| Pomperaug 2017-18 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1077 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | New Fairfield | Home - Community Baseball Field [Directions] | 4:00 p.m. | 2:30 | |
| TBA | JV Baseball | Immaculate | Away - Immaculate [Directions] | 4:15 p.m. | 2:30 | |
| TBA | JV Baseball | Bethel | Away - Parloa Field [Directions] | TBA | 2:15 | |
| TBA | JV Baseball | Newtown | Home - PHS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | Notre Dame-Fairfield | Away - Fabbri Field at Notre Dame [Directions] | TBA | 2:30 | |
| TBA | FR Baseball | Newtown | Home [Directions] | 1:00 p.m. | ||
| TBA | FR Baseball | Naugatuck | Home - Community Baseball Field [Directions] | 3:45 p.m. | 2:15 pm | |
| TBA | FR Baseball | Newtown | Home - Community Baseball Field [Directions] | 4:00 p.m. | ||
| TBA | FR Baseball | Joel Barlow | Home [Directions] | TBA | ||
| TBA | FR Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | TBA | 2:30 | |
| TBA | FR Boys Basketball | Amity | Away - Paul D. Mengold Gym at Amity HS [Directions] | 3:45 p.m. | 2:15 pm | |
| TBA | FR Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | TBA | 2:15 pm | |
| TBA | V Boys Tennis | Joel Barlow | Home - PHS Tennis Courts [Directions] | Cancelled | ||
| TBA | V Boys Tennis | Brookfield | Away - BHS Tennis Courts [Directions] | Cancelled | 2:15 pm | Non-league |
| TBA | FR Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | TBA | 9:00 am | |
| TBA | FR Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | TBA | 2:15 pm | |
| TBA | JV Field Hockey | Brookfield | Away - BHS Field Hockey Field [Directions] | TBA | 8:15 am share w/ varsity | |
| TBA | FR Field Hockey | Immaculate | Home - PHS Baseball Field [Directions] | 9:00 a.m. | ||
| TBA | FR Field Hockey | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 4:00 p.m. | 2:45 | |
| TBA | FR Field Hockey | Amity | Home - PHS Baseball Field [Directions] | 4:00 p.m. | ||
| TBA | FR Field Hockey | New Milford | Away - New Milford HS [Directions] | 4:30 p.m. | ||
| TBA | JV Girls Lacrosse | Immaculate | Away - Mustang Valley [Directions] | 5:30 p.m. | 4:15 | |
| TBA | FR Girls Soccer | Weston | Away - WHS Turf Field [Directions] | TBA | 3:00 pm | |
| TBA | JV Softball | Newtown | Home - PHS Softball Field [Directions] | 3:00 p.m. | ||
| TBA | JV Softball | Masuk | Away - Masuk HS Softball Field [Directions] | 4:15 p.m. | 2:15 pm | |
| TBA | JV Softball | Bethel | Away - Berry School Field [Directions] | 4:15 p.m. | 2:15 pm | |
| TBA | JV Softball | Newtown | Away - Treadwell Town Park [Directions] | TBA | 2:15 | |
| TBA | JV Softball | New Fairfield | Home - Community Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Brookfield | Away - BHS Softball Field [Directions] | TBA | 10:30 am | |
| TBA | JV Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 5:00 p.m. | 3:45 pm share w/varsity | |
| TBA | Unified Sports Volleyball | Oxford | Away [Directions] | 3:30 p.m. | 2:15 | return by 5:30 pm |
| Sat., 7/1 | Miscellaneous Events | Southbury Youth Baseball/American Legion | - PHS Baseball Field | 10:00 a.m. | 10:00 am - 3:00 pm | |
| Sun., 7/2 | Miscellaneous Events | Southbury Youth Baseball/American Legion | - PHS Baseball Field | 10:00 a.m. | 10:00 am - 1:00 pm | |
| Mon., 7/3 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 am - 2:30 pm | |
| Wed., 7/5 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 am - 2:30 pm | |
| Wed., 7/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:15 am | |
| Thu., 7/6 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 am - 2:30 pm | |
| Thu., 7/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:15 am | |
| Sat., 7/8 | Miscellaneous Events | Southbury Youth Baseball/American Legion | - PHS Baseball Field | 10:00 a.m. | 10:00 am - 1:00 pm | |
| Sun., 7/9 | Miscellaneous Events | Southbury Youth Baseball/American Legion | - PHS Baseball Field | 10:00 a.m. | 10:00 am - 1:00 pm | |
| Mon., 7/10 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 am - 2:30 pm | |
| Mon., 7/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:15 am | |
| Mon., 7/10 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:30 a.m. | 9:00 - 2:30 pm | |
| Tue., 7/11 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 am - 2:30 pm | |
| Tue., 7/11 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 am - 2:30 pm | |
| Tue., 7/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:15 am | |
| Tue., 7/11 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:30 a.m. | 9:00 - 2:30 pm | |
| Wed., 7/12 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 am - 2:30 pm | |
| Wed., 7/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:15 am | |
| Wed., 7/12 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:30 a.m. | 9:00 - 2:30 pm | |
| Thu., 7/13 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 am - 2:30 pm | |
| Thu., 7/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:15 am | |
| Thu., 7/13 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:30 a.m. | 9:00 - 2:30 pm | |
| Thu., 7/13 | Miscellaneous Events | Southbury Youth Baseball/American Legion | - PHS Baseball Field | 4:30 p.m. | 4:30 - 7:30 pm | |
| Fri., 7/14 | Miscellaneous Events | Nutmeg Games Gymnastics Set-Up | - PHS Main Gym | 10:00 a.m. | 10:00 am - 2:00 pm | |
| Fri., 7/14 | Miscellaneous Events | Southbury Youth Baseball/American Legion | - PHS Baseball Field | 4:30 p.m. | 4:30 - 7:30 pm | |
| Sat., 7/15 | Miscellaneous Events | Southbury Youth Baseball/American Legion | - PHS Baseball Field | 11:00 a.m. | 11:00 am - 2:00 pm | |
| Sat., 7/15 | Miscellaneous Events | Nutmeg Games Gymnastics Meet | - PHS Main Gym | 7:00 a.m. | 7:00 am - 5:00 pm | |
| Sun., 7/16 | Miscellaneous Events | Nutmeg Games Gymnastics Breakdown | - PHS Main Gym | 10:00 a.m. | 10:00 am - 2:00 pm | |
| Sun., 7/16 | Miscellaneous Events | Southbury Youth Baseball/American Legion | - PHS Baseball Field | 11:00 a.m. | 11:00 am - 4:00 pm | |
| Mon., 7/17 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 am - 2:30 pm | |
| Mon., 7/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:15 am | |
| Mon., 7/17 | Miscellaneous Events | Panther Basketball Camp | - PHS Main Gym | 9:30 a.m. | 9:30 - 2:00 pm | |
| Tue., 7/18 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 am - 2:30 pm | |
| Tue., 7/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:15 am | |
| Tue., 7/18 | Miscellaneous Events | Panther Basketball Camp | - PHS Main Gym | 9:30 a.m. | 9:30 - 2:00 pm | |
| Wed., 7/19 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 am - 2:30 pm | |
| Wed., 7/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:15 am | |
| Wed., 7/19 | Miscellaneous Events | Panther Basketball Camp | - PHS Main Gym | 9:30 a.m. | 9:30 - 2:00 pm | |
| Thu., 7/20 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 am - 2:30 pm | |
| Thu., 7/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:15 am | |
| Thu., 7/20 | Miscellaneous Events | Panther Basketball Camp | - PHS Main Gym | 9:30 a.m. | 9:30 - 2:00 pm | |
| Mon., 7/31 | Miscellaneous Events | Middle School Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 - 7:00 pm | |
