| Pomperaug 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1862 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Immaculate | Away - Immaculate High School [Directions] | 4:15 p.m. | ||
| TBA | JV Baseball | Weston | Home - Community Baseball Field [Directions] | 4:15 p.m. | ||
| TBA | JV Baseball | Notre Dame-Fairfield | Away - Fabbri Field at Notre Dame [Directions] | TBA | ||
| TBA | JV Baseball | Newtown | Away - Newtown High School Baseball Field [Directions] | TBA | ||
| TBA | FR Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | 3:45 p.m. | ||
| TBA | FR Baseball | Joel Barlow | Away - Field G (Baseball) [Directions] | TBA | ||
| TBA | FR Boys Basketball | Newtown | Home - PHS Main Gym [Directions] | 3:00 p.m. | ||
| TBA | FR Boys Basketball | Stratford | Away [Directions] | 3:30 p.m. | ||
| TBA | FR Boys Basketball | Immaculate | Away - Immaculate Gym [Directions] | TBA | ||
| TBA | V Boys Lacrosse | D-II SWC Semi-Finals | Home - Sports Complex & Track [Directions] | 5:00 p.m. | 2 Games, 5:00 and 7:00, $8 Adults, $5 Students | |
| TBA | V Boys Lacrosse | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | 7:00 p.m. | SWC Semi Final, $8 Adults, $5 Students | |
| TBA | FR Girls Basketball | Newtown | Home - PHS Main Gym [Directions] | 9:00 a.m. | ||
| TBA | FR Field Hockey | Amity | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| TBA | FR Field Hockey | Masuk | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| TBA | FR Girls Soccer | New Milford | Away [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | New Fairfield | Home - Community Softball Field [Directions] | 3:45 p.m. | The team should meet at Community Field | |
| TBA | JV Softball | Immaculate | Away - Immaculate High School [Directions] | 4:15 p.m. | ||
| TBA | JV Softball | Brookfield | Away - PTAK Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Weston | Home - Community Softball Field [Directions] | TBA | ||
| TBA | FR Softball | New Milford | Home - PHS Softball Field [Directions] | 12:30 p.m. | ||
| TBA | FR Softball | Amity | Away - Center Field - Woodbridge [Directions] | 4:00 p.m. | ||
| TBA | FR Softball | Holy Cross | Away - Holy Cross HS [Directions] | TBA | ||
| TBA | V Girls Tennis | SWC Individual Championships | Away [Directions] | 3:30 p.m. | @ Joel Barlow | |
| Mon., 7/1 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:30 pm | |
| Mon., 7/1 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 7/2 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:30 pm | |
| Tue., 7/2 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 7/2 | Miscellaneous Events | CT Seahawks Girls Softball | - PHS Softball Field | 5:45 p.m. | 5:45 - 8:00 pm | |
| Tue., 7/2 | Miscellaneous Events | CTRFHC Field Hockey Leauge | - Sports Complex & Track | 6:00 p.m. | 6:00 to 8:30 | |
| Wed., 7/3 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:30 pm | |
| Wed., 7/3 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Thu., 7/4 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Fri., 7/5 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Sat., 7/6 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 - 9:00 pm | |
| Sat., 7/6 | Miscellaneous Events | CT Seahawks Girls Softball | - PHS Softball Field | 5:45 p.m. | 5:45 - 8:00 pm | |
| Sun., 7/7 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 - 9:00 pm | |
| Mon., 7/8 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:30 pm | |
| Mon., 7/8 | Miscellaneous Events | Southbury Park & Rec Volleyball Camp | - PHS Main Gym | 8:00 a.m. | 9:00 - 12:00 pm | |
| Mon., 7/8 | Miscellaneous Events | Volleyball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 to 12:00 | |
| Mon., 7/8 | Miscellaneous Events | Mdby Park & Rec Tennis Camp | - PHS Tennis Courts | 5:00 p.m. | 5:00 - 8:15 pm | |
| Mon., 7/8 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Mon., 7/8 | Miscellaneous Events | Vacation Bible School | - Auxiliary Gym | 6:00 p.m. | 6:00 pm - 8:45 pm | |
| Tue., 7/9 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:30 pm | |
| Tue., 7/9 | Miscellaneous Events | Southbury Park & Rec Volleyball Camp | - PHS Main Gym | 8:00 a.m. | 9:00 - 12:00 pm | |
| Tue., 7/9 | Miscellaneous Events | Volleyball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 to 12:00 | |
| Tue., 7/9 | Miscellaneous Events | Mdby Park & Rec Tennis Camp | - PHS Tennis Courts | 5:00 p.m. | 5:00 - 8:15 pm | |
| Tue., 7/9 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 7/9 | Miscellaneous Events | Vacation Bible School | - Auxiliary Gym | 6:00 p.m. | 6:00 pm - 8:45 pm | |
| Tue., 7/9 | Miscellaneous Events | CTRFHC Field Hockey Leauge | - Sports Complex & Track | 6:00 p.m. | 6:00 to 8:30 | |
| Wed., 7/10 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:30 pm | |
| Wed., 7/10 | Miscellaneous Events | Southbury Park & Rec Volleyball Camp | - PHS Main Gym | 8:00 a.m. | 9:00 - 12:00 pm | |
| Wed., 7/10 | Miscellaneous Events | Volleyball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 to 12:00 | |
| Wed., 7/10 | Miscellaneous Events | Mdby Park & Rec Tennis Camp | - PHS Tennis Courts | 5:00 p.m. | 5:00 - 8:15 pm | |
| Wed., 7/10 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Wed., 7/10 | Miscellaneous Events | CT Seahawks Girls Softball | - PHS Softball Field | 5:45 p.m. | 5:45 - 8:00 pm | |
| Wed., 7/10 | Miscellaneous Events | Vacation Bible School | - Auxiliary Gym | 6:00 p.m. | 6:00 pm - 8:45 pm | |
| Thu., 7/11 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:30 pm | |
| Thu., 7/11 | Miscellaneous Events | Southbury Park & Rec Volleyball Camp | - PHS Main Gym | 8:00 a.m. | 9:00 - 12:00 pm | |
| Thu., 7/11 | Miscellaneous Events | Mdby Park & Rec Tennis Camp | - PHS Tennis Courts | 5:00 p.m. | 5:00 - 8:15 pm | |
| Thu., 7/11 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Thu., 7/11 | Miscellaneous Events | Vacation Bible School | - Auxiliary Gym | 6:00 p.m. | 6:00 pm - 8:45 pm | |
| Fri., 7/12 | Miscellaneous Events | Volleyball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 to 12:00 | |
| Fri., 7/12 | Miscellaneous Events | Mdby Park & Rec Tennis Camp | - PHS Tennis Courts | 5:00 p.m. | 5:00 - 8:15 pm | |
| Fri., 7/12 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Sat., 7/13 | Miscellaneous Events | Field Hockey Alumni Game | - Sports Complex & Track | 10:00 a.m. | 10:00 am to 1:00 pm | |
| Sat., 7/13 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 - 9:00 pm | |
| Sun., 7/14 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 - 9:00 pm | |
| Mon., 7/15 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:30 pm | |
| Mon., 7/15 | Miscellaneous Events | Mdby Park & Rec Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 - 2:00 pm | |
| Mon., 7/15 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 7/16 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:30 pm | |
| Tue., 7/16 | Miscellaneous Events | Mdby Park & Rec Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 - 2:00 pm | |
| Tue., 7/16 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 7/16 | Miscellaneous Events | CTRFHC Field Hockey Leauge | - Sports Complex & Track | 6:00 p.m. | 6:00 to 8:30 | |
| Tue., 7/16 | Miscellaneous Events | CTRFHC Field Hockey Leauge | - Sports Complex & Track | 6:00 p.m. | 6:00 to 8:30 | |
| Wed., 7/17 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:30 pm | |
| Wed., 7/17 | Miscellaneous Events | Mdby Park & Rec Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 - 2:00 pm | |
| Wed., 7/17 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Wed., 7/17 | Miscellaneous Events | CT Seahawks Girls Softball | - PHS Softball Field | 5:45 p.m. | 5:45 - 8:00 pm | |
| Thu., 7/18 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:30 pm | |
| Thu., 7/18 | Miscellaneous Events | Mdby Park & Rec Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 - 2:00 pm | |
| Thu., 7/18 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Fri., 7/19 | Miscellaneous Events | Mdby Park & Rec Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 - 2:00 pm | |
| Fri., 7/19 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Sat., 7/20 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 - 9:00 pm | |
| Sun., 7/21 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 - 9:00 pm | |
| Mon., 7/22 | Miscellaneous Events | Southbury Park & Rec Basketball Camp | - PHS Main Gym | 8:00 a.m. | 9:00 - 3:00 pm | |
| Mon., 7/22 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 7/23 | Miscellaneous Events | Southbury Park & Rec Basketball Camp | - PHS Main Gym | 8:00 a.m. | 9:00 - 3:00 pm | |
| Tue., 7/23 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 7/23 | Miscellaneous Events | CTRFHC Field Hockey Leauge | - Sports Complex & Track | 6:00 p.m. | 6:00 to 8:30 | |
| Wed., 7/24 | Miscellaneous Events | Southbury Park & Rec Basketball Camp | - PHS Main Gym | 8:00 a.m. | 9:00 - 3:00 pm | |
| Wed., 7/24 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Wed., 7/24 | Miscellaneous Events | CT Seahawks Girls Softball | - PHS Softball Field | 5:45 p.m. | 5:45 - 8:00 pm | |
| Thu., 7/25 | Miscellaneous Events | Southbury Park & Rec Basketball Camp | - PHS Main Gym | 8:00 a.m. | 9:00 - 3:00 pm | |
| Thu., 7/25 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Fri., 7/26 | Miscellaneous Events | Southbury Park & Rec Basketball Camp | - PHS Main Gym | 8:00 a.m. | 9:00 - 3:00 pm | |
| Fri., 7/26 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Sat., 7/27 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 - 9:00 pm | |
| Sun., 7/28 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 - 9:00 pm | |
| Mon., 7/29 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 7/30 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 7/30 | Miscellaneous Events | CTRFHC Field Hockey Leauge | - Sports Complex & Track | 6:00 p.m. | 6:00 to 8:30 | |
| Wed., 7/31 | Miscellaneous Events | Stby Park & Rec Swim Meet | - PHS Pool | 8:00 a.m. | 8:00 - 5:00 pm | |
| Wed., 7/31 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 8/6 | Miscellaneous Events | CTRFHC Field Hockey Leauge | - Sports Complex & Track | 6:00 p.m. | 6:00 to 8:30 | |
| Fri., 8/16 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 5:30 p.m. | 5:30 - 8:00 pm | |
| Mon., 8/19 | Miscellaneous Events | Link Crew | - Auxiliary Gym | 8:00 a.m. | 8:00 to 3:00 | |
| Mon., 8/19 | Miscellaneous Events | Soccer Camp | - Sports Complex & Track | 4:30 p.m. | ||
| Tue., 8/20 | Miscellaneous Events | Link Crew | - Auxiliary Gym | 8:00 a.m. | 8:00 to 3:00 | |
| Tue., 8/20 | Miscellaneous Events | Soccer Camp | - Sports Complex & Track | 4:30 p.m. | ||
| Tue., 8/20 | Miscellaneous Events | CPR and First Aid Class For Coaches | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 to 8:00 | |
| Wed., 8/21 | Miscellaneous Events | Freshmen Orientation | - PHS Main Gym | 7:00 a.m. | 7:00 am to 12:00 pm | |
| Wed., 8/21 | Miscellaneous Events | Freshmen Orientation | 8:00 a.m. | |||
| Wed., 8/21 | Miscellaneous Events | Soccer Camp | - Sports Complex & Track | 4:30 p.m. | ||
| Wed., 8/21 | Miscellaneous Events | Freshmen Dance by Interact Club | - PHS Main Gym | 7:30 p.m. | 7:00 set up - 8:00 pm start - 10:30 pm | |
| Thu., 8/22 | Miscellaneous Events | Soccer Camp | - Sports Complex & Track | 4:30 p.m. | ||
| Fri., 8/23 | Miscellaneous Events | Soccer Camp | - Sports Complex & Track | 4:30 p.m. | ||
| Sat., 8/24 | V Football | Sacred Heart (Scrim.) | Away | 9:30 a.m. | @ Municipal Stadium | |
| Wed., 8/28 | V Football | Bloomfield (Scrim.) | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Wed., 8/28 | FR Football | Bloomfield (Scrim.) | Home - PHS Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 8/28 | V Boys Soccer | Nonnewaug (Scrim.) | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Wed., 8/28 | V Girls Volleyball | Holy Cross (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 8/28 | JV Girls Volleyball | Holy Cross (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 8/30 | V Field Hockey | Nonnewaug (Scrim.) | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Sat., 8/31 | V Football | Amity (Scrim.) | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 8/31 | FR Football | Amity (Scrim.) | Home - Sports Complex & Track [Directions] | 12:30 p.m. | ||
| Sat., 8/31 | V Boys Soccer | Cheshire (Scrim.) | Home - Sports Complex & Track [Directions] | 6:00 p.m. | ||
| Sat., 8/31 | JV Boys Soccer | Cheshire (Scrim.) | Home - Sports Complex & Track [Directions] | 4:30 p.m. | ||
| Sun., 9/1 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 11:00 a.m. | 11:00 - 8:00 pm | |
| Mon., 9/2 | V Boys Soccer | South Kent (Scrim.) | Away | 4:00 p.m. | @ Portugese Club in Danbury | |
| Mon., 9/2 | V Field Hockey | Pomperaug Play Day | Home - Sports Complex & Track [Directions] | 9:00 a.m. | Danbury, Hall | |
| Wed., 9/4 | V Football | Southington (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Wed., 9/4 | V Boys Soccer | Bullard Havens Tech (Scrim.) | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Wed., 9/4 | V Field Hockey | Cheshire (Scrim.) | Away - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Wed., 9/4 | V Girls Volleyball | Holy Cross (Scrim.) | Away [Directions] | 3:30 p.m. | ||
| Wed., 9/4 | JV Girls Volleyball | Holy Cross (Scrim.) | Away [Directions] | 3:30 p.m. | ||
| Wed., 9/4 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | 2:15 to 3:15 | |
| Wed., 9/4 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Thu., 9/5 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Thu., 9/5 | School Holidays and Closings | Rosh Hashana - No School | ||||
| Fri., 9/6 | FR Football | Southington (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Fri., 9/6 | JV Field Hockey | New Fairfield Jamboree | Away | 4:30 p.m. | ||
| Fri., 9/6 | V Girls Soccer | Staples (Scrim.) | Away - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | ||
| Fri., 9/6 | FR Girls Soccer | Staples (Scrim.) | Home - PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Sat., 9/7 | V Boys Soccer | Amity (Scrim.) | Away [Directions] | 10:00 a.m. | ||
| Sat., 9/7 | V Field Hockey | New Fairfield Play Day | Away | 8:30 a.m. | ||
| Sat., 9/7 | V Girls Soccer | Mercy (Scrim.) | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 9/7 | JV Girls Soccer | Mercy (Scrim.) | Home - PHS Soccer Field [Directions] | 10:00 a.m. | ||
| Mon., 9/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Mon., 9/9 | Miscellaneous Events | Stby Winter Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Mon., 9/9 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Tue., 9/10 | V Boys Cross Country | Bethel, Brookfield, New Fairfield | Away - @ Bethel High School [Directions] | 4:30 p.m. | PHS 15 BETHEL 48 BROOKFIELD 19 PHS 36 NFHS 18 PHS 37 | |
| Tue., 9/10 | FR Boys Soccer | Masuk | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/10 | V Girls Cross Country | Bethel, Brookfield, New Fairfield | Away - @ Bethel High School [Directions] | 5:00 p.m. | PHS 15 BETHEL 45 PHS 15 BROOKFIELD 50 PHS 27 NFHS 31 | @ Bethel |
| Tue., 9/10 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 9/10 | JV Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 6:00 p.m. | ||
| Tue., 9/10 | V Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 5:00 p.m. | L 3-1 | Non-League Game |
| Tue., 9/10 | JV Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 3:30 p.m. | ||
| Tue., 9/10 | FR Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 6:30 p.m. | ||
| Tue., 9/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Tue., 9/10 | Miscellaneous Events | Stby Winter Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 9/11 | FR Football | Newtown | Away - Newtown High School Practice Field [Directions] | 4:30 p.m. | ||
| Wed., 9/11 | V Boys Soccer | Weston | Away - WHS Turf Field [Directions] | 7:00 p.m. | W 2-0 | |
| Wed., 9/11 | JV Boys Soccer | Weston | Home - Sports Complex & Track [Directions] | 6:30 p.m. | ||
| Wed., 9/11 | V Girls Soccer | Weston | Away - WHS Turf Field [Directions] | 5:00 p.m. | W 4-0 | |
| Wed., 9/11 | JV Girls Soccer | Weston | Home - Sports Complex & Track [Directions] | 4:30 p.m. | ||
| Wed., 9/11 | V Girls Swimming and Diving | Masuk | Home - PHS Pool [Directions] | 4:00 p.m. | Masuk 82- Pomperaug 96 | |
| Wed., 9/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Wed., 9/11 | Miscellaneous Events | Stby Winter Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 9/11 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Thu., 9/12 | V Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 3:45 p.m. | W 3-2 | Non-League Game |
| Thu., 9/12 | JV Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 5:30 p.m. | ||
| Thu., 9/12 | V Girls Volleyball | Brookfield | Away [Directions] | 5:00 p.m. | W 3-1 | Non-League Game |
| Thu., 9/12 | JV Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 3:30 p.m. | ||
| Thu., 9/12 | FR Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 6:30 p.m. | ||
| Thu., 9/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Thu., 9/12 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | 2:15 to 3:15 | |
| Thu., 9/12 | Miscellaneous Events | Stby Winter Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 9/12 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Fri., 9/13 | V Football | Newtown | Home - Sports Complex & Track [Directions] | 4:00 p.m. | L 7-26 | $5 Adults, $3 Students |
| Fri., 9/13 | JV Football | Newtown | Away - Blue and Gold Stadium [Directions] | 3:30 p.m. | Cancelled | |
| Fri., 9/13 | V Boys Soccer | Joel Barlow | Home - PHS Soccer Field [Directions] | 3:45 p.m. | L 1-3 | |
| Fri., 9/13 | V Girls Soccer | Joel Barlow | Away - Field J [Directions] | 3:45 p.m. | L 0-2 | |
| Fri., 9/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Fri., 9/13 | Miscellaneous Events | Stby Winter Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Sun., 9/15 | Miscellaneous Events | Revolution Soccer Game | - Sports Complex & Track | 1:30 p.m. | 1:30 - 3:30 pm | |
| Mon., 9/16 | V Boys Soccer | New Fairfield | Away - Rebel Turf [Directions] | 5:45 p.m. | T 3-3 | |
| Mon., 9/16 | JV Boys Soccer | New Fairfield | Away - Rebel Turf [Directions] | 3:45 p.m. | ||
| Mon., 9/16 | FR Boys Soccer | Amity | Home - Long Meadow Elementary School [Directions] | 3:45 p.m. | ||
| Mon., 9/16 | FR Field Hockey | New Milford | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 9/16 | V Girls Soccer | New Fairfield | Home - Sports Complex & Track [Directions] | 3:45 p.m. | W 9-0 | |
| Mon., 9/16 | JV Girls Soccer | New Fairfield | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 9/16 | V Girls Volleyball | Weston | Home - PHS Main Gym [Directions] | 6:00 p.m. | W 3-1 | Non-League Game |
| Mon., 9/16 | JV Girls Volleyball | Weston | Home - PHS Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 9/16 | FR Girls Volleyball | Amity | Away - Amity High School [Directions] | 5:30 p.m. | ||
| Mon., 9/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Mon., 9/16 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Tue., 9/17 | V Boys Cross Country | Lauralton Hall, Stratford, Bunnell | Home - Pomperaug High School [Directions] | 4:30 p.m. | PHS 17 Stratford 46 PHS 17 Bunnell 46 | |
| Tue., 9/17 | FR Boys Soccer | New Milford | Away [Directions] | 3:45 p.m. | ||
| Tue., 9/17 | V Girls Cross Country | Lauralton Hall, Stratford, Bunnell | Home - Pomperaug High School [Directions] | 4:30 p.m. | PHS 21 Bunnell 34 PHS 17 Lauralton Hall 38 PHS 18 Stratford 43 | |
| Tue., 9/17 | V Field Hockey | Lauralton Hall | Away - Lauralton Hall Field [Directions] | 3:45 p.m. | L 1-0 | Non-League Game |
| Tue., 9/17 | JV Field Hockey | Lauralton Hall | Away - Lauralton Hall Field [Directions] | 5:30 p.m. | ||
| Tue., 9/17 | FR Girls Soccer | New Milford | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/17 | V Girls Swimming and Diving | Oxford | Home - PHS Pool [Directions] | 4:00 p.m. | Oxford 79- Pomperaug 93 | |
| Tue., 9/17 | FR Girls Volleyball | Newtown | Away - Newtown High School Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 9/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Wed., 9/18 | FR Field Hockey | Joel Barlow | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 9/18 | V Girls Volleyball | Bunnell | Away - Bunnell [Directions] | 6:30 p.m. | L 3-1 | |
| Wed., 9/18 | JV Girls Volleyball | Bunnell | Away - Bunnell [Directions] | 5:15 p.m. | ||
| Wed., 9/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Wed., 9/18 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Thu., 9/19 | FR Football | Brookfield | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | V Boys Soccer | Bunnell | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 4-1 | $5 Adults, $3 Students |
| Thu., 9/19 | JV Boys Soccer | Bunnell | Home - PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Thu., 9/19 | V Field Hockey | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | 7:00 p.m. | W 3-0 | |
| Thu., 9/19 | JV Field Hockey | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | 5:30 p.m. | ||
| Thu., 9/19 | V Girls Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | 7:00 p.m. | T 1-1 | |
| Thu., 9/19 | JV Girls Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 9/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Thu., 9/19 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | 2:15 to 3:15 | |
| Thu., 9/19 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Fri., 9/20 | V Football | Brookfield | Away - BHS Stadium Field [Directions] | 7:00 p.m. | L 21-34 | $5 Adults, $3 Students |
| Fri., 9/20 | FR Boys Soccer | Newtown | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/20 | V Field Hockey | Lauralton Hall | Home - Sports Complex & Track [Directions] | 4:00 p.m. | L 1-0 | |
| Fri., 9/20 | JV Field Hockey | Lauralton Hall | Home - Sports Complex & Track [Directions] | 5:30 p.m. | ||