| Tue., 8/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:00 a.m. | 8:00 - 10:00 am | |
| Tue., 8/1 | Miscellaneous Events | Middle School Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 - 7:00 pm | |
| Wed., 8/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:00 a.m. | 8:00 - 10:00 am | |
| Wed., 8/2 | Miscellaneous Events | Middle School Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 - 7:00 pm | |
| Thu., 8/3 | Miscellaneous Events | Youth Swim League Championships | - PHS Pool | 6:30 a.m. | 6:30 am - 5:00 pm | |
| Thu., 8/3 | Miscellaneous Events | Stby Park & Rec Swim Championships | - PHS Pool | 7:00 a.m. | 7:00 am - 5:00 pm | |
| Thu., 8/3 | Miscellaneous Events | Middle School Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 - 7:00 pm | |
| Mon., 8/21 | Miscellaneous Events | Freshmen Orientation | - PHS Main Gym | 8:00 a.m. | 8:00 am - 12:00 noon | |
| Mon., 8/21 | Miscellaneous Events | Freshmen Dance | - PHS Main Gym | 6:00 p.m. | 6:00 - 9:30 pm | |
| Wed., 8/23 | Miscellaneous Events | CPR and First Aid Class for Coaches | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 8:00 pm | |
| Thu., 8/24 | School Holidays and Closings | Teacher Convocation | ||||
| Fri., 8/25 | School Holidays and Closings | Professional Development Day | ||||
| Sun., 8/27 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 7:30 a.m. | 7:30 am - 1:00 pm | |
| Mon., 8/28 | School Holidays and Closings | Teacher Work Day | ||||
| Tue., 8/29 | School Holidays and Closings | First Day of School | ||||
| Mon., 9/4 | School Holidays and Closings | Labor Day - No School | ||||
| Wed., 9/6 | School Holidays and Closings | Open House | ||||
| Fri., 9/8 | V Football | Newtown | Home - Sports Complex & Track [Directions] | L 0-27 | ||
| Fri., 9/8 | V Boys Soccer | Stratford | Home - Sports Complex & Track [Directions] | W 3-0 | ||
| Fri., 9/8 | JV Boys Soccer | Stratford | Home - PHS Soccer Field [Directions] | 3:30 p.m. | ||
| Fri., 9/8 | V Girls Soccer | Stratford | Away - Penders Field [Directions] | W 6-0 | 5:15 pm | |
| Fri., 9/8 | JV Girls Soccer | Stratford | Away - Penders Field [Directions] | 5:00 p.m. | 3:30 pm | |
| Fri., 9/8 | V Girls Swimming and Diving | Stratford | Away - Flood MS Pool [Directions] | 103 Pomperaug 65 Stratford 0 | 2:30 pm | |
| Fri., 9/8 | V Girls Volleyball | New Milford | Home - PHS Main Gym [Directions] | W 3-0 | Non-League | |
| Fri., 9/8 | JV Girls Volleyball | New Milford | Home - PHS Main Gym [Directions] | 4:00 p.m. | Non-League | |
| Fri., 9/8 | FR Girls Volleyball | Weston | Home - Auxiliary Gym [Directions] | 3:45 p.m. | ||
| Sat., 9/9 | JV Football | Newtown | Away - Blue and Gold Stadium [Directions] | 11:00 a.m. | 10:00 am | |
| Sat., 9/9 | FR Boys Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 9:00 a.m. | 7:45 am | |
| Sun., 9/10 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 7:30 a.m. | 7:30 am - 7:00 pm | |
| Mon., 9/11 | V Field Hockey | Bethel | Home - Sports Complex & Track [Directions] | W 3-0 | Non-League | |
| Mon., 9/11 | JV Field Hockey | Bethel | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Mon., 9/11 | FR Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 4:30 p.m. | 3:30 | |
| Mon., 9/11 | FR Girls Soccer | Weston | Away - WHS Turf Field [Directions] | 4:15 p.m. | 3:00 pm | |
| Mon., 9/11 | FR Girls Volleyball | New Fairfield | Home - Auxiliary Gym [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Boys Cross Country | Weston | Home - Sports Complex & Track [Directions] | PHS 21 Weston 39 | ||
| Tue., 9/12 | V Boys Soccer | New Fairfield | Home - Sports Complex & Track [Directions] | W 1-0 | ||
| Tue., 9/12 | JV Boys Soccer | New Fairfield | Home - PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Tue., 9/12 | V Girls Cross Country | Weston | Home - Sports Complex & Track [Directions] | PHS 15 Weston 50 | ||
| Tue., 9/12 | V Girls Soccer | New Fairfield | Away - Rebel Turf [Directions] | W 3-1 | 4:30 pm | |
| Tue., 9/12 | JV Girls Soccer | New Fairfield | Away - NFHS Komlo Field [Directions] | 4:00 p.m. | 3:00 pm | |
| Wed., 9/13 | FR Boys Soccer | Joel Barlow | Away - Field J (competition field) [Directions] | 4:00 p.m. | 2:45 | |
| Wed., 9/13 | FR Field Hockey | Brookfield | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 9/13 | V Girls Volleyball | Danbury | Home - PHS Main Gym [Directions] | L 3-2 | ||
| Wed., 9/13 | JV Girls Volleyball | Danbury | Home - PHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 9/13 | FR Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 3:30 p.m. | 2:30 | |
| Thu., 9/14 | V Boys Soccer | Bunnell | Home - Sports Complex & Track [Directions] | T 1-1 | ||
| Thu., 9/14 | JV Boys Soccer | Bunnell | Home - PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Thu., 9/14 | V Field Hockey | New Milford | Home - Sports Complex & Track [Directions] | W 2-0 | Non-League | |
| Thu., 9/14 | JV Field Hockey | New Milford | Home - Sports Complex & Track [Directions] | 3:30 p.m. | ||
| Thu., 9/14 | V Girls Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | W 4-0 | 5:30 pm | |
| Thu., 9/14 | JV Girls Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | 5:00 p.m. | 3:30 pm | |
| Thu., 9/14 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:00 p.m. | 2:00 - 3:00 pm | |
| Fri., 9/15 | V Football | Hamden | Home - Sports Complex & Track [Directions] | L 7-34 | ||
| Fri., 9/15 | FR Field Hockey | Bethel | Away - Hunt Field at Bethel HS [Directions] | 4:00 p.m. | 2:30 | |
| Fri., 9/15 | V Girls Swimming and Diving | Masuk | Home - PHS Pool [Directions] | Pomperaug 118 Masuk 67 | ||
| Fri., 9/15 | V Girls Volleyball | New Fairfield | Home - PHS Main Gym [Directions] | W 3-0 | ||
| Fri., 9/15 | JV Girls Volleyball | New Fairfield | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/15 | FR Girls Volleyball | SWC Freshmen Jamboree | Away [Directions] | Cancelled | 2:30 | @ Masuk High School |
| Sat., 9/16 | V Boys Cross Country | Wilton Invitational | Away | TBA | 7:00 am | |
| Sat., 9/16 | JV Football | Hamden | Away - HHS Turf Field #1 [Directions] | 10:30 a.m. | 8:30 am | |
| Sat., 9/16 | V Boys Soccer | Naugatuck | Away - Naugatuck HS [Directions] | W 1-0 | 5:00 pm | |
| Sat., 9/16 | JV Boys Soccer | Naugatuck | Home - Sports Complex & Track [Directions] | 3:45 p.m. | ||
| Sat., 9/16 | FR Boys Soccer | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 1:00 p.m. | 11:30 am | |
| Sat., 9/16 | V Girls Cross Country | Wilton Invitational | Away | TBA | TBA | |
| Sat., 9/16 | V Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | W 2-0 | 8:30 am share w/jv | Non-League |
| Sat., 9/16 | JV Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | 11:45 a.m. | 8:30 am share bus with varsity | |
| Sat., 9/16 | FR Girls Soccer | Masuk | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 9/16 | FR Girls Volleyball | Amity | Home - PHS Main Gym [Directions] | 12:00 p.m. | ||
| Mon., 9/18 | FR Boys Soccer | New Milford | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 9/18 | V Girls Soccer | Shelton | Home - Sports Complex & Track [Directions] | L 1-0 | ||
| Mon., 9/18 | FR Girls Soccer | Shelton | Away [Directions] | 3:45 p.m. | 3:00 pm | |
| Mon., 9/18 | V Girls Volleyball | New Milford | Away - New Milford HS [Directions] | W 3-0 | 3:45 pm share w/jv | |
| Mon., 9/18 | JV Girls Volleyball | New Milford | Away - New Milford HS [Directions] | 5:15 p.m. | 3:45 pm share w/varsity | |
| Mon., 9/18 | FR Girls Volleyball | Immaculate | Home - PHS Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | FR Football | New Milford | Away [Directions] | Cancelled | 2:15 pm | |
| Tue., 9/19 | JV Field Hockey | Immaculate | Home - Sports Complex & Track [Directions] | Cancelled | ||
| Tue., 9/19 | V Girls Swimming and Diving | Joel Barlow | Home - PHS Pool [Directions] | Pomperaug 126 Joel Barlow 59 | ||
| Wed., 9/20 | V Boys Soccer | Bethel | Away - Rourke Field [Directions] | L 6-1 | 2:15 pm share bus w/ jv | |
| Wed., 9/20 | JV Boys Soccer | Bethel | Away - Bethel MS Field [Directions] | 3:45 p.m. | 2:15 share w/varsity | |
| Wed., 9/20 | V Field Hockey | Immaculate | Home - Sports Complex & Track [Directions] | T 0-0 | ||
| Wed., 9/20 | FR Girls Soccer | Watertown | Away - Veterans Park [Directions] | 3:45 p.m. | 3:00 pm | |
| Wed., 9/20 | Miscellaneous Events | Junior Class Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 pm | |
| Thu., 9/21 | School Holidays and Closings | Rosh Hashanah - No School | ||||
| Fri., 9/22 | V Boys Cross Country | Newtown, New Fairfield, Notre Dame-Fairfield | Away - Reed School [Directions] | NHS 23 PHS 32 PHS 15 NDHS 50 PHS 19 NFHS 44 | 2:15 | |
| Fri., 9/22 | V Football | New Milford | Home - Sports Complex & Track [Directions] | W 28-26 | ||
| Fri., 9/22 | V Boys Soccer | New Milford | Home - Sports Complex & Track [Directions] | L 0-4 | ||
| Fri., 9/22 | JV Boys Soccer | New Milford | Home - PHS Soccer Field [Directions] | 3:30 p.m. | ||
| Fri., 9/22 | V Girls Cross Country | Newtown, New Fairfield, Notre Dame-Fairfield | Away [Directions] | PHS 15 NDHS 50 PHS 15 NHS 50 PHS 21 NFHS 40 | 2:15 pm | |
| Fri., 9/22 | V Girls Soccer | New Milford | Away - New Milford HS [Directions] | W 6-1 | 5:00 pm | |
| Fri., 9/22 | JV Girls Soccer | New Milford | Away - New Milford HS [Directions] | 4:30 p.m. | 2:30 pm | share w/ freshman volleyball |
| Fri., 9/22 | V Girls Swimming and Diving | New Fairfield | Home - PHS Pool [Directions] | Pomperaug 94 New Fairfield 83 | ||
| Fri., 9/22 | V Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | W 3-1 | 3:45 pm share bus w/jv | |
| Fri., 9/22 | FR Girls Volleyball | Immaculate | Away [Directions] | 3:45 p.m. | 2:30 | |
| Sat., 9/23 | V Boys Cross Country | Winding Trails Race | Away [Directions] | Cancelled | 8:00 am | |
| Sat., 9/23 | JV Football | New Milford | Away [Directions] | 11:00 a.m. | 9:00 am | |
| Sat., 9/23 | FR Boys Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | 9:00 a.m. | 8:00 am | |
| Sat., 9/23 | V Girls Cross Country | Winding Trails Race | Away [Directions] | Cancelled | TBA | |
| Sat., 9/23 | V Field Hockey | Masuk | Home - Sports Complex & Track [Directions] | W 7-0 | ||
| Sat., 9/23 | JV Field Hockey | Masuk | Home - Sports Complex & Track [Directions] | 10:30 a.m. | ||
| Sat., 9/23 | FR Field Hockey | Newtown | Home - PHS Baseball Field [Directions] | 9:00 a.m. | ||
| Sun., 9/24 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 7:30 a.m. | 7:30 am - 7:00 pm | |
| Mon., 9/25 | V Boys Soccer | Brookfield | Away - BHS Stadium Field [Directions] | T 2-2 | 2:30 pm share bus w/jv | |
| Mon., 9/25 | JV Boys Soccer | Brookfield | Away - BHS Stadium Field [Directions] | 4:00 p.m. | 2:30 share w/varsity | |
| Mon., 9/25 | FR Boys Soccer | Naugatuck | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 9/25 | V Field Hockey | New Milford | Away - New Milford HS [Directions] | W 2-0 | 3:45 share w/jv | |
| Mon., 9/25 | JV Field Hockey | New Milford | Away - New Milford HS [Directions] | 5:30 p.m. | 3:45 share w/ varsity | |
| Mon., 9/25 | V Girls Soccer | Brookfield | Home - Sports Complex & Track [Directions] | W 2-0 | ||
| Mon., 9/25 | JV Girls Soccer | Brookfield | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Mon., 9/25 | FR Girls Soccer | Naugatuck | Home - Sports Complex & Track [Directions] | 3:30 p.m. | ||
| Mon., 9/25 | V Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | W 3-2 | ||
| Mon., 9/25 | JV Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 4:00 p.m. | 2:45 pm share w/varsity | |
| Mon., 9/25 | FR Girls Volleyball | New Milford | Away - New Milford HS [Directions] | 3:45 p.m. | 2:30 | |
| Tue., 9/26 | V Boys Cross Country | Bunnell, Joel Barlow, Bethel | Home - Sports Complex & Track [Directions] | PHS 15 Barlow 48 PHS 15 Bethel 46 PHS 15 Bunnell 50 | ||
| Tue., 9/26 | V Girls Cross Country | Bunnell, Joel Barlow, Bethel | Home - Sports Complex & Track [Directions] | PHS 15 Bunnell 50 PHS 15 Barlow 48 PHS 15 Bethel 49 | ||
| Tue., 9/26 | V Girls Swimming and Diving | New Milford | Home - Pomperaug HS [Directions] | Pomperaug 96 New milford 78 | ||
| Wed., 9/27 | V Field Hockey | Weston | Away - WHS Turf Field [Directions] | T 0-0 | 3:15 pm share w/jv | |
| Wed., 9/27 | JV Field Hockey | Weston | Away - WHS Turf Field [Directions] | 5:00 p.m. | 3:15 share w/ varsity | |
| Wed., 9/27 | V Girls Volleyball | Stratford | Home - PHS Main Gym [Directions] | L 3-2 | ||
| Wed., 9/27 | JV Girls Volleyball | Stratford | Home - PHS Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 9/27 | FR Girls Volleyball | Brookfield | Home - PHS Main Gym [Directions] | 3:45 p.m. | ||
| Thu., 9/28 | V Boys Soccer | Masuk | Home - Sports Complex & Track [Directions] | L 0-7 | ||
| Thu., 9/28 | JV Boys Soccer | Masuk | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Thu., 9/28 | V Girls Soccer | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | L 3-2 | 5:00 pm | |
| Thu., 9/28 | JV Girls Soccer | Masuk | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | 4:00 p.m. | 3:00 pm | |
| Thu., 9/28 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:00 p.m. | 2:00 - 3:00 pm | |
| Mon., 10/2 | FR Girls Soccer | Weston | Home - PHS Soccer Field [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | V Girls Volleyball | Joel Barlow | Away - JBHS Lower Gym [Directions] | L 3-0 | 2:15 pm share bus w/jv | |
| Mon., 10/2 | JV Girls Volleyball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 4:00 p.m. | 2:15 pm share w/varsity | |
| Mon., 10/2 | FR Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:45 p.m. | 2:30 | |
| Tue., 10/3 | V Boys Cross Country | Masuk, Kolbe Cathedral, New Milford | Away [Directions] | PHS 28 NMHS 30 PHS 15 Masuk 48 PHS 15 KHS 50 | 2:15 pm | |
| Tue., 10/3 | V Boys Soccer | Weston | Away - WHS Turf Field [Directions] | W 2-1 | 3:30 share bus w/ jv | |
| Tue., 10/3 | JV Boys Soccer | Weston | Away - WHS Turf Field [Directions] | 5:00 p.m. | 3:30 share w/varsity | |
| Tue., 10/3 | V Girls Cross Country | Masuk, Kolbe Cathedral, New Milford | Away [Directions] | PHS 15 Masuk 50 PHS 15 Kolbe 50 PHS 15 NMHS 50 | 2:15 pm | |
| Tue., 10/3 | V Field Hockey | Joel Barlow | Home - Sports Complex & Track [Directions] | W 2-1 | ||
| Tue., 10/3 | JV Field Hockey | Joel Barlow | Home - Sports Complex & Track [Directions] | 3:30 p.m. | ||