| Fri., 9/20 | FR Field Hockey | Newtown | Away - Treadwell Town Park [Directions] | 3:30 p.m. | ||
| Fri., 9/20 | FR Girls Soccer | Newtown | Away - Treadwell Town Park--Tilson Field [Directions] | 3:45 p.m. | ||
| Fri., 9/20 | V Girls Swimming and Diving | New Fairfield | Home - PHS Pool [Directions] | 6:00 p.m. | New Fairfield 83- Pomperaug 101 | $5 Adults, $3 Students |
| Fri., 9/20 | V Girls Volleyball | Newtown | Home - PHS Main Gym [Directions] | 5:00 p.m. | L 3-0 | |
| Fri., 9/20 | JV Girls Volleyball | Newtown | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 9/20 | FR Girls Volleyball | Newtown | Home - PHS Main Gym [Directions] | 6:30 p.m. | ||
| Fri., 9/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Fri., 9/20 | School Holidays and Closings | Professional Development - Half Day | ||||
| Sat., 9/21 | V Boys Cross Country | Amherst Invitational | Away | TBA | ||
| Sat., 9/21 | JV Football | Brookfield | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 9/21 | V Boys Soccer | Watertown | Home - Sports Complex & Track [Directions] | 6:00 p.m. | W 8-0 | $5 Adults, $3 Students |
| Sat., 9/21 | JV Boys Soccer | Joel Barlow | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Sat., 9/21 | V Girls Cross Country | Amherst Invitiational | Away | TBA | ||
| Sat., 9/21 | V Girls Soccer | Naugatuck | Home - Sports Complex & Track [Directions] | 2:00 p.m. | W 2-1 | |
| Sat., 9/21 | JV Girls Soccer | Joel Barlow | Away - Field J [Directions] | 4:00 p.m. | ||
| Sat., 9/21 | FR Girls Soccer | Naugatuck | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sun., 9/22 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 11:00 a.m. | 11:00 - 8:00 pm | |
| Mon., 9/23 | FR Field Hockey | Masuk | Away - Masuk Middle Field [Directions] | 4:30 p.m. | ||
| Mon., 9/23 | V Girls Soccer | Lauralton Hall | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 1-0 | $5 Adults, $3 Students |
| Mon., 9/23 | JV Girls Soccer | Lauralton Hall | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Mon., 9/23 | V Girls Volleyball | New Milford | Away - New Milford High School [Directions] | 5:00 p.m. | W 3-1 | |
| Mon., 9/23 | JV Girls Volleyball | New Milford | Away - New Milford High School [Directions] | 3:30 p.m. | ||
| Mon., 9/23 | FR Girls Volleyball | New Milford | Away - New Milford High School [Directions] | 6:30 p.m. | ||
| Mon., 9/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Mon., 9/23 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Tue., 9/24 | V Boys Cross Country | Notre Dame-Fairfield, Immaculate, Joel Barlow | Home - Pomperaug High School [Directions] | 4:30 p.m. | PHS 15 IHS 50 PHS 15 NDHS 50 PHS 19 JBHS 42 | |
| Tue., 9/24 | V Girls Cross Country | Notre Dame-Fairfield, Immaculate, Joel Barlow | Home - Pomperaug High School [Directions] | 4:30 p.m. | PHS 15 NDHS 49 PHS 18 JBHS 40 IHS 25 PHS 30 | |
| Tue., 9/24 | V Field Hockey | Immaculate | Home - Sports Complex & Track [Directions] | 7:30 p.m. | W 1-0 | $5 Adults, $3 Students |
| Tue., 9/24 | JV Field Hockey | Immaculate | Home - Sports Complex & Track [Directions] | 5:45 p.m. | Cancelled | |
| Tue., 9/24 | V Girls Swimming and Diving | New Milford | Away - Canterbury School [Directions] | 7:00 p.m. | New Milford 75- Pomperaug 97 | |
| Tue., 9/24 | FR Girls Volleyball | New Milford | Home - PHS Main Gym [Directions] | 6:30 p.m. | ||
| Tue., 9/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Wed., 9/25 | V Girls Volleyball | Joel Barlow | Home - PHS Main Gym [Directions] | 5:00 p.m. | L 3-2 | |
| Wed., 9/25 | JV Girls Volleyball | Joel Barlow | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 9/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Wed., 9/25 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Thu., 9/26 | FR Football | New Milford | Away - New Milford High School [Directions] | 4:00 p.m. | ||
| Thu., 9/26 | V Boys Soccer | New Milford | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 2-1 | $5 Adults, $3 Students |
| Thu., 9/26 | JV Boys Soccer | New Milford | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 9/26 | FR Boys Soccer | Naugatuck | Away - Breen Field [Directions] | 3:30 p.m. | ||
| Thu., 9/26 | V Girls Soccer | New Milford | Away - New Milford High School [Directions] | 6:00 p.m. | L 1-3 | |
| Thu., 9/26 | JV Girls Soccer | New Milford | Away - New Milford High School [Directions] | 4:00 p.m. | ||
| Thu., 9/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Thu., 9/26 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | 2:15 to 3:15 | |
| Thu., 9/26 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Fri., 9/27 | V Football | New Milford | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 52-21 | $5 Adults, $3 Students |
| Fri., 9/27 | V Field Hockey | Masuk | Home - Sports Complex & Track [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 9/27 | JV Field Hockey | Masuk | Home - PHS Baseball Field [Directions] | 5:30 p.m. | ||
| Fri., 9/27 | V Girls Swimming and Diving | Brookfield | Home - PHS Pool [Directions] | 6:00 p.m. | Brookfield 87- Pomperaug 94 | $5 Adults, $3 Students |
| Fri., 9/27 | FR Girls Volleyball | Immaculate | Away - Immaculate High School [Directions] | 6:30 p.m. | ||
| Fri., 9/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Sat., 9/28 | V Boys Cross Country | Wilton Invitational | Away | TBA | ||
| Sat., 9/28 | JV Football | New Milford | Away - New Milford High School [Directions] | 10:00 a.m. | ||
| Sat., 9/28 | V Boys Soccer | Immaculate | Away - Mustang Valley [Directions] | 10:00 a.m. | W 5-1 | |
| Sat., 9/28 | JV Boys Soccer | Immaculate | Away - Immaculate High School [Directions] | 10:00 a.m. | ||
| Sat., 9/28 | V Girls Cross Country | Wilton Invitational | Away | TBA | ||
| Sat., 9/28 | FR Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 9:00 a.m. | ||
| Sat., 9/28 | V Girls Soccer | Immaculate | Home - Sports Complex & Track [Directions] | 3:45 p.m. | L 0-2 | |
| Sun., 9/29 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 11:00 a.m. | 11:00 - 8:00 pm | |
| Mon., 9/30 | V Boys Soccer | Brookfield | Home - Sports Complex & Track [Directions] | 7:00 p.m. | T 1-1 | $5 Adults, $3 Students |
| Mon., 9/30 | JV Boys Soccer | Brookfield | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Mon., 9/30 | FR Boys Soccer | Watertown | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 9/30 | FR Field Hockey | Brookfield | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 9/30 | V Girls Soccer | Brookfield | Away - BHS Stadium Field [Directions] | 7:00 p.m. | T 0-0 | |
| Mon., 9/30 | JV Girls Soccer | Brookfield | Away - BHS Stadium Field [Directions] | 5:15 p.m. | ||
| Mon., 9/30 | FR Girls Soccer | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | ||
| Mon., 9/30 | V Girls Volleyball | Masuk | Home - PHS Main Gym [Directions] | 5:00 p.m. | L 1-3 | |
| Mon., 9/30 | JV Girls Volleyball | Masuk | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 9/30 | FR Girls Volleyball | Masuk | Home - PHS Main Gym [Directions] | 6:30 p.m. | ||
| Mon., 9/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Mon., 9/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Mon., 9/30 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Tue., 10/1 | V Boys Cross Country | Masuk, Weston, Kolbe Cathedral | Away [Directions] | 4:30 p.m. | PHS 15 KHS 50 PHS 19 MASUK 42 PHS 20 WESTON 39 | |
| Tue., 10/1 | FR Boys Soccer | Holy Cross | Away - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Tue., 10/1 | V Girls Cross Country | Masuk, Weston, Kolbe Cathedral | Away [Directions] | 4:30 p.m. | PHS 15 KOLBE 50 PHS 15 MASUK 48 PHS 15 WESTON 47 | |
| Tue., 10/1 | V Field Hockey | New Milford | Away [Directions] | 3:45 p.m. | T 0-0 | |
| Tue., 10/1 | JV Field Hockey | New Milford | Away [Directions] | 5:30 p.m. | ||
| Tue., 10/1 | FR Girls Soccer | Holy Cross | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/1 | V Girls Swimming and Diving | Newtown | Away - Newtown High School Pool [Directions] | 4:00 p.m. | Newtown 86.5- Pomperaug 99.5 | |
| Tue., 10/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Tue., 10/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 10/2 | V Girls Volleyball | New Fairfield | Home - PHS Main Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Wed., 10/2 | JV Girls Volleyball | New Fairfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 10/2 | FR Girls Volleyball | Immaculate | Home - PHS Main Gym [Directions] | 6:30 p.m. | ||
| Wed., 10/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Wed., 10/2 | Miscellaneous Events | Band Practice | - Auxiliary Gym | 2:15 p.m. | 2:15 - 3:15 | |
| Wed., 10/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 10/2 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Thu., 10/3 | FR Football | Bethel | Away - @ Bethel High School [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | V Boys Soccer | Oxford | Home - Sports Complex & Track [Directions] | 3:30 p.m. | W 11-0 | |
| Thu., 10/3 | JV Boys Soccer | Oxford | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/3 | V Field Hockey | Joel Barlow | Home - Sports Complex & Track [Directions] | 7:30 p.m. | OT-L 2-1 | $5 Adults, $3 Students |
| Thu., 10/3 | JV Field Hockey | Joel Barlow | Home - Sports Complex & Track [Directions] | 5:30 p.m. | ||
| Thu., 10/3 | FR Field Hockey | Bethel | Away [Directions] | 4:30 p.m. | ||
| Thu., 10/3 | V Girls Soccer | Oxford | Away - OHS Wolverine Field [Directions] | 7:00 p.m. | W 6-1 | |
| Thu., 10/3 | JV Girls Soccer | Oxford | Away - OHS Wolverine Field [Directions] | 5:00 p.m. | ||
| Thu., 10/3 | FR Girls Soccer | Amity | Home - Long Meadow Elementary School [Directions] | 3:45 p.m. | ||
| Thu., 10/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Thu., 10/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Thu., 10/3 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | 2:15 to 3:15 | |
| Thu., 10/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 10/3 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Fri., 10/4 | V Boys Cross Country | Nonnewaug Invitational | Away | 4:00 p.m. | ||
| Fri., 10/4 | V Football | Bethel | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 20-42 | $5 Adults, $3 Students |
| Fri., 10/4 | V Girls Cross Country | Nonnewaug Invitational | Away | 4:00 p.m. | ||
| Fri., 10/4 | V Girls Swimming and Diving | Weston | Home - PHS Pool [Directions] | 6:00 p.m. | Weston 98- Pomperaug 88 | $5 Adults, $3 Students |
| Fri., 10/4 | V Girls Volleyball | Stratford | Home - PHS Main Gym [Directions] | 5:00 p.m. | W 3-1 | |
| Fri., 10/4 | JV Girls Volleyball | Stratford | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 10/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Fri., 10/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Sat., 10/5 | JV Football | Bethel | Away [Directions] | 3:00 p.m. | ||
| Sat., 10/5 | V Boys Soccer | Naugatuck | Away - Naugatuck High School [Directions] | 6:00 p.m. | L 3-4 | |
| Sat., 10/5 | FR Boys Soccer | Masuk | Away - Masuk Middle Field [Directions] | 9:00 a.m. | ||
| Sat., 10/5 | FR Girls Soccer | Masuk | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 10/5 | FR Girls Volleyball | Shelton | Away - Shelton High School Gym [Directions] | 10:30 a.m. | ||
| Sun., 10/6 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 11:00 a.m. | 11:00 - 8:00 pm | |
| Mon., 10/7 | V Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | 5:00 p.m. | L 0-3 | |
| Mon., 10/7 | JV Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Mon., 10/7 | FR Girls Volleyball | Holy Cross | Home - PHS Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 10/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Mon., 10/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Mon., 10/7 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Tue., 10/8 | V Boys Cross Country | New Milford, Oxford, Newtown | Away - New Milford High School [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Boys Soccer | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | 3:45 p.m. | W 7-1 | |
| Tue., 10/8 | FR Boys Soccer | New Milford | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/8 | V Girls Cross Country | New Milford, Oxford, Newtown | Away - New Milford High School [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Field Hockey | Weston | Away - WHS Turf Field [Directions] | 7:00 p.m. | W 5-1 | |
| Tue., 10/8 | JV Field Hockey | Weston | Away - WHS Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 10/8 | FR Field Hockey | Amity | Away - Amity High School [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Girls Soccer | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | 3:45 p.m. | W 4-1 | |
| Tue., 10/8 | V Girls Swimming and Diving | Bunnell | Home - PHS Pool [Directions] | 6:00 p.m. | Bunnell 81- Pomperaug 92 | $5 Adults, $3 Students |
| Tue., 10/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Tue., 10/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 10/9 | V Girls Volleyball | Lauralton Hall | Away - Lauralton Hall Gymnasium [Directions] | 3:30 p.m. | W 3-1 | |
| Wed., 10/9 | JV Girls Volleyball | Lauralton Hall | Away - Lauralton Hall Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 10/9 | FR Girls Volleyball | Lauralton Hall | Away - Lauralton Hall Gymnasium [Directions] | 6:30 p.m. | ||
| Wed., 10/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Wed., 10/9 | Miscellaneous Events | Band Practice | - Auxiliary Gym | 2:15 p.m. | 2:15 - 3:15 | |
| Wed., 10/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 10/9 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Thu., 10/10 | FR Football | Masuk | Away - Masuk Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 10/10 | V Boys Soccer | Kolbe Cathedral | Away - Seaside Park [Directions] | 3:45 p.m. | W 6-0 | |
| Thu., 10/10 | V Field Hockey | New Fairfield | Home - Sports Complex & Track [Directions] | 7:30 p.m. | W 2-1 | $5 Adults, $3 Students |
| Thu., 10/10 | JV Field Hockey | New Fairfield | Home - Sports Complex & Track [Directions] | 5:45 p.m. | ||
| Thu., 10/10 | V Girls Soccer | Kolbe Cathedral | Home - Sports Complex & Track [Directions] | 3:45 p.m. | W 8-0 | |
| Thu., 10/10 | V Girls Volleyball | Bethel | Away - @ Bethel High School [Directions] | 5:00 p.m. | W 3-1 | |
| Thu., 10/10 | JV Girls Volleyball | Bethel | Away - @ Bethel High School [Directions] | 3:30 p.m. | ||
| Thu., 10/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Thu., 10/10 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | 2:15 to 3:15 | |
| Thu., 10/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 10/10 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Thu., 10/10 | School Holidays and Closings | Open House | ||||
| Fri., 10/11 | V Football | Masuk | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 35-32 | $5 Adults, $3 Students |
| Fri., 10/11 | V Boys Soccer | Bethel | Away - Rourke Field [Directions] | 5:00 p.m. | L 1-0 | |
| Fri., 10/11 | JV Boys Soccer | Bethel | Away - @ Bethel High School [Directions] | 3:45 p.m. | ||
| Fri., 10/11 | FR Boys Soccer | Newtown | Away - Newtown High School Practice Field [Directions] | 3:45 p.m. | ||
| Fri., 10/11 | FR Girls Soccer | Newtown | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/11 | V Girls Swimming and Diving | Stratford | Away - Flood Middle School Pool [Directions] | 4:00 p.m. | Stratford 67- Pomperaug 91 | |
| Fri., 10/11 | FR Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 6:30 p.m. | ||
| Fri., 10/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Fri., 10/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Fri., 10/11 | School Holidays and Closings | Professional Development - Half Day | ||||
| Sat., 10/12 | JV Football | Masuk | Away - Masuk Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 10/12 | FR Boys Soccer | Amity | Away - Amity High School - Field # 2 [Directions] | 10:00 a.m. | ||
| Sat., 10/12 | V Field Hockey | Bethel | Away - @ Bethel High School [Directions] | 10:00 a.m. | OT-L 0-1 | |
| Sat., 10/12 | JV Field Hockey | Bethel | Away - @ Bethel High School [Directions] | 12:00 p.m. | ||
| Sat., 10/12 | V Girls Soccer | Bethel | Home - Sports Complex & Track [Directions] | 12:00 p.m. | W 8-1 | |
| Sat., 10/12 | JV Girls Soccer | Bethel | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 10/12 | FR Girls Volleyball | Holy Cross | Away - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Sun., 10/13 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 11:00 a.m. | 11:00 - 8:00 pm | |
| Mon., 10/14 | V Boys Soccer | Stratford | Home - Sports Complex & Track [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/14 | JV Boys Soccer | Stratford | Home - PHS Soccer Field [Directions] | 4:00 p.m. | ||
| Mon., 10/14 | V Field Hockey | Greenwich | Home - Sports Complex & Track [Directions] | 12:00 p.m. | L 2-1 | |
| Mon., 10/14 | V Girls Soccer | Stratford | Away - Penders Field [Directions] | 7:00 p.m. | W 4-0 | |
| Mon., 10/14 | JV Girls Soccer | Stratford | Away - Penders Field [Directions] | 4:00 p.m. | Cancelled | |
| Mon., 10/14 | School Holidays and Closings | Columbus Day - No School | ||||
| Tue., 10/15 | FR Field Hockey | Newtown | Home - PHS Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 10/15 | FR Girls Soccer | Masuk | Away - Masuk Middle Field [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | V Girls Volleyball | New Milford | Home - PHS Main Gym [Directions] | 5:00 p.m. | W 3-0 | Non-League Game |
| Tue., 10/15 | JV Girls Volleyball | New Milford | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 10/15 | FR Girls Volleyball | New Milford | Home - PHS Main Gym [Directions] | 6:30 p.m. | ||
| Tue., 10/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Tue., 10/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 10/15 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 10/16 | V Field Hockey | Newtown | Home - Sports Complex & Track [Directions] | 3:45 p.m. | T 2-2 | |
| Wed., 10/16 | JV Field Hockey | Newtown | Home - Sports Complex & Track [Directions] | 5:30 p.m. | ||
| Wed., 10/16 | FR Girls Soccer | Amity | Away - Center Field - Woodbridge [Directions] | 3:45 p.m. | ||
| Wed., 10/16 | V Girls Volleyball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 5:00 p.m. | W 3-0 | |
| Wed., 10/16 | JV Girls Volleyball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 3:30 p.m. | ||
| Wed., 10/16 | FR Girls Volleyball | Amity | Home - PHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Wed., 10/16 | Miscellaneous Events | Band Practice | - Auxiliary Gym | 3:30 p.m. | 3:30 to 4:30 | |
| Wed., 10/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 10/16 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Thu., 10/17 | V Boys Cross Country | SWC Championship Meet | Away [Directions] | 3:30 p.m. | @ Bethel | |
| Thu., 10/17 | V Boys Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | 7:00 p.m. | L 2-0 | |
| Thu., 10/17 | JV Boys Soccer | Newtown | Away - Treadwell Town Park--Tilson Field [Directions] | 3:45 p.m. | ||
| Thu., 10/17 | V Girls Cross Country | SWC Championship Meet | Away [Directions] | 4:00 p.m. | @ Bethel | |
| Thu., 10/17 | FR Field Hockey | New Milford | Away [Directions] | 4:30 p.m. | ||
| Thu., 10/17 | V Girls Soccer | Newtown | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 3-2 | $5 Adults, $3 Students |
| Thu., 10/17 | V Girls Swimming and Diving | Joel Barlow | Away - Western CT State University - O'Neill Center [Directions] | 4:00 p.m. | @ WCSU | |
| Thu., 10/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Thu., 10/17 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | 2:15 to 3:15 | |
| Thu., 10/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 10/17 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Thu., 10/17 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 10/18 | V Football | Woodland | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 13-42 | $5 Adults, $3 Students -- Homecoming Game |
| Fri., 10/18 | FR Boys Soccer | Naugatuck | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/18 | V Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | 3:45 p.m. | W 2-0 | |
| Fri., 10/18 | JV Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 10/18 | JV Girls Soccer | Immaculate | Home - Sports Complex & Track [Directions] | 3:45 p.m. | ||
| Fri., 10/18 | FR Girls Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 p.m. | ||
| Fri., 10/18 | V Girls Volleyball | Brookfield | Home - PHS Main Gym [Directions] | 5:00 p.m. | W 3-2 | |
| Fri., 10/18 | JV Girls Volleyball | Brookfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 10/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Fri., 10/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Sat., 10/19 | JV Football | Woodland | Away - Woodland Football Field [Directions] | 12:30 p.m. | ||
| Sat., 10/19 | FR Field Hockey | Joel Barlow | Away - Field D [Directions] | 9:00 a.m. | ||
| Sat., 10/19 | JV Girls Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 2:00 p.m. | ||
| Sat., 10/19 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 11:00 a.m. | 11:00 - 8:00 pm | |
| Sat., 10/19 | Miscellaneous Events | Save The Children Fundraiser | - Sports Complex & Track | 8:00 a.m. | 8:00 - 11:00 am | |
| Sat., 10/19 | Miscellaneous Events | Homecoming Dance | - PHS Main Gym | 7:30 p.m. | 4:30 - 11:30 pm | |
| Mon., 10/21 | V Boys Soccer | Masuk | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 3-0 | $5 Adults, $3 Students |
| Mon., 10/21 | JV Boys Soccer | Masuk | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Mon., 10/21 | V Girls Soccer | Masuk | Away - Masuk Stadium Field [Directions] | 7:00 p.m. | L 0-1 | |
| Mon., 10/21 | JV Girls Soccer | Masuk | Away - Masuk Stadium Field [Directions] | 5:00 p.m. | ||