| Tue., 10/3 | V Girls Soccer | Weston | Home - Sports Complex & Track [Directions] | W 2-1 | ||
| Tue., 10/3 | JV Girls Soccer | Weston | Home - PHS Soccer Field [Directions] | 4:30 p.m. | ||
| Tue., 10/3 | V Girls Swimming and Diving | Brookfield | Home - PHS Pool [Directions] | Pomperaug 93 Brookfield 93 | $4 Adults, $3 Students | |
| Wed., 10/4 | FR Football | Naugatuck | Home - Sports Complex & Track [Directions] | Cancelled | ||
| Wed., 10/4 | V Girls Volleyball | Weston | Home - PHS Main Gym [Directions] | W 3-1 | ||
| Wed., 10/4 | JV Girls Volleyball | Weston | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | FR Girls Volleyball | New Fairfield | Away [Directions] | 3:45 p.m. | 2:30 | |
| Thu., 10/5 | V Boys Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | L 0-1 | 5:30 | |
| Thu., 10/5 | JV Boys Soccer | Newtown | Away - Treadwell Town Park--Tilson Field [Directions] | 4:00 p.m. | 2:45 share w/varsity | |
| Thu., 10/5 | V Field Hockey | New Fairfield | Home - Sports Complex & Track [Directions] | W 6-0 | ||
| Thu., 10/5 | JV Field Hockey | New Fairfield | Home - Sports Complex & Track [Directions] | 5:30 p.m. | ||
| Thu., 10/5 | V Girls Soccer | Newtown | Home - Sports Complex & Track [Directions] | L 0-3 | ||
| Thu., 10/5 | JV Girls Soccer | Newtown | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/5 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:00 p.m. | 2:00 - 3:00 pm | |
| Fri., 10/6 | V Football | Weston | Away - WHS Stadium Field [Directions] | L 3-29 | 5:00 pm 2 buses | |
| Fri., 10/6 | FR Boys Soccer | Masuk | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/6 | FR Field Hockey | Masuk | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 10/6 | FR Girls Soccer | Masuk | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | 3:45 p.m. | 3:00 pm | |
| Fri., 10/6 | V Girls Swimming and Diving | Newtown | Away - Newtown HS Pool [Directions] | Pomperaug 95 Newtown 91 | 4:45 pm | |
| Fri., 10/6 | V Girls Volleyball | Bunnell | Home - PHS Main Gym [Directions] | W 3-0 | ||
| Fri., 10/6 | JV Girls Volleyball | Bunnell | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | FR Girls Volleyball | Newtown | Home - Auxiliary Gym [Directions] | 3:45 p.m. | ||
| Fri., 10/6 | School Holidays and Closings | Professional Development Day | ||||
| Sat., 10/7 | JV Football | Weston | Home - Sports Complex & Track [Directions] | 11:00 a.m. | Froshmore Game | |
| Sat., 10/7 | V Field Hockey | Haddam-Killingworth | Home - Sports Complex & Track [Directions] | W 5-1 | 7:00 pm | |
| Sat., 10/7 | JV Field Hockey | Haddam-Killingworth | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Sat., 10/7 | FR Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | 10:00 a.m. | 8:30 | |
| Sun., 10/8 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 7:30 a.m. | 7:30 am - 5:00 pm | |
| Mon., 10/9 | V Field Hockey | Greenwich | Home - Sports Complex & Track [Directions] | L 1-6 | ||
| Mon., 10/9 | V Girls Soccer | Bethel | Home - Sports Complex & Track [Directions] | W 1-0 | ||
| Mon., 10/9 | JV Girls Soccer | Bethel | Home - PHS Soccer Field [Directions] | Cancelled | ||
| Mon., 10/9 | School Holidays and Closings | Columbus Day - No School | ||||
| Tue., 10/10 | V Boys Soccer | Immaculate | Home - Sports Complex & Track [Directions] | W 4-3 | ||
| Tue., 10/10 | JV Boys Soccer | Immaculate | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Field Hockey | Bethel | Away - Hunt Field at Bethel HS [Directions] | W 5-0 | 3:45 share w/ JV | |
| Tue., 10/10 | JV Field Hockey | Bethel | Away - Hunt Field at Bethel HS [Directions] | 5:15 p.m. | 3:45 share w/ varsity | |
| Tue., 10/10 | V Girls Soccer | Immaculate | Away - Mustang Valley [Directions] | L 3-1 | 2:30 pm share bus w/ jv | |
| Tue., 10/10 | JV Girls Soccer | Immaculate | Away - Immaculate HS [Directions] | 4:00 p.m. | 2:30 share bus w/varsity | |
| Tue., 10/10 | V Girls Swimming and Diving | Weston | Home - PHS Pool [Directions] | Pomperaug 81 Weston 101 | $4 Adults, $3 Students | |
| Tue., 10/10 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | W 3-1 | 2:45 pm share bus w/jv | |
| Tue., 10/10 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 4:00 p.m. | 2:45 pm share w/varsity | |
| Tue., 10/10 | FR Girls Volleyball | Amity | Away - Paul D. Mengold Gym at Amity HS [Directions] | 4:00 p.m. | 2:30 | |
| Wed., 10/11 | V Boys Cross Country | Brookfield, Immaculate, Stratford | Away - BHS Track [Directions] | PHS 21 Brookfield 34 PHS 15 Stratford 50 PHS 25 Immaculate 30 | 2:15 pm | |
| Wed., 10/11 | V Girls Cross Country | Brookfield, Immaculate, Stratford | Away - BHS Track [Directions] | PHS 15 Stratford 50 PHS 17 Brookfield 46 PHS 24 Immaculate 33 | 2:15 pm | |
| Wed., 10/11 | FR Girls Soccer | New Milford | Home - PHS Soccer Field [Directions] | 3:30 p.m. | ||
| Wed., 10/11 | V Girls Volleyball | Bethel | Away - Bethel HS [Directions] | W 3-0 | 2:30 pm share bus w/jv | |
| Wed., 10/11 | JV Girls Volleyball | Bethel | Away - Bethel HS [Directions] | 4:00 p.m. | 2:30 pm share w/varsity | |
| Wed., 10/11 | FR Girls Volleyball | New Milford | Home - PHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 10/11 | Miscellaneous Events | PSAT's | - PHS Main Gym | 7:00 a.m. | 7:30 - 11:30 am | |
| Thu., 10/12 | FR Football | North Haven | Home - Sports Complex & Track [Directions] | Cancelled | ||
| Thu., 10/12 | V Boys Soccer | Kolbe Cathedral | Away - Veterans Park [Directions] | W 6-1 | 2:15 pm | |
| Thu., 10/12 | FR Field Hockey | Amity | Away - Amity HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 10/12 | V Girls Soccer | Kolbe Cathedral | Home - Sports Complex & Track [Directions] | W 10-1 | ||
| Thu., 10/12 | V Girls Volleyball | Immaculate | Home - PHS Main Gym [Directions] | W 3-0 | ||
| Thu., 10/12 | JV Girls Volleyball | Immaculate | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 10/12 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:00 p.m. | 2:00 - 3:00 pm | |
| Fri., 10/13 | V Football | North Haven | Away - Vanacore Field [Directions] | L 14-42 | 5:00 pm 2 buses | |
| Fri., 10/13 | FR Boys Soccer | New Milford | Away - New Milford HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 10/13 | FR Field Hockey | Immaculate | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 10/13 | V Girls Swimming and Diving | Bunnell | Home - PHS Pool [Directions] | Pomperaug 96 Bunnell 77 | ||
| Fri., 10/13 | FR Girls Volleyball | Masuk | Home - Auxiliary Gym [Directions] | 3:45 p.m. | ||
| Sat., 10/14 | JV Football | North Haven | Home - Sports Complex & Track [Directions] | 11:00 a.m. | ||
| Sat., 10/14 | V Boys Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | W 2-1 | 3:45 pm | |
| Sat., 10/14 | V Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | W 4-1 | 8:15 am share w/ JV | |
| Sat., 10/14 | JV Girls Soccer | Shelton | Home - Sports Complex & Track [Directions] | 1:00 p.m. | ||
| Sat., 10/14 | FR Girls Soccer | Shelton | Home - PHS Soccer Field [Directions] | 3:00 p.m. | ||
| Sun., 10/15 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 8:30 a.m. | 8:30 am - 12:30 pm | |