| Mon., 10/21 | V Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Mon., 10/21 | JV Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 10/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Mon., 10/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Mon., 10/21 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Tue., 10/22 | V Boys Cross Country | SWC JV Run | Away | 3:45 p.m. | Cancelled | |
| Tue., 10/22 | FR Boys Soccer | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | ||
| Tue., 10/22 | V Girls Cross Country | SWC JV Run | Away [Directions] | 3:45 p.m. | Cancelled | @ Bethel HS |
| Tue., 10/22 | V Field Hockey | New Milford | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 2-0 | Non-League Game, $5 Adults, $3 Students |
| Tue., 10/22 | JV Field Hockey | New Milford | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Tue., 10/22 | FR Girls Soccer | Watertown | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/22 | V Girls Swimming and Diving | Lauralton Hall | Away - Foran High School Pool [Directions] | 6:00 p.m. | ||
| Tue., 10/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Tue., 10/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 10/22 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 10/23 | V Boys Cross Country | Practice Run | Away | 3:30 p.m. | @ Wickham Park | |
| Wed., 10/23 | V Girls Cross Country | Practice Run | Away | 3:30 p.m. | @ Wickham Park | |
| Wed., 10/23 | V Girls Volleyball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Wed., 10/23 | JV Girls Volleyball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 10/23 | FR Girls Volleyball | Brookfield | Home - PHS Main Gym [Directions] | 6:30 p.m. | ||
| Wed., 10/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Wed., 10/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 10/23 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Thu., 10/24 | V Boys Cross Country | Practice Run | Away | 3:30 p.m. | @ Terrywile Park, Danbury | |
| Thu., 10/24 | FR Football | Joel Barlow | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Thu., 10/24 | FR Boys Soccer | Holy Cross | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/24 | V Girls Cross Country | Practice Run | Away | 3:30 p.m. | @ Terrywile Park, Danbury | |
| Thu., 10/24 | FR Girls Soccer | Holy Cross | Away - Upper Murray Park [Directions] | 3:45 p.m. | ||
| Thu., 10/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Thu., 10/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 10/24 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Thu., 10/24 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 10/25 | V Football | Joel Barlow | Away - Western Connecticut State University [Directions] | 7:00 p.m. | L 19-41 | |
| Fri., 10/25 | V Boys Soccer | SWC Quarter-Finals | Home - Sports Complex & Track [Directions] | 4:00 p.m. | Adults $8, Students $5 | |
| Fri., 10/25 | V Girls Soccer | Lauralton Hall | Home - Sports Complex & Track [Directions] | 6:00 p.m. | W 1-0 | $8 Adults, $5 Students |
| Fri., 10/25 | JV Girls Soccer | Newtown | Home - PHS Soccer Field [Directions] | 3:00 p.m. | ||
| Fri., 10/25 | FR Girls Soccer | Ridgefield | Home - Long Meadow Elementary School [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | V Girls Swimming and Diving | JV Invitational | Home - PHS Pool [Directions] | 6:00 p.m. | ||
| Fri., 10/25 | FR Girls Volleyball | Shelton | Home - PHS Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Fri., 10/25 | Miscellaneous Events | Pomperaug Outreach Babysitting | - Health Classroom - Room 201 | 4:00 p.m. | 4:00 - 9:00 pm | |
| Fri., 10/25 | Miscellaneous Events | Pomperaug Outreach Babysitting | - Auxiliary Gym | 4:00 p.m. | 4:00 - 9:00 pm | |
| Fri., 10/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Sat., 10/26 | V Boys Cross Country | CIAC Class L Championship | Away - Wickham Park - East Hartford [Directions] | 2:05 p.m. | ||
| Sat., 10/26 | V Girls Cross Country | CIAC Class L Championship | Away - Wickham Park - East Hartford [Directions] | 2:35 p.m. | ||
| Sat., 10/26 | V Field Hockey | SWC Quarter Finals | Home [Directions] | 10:00 a.m. | $8 Adults, $5 Students | |
| Sat., 10/26 | FR Girls Volleyball | Southington Freshmen Tournament | Away | 9:00 a.m. | ||
| Sun., 10/27 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 11:00 a.m. | 11:00 am to 8:30 pm | |
| Mon., 10/28 | JV Football | Joel Barlow | Away - Field G (Baseball) [Directions] | 4:00 p.m. | ||
| Mon., 10/28 | V Boys Soccer | SWC Semi-Finals | Home - Sports Complex & Track [Directions] | 5:00 p.m. | $8 Adults, $5 Students | |
| Mon., 10/28 | V Girls Volleyball | Bunnell | Away - Bunnell [Directions] | 5:00 p.m. | L 3-1 | @ Bunnell |
| Mon., 10/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Mon., 10/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Mon., 10/28 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Tue., 10/29 | V Field Hockey | SWC Semi-Finals | Away [Directions] | 5:30 p.m. | @ Weston, $8 Adults, $5 Students | |
| Tue., 10/29 | V Girls Soccer | Immaculate | Away [Directions] | 7:00 p.m. | W 3-2 | @ Brookfield, $8 Adults, $5 Students |
| Tue., 10/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Tue., 10/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 10/29 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 10/30 | V Boys Soccer | SWC Championship Game | Away [Directions] | 7:00 p.m. | Cancelled | @ Bunnell, $10 Adults, $5 Students |
| Wed., 10/30 | V Girls Swimming and Diving | SWC Diving Championship | Away [Directions] | 6:00 p.m. | @Masuk | |
| Wed., 10/30 | V Girls Volleyball | SWC Semi-Finals | Away [Directions] | 5:00 p.m. | Cancelled | @ Newtown |
| Wed., 10/30 | Miscellaneous Events | Blood Drive sponsored by Nat'l Honor Society | - Auxiliary Gym | 6:00 a.m. | 6:00 am - 2:30 pm | |
| Wed., 10/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Wed., 10/30 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Wed., 10/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 10/31 | FR Football | Bunnell | Away - Bunnell Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/31 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:00 p.m. | 2:00 - 3:45 pm | |
| Thu., 10/31 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Thu., 10/31 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 11/1 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 3:30 p.m. | $10 admission | |
| Fri., 11/1 | V Football | Bunnell | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 38-23 | $5 Adults, $3 Students |
| Fri., 11/1 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 4:15 p.m. | ||
| Fri., 11/1 | V Field Hockey | SWC Championship Game | Away [Directions] | 7:00 p.m. | @ Brookfield, $10 Adults, $5 Students | |
| Fri., 11/1 | V Girls Soccer | New Milford | Away [Directions] | 7:00 p.m. | W 2-1 | @ Newtown, $10 Adults, $5 Students |
| Sat., 11/2 | V Girls Swimming and Diving | SWC Swim Championship | Away [Directions] | 4:00 p.m. | $10 Adults, $5 Students | |
| Sat., 11/2 | V Girls Volleyball | Holy Cross (Scrim.) | Home - PHS Main Gym [Directions] | 8:30 a.m. | ||
| Sat., 11/2 | V Girls Volleyball | SWC Championship Game | Away [Directions] | 6:00 p.m. | Cancelled | @ Weston |
| Sat., 11/2 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 11/2 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - Auxiliary Gym | 1:30 p.m. | 1:30 - 9:00 pm | |
| Sat., 11/2 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 1:30 p.m. | 1:30 - 9:00 pm | |
| Sat., 11/2 | Miscellaneous Events | Ring Dance | 6:00 p.m. | |||
| Sat., 11/2 | School Holidays and Closings | Ring Dance | ||||
| Sun., 11/3 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 11/4 | JV Football | Bunnell | Away - Bunnell Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 11/4 | V Girls Soccer | Ledyard | Home - Sports Complex & Track [Directions] | 2:00 p.m. | W 5-1 | $8 Adults, $5 Students |
| Mon., 11/4 | V Girls Volleyball | Avon | Home - PHS Main Gym [Directions] | 6:00 p.m. | L 3-1 | $8 Adults, $5 Students |
| Mon., 11/4 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Mon., 11/4 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 11/4 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 6:15 p.m. | 6:15 - 8:30 pm | |
| Mon., 11/4 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 11/4 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/5 | V Boys Soccer | Maloney | Home - Sports Complex & Track [Directions] | 4:00 p.m. | $8 Adults, $5 Students | |
| Tue., 11/5 | V Field Hockey | Guilford | Away - Kavanaugh Turf Field at GHS [Directions] | 7:00 p.m. | ||
| Tue., 11/5 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 11/5 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 6:15 p.m. | 6:15 - 8:30 pm | |
| Tue., 11/5 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 11/6 | V Girls Soccer | RHAM | Away - RHAM High School Athletic Complex [Directions] | 2:00 p.m. | $8 Adults, $5 Students | |
| Wed., 11/6 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6 - 8:30 pm | |
| Wed., 11/6 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 11/6 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 6:15 p.m. | 6:15 - 8:30 pm | |
| Wed., 11/6 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 11/7 | FR Football | Masuk | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Thu., 11/7 | V Girls Swimming and Diving | CIAC Class M Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Thu., 11/7 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 11/7 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 11/7 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 6:15 p.m. | 6:15 - 8:30 pm | |
| Thu., 11/7 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 11/7 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 11/8 | V Boys Soccer | Torrington | Away [Directions] | 4:00 p.m. | $8 Adults, $5 Students | |
| Fri., 11/8 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 11/9 | V Boys Cross Country | New England Championship | Away - Site TBA [Directions] | TBA | ||
| Sat., 11/9 | V Football | Weston | Away - WHS Stadium Field [Directions] | 1:00 p.m. | W 21-0 | |
| Sat., 11/9 | V Girls Cross Country | New England Championship | Away - Site TBA [Directions] | TBA | ||
| Sat., 11/9 | V Girls Swimming and Diving | CIAC Class M Qualifying | Away - East Hartford [Directions] | 11:30 a.m. | ||
| Sat., 11/9 | Miscellaneous Events | Turkey Tumble | - PHS Main Gym | 7:00 a.m. | ||
| Sat., 11/9 | Miscellaneous Events | Save the Children Running Fundraiser | - Sports Complex & Track | 8:00 a.m. | 8:00 am - 12:00 noon | |
| Sat., 11/9 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 11/9 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - Auxiliary Gym | 1:30 p.m. | 1:30 - 9:00 pm | |
| Sun., 11/10 | V Boys Soccer | RHAM | Away - RHAM High School Athletic Complex [Directions] | 2:00 p.m. | ||
| Sun., 11/10 | Miscellaneous Events | Turkey Tumble | - PHS Main Gym | 7:00 a.m. | ||
| Sun., 11/10 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 11/11 | JV Football | Weston | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Mon., 11/11 | V Girls Swimming and Diving | Practice | Home - PHS Pool [Directions] | 3:15 to 6:00 | ||
| Mon., 11/11 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 11/11 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 6:15 p.m. | 6:15 - 8:30 pm | |
| Mon., 11/11 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 11/11 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/12 | V Girls Swimming and Diving | Practice | Home - PHS Pool [Directions] | 3:15 to 6:00 | ||
| Tue., 11/12 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 11/12 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 6:15 p.m. | 6:15 - 8:30 pm | |
| Tue., 11/12 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 11/13 | V Boys Soccer | Farmington | Away [Directions] | 6:30 p.m. | @ Municipal Stadium, $8 Adults, $5 Students | |
| Wed., 11/13 | V Girls Swimming and Diving | CIAC Class M Finals | Away - SCSU [Directions] | 6:00 p.m. | ||
| Wed., 11/13 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 11/13 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 11/13 | Miscellaneous Events | CIAC VOLLEYBALL TOURNAMENT NEUTRAL SITE | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 11/13 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 11/14 | FR Football | New Fairfield | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Thu., 11/14 | V Girls Swimming and Diving | Practice | Home - PHS Pool [Directions] | 3:15 to 6:00 | ||
| Thu., 11/14 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 11/14 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 6:15 p.m. | 6:15 - 8:30 pm | |
| Thu., 11/14 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 11/14 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 11/15 | V Football | New Fairfield | Away - Rebel Stadium [Directions] | 7:00 p.m. | L 15-19 | |
| Fri., 11/15 | V Girls Swimming and Diving | CIAC Open Diving | Away - Plainville HS [Directions] | 5:30 p.m. | Cancelled | |
| Fri., 11/15 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 11/15 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 6:15 p.m. | 6:15 - 8:30 pm | |
| Sat., 11/16 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Sat., 11/16 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 11/16 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - Auxiliary Gym | 1:30 p.m. | 1:30 - 9:00 pm | |
| Sat., 11/16 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 1:30 p.m. | 1:30 - 9:00 pm | |
| Sun., 11/17 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 11/17 | Miscellaneous Events | Revolution Soccer Club | - Sports Complex & Track | 2:00 p.m. | 1:30 to 4:30 | |
| Mon., 11/18 | JV Football | New Fairfield | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Mon., 11/18 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 11/18 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 6:15 p.m. | 6:15 - 8:30 pm | |
| Mon., 11/18 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 11/18 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/19 | Miscellaneous Events | CPR Class For Coaches | - Health Classroom - Room 201 | 5:00 p.m. | ||
| Tue., 11/19 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 11/19 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 6:15 p.m. | 6:15 - 8:30 pm | |
| Tue., 11/19 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 11/20 | FR Football | Oxford | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Wed., 11/20 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 6:00 p.m. | 6:00 - 9:00 pm | |
| Wed., 11/20 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 11/20 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 6:15 p.m. | 6:15 - 8:30 pm | |
| Wed., 11/20 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 11/21 | V Football | SWC Championship Game | Away [Directions] | 7:00 p.m. | Cancelled | @Brookfield |
| Thu., 11/21 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 11/21 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 6:15 p.m. | 6:15 - 8:30 pm | |
| Thu., 11/21 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 11/21 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 11/22 | JV Football | Oxford | Home - Sports Complex & Track [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 11/22 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 6:00 p.m. | 6:00 - 9:00 pm | |
| Fri., 11/22 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 11/22 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 6:15 p.m. | 6:15 - 8:30 pm | |
| Sat., 11/23 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 11/23 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - Auxiliary Gym | 1:30 p.m. | 1:30 - 9:00 pm | |
| Sat., 11/23 | Miscellaneous Events | Southbury Park & Rec Travel Basketball | - PHS Main Gym | 1:30 p.m. | 1:30 - 9:00 pm | |
| Sun., 11/24 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 11/25 | Miscellaneous Events | PAC Swim Pictures | - Health Classroom - Room 201 | 4:00 p.m. | 4:00 - 9:00 pm (Swim Team Pictures) | |
| Mon., 11/25 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 11/25 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 11/25 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/26 | V Football | Oxford | Away - OHS Wolverine Field (Turf) [Directions] | 5:00 p.m. | L 12-28 | |
| Tue., 11/26 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 11/26 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 11/27 | School Holidays and Closings | Thanksgiving Break - Half Day | ||||
| Thu., 11/28 | School Holidays and Closings | Thanksgiving | ||||
| Sat., 11/30 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/1 | V Girls Basketball | Nonnewaug (Scrim.) | Home - PHS Main Gym [Directions] | 11:00 a.m. | ||
| Sun., 12/1 | V Girls Basketball | Watertown (Scrim.) | Home - PHS Main Gym [Directions] | 11:00 a.m. | ||
| Sun., 12/1 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 12/2 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 12/2 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 12/2 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 12/2 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/3 | V Girls Basketball | Trumbull (Scrim.) | Home - PHS Main Gym [Directions] | 5:00 p.m. | Also Nonnewaug | |
| Tue., 12/3 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/3 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 12/3 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 12/4 | V Girls Basketball | Daniel Hand (Scrim.) | Away - Polson Gym/DHHS Campus [Directions] | 6:30 p.m. | ||
| Wed., 12/4 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 12/4 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 12/4 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 12/5 | V Boys Basketball | Wilby (Scrim.) | Home - PHS Main Gym [Directions] | 6:30 p.m. | ||
| Thu., 12/5 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 12/5 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 12/5 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 12/5 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 12/6 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 12/6 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 12/6 | Miscellaneous Events | Pomperaug Youth Wrestlin | - Auxiliary Gym | 6:15 p.m. | ||
| Fri., 12/6 | School Holidays and Closings | Professional Development - Half Day | ||||
| Sat., 12/7 | V Girls Basketball | Career Magnet (Scrim.) | Away - Career High School [Directions] | 10:00 a.m. | ||
| Sat., 12/7 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 12/7 | Miscellaneous Events | CIAC FOOTBALL PLAYOFF GAME | Home - Sports Complex & Track [Directions] | 2:00 p.m. | ||
| Sun., 12/8 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 12/9 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 12/9 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 12/9 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 12/9 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/10 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | Cancelled | ||
| Tue., 12/10 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/10 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 12/10 | Miscellaneous Events | Stby Park & Rec HS Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 12/10 | Miscellaneous Events | Southbury Park and Rec HS Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 to 8:30 | |
| Tue., 12/10 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 12/11 | V Boys Basketball | Nonnewaug (Scrim.) | Away - Nonnewaug High School [Directions] | 7:00 p.m. | ||
| Wed., 12/11 | V Boys Ice Hockey | Shepaug Jamboree | Away - The Gunnery | 7:40 p.m. | ||
| Wed., 12/11 | V Boys Indoor Track | Wesleyan Meet | Away | 4:30 p.m. | ||
| Wed., 12/11 | V Girls Basketball | Brookfield | Away [Directions] | 5:15 p.m. | W 51-34 | vs. Brookfield |
| Wed., 12/11 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 12/11 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 12/11 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 12/12 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 12/12 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 12/12 | FR Girls Basketball | Thomaston | Away [Directions] | 6:00 p.m. | ||
| Thu., 12/12 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 12/12 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 12/12 | Miscellaneous Events | Stby Park & Rec HS Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 - 9:30 pm | |
| Thu., 12/12 | Miscellaneous Events | Southbury Park and Rec HS Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 to 8:30 | |
| Thu., 12/12 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 12/12 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 12/13 | V Boys Basketball | Holy Cross (Scrim.) | Home - PHS Main Gym [Directions] | 2:30 p.m. | ||
| Fri., 12/13 | FR Boys Basketball | Brookfield (Scrim.) | Away [Directions] | 3:30 p.m. | ||
| Fri., 12/13 | V Girls Basketball | Norwich Free Academy | Away [Directions] | 7:00 p.m. | L 58-83 | |
| Fri., 12/13 | FR Girls Basketball | Brookfield | Away [Directions] | 3:30 p.m. | ||
| Fri., 12/13 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 12/13 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 12/13 | Miscellaneous Events | Pomperaug Youth Wrestlin | - Auxiliary Gym | 6:15 p.m. | ||
| Sat., 12/14 | V Boys Ice Hockey | Shelton Jamboree | Away - The Rinks at Shelton | 6:00 p.m. | ||
| Sat., 12/14 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | cancelled | ||
| Sat., 12/14 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | cancelled | ||