| Mon., 10/16 | FR Boys Soccer | Newtown | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 10/16 | FR Field Hockey | Newtown | Away - Treadwell Town Park [Directions] | 4:00 p.m. | 3:00 | share bus w/ freshman girls soccer |
| Mon., 10/16 | FR Girls Soccer | Newtown | Away - Treadwell Town Park--Tilson Field [Directions] | 3:45 p.m. | 3:00 pm | share bus w/ freshman field hockey |
| Mon., 10/16 | V Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | L 3-1 | 2:45 pm share bus w/jv | |
| Mon., 10/16 | JV Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 4:00 p.m. | 2:45 pm share w/varsity | |
| Mon., 10/16 | FR Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 3:45 p.m. | 2:30 | |
| Tue., 10/17 | V Boys Soccer | Joel Barlow | Home - Sports Complex & Track [Directions] | L 2-0 | ||
| Tue., 10/17 | JV Boys Soccer | Joel Barlow | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Field Hockey | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | W 1-0(OT) | 3:00 share w/ JV | |
| Tue., 10/17 | JV Field Hockey | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 4:15 p.m. | 3:00 share w/ varsity | |
| Tue., 10/17 | V Girls Soccer | Joel Barlow | Away - Field I (Stadium) [Directions] | W 5-2 | 2:30 pm share bus w/jv | |
| Tue., 10/17 | JV Girls Soccer | Joel Barlow | Away - Field I (Stadium) [Directions] | 5:30 p.m. | 2:30 share bus w/varsity | |
| Tue., 10/17 | V Girls Swimming and Diving | Immaculate | Away - O'Neill Center, WCSU, Danbury [Directions] | Pomperaug 100 Immaculate 81 | 2:30 pm | |
| Tue., 10/17 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:10-3:00 p.m. | ||
| Wed., 10/18 | FR Field Hockey | New Milford | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 10/18 | V Girls Volleyball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | W 3-0 | ||
| Wed., 10/18 | JV Girls Volleyball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | FR Girls Volleyball | Weston | Away - WHS Old Gymnasium [Directions] | 3:45 p.m. | 2:15 | |
| Thu., 10/19 | FR Football | Bethel | Away - DeSantis Field at Bethel HS [Directions] | Cancelled | 2:15 pm | |
| Thu., 10/19 | V Boys Soccer | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | W 3-1 | 2:15 pm | |
| Thu., 10/19 | V Girls Soccer | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | T 1-1 | ||
| Thu., 10/19 | FR Girls Soccer | Watertown | Home - Pomperaug HS [Directions] | 3:45 p.m. | ||
| Thu., 10/19 | V Girls Volleyball | Notre Dame-Fairfield | Home - Pomperaug HS [Directions] | W 3-0 | Yes | |
| Thu., 10/19 | JV Girls Volleyball | Notre Dame-Fairfield | Home - Pomperaug HS [Directions] | 4:00 p.m. | Yes | |
| Thu., 10/19 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:00 p.m. | 2:00 - 3:00 pm | |
| Thu., 10/19 | Miscellaneous Events | Girls Soccer Senior Night | - Health Classroom - Room 201 | 8:30 p.m. | ||
| Fri., 10/20 | V Football | Bethel | Home - Sports Complex & Track [Directions] | W 19-6 | ||
| Fri., 10/20 | FR Girls Volleyball | SWC Freshmen Jamboree | Home - PHS Main Gym [Directions] | 3:30 p.m. | Main gym and Auxiliary Gym | |
| Sat., 10/21 | JV Football | Bethel | Away - Bethel HS [Directions] | 11:00 a.m. | 9:30 am | Froshmore game |
| Sat., 10/21 | FR Boys Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 9:00 a.m. | 8:00 am | |
| Sat., 10/21 | Miscellaneous Events | Homecoming Dance | - Cafeteria | 7:00 p.m. | 7:00 - 10:00 pm | |
| Sun., 10/22 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 10:00 a.m. | 10:00 am - 5:00 pm | |
| Mon., 10/23 | V Boys Soccer | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | L 0-5 | 3:15 pm share w/jv | Non-League |
| Mon., 10/23 | JV Boys Soccer | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 5:00 p.m. | 3:15 share w/varsity | |
| Mon., 10/23 | V Field Hockey | Wamogo | Home - Sports Complex & Track [Directions] | W 9-1 | ||
| Mon., 10/23 | JV Field Hockey | Wamogo | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Mon., 10/23 | V Girls Volleyball | Bethel | Home - PHS Main Gym [Directions] | W 3-0 | Non-League | |
| Mon., 10/23 | JV Girls Volleyball | Bethel | Home - PHS Main Gym [Directions] | 4:00 p.m. | Non-League | |
| Tue., 10/24 | FR Boys Soccer | Joel Barlow | Home - PHS Soccer Field [Directions] | Cancelled | ||
| Tue., 10/24 | Miscellaneous Events | Unified Soccer | Home - Auxiliary Gym [Directions] | 2:30 p.m. | ||
| Wed., 10/25 | V Field Hockey | Newtown | Home - Sports Complex & Track [Directions] | W 2-1 | ||
| Wed., 10/25 | JV Field Hockey | Newtown | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Wed., 10/25 | V Girls Swimming and Diving | SWC Diving Championships | Away | 5:30 p.m. | 3:15 | @ New Fairfield |
| Wed., 10/25 | V Girls Volleyball | Southington | Away - West Gym [Directions] | L 3-0 | 3:30 pm share bus w/jv | |
| Wed., 10/25 | JV Girls Volleyball | Southington | Away - West Gym [Directions] | 5:00 p.m. | 3:30 pm share bus w/varsity | |
| Wed., 10/25 | FR Girls Volleyball | Southington | Away - East Gym [Directions] | 5:00 p.m. | 3:15 pm | |
| Wed., 10/25 | Miscellaneous Events | Red Cross Blood Drive | - Auxiliary Gym | 6:30 a.m. | 6:30 am - 2:00 pm | |
| Thu., 10/26 | V Boys Cross Country | Danbury Freshmen Invitational | Away | 4:30 p.m. | 2:30 pm | |
| Thu., 10/26 | FR Football | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 6:45 p.m. | 5:00 pm | Froshmore game |
| Thu., 10/26 | FR Boys Soccer | New Milford | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/26 | V Girls Cross Country | Danbury Freshmen Race | Away | 4:30 p.m. | 2:30 pm | |
| Thu., 10/26 | FR Girls Soccer | New Milford | Away [Directions] | 3:45 p.m. | 3:00 pm | |
| Fri., 10/27 | V Football | Masuk | Home - Sports Complex & Track [Directions] | L 6-54 | ||
| Sat., 10/28 | JV Football | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | Cancelled | Yes | |
| Sat., 10/28 | Miscellaneous Events | SWC Field Hockey Quarterfinals | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Sat., 10/28 | Miscellaneous Events | SWC Field Hockey Quarterfinals | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Sun., 10/29 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 10:00 a.m. | 10:00 am - 2:00 pm | |
| Tue., 10/31 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Thu., 11/2 | FR Football | Bunnell | Home - Sports Complex & Track [Directions] | 4:00 p.m. | Froshmore Game | |
| Fri., 11/3 | V Football | Bunnell | Away - Bunnell Turf Field [Directions] | L 15-41 | 5:00 pm 2 buses | |
| Fri., 11/3 | Miscellaneous Events | Winter Cheerleading tryouts | - Auxiliary Gym | 2:30-5:00 p.m. | ||
| Sat., 11/4 | JV Football | Bunnell | Home - Sports Complex & Track [Directions] | Cancelled | ||
| Sat., 11/4 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 11:00 a.m. | 11:00 am - 1:00 pm | |
| Sun., 11/5 | Miscellaneous Events | Nonnewaug Field Hockey practice | - Sports Complex & Track | 8:00 a.m. | ||
| Sun., 11/5 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 12:00 p.m. | 12:00 - 1:00 pm | |
| Mon., 11/6 | Miscellaneous Events | Cheerleading Practice | - Auxiliary Gym | 2:15 p.m. | ||
| Tue., 11/7 | School Holidays and Closings | Professional Development Day | ||||
| Wed., 11/8 | Miscellaneous Events | Cheerleading practice | - Auxiliary Gym | 6:00 p.m. | ||
| Thu., 11/9 | FR Football | Stratford | Home - Sports Complex & Track [Directions] | Cancelled | ||
| Fri., 11/10 | V Football | Stratford | Away - Penders Field [Directions] | L 7-20 | 5:00 pm 2 buses | |
| Fri., 11/10 | Miscellaneous Events | Turkey Tumble Set-Up | - PHS Main Gym | 3:00 p.m. | 3:00 - 10:00 pm | |
| Sat., 11/11 | JV Football | Stratford | Home - Sports Complex & Track [Directions] | 11:00 a.m. | Froshmore Game | |
| Sat., 11/11 | Miscellaneous Events | Turkey Tumble Gymnastics | - PHS Main Gym | 6:30 a.m. | 6:30 am - 9:00 pm | |
| Sat., 11/11 | Miscellaneous Events | Ring Dance | - Pomperaug HS | 6:00 p.m. | ||
| Sun., 11/12 | Miscellaneous Events | Turkey Tumble Gymnastics | - PHS Main Gym | 7:00 a.m. | 7:00 am - 6:00 pm | |
| Mon., 11/13 | Miscellaneous Events | Baseball Preseason Meeting | - Health Classroom - Room 201 | 6:30 p.m. | 6:30 - 7:30 pm | |
| Wed., 11/15 | Miscellaneous Events | Pre-season conditioning | - PHS Main Gym | 2:30-4:00 p.m. | ||
| Fri., 11/17 | FR Football | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | 4:00 p.m. | Froshmore Game | |
| Fri., 11/17 | Miscellaneous Events | Pre-season conditioning | - PHS Main Gym | 2:30-4:00 p.m. | ||
| Sat., 11/18 | Miscellaneous Events | Senior Semi-Formal | 6:00 p.m. | |||
| Mon., 11/20 | Miscellaneous Events | Cheerleading practice | - Auxiliary Gym | 2:15 p.m. | ||
| Mon., 11/20 | Miscellaneous Events | CPR and 1st Aid Class | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 8:00 pm | |
| Mon., 11/20 | Miscellaneous Events | Pre-season conditioning | - PHS Main Gym | 6:30-8:00 p.m. | ||
| Tue., 11/21 | Miscellaneous Events | Pre-season conditioning | - PHS Main Gym | 6:30-8:00 p.m. | ||
| Wed., 11/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 11:30 a.m. | 11:30 am - 3:00 pm | |
| Wed., 11/22 | School Holidays and Closings | Early Dismissal | ||||
| Thu., 11/23 | V Football | Notre Dame-Fairfield | Away - McCarty Stadium at Notre Dame [Directions] | W 13-12 | 8:00 am 2 buses | |
| Thu., 11/23 | School Holidays and Closings | Thanksgiving Day | ||||
| Fri., 11/24 | School Holidays and Closings | Thanksgiving Recess - No School | ||||
| Mon., 11/27 | Miscellaneous Events | Cheerleading practice | - Auxiliary Gym | 2:15 p.m. | ||
| Thu., 11/30 | Miscellaneous Events | Health Department Meeting | - Health Classroom - Room 201 | 3:15 p.m. | 3:15 - 4:15 pm | |
| Fri., 12/1 | Miscellaneous Events | Pop Warner Cheerleaders Meeting | - Health Classroom - Room 201 | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 12/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 pm | |
| Fri., 12/1 | Miscellaneous Events | Middlebury Park & Rec Travel Bball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 12/4 | Miscellaneous Events | Pop Warner Cheerleaders Meeting | - Health Classroom - Room 201 | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 12/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 pm | |
| Mon., 12/4 | Miscellaneous Events | Middlebury Park & Rec Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/5 | Miscellaneous Events | Park & Rec CPR Training | - Health Classroom - Room 201 | 2:30 p.m. | 2:30 - 4:40 pm | |
| Tue., 12/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 pm | |
| Tue., 12/5 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Wed., 12/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 pm | |
| Thu., 12/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 pm | |
| Thu., 12/7 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Fri., 12/8 | School Holidays and Closings | 1/2 Professional Development Day | ||||
| Mon., 12/11 | V Girls Basketball | St. Joseph | Home - PHS Main Gym [Directions] | W 58-36 | SWC - FCIAC Challenge $% Adult and $3 Student Admission | |
| Mon., 12/11 | Miscellaneous Events | SWC-FCIAC Challenge-Girls Basketball | Home - PHS Main Gym [Directions] | 5:00 p.m. | Danbury vs Newtown | |
| Mon., 12/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 pm | |
| Mon., 12/11 | Miscellaneous Events | Middlebury Park & Rec Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 pm | |
| Tue., 12/12 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Tue., 12/12 | Miscellaneous Events | Southbury Park & Rec High School Bball Tryouts | - PHS Main Gym | 7:00 p.m. | 7:00 - 10:00 pm | |
| Wed., 12/13 | V Wrestling | New Fairfield | Home - Auxiliary Gym [Directions] | New Fairfield 21, Pomperaug 57 | ||
| Wed., 12/13 | JV Wrestling | New Fairfield | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/13 | V Girls Basketball | Danbury | Home - PHS Main Gym [Directions] | W 62-44 | SWC - FCIAC Challenge $5 Adult and $3 Student Admission | |
| Wed., 12/13 | Miscellaneous Events | SWC-FCIAC Challenge-Girls Basketball | Home - PHS Main Gym [Directions] | 5:00 p.m. | St. Joe's vs Newtown | |
| Wed., 12/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 pm | |
| Thu., 12/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 pm | |
| Thu., 12/14 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Thu., 12/14 | Miscellaneous Events | Stby Park & Rec Youth Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 12/15 | Miscellaneous Events | Wrestling Parents Set Up Refreshments | - Health Classroom - Room 201 | 5:30 p.m. | ||
| Sat., 12/16 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | W 9-1 | ||
| Sat., 12/16 | V Wrestling | Pomperaug Holiday Invitational | Home - PHS Main Gym [Directions] | 9:00 a.m. | $5 Adult & $3 Student Admission | |
| Sat., 12/16 | JV Wrestling | Pomperaug Holiday Invitational | Home - PHS Main Gym [Directions] | 9:00 a.m. | ||
| Mon., 12/18 | V Girls Basketball | New Fairfield | Home - PHS Main Gym [Directions] | W 46-27 | Non-League $5 Adult and $3 Student Admission | |
| Mon., 12/18 | JV Girls Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/18 | FR Girls Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 12/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 pm | |
| Mon., 12/18 | Miscellaneous Events | Middlebury Park & Rec Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/19 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Away - Weston MS Pool [Directions] | 6:30 p.m. | 4:30 | |
| Tue., 12/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 pm | |
| Tue., 12/19 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Tue., 12/19 | Miscellaneous Events | Southbury Park & Rec High School Bball Tryouts | - PHS Main Gym | 7:00 p.m. | 7:00 - 10:00 pm | |
| Wed., 12/20 | V Boys Basketball | Wilton | Home - PHS Main Gym [Directions] | W 51-49 OT | Non-league, $5 Adult & $3 Student Admission | |
| Wed., 12/20 | JV Boys Basketball | Wilton | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/20 | FR Boys Basketball | Wilton | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 12/20 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Away - Enfield Twin Rinks [Directions] | W 7-2 | ||
| Wed., 12/20 | V Wrestling | Masuk | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/20 | V Girls Basketball | Cromwell | Away [Directions] | W 51-48 | 4:00 | 3's for Charity Tournament-Newtown, $5 Adult and $3 Student Admission |