| Sat., 12/14 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/15 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 12/16 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 12/16 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 12/16 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 12/16 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 12/16 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 12/16 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/17 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Tue., 12/17 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Tue., 12/17 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/17 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 12/17 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 12/18 | V Boys Ice Hockey | Stamford | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | L 2-3 | |
| Wed., 12/18 | V Boys Swimming and Diving | Newtown | Home - PHS Pool [Directions] | 7:00 p.m. | Adults $5, Students $3 | |
| Wed., 12/18 | V Wrestling | Masuk | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/18 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 12/18 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 12/18 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 12/19 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 12/19 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 12/19 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 12/19 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 12/19 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 12/19 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 12/20 | V Boys Basketball | Middletown | Away - Middletown High School [Directions] | 7:00 p.m. | W 75 - 54 | |
| Fri., 12/20 | JV Boys Basketball | Middletown | Away - Middletown High School [Directions] | 5:15 p.m. | ||
| Fri., 12/20 | FR Boys Basketball | Middletown | Away - Middletown High School [Directions] | 4:00 p.m. | ||
| Fri., 12/20 | V Boys Indoor Track | New Haven Qualifier | Away | 4:00 p.m. | @ Floyd Little Athletic Center | |
| Fri., 12/20 | V Boys Swimming and Diving | Bunnell-Stratford | Home - PHS Pool [Directions] | 5:00 p.m. | Adults $5, Students $3 | |
| Fri., 12/20 | V Competitive Cheerleading | Brookfield | Home - PHS Main Gym [Directions] | 7:00 p.m. | Arrive by 6:00 | |
| Fri., 12/20 | V Girls Basketball | Brookfield | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 66-30 | Adults $5, Students $3 |
| Fri., 12/20 | JV Girls Basketball | Brookfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/20 | FR Girls Basketball | Brookfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 12/20 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 12/20 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 12/21 | FR Boys Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 11:00 a.m. | ||
| Sat., 12/21 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | 6:00 p.m. | L 0-4 | |
| Sat., 12/21 | V Boys Indoor Track | New Haven Qualifier | Away | 9:00 a.m. | Floyd Little Athletic Center | |
| Sat., 12/21 | V Wrestling | Pomperaug Tournament | Home - PHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/21 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 8:00 am to 10:30 | ||
| Sat., 12/21 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 8:00 to 10:30 | ||
| Sat., 12/21 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/22 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 12/23 | V Boys Basketball | Newtown | Home - PHS Main Gym [Directions] | 7:15 p.m. | W 37 - 33 | Adults $5, Students $3, Non-League Game |
| Mon., 12/23 | JV Boys Basketball | Newtown | Home - PHS Main Gym [Directions] | 5:15 p.m. | Adults $5, Students $3 | |
| Mon., 12/23 | FR Boys Basketball | Newtown | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 12/23 | JV Wrestling | Nonnewaug | Away [Directions] | 9:00 a.m. | ||
| Mon., 12/23 | V Competitive Cheerleading | Newtown | Home - PHS Main Gym [Directions] | 7:00 p.m. | Arrive by 6:00 | |
| Mon., 12/23 | JV Competitive Cheerleading | Newtown | Home - PHS Main Gym [Directions] | 5:15 p.m. | Arrive by 4:30 | |
| Mon., 12/23 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 12/23 | School Holidays and Closings | Holiday Vacation | ||||
| Tue., 12/24 | School Holidays and Closings | Holiday Vacation | ||||
| Wed., 12/25 | School Holidays and Closings | Christmas Day | ||||
| Thu., 12/26 | School Holidays and Closings | Holiday Vacation | ||||
| Fri., 12/27 | V Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 7:00 p.m. | W 72 - 48 | |
| Fri., 12/27 | JV Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/27 | V Girls Basketball | Trinity Catholic | Away | TBA | W 68-22 | |
| Fri., 12/27 | School Holidays and Closings | Holiday Vacation | ||||
| Sat., 12/28 | V Boys Basketball | Jonathan Law | Away - Jonathan Law Old Gym [Directions] | 5:00 p.m. | W 75 - 35 | |
| Sat., 12/28 | JV Boys Basketball | Jonathan Law | Away - Jonathan Law Old Gym [Directions] | 3:15 p.m. | ||
| Sat., 12/28 | FR Boys Basketball | Jonathan Law | Away - Jonathan Law Old Gym [Directions] | 1:30 p.m. | ||
| Sat., 12/28 | V Boys Indoor Track | Varsity Development Meet | Away | 4:00 p.m. | @ Wilton High School | |
| Sat., 12/28 | V Wrestling | Frank Chaves Farmington Valley Invitational | Away [Directions] | 9:00 a.m. | @ Simsbury HS | |
| Sat., 12/28 | V Girls Basketball | Sacred Heart Academy | Away [Directions] | TBA | W 49-41 | |
| Sat., 12/28 | FR Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 9:30 a.m. | ||
| Sat., 12/28 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/29 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 12/30 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | 8:00 p.m. | L 0-8 | |
| Mon., 12/30 | V Boys Swimming and Diving | New Milford | Home [Directions] | 4:00 p.m. | ||
| Mon., 12/30 | School Holidays and Closings | Holiday Vacation | ||||
| Tue., 12/31 | School Holidays and Closings | Holiday Vacation | ||||
| Wed., 1/1 | School Holidays and Closings | New Year's Day | ||||
| Thu., 1/2 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | Cancelled | ||
| Thu., 1/2 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | Cancelled | ||
| Thu., 1/2 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/2 | Miscellaneous Events | Southbury P&R Swim Team | - PHS Pool | 5:30 p.m. | 5:30 to8:45 | |
| Thu., 1/2 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/2 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 1/2 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 1/3 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/3 | Miscellaneous Events | Southbury P&R Swim Team | - PHS Pool | 5:30 p.m. | 5:30 to8:45 | |
| Fri., 1/3 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 1/4 | V Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 7:00 p.m. | W 72 - 63 | Non-League Game |
| Sat., 1/4 | JV Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/4 | FR Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 3:30 p.m. | ||
| Sat., 1/4 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | L 0-4 | |
| Sat., 1/4 | V Boys Indoor Track | SWC Developmental @ Weslyan | Away | 10:00 a.m. | ||
| Sat., 1/4 | V Wrestling | Newtown | Away - Trumbull High School [Directions] | 10:00 a.m. | ||
| Sat., 1/4 | V Wrestling | Trumbull Duals | Away | 10:00 a.m. | 9:00 Weigh ins | |
| Sat., 1/4 | JV Wrestling | Bristol Eastern | Away [Directions] | 9:00 a.m. | Cancelled | |
| Sat., 1/4 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 9:00 am to 11:30 | ||
| Sat., 1/4 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 9:00 to 11:30 | ||
| Sat., 1/4 | V Girls Gymnastics | Pomperaug Invitational | Home - PHS Main Gym [Directions] | 9:00 a.m. | Hand-140.7; Ludlowe-131.55; Farmington- 130.45; Newtown- 128.8; Glastonbury- 127.15; Staples- 126.3; New Milford- 124.6; Darien- 123.25; PHS- 122.6; Nonnewaug- 122.05; Hall- 118.2; Conard- 116.95; Oxford-70.5 | |
| Sat., 1/4 | V Girls Indoor Track | SWC Developmental @ Weslyan | Away | 10:00 a.m. | ||
| Sat., 1/4 | Miscellaneous Events | Southbury Park and Rec Basketball | - Auxiliary Gym | 11:30 a.m. | 11:30 am to 9:00 pm | |
| Sat., 1/4 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/5 | Miscellaneous Events | Southbury Park and Rec Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 to 5:00 pm | |
| Sun., 1/5 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 1/6 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 1/6 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 1/6 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 1/6 | Miscellaneous Events | Southbury P&R Swim Team | - PHS Pool | 5:30 p.m. | 5:30 to8:45 | |
| Mon., 1/6 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 1/6 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 1/6 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/7 | V Boys Basketball | Masuk | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 57 - 47 | Adults $5, Students $3 |
| Tue., 1/7 | JV Boys Basketball | Masuk | Home - PHS Main Gym [Directions] | 5:15 p.m. | Adults $5, Students $3 | |
| Tue., 1/7 | FR Boys Basketball | Masuk | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/7 | V Boys Swimming and Diving | New Fairfield | Away - New Fairfield HS [Directions] | 4:00 p.m. | ||
| Tue., 1/7 | V Competitive Cheerleading | Masuk | Home - PHS Main Gym [Directions] | 7:00 p.m. | Arrive by 6:00 | |
| Tue., 1/7 | V Girls Basketball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 7:00 p.m. | L 54-41 | |
| Tue., 1/7 | JV Girls Basketball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 5:15 p.m. | ||
| Tue., 1/7 | FR Girls Basketball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 3:30 p.m. | ||
| Tue., 1/7 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/7 | Miscellaneous Events | Southbury P&R Swim Team | - PHS Pool | 5:30 p.m. | 5:30 to8:45 | |
| Tue., 1/7 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 1/7 | Miscellaneous Events | PHS Softball Parent Assoc. Softball Camp | - Auxiliary Gym | 7:30 p.m. | 7:30 - 9:00 pm | |
| Tue., 1/7 | Miscellaneous Events | Softball Clinic | - Auxiliary Gym | 7:30 p.m. | 7:30 to 9:00 | |
| Tue., 1/7 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 1/8 | V Boys Ice Hockey | Cheshire | Away - Wesleyan University Ice Rink [Directions] | 6:00 p.m. | L 2-5 | |
| Wed., 1/8 | V Boys Indoor Track | SWC JV Development Meet | Away | 3:00 p.m. | Danbury Dome | |
| Wed., 1/8 | V Wrestling | New Milford | Away - New Milford High School [Directions] | 6:00 p.m. | ||
| Wed., 1/8 | V Girls Basketball | New Milford | Away - New Milford High School [Directions] | 7:00 p.m. | W 66-33 | |
| Wed., 1/8 | JV Girls Basketball | New Milford | Away - New Milford High School [Directions] | 5:15 p.m. | ||
| Wed., 1/8 | FR Girls Basketball | New Milford | Away - New Milford High School [Directions] | 3:30 p.m. | ||
| Wed., 1/8 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/8 | Miscellaneous Events | Southbury P&R Swim Team | - PHS Pool | 5:30 p.m. | 5:30 to8:45 | |
| Wed., 1/8 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 1/8 | Miscellaneous Events | Middlebury Park and Rec Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 to 9:00 pm | |
| Wed., 1/8 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 1/9 | V Co-ed Alpine Skiing | Ski Race | Away | 4:00 p.m. | @ Mt. Southington | |
| Thu., 1/9 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 1/9 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 1/9 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/9 | Miscellaneous Events | Southbury P&R Swim Team | - PHS Pool | 5:30 p.m. | 5:30 to8:45 | |
| Thu., 1/9 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/9 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 1/9 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 1/10 | V Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 7:00 p.m. | W 80 - 38 | |
| Fri., 1/10 | JV Boys Basketball | Oxford | Away - OHS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/10 | FR Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 3:30 p.m. | ||
| Fri., 1/10 | V Competitive Cheerleading | Oxford | Home - PHS Main Gym [Directions] | 7:00 p.m. | Arrive by 6:00 | |
| Fri., 1/10 | JV Competitive Cheerleading | Oxford | Home - PHS Main Gym [Directions] | 5:15 p.m. | Arrive by 4:30 | |
| Fri., 1/10 | V Girls Basketball | Oxford | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 52-30 | Adults $5, Students $3 |
| Fri., 1/10 | JV Girls Basketball | Oxford | Home [Directions] | 5:15 p.m. | ||
| Fri., 1/10 | FR Girls Basketball | Masuk | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/10 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/10 | Miscellaneous Events | Southbury P&R Swim Team | - PHS Pool | 5:30 p.m. | 5:30 to8:45 | |
| Fri., 1/10 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 1/11 | V Boys Ice Hockey | New Milford | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | L 2-7 | |
| Sat., 1/11 | V Wrestling | Xavier Duals | Away [Directions] | 9:00 a.m. | ||
| Sat., 1/11 | V Competitive Cheerleading | Oxford HS Spirit Spectacular | Away | 9:00 a.m. | ||
| Sat., 1/11 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 8:00 am to 10:30 | ||
| Sat., 1/11 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 8:00 am to 10:30 | ||
| Sat., 1/11 | JV Competitive Cheerleading | Oxford | Away [Directions] | TBA | ||
| Sat., 1/11 | Miscellaneous Events | Southbury Park and Rec Basketball | - Auxiliary Gym | 11:30 a.m. | 11:30 am to 9:00 pm | |
| Sat., 1/11 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/12 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 1:00 to 5:00 pm | ||
| Sun., 1/12 | Miscellaneous Events | Pomp Youth Softball Instructional Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 10:00 am | |
| Sun., 1/12 | Miscellaneous Events | Southbury Park and Rec Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 to 5:00 pm | |
| Sun., 1/12 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 1/13 | V Boys Ice Hockey | Wilton | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | T 2-2 (OT) | |
| Mon., 1/13 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 1/13 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 1/13 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 1/13 | Miscellaneous Events | Southbury P&R Swim Team | - PHS Pool | 5:30 p.m. | 5:30 to8:45 | |
| Mon., 1/13 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 1/13 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 1/13 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/14 | V Boys Swimming and Diving | Bethel | Home - PHS Pool [Directions] | 4:30 p.m. | ||
| Tue., 1/14 | V/JV Competitive Cheerleading | Practice | Home - PHS Main Gym [Directions] | 6:00 pm | ||
| Tue., 1/14 | V Competitive Cheerleading | Kolbe Cathedral | Home - PHS Main Gym [Directions] | 7:00 p.m. | Cancelled | Arrive by 6:00 |
| Tue., 1/14 | V Girls Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | 6:15 p.m. | L 62-59 | |
| Tue., 1/14 | JV Girls Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | 4:30 p.m. | ||
| Tue., 1/14 | V Girls Gymnastics | Weston, Joel Barlow, Nonnewaug | Home - Auxiliary Gym [Directions] | 6:00 p.m. | 125.1 | |
| Tue., 1/14 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/14 | Miscellaneous Events | Southbury P&R Swim Team | - PHS Pool | 5:30 p.m. | 5:30 to8:45 | |
| Tue., 1/14 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 1/14 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 1/15 | V Boys Basketball | Kolbe Cathedral | Away - Sheehan Center [Directions] | 6:00 p.m. | L 62 - 65 | |
| Wed., 1/15 | JV Boys Basketball | Kolbe Cathedral | Away - Sheehan Center [Directions] | 4:15 p.m. | Adults $5, Students $3 | |
| Wed., 1/15 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | 8:00 p.m. | L 2-4 | |
| Wed., 1/15 | V Boys Indoor Track | SWC JV Meet | Away | 3:00 p.m. | Danbury Dome | |
| Wed., 1/15 | V Wrestling | Bunnell | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/15 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/15 | Miscellaneous Events | Southbury P&R Swim Team | - PHS Pool | 5:30 p.m. | 5:30 to8:45 | |
| Wed., 1/15 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 1/15 | Miscellaneous Events | Middlebury Park and Rec Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 to 9:00 pm | |
| Wed., 1/15 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 1/16 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 1/16 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 1/16 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 | |
| Thu., 1/16 | Miscellaneous Events | Southbury P&R Swim Team | - PHS Pool | 5:30 p.m. | 5:30 to8:45 | |
| Thu., 1/16 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/16 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 1/16 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Thu., 1/16 | School Holidays and Closings | Mid Year Exams | ||||
| Fri., 1/17 | V Boys Basketball | Bunnell | Away - Bunnell [Directions] | 7:00 p.m. | L 58 - 74 | |
| Fri., 1/17 | JV Boys Basketball | Bunnell | Away - Bunnell [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Boys Basketball | Bunnell | Away - Bunnell [Directions] | 3:30 p.m. | ||
| Fri., 1/17 | V Boys Swimming and Diving | Naugatuck, Conard | Home - PHS Pool [Directions] | 4:30 p.m. | ||
| Fri., 1/17 | V Boys Swimming and Diving | Naugatuck, Conard | Away [Directions] | 7:00 p.m. | Cancelled | |
| Fri., 1/17 | JV Wrestling | JV Developmental | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/17 | V Competitive Cheerleading | Bunnell | Home - PHS Main Gym [Directions] | 7:00 p.m. | Arrive by 6:00 | |
| Fri., 1/17 | JV Competitive Cheerleading | Bunnell | Home - PHS Main Gym [Directions] | 5:15 p.m. | Arrive by 4:30 | |
| Fri., 1/17 | V Girls Basketball | Bunnell | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 70-53 | Adults $5, Students $3 |
| Fri., 1/17 | JV Girls Basketball | Bunnell | Home - Pomperaug HS [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Girls Basketball | Bunnell | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/17 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 | |
| Fri., 1/17 | Miscellaneous Events | Southbury P&R Swim Team | - PHS Pool | 5:30 p.m. | 5:30 to8:45 | |
| Fri., 1/17 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 1/17 | School Holidays and Closings | Mid Year Exams | ||||
| Sat., 1/18 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavilion [Directions] | 1:00 p.m. | L 0-2 | |
| Sat., 1/18 | V Wrestling | Lyman Memorial/Windham Tech | Away [Directions] | 10:00 a.m. | ||
| Sat., 1/18 | V Competitive Cheerleading | Watertown Invitational | Away | TBA | @ Watertown | |
| Sat., 1/18 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 8:00 to 10:30 | ||
| Sat., 1/18 | V Girls Basketball | Newtown | Away - W.C.S.U. [Directions] | 7:00 p.m. | W 43-38 | |
| Sat., 1/18 | Miscellaneous Events | Southbury Park and Rec Basketball | - Auxiliary Gym | 11:30 a.m. | 11:30 am to 9:00 pm | |
| Sat., 1/18 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/19 | Miscellaneous Events | Pomp Youth Softball Instructional Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 10:00 am | |
| Sun., 1/19 | Miscellaneous Events | Southbury Park and Rec Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 to 5:00 pm | |
| Sun., 1/19 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 1/20 | V Boys Indoor Track | SWC Developmental @ Weslyan | Away | 9:00 a.m. | ||
| Mon., 1/20 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 1/20 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | tba | ||
| Mon., 1/20 | V Girls Indoor Track | SWC Developmental @ Weslyan | Away | 9:00 a.m. | ||
| Mon., 1/20 | Miscellaneous Events | Youth Basketball Clinic | - PHS Main Gym | 9:00 a.m. | 9:00 am to 12:00 noon | |
| Mon., 1/20 | Miscellaneous Events | Southbury P&R Swim Team | - PHS Pool | 5:30 p.m. | 5:30 to8:45 | |
| Mon., 1/20 | School Holidays and Closings | Martin Luther King Day - No School | ||||
| Tue., 1/21 | Miscellaneous Events | Youth Basketball Clinic | - PHS Main Gym | 9:00 a.m. | 9:00 am to 12:00 noon | |
| Wed., 1/22 | V Boys Ice Hockey | North Haven | Away - Northford Ice Pavilion [Directions] | 8:30 p.m. | L 0-5 | |
| Wed., 1/22 | V Boys Indoor Track | SWC JV Development Meet | Away | 3:00 p.m. | Cancelled | |
| Wed., 1/22 | V Co-ed Alpine Skiing | Ski Race | Away | 4:00 p.m. | Cancelled | @ Mt. Southington |
| Wed., 1/22 | V Competitive Cheerleading | Newtown | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/22 | V Girls Gymnastics | Jonathan Law | Away [Directions] | 7:00 p.m. | Cancelled | |
| Wed., 1/22 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 | |
| Wed., 1/22 | Miscellaneous Events | Southbury Park and Rec Swim Team | - PHS Pool | 5:45 p.m. | 5:30 to 8:45 | |
| Wed., 1/22 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 1/22 | Miscellaneous Events | Middlebury Park and Rec Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 to 9:00 pm | |
| Wed., 1/22 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Wed., 1/22 | School Holidays and Closings | Mid Year Exams | ||||
| Thu., 1/23 | V Boys Basketball | Weston | Home - PHS Main Gym [Directions] | 7:00 p.m. | L 65 - 68 | Adults $5, Students $3 |
| Thu., 1/23 | JV Boys Basketball | Weston | Home - PHS Main Gym [Directions] | 5:15 p.m. | Adults $5, Students $3 | |
| Thu., 1/23 | FR Boys Basketball | Weston | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 1/23 | V Boys Swimming and Diving | Brookfield | Home - PHS Pool [Directions] | 7:00 p.m. | Adults $5, Students $3 | |
| Thu., 1/23 | V Competitive Cheerleading | Weston | Home - PHS Main Gym [Directions] | 7:00 p.m. | Arrive by 6:00 | |
| Thu., 1/23 | JV Competitive Cheerleading | Weston | Home - PHS Main Gym [Directions] | 5:15 p.m. | Arrive by 4:30 | |
| Thu., 1/23 | V Girls Gymnastics | New Milford, Nonnewaug | Away - New Milford High School [Directions] | 5:00 p.m. | 122.75 | |
| Thu., 1/23 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 | |