| Wed., 12/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 pm | |
| Thu., 12/21 | V Girls Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | W 47-35 | 5:00 pm | Newtown or Hillhouse |
| Thu., 12/21 | FR Girls Basketball | Danbury | Home - PHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 pm | |
| Thu., 12/21 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Thu., 12/21 | Miscellaneous Events | Stby Park & Rec Travel Bball Practice | 7:00 p.m. | 7:00 - 9:00 pm | ||
| Fri., 12/22 | Miscellaneous Events | Middlebury Park & Rec Travel Bball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 12/23 | V Boys Basketball | Wilby | Home - PHS Main Gym [Directions] | W 61-56 | Non-league,$5 Adult & $3 Student Admission | |
| Sat., 12/23 | JV Boys Basketball | Wilby | Home - PHS Main Gym [Directions] | 12:45 p.m. | ||
| Sat., 12/23 | FR Boys Basketball | Wilby | Home - PHS Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 12/23 | V Boys Ice Hockey | East Haven Coop | Home - Taft-Mays Rink [Directions] | T 1-1(OT) | ||
| Sat., 12/23 | V Wrestling | Frank Chaves Farmington Valley Invitational | Away [Directions] | 9:00 a.m. | 6:30 am | |
| Sat., 12/23 | JV Wrestling | Frank Chaves Farmington Valley Invitational | Away [Directions] | 9:00 a.m. | Yes | |
| Mon., 12/25 | School Holidays and Closings | Christmas Day | ||||
| Tue., 12/26 | V Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | W 60-57 | 4:00 pm share w/jv | Non-league |
| Tue., 12/26 | JV Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 5:30 p.m. | 4:00 pm share bus w/varsity | |
| Tue., 12/26 | School Holidays and Closings | Winter Recess - No School | ||||
| Wed., 12/27 | V Boys Basketball | Avon | Away - Nonnewaug HS Gym [Directions] | W 57-53 | 5:30 | Non-league (Home team)Nonnewaug Tournament |
| Wed., 12/27 | JV Girls Basketball | Capital Prep | Away [Directions] | Cancelled | 10:30 | |
| Wed., 12/27 | School Holidays and Closings | Winter Recess - No School | ||||
| Thu., 12/28 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | W 4-1 | ||
| Thu., 12/28 | School Holidays and Closings | Winter Recess - No School | ||||
| Fri., 12/29 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | W 79-68 | 5:30 | Non-league |
| Fri., 12/29 | FR Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 1:30 p.m. | 12:15 pm | |
| Fri., 12/29 | FR Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 3:00 p.m. | 1:45 pm | |
| Fri., 12/29 | School Holidays and Closings | Winter Recess - No School | ||||
| Sat., 12/30 | V Boys Ice Hockey | North Branford | Home - Taft-Mays Rink [Directions] | W 2-0 | ||
| Sat., 12/30 | V Boys Indoor Track | Wintergreen Invitational Meet | Away | 9:00 a.m. | 7:30 am | @ Southern CT State Univ. |
| Sat., 12/30 | V Wrestling | Trumbull Tournament | Away | 9:00 a.m. | 7:00 am | |
| Sat., 12/30 | JV Wrestling | Trumbull Tournament | Away | 9:00 a.m. | 7:00 am | |
| Mon., 1/1 | School Holidays and Closings | New Year's Day | ||||
| Tue., 1/2 | V Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | W 66-56 OT | 4:00 pm share w/ JV | Non-League |
| Tue., 1/2 | JV Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/2 | FR Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 1/2 | V Girls Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | L 58-66 | $5 Adult & $3 Student Admission | |
| Tue., 1/2 | JV Girls Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/2 | FR Girls Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/2 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Tue., 1/2 | Miscellaneous Events | Stby Park & Rec Youth Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 9:45 pm | |
| Wed., 1/3 | V Boys Ice Hockey | Cheshire | Away - Wesleyan University Ice Rink [Directions] | W 1-0 | ||
| Wed., 1/3 | V Boys Indoor Track | Tournament Game - Opponent Not Known | Away | Cancelled | ||
| Wed., 1/3 | V Boys Swimming and Diving | Bethel | Away - WCSU Pool [Directions] | 5:00 p.m. | 2:30 | |
| Wed., 1/3 | V Wrestling | New Milford | Away - New Milford HS [Directions] | 6:00 p.m. | 4:30 pm | |
| Wed., 1/3 | JV Wrestling | New Milford | Away - New Milford HS [Directions] | 6:00 p.m. | 4:30 pm | |
| Wed., 1/3 | V Co-ed Alpine Skiing | Race Day | Away | 3:00 p.m. | 2:20 pm | Mt. Southington |
| Thu., 1/4 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Thu., 1/4 | Miscellaneous Events | Stby Park & Rec Youth Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 9:45 pm | |
| Fri., 1/5 | Miscellaneous Events | Middlebury Park & Rec Travel Bball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 1/6 | V Boys Basketball | Amity | Away - Paul D. Mengold Gym at Amity HS [Directions] | L 47-64 | 4:00 pm share w/ | Non-league |
| Sat., 1/6 | JV Boys Basketball | Amity | Away - Paul D. Mengold Gym at Amity HS [Directions] | 5:15 p.m. | ||
| Sat., 1/6 | V Boys Ice Hockey | Farmington Valley Generals | Home - Taft-Mays Rink [Directions] | L 2-5 | ||
| Sat., 1/6 | V Boys Indoor Track | SWC Developmental | Away | 8:00 a.m. | 7:00 am | @ Wesleyan Univ. |
| Sat., 1/6 | V Wrestling | Bristol Central Invitational | Away | 9:00 a.m. | 7:00 am | |
| Sat., 1/6 | JV Wrestling | Bristol Eastern Tournament | Away | 9:30 a.m. | 7:00 | |
| Sat., 1/6 | V Girls Basketball | Bethel | Away - Bethel HS [Directions] | W 68-56 | 1:00 pm | |
| Sat., 1/6 | JV Girls Basketball | Bethel | Away - Bethel HS [Directions] | 2:15 p.m. | 1:00 pm | |
| Sat., 1/6 | V Girls Gymnastics | Pomperaug Invitational | Home - PHS Main Gym [Directions] | 129.1 | $5 Adult & $3 Student Admission | |
| Sat., 1/6 | Miscellaneous Events | Stby Park & Rec Youth Bball | - Auxiliary Gym | 12:45 p.m. | 12:45 - 9:00 pm | |
| Sun., 1/7 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 1/7 | Miscellaneous Events | Stby Park & Rec Youth Bball | - PHS Main Gym | 1:15 p.m. | 1:15 - 9:00 pm | |
| Mon., 1/8 | Miscellaneous Events | PHS Parent Softball Association | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 1/8 | Miscellaneous Events | Middlebury Park & Rec Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/9 | V Boys Basketball | Bunnell | Home - PHS Main Gym [Directions] | W 84-68 | $5 Adult & $3 Student Admission | |
| Tue., 1/9 | JV Boys Basketball | Bunnell | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/9 | FR Boys Basketball | Bunnell | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/9 | V Boys Swimming and Diving | Bunnell-Stratford | Home - PHS Pool [Directions] | 4:30 p.m. | ||
| Tue., 1/9 | V Girls Basketball | Bunnell | Away - Bunnell [Directions] | W 73-53 | 4:00 | |
| Tue., 1/9 | JV Girls Basketball | Bunnell | Away - Bunnell [Directions] | 5:15 p.m. | ||
| Tue., 1/9 | V Girls Gymnastics | Jonathan Law, Joel Barlow, Nonnewaug | Away - Jonathan Law HS Old Gym [Directions] | 127.95 | ||
| Tue., 1/9 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Tue., 1/9 | Miscellaneous Events | Lacrosse Parents Meeting | - Health Classroom - Room 201 | 6:00-7:00 p.m. | ||
| Wed., 1/10 | V Boys Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | 2:15 pm | @ Danbury Dome |
| Wed., 1/10 | V Wrestling | Bethel | Away - Bethel HS [Directions] | 5:30 p.m. | 4:30 pm | |
| Wed., 1/10 | V Co-ed Alpine Skiing | Race Day | Away | 3:00 p.m. | 2:20 pm | @ Mt. Southington |
| Wed., 1/10 | Miscellaneous Events | Stby Park & Rec Bball Practice | - Auxiliary Gym | 7:00 p.m. | ||
| Thu., 1/11 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Thu., 1/11 | Miscellaneous Events | Stby Park & Rec Bball Practice | - Auxiliary Gym | 7:00 p.m. | ||
| Fri., 1/12 | V Boys Basketball | Immaculate | Away - Immaculate HS [Directions] | L 41-47 | 4:00 pm share w/ JV | |
| Fri., 1/12 | JV Boys Basketball | Immaculate | Away - Immaculate HS [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | FR Boys Basketball | Immaculate | Away - Immaculate HS [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 1/12 | V Boys Swimming and Diving | Brookfield | Home - PHS Pool [Directions] | 7:00 p.m. | $5 Adult and $3 Student Admission | |
| Fri., 1/12 | JV Wrestling | JV Development Night | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Girls Basketball | Immaculate | Home - PHS Main Gym [Directions] | W 58-43 | $5 Adult & $3 Student Admission | |
| Fri., 1/12 | JV Girls Basketball | Immaculate | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | FR Girls Basketball | Immaculate | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/12 | Miscellaneous Events | Middlebury Park & Rec Travel Bball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 1/13 | V Boys Indoor Track | SCC Meet | Away | Cancelled | TBA | |
| Sat., 1/13 | V Wrestling | Colter Abely Mid Season Classic | Away [Directions] | Cancelled | 7:00 am | Mercy |
| Sat., 1/13 | JV Wrestling | Colter Abely Mid Season Classic | Away [Directions] | 9:00 a.m. | 7:00 am | Mercy |
| Sat., 1/13 | Miscellaneous Events | Civil Air Patrol - Water Saves | - PHS Pool | 12:00 p.m. | 12:00 - 2:00 pm | |
| Sat., 1/13 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sun., 1/14 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 1/14 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Mon., 1/15 | V Boys Ice Hockey | Trinity Catholic | Home - Taft-Mays Rink [Directions] | W 302 | ||
| Mon., 1/15 | V Boys Indoor Track | Wesleyan SWC Development Meet # 2 | Away | 9:00 a.m. | 7:30 am | |
| Mon., 1/15 | V Girls Gymnastics | Fairfield Ludlowe, Trumbull, Nonnewaug, Fairfield Warde | Away - Gymnastics & Cheer Academy [Directions] | 126.9 | ||
| Mon., 1/15 | V Girls Indoor Track | Wesleyan SWC Development Meet #2 | Away | 9:00 a.m. | 7:30 am share w/boys | |
| Mon., 1/15 | School Holidays and Closings | Martin Luther King Day - No School | ||||
| Tue., 1/16 | V Boys Basketball | New Fairfield | Home - PHS Main Gym [Directions] | W 66-47 | $5 Adult & $3 Student Admission | |
| Tue., 1/16 | JV Boys Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/16 | FR Boys Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/16 | V Boys Swimming and Diving | Masuk | Away - Masuk Pool [Directions] | 4:00 p.m. | 2:15 | |
| Tue., 1/16 | V Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | W 71-37 | 4:00 | |
| Tue., 1/16 | JV Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/16 | FR Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | 3:30 p.m. | 2:15 | |
| Tue., 1/16 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Wed., 1/17 | JV Wrestling | Newtown | Away [Directions] | Cancelled | 4:45 pm | |
| Wed., 1/17 | Miscellaneous Events | Middlebury Travel Bball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 1/18 | V Wrestling | Newtown | Away - Newtown HS Gymnasium [Directions] | 7:00 p.m. | 5:15 pm | |
| Thu., 1/18 | Miscellaneous Events | Football Team Meeting | - Health Classroom - Room 201 | 3:00 p.m. | 3:00 - 3:30 pm | |
| Thu., 1/18 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Fri., 1/19 | V Boys Indoor Track | Yale Interscholastic Track Classic | Away | TBA | 11:45 am | |
| Fri., 1/19 | JV Wrestling | JV Development Night | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Stratford | Home - PHS Main Gym [Directions] | W 77-40 | $5 Adult & $3 Student Admission | |
| Fri., 1/19 | JV Girls Basketball | Stratford | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/19 | FR Girls Basketball | Weston | Away - WHS Gymnasium [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 1/19 | Miscellaneous Events | Middlebury Park & Rec Travel Bball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Fri., 1/19 | Miscellaneous Events | Kinetic Kids Invitational Set Up | - PHS Main Gym | 9:00 p.m. | 8:00 - 10:00 pm | |
| Sat., 1/20 | V Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | L 54-62 | 10:15 am share w/ JV | |
| Sat., 1/20 | JV Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 11:30 a.m. | ||
| Sat., 1/20 | V Boys Ice Hockey | Branford | Home - Taft-Mays Rink [Directions] | W 6-1 | ||
| Sat., 1/20 | V Boys Indoor Track | Yale Interscholastic Track Classic | Away | 10:00 a.m. | 8:30 am | |
| Sat., 1/20 | V Wrestling | Granby Memorial, East Lyme/Norwich Tech, New Britain, New Haven Wrestling | Away - Granby Memorial HS [Directions] | 10:00 a.m. | 6:45 am | weigh ins @ 9:00 am |
| Sat., 1/20 | JV Wrestling | Granby Memorial | Away [Directions] | Cancelled | 7:30 am | weigh ins @ 9:00 am |
| Sat., 1/20 | FR Girls Basketball | St. Paul Catholic | Home - Auxiliary Gym [Directions] | 9:30 a.m. | ||
| Sat., 1/20 | Miscellaneous Events | Kinetic Kids Invitational | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sat., 1/20 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sun., 1/21 | Miscellaneous Events | Kinetic Kids Invitational | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sun., 1/21 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 1/21 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Mon., 1/22 | V Boys Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | W 81-56 | $5 Adult & $3 Student Admission | |
| Mon., 1/22 | JV Boys Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/22 | FR Boys Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 1/22 | V Girls Basketball | Joel Barlow | Away - JBHS Lower Gym [Directions] | W 65-48 | 3:45 | |
| Mon., 1/22 | JV Girls Basketball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/22 | FR Girls Basketball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 3:30 p.m. | 2:15 | |
| Mon., 1/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 1/22 | Miscellaneous Events | PHS Parent Softball Association | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 1/22 | Miscellaneous Events | Middlebury Park & Rec Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/23 | V Girls Gymnastics | New Milford, Joel Barlow, Nonnewaug | Home - Auxiliary Gym [Directions] | 129.5 | ||
| Tue., 1/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/23 | Miscellaneous Events | Boys Swim Team & Parents Meeting | - Health Classroom - Room 201 | 6:00 p.m. | 6:00 - 7:00 pm | |
| Tue., 1/23 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Wed., 1/24 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | W 5-1 | ||
| Wed., 1/24 | V Boys Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | 2:15 pm | @ Danbury Dome |
| Wed., 1/24 | V Boys Swimming and Diving | Weston | Home - PHS