| Thu., 1/23 | Miscellaneous Events | Southbury Park and Rec Swim Team | - PHS Pool | 5:45 p.m. | 5:30 to 8:45 | |
| Thu., 1/23 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/23 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 1/23 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Thu., 1/23 | School Holidays and Closings | Mid Year Exams | ||||
| Thu., 1/23 | School Holidays and Closings | End of 2nd Marking Period | ||||
| Fri., 1/24 | JV Wrestling | JV Developmental | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/24 | ALL Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 4:30 to 6:30 | ||
| Fri., 1/24 | V Girls Basketball | Weston | Away - WHS Gymnasium [Directions] | 7:00 p.m. | W 70-23 | |
| Fri., 1/24 | JV Girls Basketball | Weston | Away - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/24 | FR Girls Basketball | Newtown | Away - Newtown High School Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 1/24 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 | |
| Fri., 1/24 | Miscellaneous Events | Southbury Park and Rec Swim Team | - PHS Pool | 5:45 p.m. | 5:30 to 8:45 | |
| Fri., 1/24 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 1/25 | V Boys Basketball | Newtown | Away - Newtown High School Gymnasium [Directions] | 1:00 p.m. | L 46 - 48 | |
| Sat., 1/25 | JV Boys Basketball | Newtown | Away - Newtown High School Gymnasium [Directions] | 11:15 a.m. | ||
| Sat., 1/25 | V Boys Indoor Track | JV Development Meet | Away [Directions] | 3:00 p.m. | Cancelled | @ Wilton HS |
| Sat., 1/25 | V Wrestling | Rodney Smith Invitational | Away [Directions] | 9:00 a.m. | Cancelled | @ East Windsor HS |
| Sat., 1/25 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 8:00 am to 10:30 | ||
| Sat., 1/25 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 8:00 to 10:30 | ||
| Sat., 1/25 | V Girls Indoor Track | SWC Developmental | Away | TBA | Cancelled | |
| Sat., 1/25 | Miscellaneous Events | Southbury Park and Rec Basketball | - Auxiliary Gym | 11:30 a.m. | 11:30 am to 9:00 pm | |
| Sat., 1/25 | Miscellaneous Events | Kinetic Kids Gymnastic Meet | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sat., 1/25 | Miscellaneous Events | Kinetic Kids Gymnatic Meet | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sat., 1/25 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 1/25 | Miscellaneous Events | Senior Semi Formal | 6:00 p.m. | |||
| Sun., 1/26 | Miscellaneous Events | Kinetic Kids Gymnastic Meet | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sun., 1/26 | Miscellaneous Events | Kinetic Kids Gymnatic Meet | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sun., 1/26 | Miscellaneous Events | Southbury Park and Rec Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 to 5:00 pm | |
| Sun., 1/26 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 1/27 | V Wrestling | Stratford | Away - Needham Memorial Gymnasium [Directions] | 6:00 p.m. | ||
| Mon., 1/27 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 1/27 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 1/27 | Miscellaneous Events | Adult Yoga | - Health Classroom - Room 201 | 2:30 p.m. | 2:30 - 4:00 pm | |
| Mon., 1/27 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 | |
| Mon., 1/27 | Miscellaneous Events | Southbury Park and Rec Swim Team | - PHS Pool | 5:45 p.m. | 5:30 to 8:45 | |
| Mon., 1/27 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 1/27 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 1/27 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/28 | V Boys Basketball | Joel Barlow | Away - Lower Gym [Directions] | 7:00 p.m. | W 53 - 33 | |
| Tue., 1/28 | JV Boys Basketball | Joel Barlow | Away - Lower Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/28 | V Boys Swimming and Diving | Oxford | Home - PHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 1/28 | V Competitive Cheerleading | Joel Barlow | Home - PHS Main Gym [Directions] | 7:00 p.m. | Arrive by 6:00 | |
| Tue., 1/28 | V Girls Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 51-44 | Adults $5, Students $3 |
| Tue., 1/28 | JV Girls Basketball | Joel Barlow | Home [Directions] | 5:15 p.m. | ||
| Tue., 1/28 | FR Girls Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/28 | V Girls Gymnastics | Oxford, Newtown, Nonnewaug | Home - Auxiliary Gym [Directions] | 6:00 p.m. | 126.7 | |
| Tue., 1/28 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 | |
| Tue., 1/28 | Miscellaneous Events | Southbury Park and Rec Swim Team | - PHS Pool | 5:45 p.m. | 5:30 to 8:45 | |
| Tue., 1/28 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 1/28 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 1/29 | V Boys Ice Hockey | Danbury | Away - Danbury Ice Arena [Directions] | 7:40 p.m. | W 7-3 | |
| Wed., 1/29 | V Wrestling | Joel Barlow | Away - Upper Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/29 | V Co-ed Alpine Skiing | Ski Race | Away | 4:00 p.m. | ||
| Wed., 1/29 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 | |
| Wed., 1/29 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 1/29 | Miscellaneous Events | Middlebury Park and Rec Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 to 9:00 pm | |
| Wed., 1/29 | Miscellaneous Events | Pomp Youth Softball Instructional Clinic | - Auxiliary Gym | 7:00 p.m. | 7:00 to 9:00 | |
| Wed., 1/29 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 1/30 | FR Boys Basketball | Practice | Home - Auxiliary Gym [Directions] | 2:30 pm | ||
| Thu., 1/30 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 1/30 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 1/30 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 | |
| Thu., 1/30 | Miscellaneous Events | Southbury Park and Rec Swim Team | - PHS Pool | 5:45 p.m. | 5:30 to 8:45 | |
| Thu., 1/30 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/30 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 1/30 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 1/31 | V Boys Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 7:00 p.m. | L 51 - 53 | Adults $5, Students $3 |
| Fri., 1/31 | JV Boys Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | Adults $5, Students $3 | |
| Fri., 1/31 | V Boys Swimming and Diving | Cheshire | Home - PHS Pool [Directions] | 6:30 p.m. | $5 Adults, $3 Students | |
| Fri., 1/31 | JV Wrestling | JV Developmental | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/31 | V Competitive Cheerleading | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/31 | JV Competitive Cheerleading | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/31 | V Girls Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 7:00 p.m. | L 63-62 | |
| Fri., 1/31 | JV Girls Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 5:15 p.m. | ||
| Fri., 1/31 | Miscellaneous Events | Winter Swim Team - PAC | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 | |
| Fri., 1/31 | Miscellaneous Events | Southbury Park and Rec Swim Team | - PHS Pool | 5:45 p.m. | 5:30 to 8:45 | |
| Fri., 1/31 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 2/1 | FR Boys Basketball | Joel Barlow | Away - Lower Gym [Directions] | 2:00 p.m. | ||
| Sat., 2/1 | V Boys Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | 3:00 p.m. | L 1-10 | |
| Sat., 2/1 | V Boys Indoor Track | SWC Championship @ Hillhouse | Away | 5:00 p.m. | ||
| Sat., 2/1 | V Wrestling | Brookfield/Shepaug, Gilbert/Torrington, Platt Tech | Home - Auxiliary Gym [Directions] | 10:00 a.m. | 9:00 weigh in | |
| Sat., 2/1 | V Competitive Cheerleading | SWC Championship | Away [Directions] | 4:00 p.m. | @ Newtown High School | |
| Sat., 2/1 | ALL Competitive Cheerleading | Practice | Home - Sports Complex & Track [Directions] | 8:00 to 10:30 | ||
| Sat., 2/1 | V Girls Indoor Track | SWC Championship @ Hillhouse | Away | 5:00 p.m. | ||
| Sat., 2/1 | Miscellaneous Events | Southbury Park and Rec Basketball | - Auxiliary Gym | 11:30 a.m. | 11:30 am to 9:00 pm | |
| Sat., 2/1 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/2 | Miscellaneous Events | Pomp Youth Softball Instructional Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 10:00 am | |
| Sun., 2/2 | Miscellaneous Events | Southbury Park and Rec Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 to 6:00 pm | |
| Sun., 2/2 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 2/3 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | cancelled | cancelled | |
| Mon., 2/3 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | cancelled | cancelled | |
| Mon., 2/3 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 2/3 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 2/3 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 2/3 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/4 | V Competitive Cheerleading | Lauralton Hall | Home - PHS Main Gym [Directions] | 7:00 p.m. | Arrive by 6:00 | |
| Tue., 2/4 | V Girls Basketball | Lauralton Hall | Home - PHS Main Gym [Directions] | 7:00 p.m. | L 63-45 | Adults $5, Students $3 |
| Tue., 2/4 | JV Girls Basketball | Lauralton Hall | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/4 | FR Girls Basketball | Lauralton Hall | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/4 | V Girls Gymnastics | Lauralton Hall, Nonnewaug, Darien | Home - Auxiliary Gym [Directions] | 6:00 p.m. | 128.75 | |
| Tue., 2/4 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 2/4 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 2/4 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 2/5 | V Co-ed Alpine Skiing | Ski Race | Away | 3:00 p.m. | ||
| Wed., 2/5 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 2/5 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 2/5 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 2/6 | V Boys Ice Hockey | Farmington Valley Generals | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | W 8-5 | |
| Thu., 2/6 | V Boys Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Thu., 2/6 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Away - Western CT State University - O'Neill Center [Directions] | 4:00 p.m. | ||
| Thu., 2/6 | V Wrestling | Weston | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Thu., 2/6 | V Co-ed Alpine Skiing | Ski Race | Away | 4:00 p.m. | ||
| Thu., 2/6 | V/JV Competitive Cheerleading | Practice | Home - PHS Main Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 2/6 | V Girls Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Thu., 2/6 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 2/6 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 2/6 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 2/6 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 2/7 | V Boys Basketball | Bethel | Away - Bethel High School [Directions] | 7:00 p.m. | W 63 - 61 | |
| Fri., 2/7 | JV Boys Basketball | Bethel | Away [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | FR Boys Basketball | Bethel | Away - Bethel High School [Directions] | 3:30 p.m. | ||
| Fri., 2/7 | V/JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 5:00 to 7:00 pm | ||
| Fri., 2/7 | V Competitive Cheerleading | Bethel | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 2/7 | JV Competitive Cheerleading | Bethel | Home - PHS Main Gym [Directions] | 5:15 p.m. | Arrive by 4:30 | |
| Fri., 2/7 | V Girls Basketball | Bethel | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 75-53 | Adults $5, Students $3 |
| Fri., 2/7 | JV Girls Basketball | Bethel | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | FR Girls Basketball | Bethel | Home - PHS Main Gym [Directions] | 3:30 p.m. | Cancelled | |
| Fri., 2/7 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 2/7 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 2/8 | V Boys Basketball | Nonnewaug | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 76 - 37 | Adults $5, Students $3 |
| Sat., 2/8 | JV Boys Basketball | Nonnewaug | Home - PHS Main Gym [Directions] | 5:15 p.m. | Adults $5, Students $3 | |
| Sat., 2/8 | FR Boys Basketball | Sacred Heart | Away - Sacred Heart - Alumni Hall | 2:00 p.m. | ||
| Sat., 2/8 | V Boys Ice Hockey | North Branford | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | W 3-1 | |
| Sat., 2/8 | V Wrestling | Seymour, Branford, Maloney, Seymour | Away [Directions] | 10:00 a.m. | @ Maloney | |
| Sat., 2/8 | V Competitive Cheerleading | Woodland Competion | Away | 11:00 a.m. | ||
| Sat., 2/8 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 8:00 am to 10:30 | ||
| Sat., 2/8 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 8:00 to 10:30 | ||
| Sat., 2/8 | V Girls Basketball | Newtown | Home - PHS Main Gym [Directions] | 3:30 p.m. | W 52-41 | Adults $5, Students $3 |
| Sat., 2/8 | JV Girls Basketball | Newtown | Home - PHS Main Gym [Directions] | 1:45 p.m. | ||
| Sat., 2/8 | Miscellaneous Events | Southbury Park and Rec Basketball | - Auxiliary Gym | 11:30 a.m. | 11:30 am to 9:00 pm | |
| Sat., 2/8 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/9 | Miscellaneous Events | Pomp Youth Softball Instructional Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 10:00 am | |
| Sun., 2/9 | Miscellaneous Events | Southbury Park and Rec Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 to 5:00 pm | |
| Sun., 2/9 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 2/10 | V Wrestling | Oxford | Away - OHS-Main Gym [Directions] | 7:00 p.m. | Cancelled | |
| Mon., 2/10 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 2/10 | JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 2/10 | V Girls Gymnastics | Jonathan Law | Away - Jonathan Law Old Gym [Directions] | 6:00 p.m. | 125.25 | |
| Mon., 2/10 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 2/10 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 2/10 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 2/10 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/11 | V Boys Basketball | Immaculate | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 60 - 46 | Adults $5, Students $3 |
| Tue., 2/11 | JV Boys Basketball | Immaculate | Home - PHS Main Gym [Directions] | 5:15 p.m. | Adults $5, Students $3 | |
| Tue., 2/11 | V Boys Swimming and Diving | Masuk | Home - PHS Pool [Directions] | 6:30 p.m. | Adults $5, Students $3 | |
| Tue., 2/11 | V Competitive Cheerleading | Immaculate | Home - PHS Main Gym [Directions] | 7:00 p.m. | Arrive by 6:00 | |
| Tue., 2/11 | V Girls Basketball | Immaculate | Away - Immaculate High School [Directions] | 7:00 p.m. | W 71-60 | |
| Tue., 2/11 | JV Girls Basketball | Immaculate | Away - Immaculate High School [Directions] | 5:15 p.m. | ||
| Tue., 2/11 | FR Girls Basketball | Immaculate | Away - Immaculate High School [Directions] | 3:30 p.m. | Cancelled | |
| Tue., 2/11 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 2/11 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 2/11 | Miscellaneous Events | PHS Softball Parent Assoc. Softball Camp | - Auxiliary Gym | 7:30 p.m. | 7:30 - 9:00 pm | |
| Tue., 2/11 | Miscellaneous Events | Softball Clinic | - Auxiliary Gym | 7:30 p.m. | 7:30 to 9:00 | |
| Tue., 2/11 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 2/12 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - Gunnery Rink [Directions] | 8:15 p.m. | W 3-2 (OT) | |
| Wed., 2/12 | V Boys Swimming and Diving | Trip to Florida | Away | 8:15 a.m. | ||
| Wed., 2/12 | V Competitive Cheerleading | Stratford | Home - PHS Main Gym [Directions] | 6:00 p.m. | Arrive by 5:00 | |
| Wed., 2/12 | JV Competitive Cheerleading | Stratford | Home - Sports Complex & Track [Directions] | 5:15 p.m. | JV Game | |
| Wed., 2/12 | V Girls Basketball | Stratford | Home - PHS Main Gym [Directions] | 6:00 p.m. | W 62-39 | Adults $5, Students $3 |
| Wed., 2/12 | JV Girls Basketball | Stratford | Home - PHS Main Gym [Directions] | 4:15 p.m. | ||
| Wed., 2/12 | Miscellaneous Events | Adult Yoga | - Health Classroom - Room 201 | 2:30 p.m. | 2:30 - 4:00 pm | |
| Wed., 2/12 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 2/12 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 2/12 | Miscellaneous Events | Middlebury Park and Rec Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 to 9:00 pm | |
| Wed., 2/12 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 2/13 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 2/13 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 2/13 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 2/13 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Thu., 2/13 | School Holidays and Closings | Professional Development - Half Day | ||||
| Fri., 2/14 | V Boys Ice Hockey | Branford | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | L 1-7 | |
| Fri., 2/14 | School Holidays and Closings | Presidents Weekend - No School | ||||
| Sat., 2/15 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/15 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/15 | Miscellaneous Events | Revolution United Soccer | - Sports Complex & Track | 9:45 a.m. | 9:45 to 12:00 | |
| Sat., 2/15 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/16 | V Wrestling | SWC Championships | Home - PHS Main Gym [Directions] | 12:30 p.m. | ||
| Sun., 2/16 | V Wrestling | SWC Wrestling Tournament | Home - Auxiliary Gym [Directions] | 12:30 p.m. | ||
| Sun., 2/16 | Miscellaneous Events | Pomp Youth Softball Instructional Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 10:00 am | |
| Sun., 2/16 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/16 | Miscellaneous Events | Revolution United Soccer | - Sports Complex & Track | 1:45 p.m. | 2:30 to 5:00 | |
| Mon., 2/17 | JV Wrestling | Panther JV Tournament | Home - PHS Main Gym [Directions] | 9:00 a.m. | ||
| Mon., 2/17 | V Girls Gymnastics | Jonathan Law | Home - Auxiliary Gym [Directions] | 10:00 a.m. | 120.3 | |
| Mon., 2/17 | School Holidays and Closings | Presidents Weekend - No School | ||||
| Tue., 2/18 | V Boys Swimming and Diving | Return Trip From Florida | Away | 4:25 p.m. | ||
| Tue., 2/18 | V Competitive Cheerleading | New Fairfield | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Tue., 2/18 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 2/18 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 2/18 | Miscellaneous Events | PHS Softball Parent Assoc. Softball Camp | - Auxiliary Gym | 7:30 p.m. | 7:30 - 9:00 pm | |
| Tue., 2/18 | Miscellaneous Events | Softball Clinic | - Auxiliary Gym | 7:30 p.m. | 7:30 to 9:00 | |
| Tue., 2/18 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 2/19 | V Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 7:00 p.m. | L 51 - 58 | |
| Wed., 2/19 | JV Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/19 | FR Boys Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 2/19 | V Boys Ice Hockey | Amity | Away - Bennett Rink - West Haven [Directions] | 6:00 p.m. | L 3-5 | |
| Wed., 2/19 | V/JV Wrestling | Practice | Home - Wrestling Room [Directions] | 2:30 pm | ||
| Wed., 2/19 | V Co-ed Alpine Skiing | Practice | Home - Mt. Southington [Directions] | CANCELLED | ||
| Wed., 2/19 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:00 to 8:30 | ||
| Wed., 2/19 | V Girls Basketball | New Fairfield | Away - New Fairfield HS [Directions] | 7:00 p.m. | W 73-62 | |
| Wed., 2/19 | JV Girls Basketball | New Fairfield | Away [Directions] | 5:15 p.m. | ||
| Wed., 2/19 | FR Girls Basketball | New Fairfield | Away [Directions] | 3:30 p.m. | ||
| Wed., 2/19 | V Girls Gymnastics | SWC Championships | Away | 5:00 p.m. | 127.3 | |
| Wed., 2/19 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 2/19 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 2/19 | Miscellaneous Events | Middlebury Park and Rec Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 to 9:00 pm | |
| Wed., 2/19 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 2/20 | FR Boys Basketball | Practice | Home - Auxiliary Gym [Directions] | 2:30 pm | ||
| Thu., 2/20 | V/JV Wrestling | Practice | Home - Wrestling Room [Directions] | 2:30 pm | ||
| Thu., 2/20 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 2/20 | FR Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/20 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 2/20 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 2/20 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 2/20 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 2/21 | V Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 7:00 p.m. | W 72 - 64 | |
| Fri., 2/21 | JV Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/21 | FR Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/21 | V Boys Ice Hockey | Guilford | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | W 2-1 | |
| Fri., 2/21 | V Boys Swimming and Diving | Practice | Home - PHS Pool [Directions] | 2:30 pm | ||
| Fri., 2/21 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 4:30 p.m. | ||
| Fri., 2/21 | V/JV Girls Basketball | Practice | Home - PHS Main Gym [Directions] | 4:00 pm | ||
| Fri., 2/21 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 2/21 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 2/22 | V Boys Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 5:00 p.m. | W 42 - 36 | Adults $5, Students $3 |
| Sat., 2/22 | JV Boys Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 3:15 p.m. | Adults $5, Students $3 | |
| Sat., 2/22 | FR Boys Basketball | Practice | Home - PHS Main Gym [Directions] | 9:00 am | ||
| Sat., 2/22 | V Boys Ice Hockey | New Fairfield | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | L 3-5 | Senior Night |
| Sat., 2/22 | V Boys Swimming and Diving | Practice | Home - PHS Pool [Directions] | 8:00 am | ||
| Sat., 2/22 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 9:15 a.m. | ||
| Sat., 2/22 | V/JV Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 8:00 am to 10:30 pm | ||
| Sat., 2/22 | V Competitive Cheerleading | Varsity Competition | Away | TBA | Cancelled | |
| Sat., 2/22 | V Girls Basketball | SWC Quarter Final | Away | 5:00 p.m. | @ Lauralton Hall, $8 Adults, $5 Students | |
| Sat., 2/22 | Miscellaneous Events | Southbury Park and Rec Basketball | - Auxiliary Gym | 11:30 a.m. | 11:30 am to 9:00 pm | |
| Sat., 2/22 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/23 | V/JV Boys Basketball | Practice | Home - PHS Main Gym [Directions] | 9:00 am | ||
| Sun., 2/23 | V/JV Girls Basketball | Practice | Home - PHS Main Gym [Directions] | 11:00 am | ||
| Sun., 2/23 | Miscellaneous Events | Pomp Youth Softball Instructional Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 10:00 am | |
| Sun., 2/23 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 2/24 | V/JV Boys Basketball | Practice | Home - PHS Main Gym [Directions] | 2:30 | ||
| Mon., 2/24 | FR Boys Basketball | Practice | Home - Auxiliary Gym [Directions] | 2:30 | ||
| Mon., 2/24 | V Boys Swimming and Diving | Practice | Home - PHS Pool [Directions] | 2:30 pm | ||
| Mon., 2/24 | V/JV Wrestling | Practice | Home - Wrestling Room [Directions] | 2:30 pm | ||
| Mon., 2/24 | V Co-ed Alpine Skiing | Ski Race | Away | 4:00 p.m. | ||
| Mon., 2/24 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 2/24 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 2/24 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 2/24 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 2/24 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/25 | V Boys Basketball | New Milford | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 46 - 41 | Adults $5, Students $3 |
| Tue., 2/25 | JV Boys Basketball | New Milford | Home - PHS Main Gym [Directions] | 5:15 p.m. | Adults $5, Students $3 | |
| Tue., 2/25 | FR Boys Basketball | New Milford | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/25 | V Boys Swimming and Diving | Weston | Away - Weston Middle School Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/25 | V/JV Wrestling | Practice | Home - Wrestling Room [Directions] | 2:30 pm | ||
| Tue., 2/25 | V Competitive Cheerleading | New Milford | Home - PHS Main Gym [Directions] | 7:00 p.m. | Arrive by 6:00 | |
| Tue., 2/25 | V Girls Basketball | SWC Semi Finals | Away | TBA | Cancelled | @ Bethel HS, $8 Adults, $5 Students |
| Tue., 2/25 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 2/25 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 2/25 | Miscellaneous Events | PHS Softball Parent Assoc. Softball Camp | - Auxiliary Gym | 7:30 p.m. | 7:30 - 9:00 pm | |
| Tue., 2/25 | Miscellaneous Events | Softball Clinic | - Auxiliary Gym | 7:30 p.m. | 7:30 to 9:00 | |
| Tue., 2/25 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 2/26 | V/JV Boys Basketball | Practice | Home - PHS Main Gym [Directions] | 2:30 | ||
| Wed., 2/26 | V Boys Ice Hockey | Daniel Hand | Away - Northford Ice Pavilion [Directions] | 6:00 p.m. | L 1-6 | |
| Wed., 2/26 | V Boys Swimming and Diving | Practice | Home - PHS Pool [Directions] | 2:30 pm | ||
| Wed., 2/26 | V Boys Swimming and Diving | Practice | Home - Health Classroom - Room 201 [Directions] | 5:30 to 7:30 | ||
| Wed., 2/26 | V/JV Wrestling | Practice | Home - Wrestling Room [Directions] | 2:30 pm | ||
| Wed., 2/26 | V/JV Girls Basketball | Practice | Home - PHS Main Gym [Directions] | 4:30 pm | ||
| Wed., 2/26 | Miscellaneous Events | PAC Meeting | - Health Classroom - Room 201 | 5:30 p.m. | ||
| Wed., 2/26 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 2/26 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 2/26 | Miscellaneous Events | Middlebury Park and Rec Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 to 9:00 pm | |
| Wed., 2/26 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 2/27 | V/JV Boys Basketball | Practice | Home - PHS Main Gym [Directions] | 2:30 | ||
| Thu., 2/27 | V/JV Wrestling | Practice | Home - Wrestling Room [Directions] | 2:30 pm | ||
| Thu., 2/27 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 2/27 | V/JV Girls Basketball | Practice | Home - PHS Main Gym [Directions] | 4:30 pm | ||
| Thu., 2/27 | V Girls Basketball | SWC Championship Game | Away | 7:30 p.m. | Cancelled | @ Masuk, $10 Adults, $5 Students |
| Thu., 2/27 | Miscellaneous Events | PAC Meeting | - Health Classroom - Room 201 | 5:30 p.m. | ||
| Thu., 2/27 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 2/27 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 2/27 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 2/27 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 2/28 | V/JV Boys Basketball | Practice | Home - PHS Main Gym [Directions] | 2:30 | ||
| Fri., 2/28 | V Boys Swimming and Diving | Practice | Home - PHS Pool [Directions] | 2:30 pm | ||
| Fri., 2/28 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | ||
| Fri., 2/28 | V/JV Girls Basketball | Practice | Home - PHS Main Gym [Directions] | 4:30 pm | ||
| Fri., 2/28 | Miscellaneous Events | Stby Park & Rec Swim Team Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 2/28 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 3/1 | V Boys Basketball | SWC Quarter Finals | Away | TBA | @ Bunnell, $8 Adults, $5 Students | |
| Sat., 3/1 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 10:30 a.m. | ||
| Sat., 3/1 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:15 a.m. | ||
| Sat., 3/1 | V Competitive Cheerleading | Cheer Competion | Away | 3:00 p.m. | ||
| Sat., 3/1 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 8:00 am to 10:30 | ||
| Sat., 3/1 | V Girls Gymnastics | CIAC Class Meet | Home - PHS Main Gym [Directions] | TBA | ||
| Sat., 3/1 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 10:30 a.m. | ||
| Sat., 3/1 | Miscellaneous Events | Southbury Park and Rec Basketball | - Auxiliary Gym | 11:30 a.m. | 11:30 am to 9:00 pm | |
| Sat., 3/1 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/2 | Miscellaneous Events | Pomp Youth Softball Instructional Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 10:00 am | |
| Sun., 3/2 | Miscellaneous Events | Southbury Park and Rec Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 to 5:00 pm | |
| Sun., 3/2 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 3/3 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 3/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:00 pm | |
| Mon., 3/3 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 3/3 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 3/3 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/4 | V Boys Basketball | SWC Semi Finals | Away | TBA | Cancelled | @ Newtown, $8 Adults, $5 students |
| Tue., 3/4 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 7:30 | ||
| Tue., 3/4 | V Competitive Cheerleading | Hillhouse | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Tue., 3/4 | V Girls Basketball | Hillhouse | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Tue., 3/4 | V Field Hockey | Practice | Home - Health Classroom - Room 201 [Directions] | 3:00 pm | Captain Meeting | |
| Tue., 3/4 | Miscellaneous Events | CPR Class for Coaches | - Health Classroom - Room 201 | 5:00 p.m. | ||
| Tue., 3/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:00 pm | |
| Tue., 3/4 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 3/4 | Miscellaneous Events | PHS Softball Parent Assoc. Softball Camp | - Auxiliary Gym | 7:30 p.m. | 7:30 - 9:00 pm | |
| Tue., 3/4 | Miscellaneous Events | Softball Clinic | - Auxiliary Gym | 7:30 p.m. | 7:30 to 9:00 | |
| Tue., 3/4 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 3/5 | V Boys Swimming and Diving | SWC Diving Championships | Away | 6:00 p.m. | @ New Fairfield, Adults $10, Students $5 | |
| Wed., 3/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:00 pm | |
| Wed., 3/5 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 3/5 | Miscellaneous Events | Middlebury Park and Rec Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 to 9:00 pm | |
| Wed., 3/5 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 3/6 | V Boys Basketball | SWC Championship Game | Home - PHS Main Gym [Directions] | 7:30 p.m. | Cancelled | $10 Adults, $5 Students |
| Thu., 3/6 | V Co-ed Alpine Skiing | Practice | Home - Mohawk [Directions] | 4:00 pm | ||
| Thu., 3/6 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 3/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:00 pm | |
| Thu., 3/6 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 3/6 | Miscellaneous Events | SWC Boys Championship Game | - PHS Main Gym | 6:00 p.m. | Game @ 7:00 pm | |
| Thu., 3/6 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 3/6 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 3/7 | V Boys Swimming and Diving | SWC Swim Championships, Adults $10, Students $5 | Away | 6:00 p.m. | ||
| Fri., 3/7 | V Wrestling | New England Championships | Away - Providence Career and Technical Center | 4:30 p.m. | Cancelled | |
| Fri., 3/7 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 2:30 to 3:30 | ||
| Fri., 3/7 | V Competitive Cheerleading | State Competition Date | Away [Directions] | 6:15 p.m. | Snow date March 9, 11:00 am | |
| Fri., 3/7 | V Girls Basketball | Wilton | Away [Directions] | 7:00 p.m. | ||
| Fri., 3/7 | Miscellaneous Events | Rochambeau March Madness | - PHS Main Gym | 5:00 p.m. | ||
| Fri., 3/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:00 pm | |
| Fri., 3/7 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 3/8 | V Boys Swimming and Diving | JV Invitational | Home - PHS Pool [Directions] | 3:00 p.m. | ||
| Sat., 3/8 | V Wrestling | New England Championships | Away - Providence Career and Technical Center | 9:15 a.m. | Cancelled | |
| Sat., 3/8 | V Competitive Cheerleading | State Competition Date | Away | TBA | Cancelled | |
| Sat., 3/8 | V Girls Gymnastics | CIAC Open | Away | TBA | ||
| Sat., 3/8 | Miscellaneous Events | Middlebury Park and Rec Basketball | - PHS Main Gym | 11:00 a.m. | ||
| Sat., 3/8 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/9 | V Competitive Cheerleading | State Competition Date | Away | TBA | ||
| Sun., 3/9 | Miscellaneous Events | Pomp Youth Softball Instructional Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 10:00 am | |
| Sun., 3/9 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 3/10 | V Boys Basketball | Stratford | Home - PHS Main Gym [Directions] | 7:00 p.m. | $8 Adults, $5 students | |
| Mon., 3/10 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 3/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:00 pm | |
| Mon., 3/10 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 3/10 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 3/10 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/11 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Tue., 3/11 | ALL Girls Basketball | Practice | Home - Health Classroom - Room 201 [Directions] | 4:30 pm | End of season meeting | |
| Tue., 3/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:00 pm | |
| Tue., 3/11 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 3/11 | Miscellaneous Events | Softball Clinic | - Auxiliary Gym | 7:30 p.m. | 7:30 to 9:00 | |
| Tue., 3/11 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 3/12 | Miscellaneous Events | Adult Yoga | - Health Classroom - Room 201 | 2:30 p.m. | 2:30 - 4:15 pm | |
| Wed., 3/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:00 pm | |
| Wed., 3/12 | Miscellaneous Events | Middlebury Park and Rec Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 to 9:00 pm | |
| Wed., 3/12 | Miscellaneous Events | Softball Clinic | - Auxiliary Gym | 7:30 p.m. | 7:30 - 9:00 pm | |
| Wed., 3/12 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 3/13 | V Boys Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Thu., 3/13 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 3/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:00 pm | |
| Thu., 3/13 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 3/13 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 3/13 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 3/14 | Miscellaneous Events | Pomperaug Outreach Club Babysitting | - Auxiliary Gym | 4:00 p.m. | 4:00 - 9:00 pm | |
| Fri., 3/14 | Miscellaneous Events | Memorial March Madness | - PHS Main Gym | 5:00 p.m. | ||
| Fri., 3/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:00 pm | |
| Fri., 3/14 | Miscellaneous Events | Pomoperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 3/15 | V Boys Swimming and Diving | CIAC Class L Qualifying | Away - Cornerstone Pool [Directions] | 6:15 p.m. | ||
| Sat., 3/15 | V Girls Gymnastics | New England Tournament | Away | TBA | ||
| Sat., 3/15 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/16 | Miscellaneous Events | Pomp Youth Softball Instructional Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 10:00 am | |
| Sun., 3/16 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 3/17 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 3/17 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 3/17 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/18 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Tue., 3/18 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 3/19 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Wesleyan Univ. [Directions] | 7:15 p.m. | @ Weslyan University, $10 Adults, $5 Students | |
| Wed., 3/19 | Miscellaneous Events | Middlebury Park and Rec Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 to 9:00 pm | |
| Wed., 3/19 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 3/20 | V Boys Swimming and Diving | CIAC Open Diving | Away - Middletown [Directions] | 5:30 p.m. | Cancelled | |
| Thu., 3/20 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | TBA | Trip to Airport | |
| Thu., 3/20 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 3/20 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Fri., 3/21 | V Boys Indoor Track | Practice | Home - Health Classroom - Room 201 [Directions] | 2:15 pm | End of Year Meeting & Awards | |
| Fri., 3/21 | V Girls Indoor Track | Practice | Home - Health Classroom - Room 201 [Directions] | 2:30 pm | 2:30 - 4:30 pm | |
| Fri., 3/21 | Miscellaneous Events | Blood Drive | - Auxiliary Gym | 6:00 a.m. | 6:00 am to 2:00 pm | |
| Fri., 3/21 | Miscellaneous Events | Softball Camp | - Auxiliary Gym | 7:30 p.m. | 7:30 - 9:00 pm | |
| Sat., 3/22 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Sat., 3/22 | Miscellaneous Events | SMART - Community Conversion | - Auxiliary Gym | 8:00 a.m. | 8:00 - 1:00 pm | |
| Sat., 3/22 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/23 | Miscellaneous Events | Pomp Youth Softball Instructional Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 10:00 am | |
| Sun., 3/23 | Miscellaneous Events | Tailgator's Lacrosse Club | - Sports Complex & Track | 9:00 a.m. | 9:00 am to 11:00 am | |
| Sun., 3/23 | Miscellaneous Events | Revolution Soccer Game | - Sports Complex & Track | 12:00 p.m. | 11:00 to 2:00 | |
| Sun., 3/23 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 3/24 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Mon., 3/24 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/25 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Wed., 3/26 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:00 p.m. | 8:00 - 10:00 pm | |
| Thu., 3/27 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 3/27 | V Softball | Seymour (Scrim.) | Away - Seymour HS [Directions] | 4:00 p.m. | ||
| Thu., 3/27 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 3/27 | Miscellaneous Events | Stby Park & Rec Mens Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:15 pm | |
| Sat., 3/29 | V Baseball | Danbury (Scrim.) | Away [Directions] | 10:30 a.m. | ||
| Sat., 3/29 | V Boys Lacrosse | Hamden Jamboree | Away | 10:30 a.m. | ||
| Sat., 3/29 | V Girls Lacrosse | Pomperaug Play Day | Home - Sports Complex & Track [Directions] | 12:00 p.m. | 8:30 am to 3:30 pm | |
| Sat., 3/29 | V Softball | Holy Cross (Scrim.) | Home - Community Softball Field [Directions] | 1:00 p.m. | ||
| Sat., 3/29 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/30 | Miscellaneous Events | Revolution Soccer Game | - Sports Complex & Track | 11:00 a.m. | 10:00 to 1:00 | |
| Sun., 3/30 | Miscellaneous Events | Pomp Youth Softball Instructional Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 10:00 am | |
| Mon., 3/31 | V/JV Boys Golf | Practice | Home - Heritage Village C.C. [Directions] | Cancelled | ||
| Mon., 3/31 | Miscellaneous Events | Adult Yoga | - Health Classroom - Room 201 | 2:45 p.m. | 2:45 - 4:00 pm | |
| Mon., 3/31 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/1 | V Baseball | Torrington (Scrim.) | Home - PHS Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 4/2 | V Baseball | Naugatuck (Scrim.) | Away - Rotary Field [Directions] | 3:30 p.m. | ||
| Wed., 4/2 | V Boys Golf | Oxford Greens Clinic | Away | 3:00 p.m. | ||
| Wed., 4/2 | V Softball | Watertown (Scrim.) | Home - Community Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/2 | Miscellaneous Events | Adult Yoga | - Health Classroom - Room 201 | 2:45 p.m. | 2:45 - 4:00 pm | |
| Thu., 4/3 | V Baseball | Bristol Central (Scrim.) | Home - Community Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 4/3 | Miscellaneous Events | Girls Swim Team Meeting | - Health Classroom - Room 201 | 2:30 p.m. | ||
| Fri., 4/4 | V Girls Lacrosse | Farmington (Scrim.) | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Fri., 4/4 | JV Girls Lacrosse | Farmington (Scrim.) | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Fri., 4/4 | V Girls Tennis | Shelton (Scrim.) | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 4/4 | Miscellaneous Events | Dodgeball for Diabetes | - PHS Main Gym | 6:00 p.m. | ||
| Sat., 4/5 | V Baseball | Jamboree @ Weston | Away [Directions] | 10:00 a.m. | ||
| Sat., 4/5 | V Boys Lacrosse | Watertown (Scrim.) | Away - John J. Mills Complex @ Watertown High School [Directions] | 11:00 a.m. | ||
| Sat., 4/5 | JV Boys Lacrosse | Watertown (Scrim.) | Away [Directions] | 11:00 a.m. | ||
| Sat., 4/5 | V Girls Lacrosse | Hamden Play Day | Away | TBA | 8:00 am to 4:00 pm | |
| Sat., 4/5 | V Softball | Nonnewaug (Scrim.) | Home - PHS Softball Field [Directions] | 1:00 p.m. | ||
| Sun., 4/6 | Miscellaneous Events | Southbury Soccer Club | - Sports Complex & Track | 3:00 p.m. | 3:00 - 5:00 pm | |
| Mon., 4/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:00 pm | |
| Mon., 4/7 | Miscellaneous Events | Adult Yoga | - Health Classroom - Room 201 | 2:45 p.m. | 2:45 - 4:00 pm | |
| Mon., 4/7 | Miscellaneous Events | Mdbly Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:00 pm | |
| Wed., 4/9 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | 4:15 p.m. | W 11-9 | |
| Wed., 4/9 | JV Baseball | Ridgefield | Home - Community Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/9 | FR Baseball | Newtown | Away - Newtown High School Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 4/9 | V Boys Lacrosse | New Milford | Away - New Milford High School [Directions] | 6:00 p.m.m | L 17-7 | |
| Wed., 4/9 | JV Boys Lacrosse | New Milford | Away - New Milford High School [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Girls Lacrosse | Immaculate | Away - Mustang Valley [Directions] | 4:15 p.m. | L 5-15 | |
| Wed., 4/9 | JV Girls Lacrosse | Immaculate | Away - Mustang Valley [Directions] | 5:30 p.m. | ||
| Wed., 4/9 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:15 p.m. | W 10 - 0 | |
| Wed., 4/9 | JV Softball | Ridgefield | Home - PHS Softball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/9 | V Girls Tennis | Brookfield | Away - BHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | Non league game |
| Wed., 4/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:00 pm | |
| Wed., 4/9 | Miscellaneous Events | Adult Yoga | - Health Classroom - Room 201 | 2:45 p.m. | 2:45 - 4:00 pm | |
| Thu., 4/10 | JV Baseball | Masuk | Home - Community Baseball Field [Directions] | 4:15 p.m. | ||
| Thu., 4/10 | V Boys Outdoor Track | Newtown (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Thu., 4/10 | V Girls Outdoor Track | Newtown (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Thu., 4/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:00 pm | |
| Fri., 4/11 | V Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | 3:30 p.m. | L 5-7 | Non league game |
| Fri., 4/11 | JV Baseball | New Fairfield | Home - Community Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/11 | FR Baseball | Masuk | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 4/11 | V Boys Tennis | Bunnell | Away - Bunnell Tennis Courts [Directions] | 4:00 p.m. | W 6 - 1 | |
| Fri., 4/11 | V Girls Lacrosse | Weston | Away - WHS Turf Field [Directions] | 6:00 p.m. | L 8-18 | |
| Fri., 4/11 | JV Girls Lacrosse | Weston | Away - WHS Turf Field [Directions] | 4:30 p.m. | ||
| Fri., 4/11 | V Softball | Joel Barlow | Home - PHS Softball Field [Directions] | 4:15 p.m. | W 10 - 1 | Non-League Game |
| Fri., 4/11 | V Girls Tennis | Bunnell | Home - PHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Fri., 4/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:00 pm | |
| Sat., 4/12 | V Baseball | Holy Cross | Home - PHS Baseball Field [Directions] | 1:00 p.m. | W 5-4 | |
| Sat., 4/12 | FR Baseball | Stratford | Away - Penders Field [Directions] | 3:00 p.m. | ||
| Sat., 4/12 | V Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 1:00 p.m. | L 6-7 | |
| Sat., 4/12 | JV Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 3:00 p.m. | ||
| Sat., 4/12 | V Girls Lacrosse | Bethel | Home - Sports Complex & Track [Directions] | 4:00 p.m. | L 8-15 | non league game |
| Sat., 4/12 | JV Girls Lacrosse | Bethel | Home - Sports Complex & Track [Directions] | 2:30 p.m. | ||
| Sat., 4/12 | V Softball | Lauralton Hall | Home - PHS Softball Field [Directions] | 3:30 p.m. | L 17 - 1 | |
| Sat., 4/12 | JV Softball | Lauralton Hall | Away - Lauralton Hall Field [Directions] | 4:30 p.m.. | ||
| Sat., 4/12 | FR Softball | Stratford | Away - King Street Field [Directions] | 4:15 p.m. | Cancelled | |
| Mon., 4/14 | V Baseball | Masuk | Away - John Giampaolo Field @ Masuk [Directions] | 12:00 p.m. | L 1-0 | Non league game |
| Mon., 4/14 | FR Baseball | New Milford | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 4/14 | V Boys Lacrosse | Stratford | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 14-10 | |
| Mon., 4/14 | JV Boys Lacrosse | Stratford | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Mon., 4/14 | V Boys Tennis | Stratford | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | W 6 - 1 | |
| Mon., 4/14 | V Softball | New Milford | Away - New Milford High School [Directions] | 4:15 p.m. | W 4-3 | Non league game |
| Mon., 4/14 | JV Softball | New Milford | Home - Community Softball Field [Directions] | 3:45 p.m. | The team should meet at Community Field | |
| Mon., 4/14 | V Girls Tennis | Stratford | Away - Short Beach Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Mon., 4/14 | Miscellaneous Events | PAC Swimming | - PHS Pool | 8:00 a.m. | 8:00 am to 10:30 am | |
| Mon., 4/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 9:00 a.m. | 9:00 - 11:30 am | |
| Mon., 4/14 | Miscellaneous Events | Middlebury Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 4/14 | School Holidays and Closings | Spring Recess | ||||
| Tue., 4/15 | Miscellaneous Events | PAC Swimming | - PHS Pool | 8:00 a.m. | 8:00 am to 10:30 am | |
| Tue., 4/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 9:00 a.m. | 9:00 - 11:30 am | |
| Tue., 4/15 | Miscellaneous Events | Mdby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 3:00 pm | |
| Tue., 4/15 | Miscellaneous Events | Mdby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 3:00 pm | |
| Tue., 4/15 | School Holidays and Closings | Spring Recess | ||||
| Wed., 4/16 | V Boys Tennis | Immaculate | Away - Rogers Park [Directions] | 3:30 p.m. | W 6 - 1 | |
| Wed., 4/16 | V Girls Lacrosse | Brookfield | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 5-9 | |
| Wed., 4/16 | JV Girls Lacrosse | Brookfield | Home - Sports Complex & Track [Directions] | 5:30 p.m. | ||
| Wed., 4/16 | V Girls Tennis | Immaculate | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Wed., 4/16 | Miscellaneous Events | PAC Swimming | - PHS Pool | 8:00 a.m. | 8:00 am to 10:30 am | |
| Wed., 4/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 9:00 a.m. | 9:00 - 11:30 am | |
| Wed., 4/16 | School Holidays and Closings | Spring Recess | ||||
| Thu., 4/17 | V Baseball | New Fairfield | Home - PHS Baseball Field [Directions] | 4:15 p.m. | W 2-1 | |
| Thu., 4/17 | V Boys Golf | Joel Barlow | Away - Redding Country Club [Directions] | 3:00 p.m. | Pomperaug 158 Joel Barlow 182 | Non-League Game |
| Thu., 4/17 | V Boys Lacrosse | Masuk | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 13-8 | |
| Thu., 4/17 | JV Boys Lacrosse | Masuk | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 4/17 | V Softball | New Fairfield | Home - PHS Softball Field [Directions] | 4:15 p.m. | W 18-1 | |
| Thu., 4/17 | Miscellaneous Events | PAC Swimming | - PHS Pool | 8:00 a.m. | 8:00 am to 10:30 am | |
| Thu., 4/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 9:00 a.m. | 9:00 - 11:30 am | |
| Thu., 4/17 | Miscellaneous Events | Mdby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 3:00 pm | |
| Thu., 4/17 | Miscellaneous Events | Mdby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 3:00 pm | |
| Thu., 4/17 | Miscellaneous Events | Connecticut Football Club | - PHS Soccer Field | 5:30 p.m. | Club Soccer Practice | |
| Thu., 4/17 | School Holidays and Closings | Spring Recess | ||||
| Fri., 4/18 | School Holidays and Closings | Good Friday | ||||
| Sat., 4/19 | JV Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | 1:00 p.m. | ||
| Sat., 4/19 | FR Baseball | New Fairfield | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| Sat., 4/19 | V Boys Lacrosse | Lewis Mills | Away - Lewis Mills Lacrosse Field [Directions] | 10:00 a.m. | L 13-14 | |
| Sat., 4/19 | JV Boys Lacrosse | Lewis Mills | Away - Lewis Mills Lacrosse Field [Directions] | 11:30 a.m. | ||
| Sat., 4/19 | V Girls Lacrosse | Masuk | Home - Sports Complex & Track [Directions] | 11:00 a.m. | W 16-6 | |
| Sat., 4/19 | JV Girls Lacrosse | Masuk | Home - Sports Complex & Track [Directions] | 9:00 a.m. | ||
| Sat., 4/19 | JV Softball | New Fairfield | Away - NFHS Softball Field [Directions] | 10:00 a.m. | ||
| Mon., 4/21 | V Baseball | Joel Barlow | Away - Field G (Baseball) [Directions] | 4:15 p.m. | W 6-3 | |
| Mon., 4/21 | V Boys Lacrosse | Newtown | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 3-12 | |
| Mon., 4/21 | JV Boys Lacrosse | Newtown | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Mon., 4/21 | V Boys Tennis | New Fairfield | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | W 6 - 1 | |
| Mon., 4/21 | V Girls Outdoor Track | Newtown, Immaculate, Oxford | Away - Blue and Gold Stadium [Directions] | 4:00 p.m. | NHS 114 PHS 36 PHS 94 IHS 47 OHS 85 PHS 56 | |
| Mon., 4/21 | V Softball | Joel Barlow | Away - Field E (Softball) [Directions] | 4:15 p.m. | W 3-1 | |
| Mon., 4/21 | V Girls Tennis | New Fairfield | Away - New Fairfield HS [Directions] | 3:45 p.m. | L 2-5 | |
| Mon., 4/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:00 pm | |
| Mon., 4/21 | Miscellaneous Events | Middlebury Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/22 | V Baseball | Bunnell | Home - PHS Baseball Field [Directions] | 4:15 p.m. | L 5-0 | Non league game |
| Tue., 4/22 | JV Baseball | Joel Barlow | Home - Community Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 4/22 | V Boys Golf | Stratford | Home - Heritage Village C.C. [Directions] | 3:00 p.m. | Pomperaug 148 Startford 200 | |
| Tue., 4/22 | V Boys Outdoor Track | Newtown, Immaculate, Oxford | Home - Sports Complex & Track [Directions] | 4:00 p.m. | (P)121 (I) 27 (P) 88.5 (n) 60.5 (P) 105 (o) 45 | |
| Tue., 4/22 | JV Softball | Joel Barlow | Home - Community Softball Field [Directions] | 3:45 p.m. | ||
| Tue., 4/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:00 pm | |
| Wed., 4/23 | V Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | 4:15 p.m. | L 5-4 | |
| Wed., 4/23 | FR Baseball | Weston | Home - Community Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/23 | V Boys Golf | Bunnell | Away - Oronoque Country Club [Directions] | 3:00 p.m. | Pomperaug 163 Bunnell 193 | |
| Wed., 4/23 | V Boys Tennis | Brookfield | Away - BHS Tennis Courts [Directions] | 3:45 p.m. | W 6 - 1 | |
| Wed., 4/23 | V Softball | Bunnell | Away - Bunnell Softball Field [Directions] | 4:15 p.m. | W 13 - 1 | |
| Wed., 4/23 | V Girls Tennis | Brookfield | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Wed., 4/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:00 pm | |
| Wed., 4/23 | Miscellaneous Events | College Fair Set-Up | - PHS Main Gym | 2:30 p.m. | set-up | |
| Wed., 4/23 | Miscellaneous Events | College Fair | 6:00 p.m. | 6:00 - 11:00 pm | ||
| Thu., 4/24 | JV Baseball | Bunnell | Home - Community Baseball Field [Directions] | 4:15 p.m. | ||
| Thu., 4/24 | V Boys Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 3:00 p.m. | Pomperaug 160 Brookfield 182 | |
| Thu., 4/24 | V Boys Lacrosse | Immaculate | Home - Sports Complex & Track [Directions] | 5:15 p.m. | W 14-9 | |
| Thu., 4/24 | JV Boys Lacrosse | Immaculate | Home - Sports Complex & Track [Directions] | 5:00 p.m. | Cancelled | |
| Thu., 4/24 | V Boys Tennis | New Milford | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | W 6 - 1 | |
| Thu., 4/24 | V Girls Lacrosse | New Milford | Away - New Milford High School [Directions] | 6:00 p.m. | W 8-6 | |
| Thu., 4/24 | JV Girls Lacrosse | New Milford | Away - New Milford High School [Directions] | 4:30 p.m. | ||
| Thu., 4/24 | JV Softball | Bunnell | Home - Community Softball Field [Directions] | 4:15 p.m. | ||
| Thu., 4/24 | V Girls Tennis | New Milford | Away - New Milford High School [Directions] | 3:45 p.m. | W 6-1 | |
| Thu., 4/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Thu., 4/24 | Miscellaneous Events | Region 15 Art Show Set-Up | - PHS Main Gym | 7:30 a.m. | 7:30 - 7:00 pm | |
| Thu., 4/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:00 pm | |
| Thu., 4/24 | Miscellaneous Events | Connecticut Football Club | - PHS Soccer Field | 5:30 p.m. | Club Soccer Practice | |
| Fri., 4/25 | FR Baseball | Brookfield | Away - BHS Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 4/25 | V Boys Outdoor Track | O'Grady Relays | Away [Directions] | 6:00 p.m. | @ Danbury HS | |
| Fri., 4/25 | V Girls Outdoor Track | O'Grady Relays | Away [Directions] | 6:00 p.m. | @ Danbury HS | |
| Fri., 4/25 | Miscellaneous Events | Region 15 Art Show | - PHS Main Gym | 7:30 a.m. | 7:30 - 9:30 pm | |
| Fri., 4/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:00 pm | |
| Sat., 4/26 | V Boys Outdoor Track | O'Grady Relays | Away [Directions] | 9:00 a.m. | @ Danbury HS | |
| Sat., 4/26 | V Girls Lacrosse | Southington | Home - Sports Complex & Track [Directions] | 10:00 a.m. | L 8-11 | |
| Sat., 4/26 | JV Girls Lacrosse | Southington | Home - Sports Complex & Track [Directions] | 11:15 a.m. | ||
| Sat., 4/26 | V Girls Outdoor Track | O'Grady Relays | Away [Directions] | 9:00 a.m. | @ Danbury HS | |
| Sat., 4/26 | Miscellaneous Events | Region 15 Art Show | - PHS Main Gym | 9:00 a.m. | 9:00 - 3:00 pm | |
| Sun., 4/27 | Miscellaneous Events | Revolution Soccer | - Sports Complex & Track | 2:00 p.m. | 1:30 to 3:30 | |
| Mon., 4/28 | V Baseball | Newtown | Away - Baseball Field at Fairfield Hills Complex [Directions] | 3:45 p.m. | W 5-1 | League Game, Newtown is Home |
| Mon., 4/28 | V Baseball | Newtown | Away - Baseball Field at Fairfield Hills Complex [Directions] | 6:30 p.m. | L 6-8 | Pomperaug is the Home Team, This is the Non League game |
| Mon., 4/28 | FR Baseball | Bethel | Home - Community Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 4/28 | V Boys Golf | New Fairfield | Away - River Oaks [Directions] | 3:00 p.m. | Pomperaug 145 New Fairfield 204 | |
| Mon., 4/28 | V Boys Lacrosse | Southington | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 3-12 | |
| Mon., 4/28 | JV Boys Lacrosse | Southington | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Mon., 4/28 | V Boys Tennis | Joel Barlow | Away - Tennis Courts [Directions] | 3:45 p.m. | W 4 - 3 | |
| Mon., 4/28 | V Girls Outdoor Track | Bethel, New Fairfield, Bunnell | Away - DeSantis Field at Bethel High School [Directions] | 4:00 p.m. | Bethel 81 PHS 68 PHS 94 NFHS 45 PHS 73 Bunnell 73 | |
| Mon., 4/28 | V Softball | Newtown | Away - Treadwell Town Park [Directions] | 5:00 p.m. | W 6 - 3 | Non league game, Pomperaug will bat as the home team |
| Mon., 4/28 | V Softball | Newtown | Away - Treadwell Town Park [Directions] | 7:00 p.m. | W 2 - 1 | |
| Mon., 4/28 | V Girls Tennis | Joel Barlow | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Mon., 4/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:00 pm | |
| Mon., 4/28 | Miscellaneous Events | Middlebury Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/29 | JV Baseball | Newtown | Home - Community Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 4/29 | V Boys Golf | Immaculate | Home - Heritage Village C.C. [Directions] | 3:00 p.m. | Pomperaug 156 Immaculate 212 | |
| Tue., 4/29 | V Boys Outdoor Track | Bunnell, New Fairfield, Bethel | Away - Bunnell Track [Directions] | 4:00 p.m. | (P) 62 (Bunnell) 88 (P) 52.5 (NF) 97.5 (P) 68.5 (Bethel) 81.5 | |
| Tue., 4/29 | V Boys Tennis | Bethel | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 4/29 | V Girls Lacrosse | Joel Barlow | Away - Joel Barlow High School [Directions] | 4:30 p.m. | L 9-17 | |
| Tue., 4/29 | JV Girls Lacrosse | Joel Barlow | Away - Joel Barlow High School [Directions] | 6:00 p.m. | ||
| Tue., 4/29 | JV Softball | Newtown | Home - Community Softball Field [Directions] | 3:45 p.m. | ||
| Tue., 4/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:00 pm | |
| Wed., 4/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:00 pm | |
| Thu., 5/1 | V Boys Lacrosse | Bunnell-Stratford | Away - Bunnell Turf Field [Directions] | 7:00 p.m. | W 17-7 | |
| Thu., 5/1 | JV Boys Lacrosse | Bunnell-Stratford | Away - Bunnell Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 5/1 | V Boys Tennis | Weston | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | L 2 - 5 | |
| Thu., 5/1 | V Girls Lacrosse | New Fairfield | Home - Sports Complex & Track [Directions] | 4:30 p.m. | L 8-21 | |
| Thu., 5/1 | JV Girls Lacrosse | New Fairfield | Home - Sports Complex & Track [Directions] | 6:30 p.m. | ||
| Thu., 5/1 | V Girls Tennis | Weston | Away - WHS Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Thu., 5/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Thu., 5/1 | Miscellaneous Events | Connecticut Football Club | - PHS Soccer Field | 5:30 p.m. | Club Soccer Practice | |
| Fri., 5/2 | V Baseball | New Milford | Home - PHS Baseball Field [Directions] | 4:15 p.m. | L 9-7 | |
| Fri., 5/2 | JV Baseball | Masuk | Away - John Giampaolo Field @ Masuk [Directions] | 4:15 p.m. | ||
| Fri., 5/2 | FR Baseball | Newtown | Home - Community Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 5/2 | V Girls Lacrosse | Lauralton Hall | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 12-9 | non league game |
| Fri., 5/2 | JV Girls Lacrosse | Lauralton Hall | Home - Sports Complex & Track [Directions] | 5:30 p.m. | ||
| Fri., 5/2 | V Softball | New Milford | Home - PHS Softball Field [Directions] | 4:15 p.m. | W 7 - 6 | |
| Fri., 5/2 | V Girls Tennis | Bethel | Away - Bethel High School [Directions] | 3:45 p.m. | L 3-4 | |
| Fri., 5/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Sat., 5/3 | JV Baseball | New Milford | Away - New Milford High School [Directions] | 10:00 a.m. | ||
| Sat., 5/3 | FR Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 5/3 | V Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 3:00 p.m. | L 14-20 | |
| Sat., 5/3 | JV Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 4:30 p.m. | ||
| Sat., 5/3 | JV Softball | New Milford | Away - New Milford High School [Directions] | 10:00 a.m. | ||
| Sun., 5/4 | Miscellaneous Events | Pomperaug Lacrosse Association Honor The Game Day | - Sports Complex & Track | 7:00 a.m. | 7:00 am - 6:30 pm | |
| Sun., 5/4 | Miscellaneous Events | Pomperaug Lacrosse Association Honor The Game Day | - PHS Soccer Field | 7:00 a.m. | 7:00 am - 6:30 pm | |
| Mon., 5/5 | V Baseball | Stratford | Away - Penders Field [Directions] | 7:00 p.m. | W 6-5 | |
| Mon., 5/5 | FR Baseball | Masuk | Away - Wolfe Park [Directions] | 3:45 p.m. | ||
| Mon., 5/5 | V Boys Golf | Newtown | Home - Heritage Village C.C. [Directions] | 3:00 p.m. | Pomperaug 170 Newtown 171 | |
| Mon., 5/5 | V Boys Tennis | Newtown | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | L 3 - 4 | |
| Mon., 5/5 | V Girls Outdoor Track | Joel Barlow, New Milford, Weston | Home - Sports Complex & Track [Directions] | 4:15 p.m. | WHS 91 1/2 PHS 58 1/2 JBHS 91 PHS 55 NMHS 84 1/2 PHS 61 1/2 | |
| Mon., 5/5 | V Softball | Stratford | Away - DeLuca Field [Directions] | 7:00 p.m. | W 12 - 2 | |
| Mon., 5/5 | FR Softball | Nonnewaug | Home - PHS Softball Field [Directions] | 3:45 p.m. | ||
| Mon., 5/5 | V Girls Tennis | Newtown | Away - Newtown High School [Directions] | 3:45 p.m. | L 0-7 | |
| Mon., 5/5 | Miscellaneous Events | AP Testing in the Auxiliary Gym | - Auxiliary Gym | 12:00 p.m. | 12:00 to 2:30 pm | |
| Mon., 5/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Mon., 5/5 | Miscellaneous Events | Middlebury Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 5/6 | V Baseball | Masuk | Home - PHS Baseball Field [Directions] | 4:15 p.m. | W 7-3 | |
| Tue., 5/6 | JV Baseball | Stratford | Home - Community Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/6 | V Boys Lacrosse | Notre Dame-Fairfield | Away - McCarty Stadium at Notre Dame [Directions] | 4:00 p.m. | L 13-14 | |
| Tue., 5/6 | JV Boys Lacrosse | Notre Dame-Fairfield | Away - McCarty Stadium at Notre Dame [Directions] | 5:30 p.m. | ||
| Tue., 5/6 | V Boys Outdoor Track | Weston, New Milford, Joel Barlow | Away - WHS Track [Directions] | 4:00 p.m. | P(66) W(84) P(60) NM (90) P(104) JB(43) | |
| Tue., 5/6 | V Girls Lacrosse | Newtown | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 2-14 | |
| Tue., 5/6 | JV Girls Lacrosse | Newtown | Home - Sports Complex & Track [Directions] | 5:30 p.m. | ||
| Tue., 5/6 | V Softball | Masuk | Home - PHS Softball Field [Directions] | 4:15 p.m. | L 0-8 | |
| Tue., 5/6 | JV Softball | Stratford | Home - Community Softball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Tue., 5/6 | Miscellaneous Events | Ultimate Frisbee Club Competition | - PHS Soccer Field | 4:30 p.m. | 4:30 - 7:00 pm | |
| Wed., 5/7 | V Baseball | Bethel | Away - Hunt Field at Bethel High School [Directions] | 5:30 p.m. | W 6-4 | |
| Wed., 5/7 | JV Baseball | Bethel | Home - Community Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/7 | FR Baseball | Stratford | Home - PHS Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/7 | V Boys Golf | Bethel | Home - Heritage Village C.C. [Directions] | 3:00 p.m. | Pomperaug 150 Bethel 201 | |
| Wed., 5/7 | V Boys Tennis | Masuk | Away - Wolfe Park Tennis Courts [Directions] | 3:45 p.m. | W 7 - 0 | |
| Wed., 5/7 | V Softball | Bethel | Away - Kasack Field at Johnson School [Directions] | 5:30 p.m. | W 7 - 4 | |
| Wed., 5/7 | JV Softball | Bethel | Home - Community Softball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/7 | FR Softball | Stratford | Home - Community Softball Field [Directions] | 4:15 p.m. | Cancelled | |
| Wed., 5/7 | V Girls Tennis | Masuk | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Wed., 5/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Thu., 5/8 | V Boys Golf | Weston | Home - Heritage Village C.C. [Directions] | 3:00 p.m. | Pomperaug 154 Weston 172 | |
| Thu., 5/8 | V Boys Lacrosse | Weston | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 8-19 | |
| Thu., 5/8 | JV Boys Lacrosse | Weston | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 5/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Fri., 5/9 | FR Baseball | New Milford | Away - New Milford High School [Directions] | 3:45 p.m. | ||
| Fri., 5/9 | FR Softball | New Milford | Away - New Milford High School [Directions] | 3:45 p.m. | ||
| Fri., 5/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Fri., 5/9 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Sat., 5/10 | V Boys Lacrosse | Hall | Home - Sports Complex & Track [Directions] | 12:00 p.m. | L 3-14 | |
| Sat., 5/10 | JV Boys Lacrosse | Hall | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 5/10 | V Girls Lacrosse | Bunnell | Away - Bunnell Turf Field [Directions] | 12:00 p.m. | W 14-8 | |
| Sun., 5/11 | Miscellaneous Events | Revolution Soccer | - Sports Complex & Track | 11:30 a.m. | 11:30 to 3:30 | |
| Mon., 5/12 | V Boys Lacrosse | Practice | Home - Sports Complex & Track [Directions] | 4:30 | ||
| Mon., 5/12 | JV Boys Lacrosse | Practice | Home - PHS Soccer Field [Directions] | 4:30 | ||
| Mon., 5/12 | V Boys Tennis | Newtown | Away - Newtown High School [Directions] | 3:45 p.m. | W 5 - 2 | non-league match |
| Mon., 5/12 | V Girls Lacrosse | Mercy | Away - Mercy [Directions] | 4:15 p.m. | W 10-8 | |
| Mon., 5/12 | JV Girls Lacrosse | Mercy | Away - Mercy [Directions] | 5:30 p.m. | ||
| Mon., 5/12 | V Girls Outdoor Track | Masuk, Lauralton Hall, Stratford | Away - Masuk HS Track [Directions] | 4:30 p.m. | PHS 115 Stratford 26 PHS 115 L. Hall 26 PHS 93.5 Masuk 52.5 | |
| Mon., 5/12 | V Girls Tennis | Lauralton Hall | Away - Eisenhower Park [Directions] | 3:45 p.m. | L 1-6 | |
| Mon., 5/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Mon., 5/12 | Miscellaneous Events | Middlebury Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 5/13 | V Baseball | Kolbe Cathedral | Away - Veterans Park [Directions] | 4:15 p.m. | W 6-0 | |
| Tue., 5/13 | V Boys Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | Pomperaug 169 Masuk 180 | |
| Tue., 5/13 | V Boys Lacrosse | New Fairfield | Away - Rebel Stadium [Directions] | 4:00 p.m. | L 4-10 | |
| Tue., 5/13 | JV Boys Lacrosse | New Fairfield | Away - Rebel Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/13 | V Boys Outdoor Track | Stratford, Masuk | Away - Bunnell High School Track [Directions] | 4:00 p.m. | P 106 S 44 P 57 M 96 | @ Bunnell High School |
| Tue., 5/13 | ALL Competitive Cheerleading | Practice | Home - Health Classroom - Room 201 [Directions] | 6:00 to 7:00 pm | Parent Organizational Meeting | |
| Tue., 5/13 | V Softball | Kolbe Cathedral | Away - Seaside Park [Directions] | 4:15 p.m. | W 15 - 4 | |
| Tue., 5/13 | V Girls Tennis | Notre Dame-Fairfield | Home - PHS Tennis Courts [Directions] | 3:30 p.m. | W 6-1 | |
| Tue., 5/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Wed., 5/14 | V Baseball | Oxford | Home - Dodd Stadium, Norwich [Directions] | 6:00 p.m. | W 4-3 | |
| Wed., 5/14 | V Boys Golf | Joel Barlow | Home - Heritage Village C.C. [Directions] | 3:00 p.m. | Pomperaug 154 Barlow 180 | |
| Wed., 5/14 | V/JV Boys Lacrosse | Practice | Home - PHS Soccer Field [Directions] | 4:30 | ||
| Wed., 5/14 | V Boys Tennis | Joel Barlow | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | L 3 - 4 | non league match |
| Wed., 5/14 | V Girls Lacrosse | Housatonic Regional | Home - Sports Complex & Track [Directions] | 5:00 p.m. | W 15-13 | |
| Wed., 5/14 | V Softball | Oxford | Home - PHS Softball Field [Directions] | 4:15 p.m. | L 0-2 | |
| Wed., 5/14 | V Girls Tennis | Bunnell | Away - Bunnell Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | Non league game |
| Wed., 5/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Wed., 5/14 | School Holidays and Closings | Professional Development - Half Day | ||||
| Thu., 5/15 | V Baseball | Notre Dame-Fairfield | Home - PHS Baseball Field [Directions] | 4:15 p.m. | W 6-0 | |
| Thu., 5/15 | JV Baseball | Oxford | Away - OHS Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 5/15 | V Boys Golf | New Milford | Home - Heritage Village C.C. [Directions] | 3:45 p.m. | Pomperaug 156 New Milford 186 | |
| Thu., 5/15 | V Boys Lacrosse | Bethel | Away - DeSantis Field at Bethel High School [Directions] | 7:00 p.m. | L 6-9 | |
| Thu., 5/15 | JV Boys Lacrosse | Bethel | Away - DeSantis Field at Bethel High School [Directions] | 5:30 p.m. | ||
| Thu., 5/15 | V Softball | Notre Dame-Fairfield | Home - PHS Softball Field [Directions] | 4:15 p.m. | W 9-1 | |
| Thu., 5/15 | JV Softball | Oxford | Away - OHS Softball Field [Directions] | 3:45 p.m. | ||
| Thu., 5/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Thu., 5/15 | Miscellaneous Events | Connecticut Football Club | - PHS Soccer Field | 5:30 p.m. | Club Soccer Practice | |
| Fri., 5/16 | V Boys Lacrosse | Practice | Home - Sports Complex & Track [Directions] | 4:30 | ||
| Fri., 5/16 | JV Boys Lacrosse | Practice | Home - PHS Soccer Field [Directions] | 4:30 | ||
| Fri., 5/16 | V Girls Tennis | Practice | Home - Room 400 [Directions] | 2:30 pm | Meet in Room 400 after school | |
| Fri., 5/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Sat., 5/17 | V Baseball | Brookfield | Home - PHS Baseball Field [Directions] | 12:00 p.m. | W 5-0 | |
| Sat., 5/17 | V Baseball | SWC Mandatory Make Up Date | Home - PHS Baseball Field [Directions] | TBA | ||
| Sat., 5/17 | V Softball | Brookfield | Home - PHS Softball Field [Directions] | 12:00 p.m. | W 3 - 2 | |
| Sat., 5/17 | V Softball | SWC Mandatory Make Up Date | Home - PHS Softball Field [Directions] | TBA | ||
| Sat., 5/17 | JV Softball | Masuk | Away - Masuk Upper Softball Field [Directions] | 12:00 p.m. | ||
| Sun., 5/18 | V Girls Tennis | Practice | Home - PHS Tennis Courts [Directions] | 9:00 to 12:00 | ||
| Sun., 5/18 | Miscellaneous Events | Revolution Soccer | - Sports Complex & Track | 10:00 a.m. | 9:30 to 11:30 | |
| Sun., 5/18 | Miscellaneous Events | Revolution United Soccer Game | - Sports Complex & Track | 9:30 a.m. | 9:30 - 11:30 am | |
| Mon., 5/19 | V Baseball | Immaculate | Home - PHS Baseball Field [Directions] | 4:30 p.m. | W 4-1 | |
| Mon., 5/19 | FR Baseball | Bethel | Away - Parloa Field [Directions] | 3:45 p.m. | ||
| Mon., 5/19 | V Boys Golf | Notre Dame-Fairfield | Away - Fairchild Wheeler Golf Course [Directions] | 3:00 p.m. | Pomperaug 151 Notre dame 181 | |
| Mon., 5/19 | V/JV Boys Lacrosse | Practice | Home - Long Meadow Elementary School [Directions] | 4:30 | ||
| Mon., 5/19 | V Boys Tennis | SWC Team Semi-Finals | Away [Directions] | 3:45 p.m. | ||
| Mon., 5/19 | V Girls Outdoor Track | Notre Dame-Fairfield, Brookfield, Kolbe Cathedral | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Softball | Immaculate | Home - PHS Softball Field [Directions] | 4:30 p.m. | W 14-7 | |
| Mon., 5/19 | JV Softball | Newtown | Away - Newtown High School Softball Field [Directions] | 3:45 p.m. | ||
| Mon., 5/19 | V Girls Tennis | SWC Team Semi-Finals | Away | 3:30 p.m. | ||
| Mon., 5/19 | V Girls Tennis | Practice | Home - PHS Tennis Courts [Directions] | 4:15 pm | 4:15 to 6:00 | |
| Mon., 5/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:00 pm | |
| Mon., 5/19 | Miscellaneous Events | Mdby Park & Rec Lifeguarding Certification | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 7:00 pm | |
| Mon., 5/19 | Miscellaneous Events | Mdby Park & Rec Lifeguarding Certification | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 5/19 | Miscellaneous Events | Middlebury Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 5/20 | V Baseball | Weston | Away - Revson Field, Weston [Directions] | 4:15 p.m. | L 5-3 | |
| Tue., 5/20 | V Boys Golf | New Milford | Away - Candlewood Valley [Directions] | 3:00 p.m. | Pomperaug 152 New Milford 162 | Non-League Game |
| Tue., 5/20 | V/JV Boys Lacrosse | Practice | Home - PHS Soccer Field [Directions] | 4:30 | ||
| Tue., 5/20 | V Boys Outdoor Track | Brookfield, Notre Dame-Fairfield, Kolbe Cathedral | Away [Directions] | 4:00 p.m. | P (64) B (86) P (134) K (15) P (122) ND (24) | |
| Tue., 5/20 | V Boys Tennis | SWC Team Championship | Away | 3:30 p.m. | ||
| Tue., 5/20 | V Girls Lacrosse | Shelton | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 10-8 | |
| Tue., 5/20 | JV Girls Lacrosse | Shelton | Home - Sports Complex & Track [Directions] | 5:30 p.m. | ||
| Tue., 5/20 | V Softball | Weston | Away - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | W 10-2 | |
| Tue., 5/20 | V Girls Tennis | Practice | Home - PHS Tennis Courts [Directions] | 4:15 pm | 4:15 - 6:00 pm | |
| Tue., 5/20 | Miscellaneous Events | SMART Presentation to Students | - PHS Main Gym | 1:00 p.m. | set up @ 12:00 | |
| Tue., 5/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:00 pm | |
| Tue., 5/20 | Miscellaneous Events | Mdby Park & Rec Lifeguarding Certification | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 7:00 pm | |
| Tue., 5/20 | Miscellaneous Events | S.M.A.R.T. EVENT | - PHS Main Gym | 6:00 p.m. | 6:00 set-up. 7:00 event begins | |
| Tue., 5/20 | Miscellaneous Events | Mdby Park & Rec Lifeguarding Certification | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 5/21 | JV Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/21 | FR Baseball | Bunnell | Home - Community Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/21 | V/JV Boys Lacrosse | Practice | Home - PHS Soccer Field [Directions] | 4:30 | ||
| Wed., 5/21 | V Girls Lacrosse | Amity | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 13-15 | |
| Wed., 5/21 | JV Girls Lacrosse | Amity | Home - Sports Complex & Track [Directions] | 5:30 p.m. | ||
| Wed., 5/21 | V Softball | New Fairfield | Away - NFHS Softball Field [Directions] | 4:00 p.m. | W 16-1 | Non league game |
| Wed., 5/21 | V Girls Tennis | SWC Team Championships | Away | 3:30 p.m. | ||
| Wed., 5/21 | V Girls Tennis | Practice | Home - PHS Tennis Courts [Directions] | 4:15 pm | 4:15 - 6:00 pm | |
| Wed., 5/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:00 pm | |
| Wed., 5/21 | Miscellaneous Events | Mdby Park & Rec Lifeguarding Certification | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 7:00 pm | |
| Wed., 5/21 | Miscellaneous Events | Mdby Park & Rec Lifeguarding Certification | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 5/22 | V Boys Lacrosse | Danbury | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 4-13 | |
| Thu., 5/22 | JV Boys Lacrosse | Danbury | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 5/22 | V Boys Tennis | Practice | Home - Auxiliary Gym [Directions] | 2:30 pm | 2:30 - 4:15 pm | |
| Thu., 5/22 | V Girls Outdoor Track | Staples Qualifier | Away [Directions] | 5:00 p.m. | Cancelled | @ Staples High School |
| Thu., 5/22 | V Girls Tennis | Practice | Home - PHS Tennis Courts [Directions] | 4:15 pm | 4:15 - 6:00 pm | |
| Thu., 5/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:00 pm | |
| Thu., 5/22 | Miscellaneous Events | Mdby Park & Rec Lifeguarding Certification | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 7:00 pm | |
| Thu., 5/22 | Miscellaneous Events | Connecticut Football Club | - PHS Soccer Field | 5:30 p.m. | Club Soccer Practice | |
| Thu., 5/22 | Miscellaneous Events | Mdby Park & Rec Lifeguarding Certification | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Fri., 5/23 | FR Baseball | Brookfield | Home - Community Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 5/23 | V Boys Golf | Practice Round at Fairview Farms | Away | 12:30 p.m. | ||
| Fri., 5/23 | V Boys Lacrosse | Practice | Home - Sports Complex & Track [Directions] | 6:30 | ||
| Fri., 5/23 | V Boys Tennis | Practice | Home - PHS Tennis Courts [Directions] | 2:30 pm | 2:30 - 4:15 pm | |
| Fri., 5/23 | V Girls Lacrosse | SWC Quarter-Finals | Away [Directions] | 5:00 p.m. | @ New Fairfield, $8 Adults, $5 Students | |
| Fri., 5/23 | V Girls Tennis | Practice | Home - PHS Tennis Courts [Directions] | 4:15 pm | 4:15 - 6:00 pm | |
| Fri., 5/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Sat., 5/24 | Miscellaneous Events | Rochambeau Intramural Track | Home - Sports Complex & Track [Directions] | 9:00 a.m. | 9:00 am to 12:00 pm | |
| Sun., 5/25 | V Girls Tennis | Practice | Home - PHS Tennis Courts [Directions] | 9:00 to 12:00 | ||
| Mon., 5/26 | V Baseball | SWC Quarter-Finals | Home - PHS Baseball Field [Directions] | 1:00 p.m. | $8 Adults, $5 Students | |
| Mon., 5/26 | V Boys Lacrosse | Practice | Home - Sports Complex & Track [Directions] | 11:00 am | ||
| Mon., 5/26 | JV Boys Lacrosse | Practice | Home - Sports Complex & Track [Directions] | 1:00 pm | ||
| Mon., 5/26 | V Softball | Newtown | Home - PHS Softball Field [Directions] | 12:00 p.m. | L 0-1 | SWC Quarter Finals, $8 Adults, $5 Students |
| Mon., 5/26 | School Holidays and Closings | Memorial Day | ||||
| Tue., 5/27 | V Boys Golf | Coaches Cup Tournament | Away | 3:00 p.m. | ||
| Tue., 5/27 | V Boys Lacrosse | Practice | Home - Sports Complex & Track [Directions] | 6:30 | ||
| Tue., 5/27 | V Boys Outdoor Track | Practice | Home - Sports Complex & Track [Directions] | 2:30 pm | ||
| Tue., 5/27 | V Boys Tennis | SWC Individual Championships | Away | 3:30 p.m. | Cancelled | @ Roger's Park in Danbury |
| Tue., 5/27 | V Girls Lacrosse | D-II SWC Semi-Finals | Away | TBA | Cancelled | @ New Fairfield, $8 Adults, $5 Students |
| Tue., 5/27 | V Girls Outdoor Track | Practice | Home - Sports Complex & Track [Directions] | 2:30 pm | ||
| Tue., 5/27 | V Softball | SWC Semi-Finals | Away | 4:00 p.m. | Cancelled | DeLuca in Stratford at Sacred University, $8 Adults, $5 Students Heart Univ. |
| Tue., 5/27 | V Girls Tennis | Practice | Home - PHS Tennis Courts [Directions] | 2:30 pm | 2:30 - 5:00 pm | |
| Tue., 5/27 | V Girls Tennis | SWC Individual Championships | Away [Directions] | 3:30 p.m. | Cancelled | @ Joel Barlow |
| Tue., 5/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Wed., 5/28 | V Girls Lacrosse | D-I SWC Championship Game | Home - Sports Complex & Track [Directions] | 5:00 p.m. | $10 Adults, $5 Students | |
| Wed., 5/28 | V Softball | SWC Championship Game | Away | 7:00 p.m. | Cancelled | DeLuca Field in Stratford, $10 Adults, $5 Students |
| Wed., 5/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Wed., 5/28 | Miscellaneous Events | SWC D-II Semi Finals | - Sports Complex & Track | 5:00 p.m. | 5:00 and 7:00 | |
| Wed., 5/28 | Miscellaneous Events | SWC D-I Championship Double Header | Home - Sports Complex & Track [Directions] | 5:00 p.m. | Girls at 5:00 Boys at 7:00 | |
| Thu., 5/29 | V Baseball | SWC Semi-Finals | Away | 5:00 p.m. | @ Bethel, $8 Adults, $5 Students | |
| Thu., 5/29 | V Baseball | SWC Championship Game | Away [Directions] | 7:00 p.m. | @ Bethel HS, $10 Adults, $5 Students | |
| Thu., 5/29 | V Boys Lacrosse | D-II SWC Championship Game | Home - Sports Complex & Track [Directions] | 7:00 p.m. | $8 Adults, $5 Students | |
| Thu., 5/29 | V Boys Outdoor Track | South-West Conference Championships | Away [Directions] | 2:00 p.m. | at Bunnell HS | |
| Thu., 5/29 | V Boys Tennis | SWC Individual Championships | Away | 12:00 p.m. | @ Rogers Park in Danbury | |
| Thu., 5/29 | V Girls Lacrosse | Practice | Home - PHS Soccer Field [Directions] | 4:30 - 6:30 | ||
| Thu., 5/29 | V Girls Lacrosse | D - I SWC Championship rain date | Home - Sports Complex & Track [Directions] | 5:00 p.m. | $10 Adults, $5 Students | |
| Thu., 5/29 | V Girls Outdoor Track | South-West Conference Championships | Away [Directions] | 2:00 p.m. | at Bunnell HS | |
| Thu., 5/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Thu., 5/29 | Miscellaneous Events | SWC D-I Lacrosse Championship | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 5/29 | Miscellaneous Events | Connecticut Football Club | - PHS Soccer Field | 5:30 p.m. | Club Soccer Practice | |
| Fri., 5/30 | V Boys Golf | SWC Championship | Away | 7:30 a.m. | @ Ridgewood CC, Danbury | |
| Fri., 5/30 | V Boys Lacrosse | D-II SWC Championship Game Rain Date | Away [Directions] | 6:00 p.m. | at Newtown, $10 Adults, $5 Students | |
| Fri., 5/30 | V Boys Outdoor Track | Practice | Home - Sports Complex & Track [Directions] | 2:30 pm | ||
| Fri., 5/30 | V Boys Tennis | Practice | Home - PHS Tennis Courts [Directions] | 4:15 pm | 4:15 - 6:00 pm | |
| Fri., 5/30 | V Girls Lacrosse | Sheehan | Home - Sports Complex & Track [Directions] | 5:30 p.m. | CIAC Tournament Game | |
| Fri., 5/30 | V Girls Outdoor Track | Practice | Home - Sports Complex & Track [Directions] | 2:30 pm | ||
| Fri., 5/30 | V Softball | Practice | Home - Auxiliary Gym [Directions] | 2:30 pm | ||
| Fri., 5/30 | V Girls Tennis | Practice | Home - PHS Tennis Courts [Directions] | 2:30 pm | 2:30 - 5:00 pm | |
| Fri., 5/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Sat., 5/31 | V Boys Tennis | CIAC Tournament | Away | 8:00 a.m. | ||
| Sat., 5/31 | ALL Girls Lacrosse | Practice | Home - Sports Complex & Track [Directions] | 10:00 to 12:00 | ||
| Sun., 6/1 | V Girls Tennis | Practice | Home - PHS Tennis Courts [Directions] | 2:30 pm | 2:30 - 5:00 pm | |
| Sun., 6/1 | School Holidays and Closings | Junior/Senior Prom | ||||
| Mon., 6/2 | V Baseball | Woodstock Academy | Home - PHS Baseball Field [Directions] | 3:30 p.m. | CIAC Tournament Game | |
| Mon., 6/2 | ALL Football | Practice | Home - Sports Complex & Track [Directions] | 4:30 to 6:30 | ||
| Mon., 6/2 | V Boys Golf | Weston | Away - Aspetuck Valley Country Club [Directions] | 3:00 p.m. | Pomperaug 165 Weston171 | Non-League Game |
| Mon., 6/2 | V Boys Outdoor Track | CIAC Class L Championship | Away - Middletown HS [Directions] | 2:30 p.m. | ||
| Mon., 6/2 | V Girls Lacrosse | Practice | Home - Sports Complex & Track [Directions] | 6:30 | ||
| Mon., 6/2 | V Girls Outdoor Track | CIAC Class L Championship | Away - Middletown HS [Directions] | 2:30 p.m. | ||
| Mon., 6/2 | School Holidays and Closings | Teacher Work Day - Early Release | ||||
| Tue., 6/3 | V Baseball | Notre Dame-West Haven | Away - Quigley Stadium [Directions] | 3:30 p.m. | ||
| Tue., 6/3 | FR Baseball | Practice | Home - Health Classroom - Room 201 [Directions] | 2:15 pm | ||
| Tue., 6/3 | ALL Football | Practice | Home - Sports Complex & Track [Directions] | 4:30 to 6:30 | ||
| Tue., 6/3 | V Boys Golf | Nonnewaug | Home - Heritage Village C.C. [Directions] | 3:00 p.m. | Cancelled | |
| Tue., 6/3 | V Boys Lacrosse | Practice | Home - Sports Complex & Track [Directions] | 6:30 to 8:30 | ||
| Tue., 6/3 | V Girls Lacrosse | Joel Barlow | Away [Directions] | 5:00 p.m. | ||
| Tue., 6/3 | V Softball | Windsor | Home - PHS Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 6/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Wed., 6/4 | ALL Football | Practice | Home - Sports Complex & Track [Directions] | 6:30 to 8:30 | ||
| Wed., 6/4 | V Boys Lacrosse | Practice | Home - Sports Complex & Track [Directions] | 4:30 | ||
| Wed., 6/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Wed., 6/4 | Miscellaneous Events | CPR Class for Coaches | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 to 8:00 | |
| Thu., 6/5 | ALL Football | Practice | Home - Sports Complex & Track [Directions] | 6:30 to 8:30 | ||
| Thu., 6/5 | V Boys Lacrosse | Practice | Home - Sports Complex & Track [Directions] | 4:30 | ||
| Thu., 6/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Thu., 6/5 | Miscellaneous Events | Connecticut Football Club | - PHS Soccer Field | 5:30 p.m. | Club Soccer Practice | |
| Fri., 6/6 | V Baseball | CIAC Tournament | Home - PHS Baseball Field [Directions] | TBA | Cancelled | |
| Fri., 6/6 | ALL Football | Practice | Home - Sports Complex & Track [Directions] | 4:30 to 6:30 | ||
| Fri., 6/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Fri., 6/6 | Miscellaneous Events | Kinetic Kids Gymnastic Show Set-Up | - PHS Main Gym | 3:00 p.m. | 3:00 - 7:00 pm | |
| Fri., 6/6 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Sat., 6/7 | Miscellaneous Events | Kinetic Kids Gymnastics Exhibition | - PHS Main Gym | 11:00 a.m. | 11:00 - 5:00 pm | |
| Sat., 6/7 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Sun., 6/8 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Mon., 6/9 | ALL Football | Practice | Home - Sports Complex & Track [Directions] | 4:30 to 6:30 | ||
| Mon., 6/9 | V Boys Outdoor Track | CIAC Open Championship | Away - Middletown [Directions] | 1:30 p.m. | ||
| Mon., 6/9 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Mon., 6/9 | V Girls Outdoor Track | CIAC Open Championship | Away - Middletown [Directions] | 1:30 p.m. | ||
| Mon., 6/9 | Miscellaneous Events | Field Hockey Team Meeting | - Health Classroom - Room 201 | 2:15 p.m. | ||
| Mon., 6/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Tue., 6/10 | ALL Football | Practice | Home - Sports Complex & Track [Directions] | 4:30 to 6:30 | ||
| Tue., 6/10 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Tue., 6/10 | Miscellaneous Events | Volleyball Team Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 pm | |
| Tue., 6/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Tue., 6/10 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Wed., 6/11 | ALL Football | Practice | Home - Sports Complex & Track [Directions] | 4:30 to 6:30 | ||
| Wed., 6/11 | V Boys Golf | CIAC Division II Championship | Away | TBA | @ Fairview Farms | |
| Wed., 6/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Wed., 6/11 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Thu., 6/12 | ALL Football | Practice | Home - Sports Complex & Track [Directions] | 4:30 to 6:30 | ||
| Thu., 6/12 | V Competitive Cheerleading | Practice | Home - Auxiliary Gym [Directions] | 6:15 to 8:30 | ||
| Thu., 6/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Thu., 6/12 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Thu., 6/12 | Miscellaneous Events | Connecticut Football Club | - PHS Soccer Field | 5:30 p.m. | Club Soccer Practice | |
| Thu., 6/12 | Miscellaneous Events | CT Seahawks Softball | - PHS Softball Field | 5:45 p.m. | 5:45 - 7:45 pm | |
| Thu., 6/12 | Miscellaneous Events | Cross Country Team Meeting | - PHS Main Gym | 6:30 p.m. | ||
| Fri., 6/13 | ALL Football | Practice | Home - Sports Complex & Track [Directions] | 6:00 pm | Intra squad scrimmage | |
| Fri., 6/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Sat., 6/14 | V Boys Outdoor Track | New England Championship | Away - Norwell (MA) HS | TBA | ||
| Sat., 6/14 | V Girls Outdoor Track | New England Championship | Away | 10:00 a.m. | ||
| Sat., 6/14 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Sun., 6/15 | Miscellaneous Events | CFC Soccer Tournament | - Sports Complex & Track | 7:30 a.m. | 7:30 am - 5:00 pm | |
| Sun., 6/15 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Tue., 6/17 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - USCG Academy [Directions] | 11:00 a.m. | ||
| Tue., 6/17 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - USCG Academy | 11:30 a.m. | ||
| Wed., 6/18 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Willowbrook Park - New Britain [Directions] | 11:00 a.m. | ||
| Wed., 6/18 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - USCG Academy [Directions] | 11:00 a.m. | ||
| Wed., 6/18 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Thu., 6/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Thu., 6/19 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Thu., 6/19 | Miscellaneous Events | Connecticut Football Club | - PHS Soccer Field | 5:30 p.m. | Club Soccer Practice | |
| Fri., 6/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Fri., 6/20 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Sat., 6/21 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Sun., 6/22 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Mon., 6/23 | Miscellaneous Events | Stby Park & Rec Field Hockey Camp | - PHS Field Hockey Field | 9:00 a.m. | 9:00 am - 12:00 pm | |
| Mon., 6/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Mon., 6/23 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 6/24 | Miscellaneous Events | Cheerleading Skills Camp | - PHS Main Gym | 8:00 a.m. | 8:00 am - 6:00 pm | |
| Tue., 6/24 | Miscellaneous Events | Stby Park & Rec Field Hockey Camp | - PHS Field Hockey Field | 9:00 a.m. | 9:00 am - 12:00 pm | |
| Tue., 6/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Tue., 6/24 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Wed., 6/25 | Miscellaneous Events | Cheerleading Skills Camp | - PHS Main Gym | 8:00 a.m. | 8:00 am - 6:00 pm | |
| Wed., 6/25 | Miscellaneous Events | Stby Park & Rec Field Hockey Camp | - PHS Field Hockey Field | 9:00 a.m. | 9:00 am - 12:00 pm | |
| Wed., 6/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Wed., 6/25 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Thu., 6/26 | Miscellaneous Events | Cheerleading Skills Camp | - PHS Main Gym | 8:00 a.m. | 8:00 am - 6:00 pm | |
| Thu., 6/26 | Miscellaneous Events | Stby Park & Rec Field Hockey Camp | - PHS Field Hockey Field | 9:00 a.m. | 9:00 am - 12:00 pm | |
| Thu., 6/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Thu., 6/26 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Thu., 6/26 | Miscellaneous Events | CT Seahawks Softball | - PHS Softball Field | 5:45 p.m. | 5:45 - 7:45 pm | |
| Fri., 6/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | ||
| Fri., 6/27 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Sat., 6/28 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Sun., 6/29 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |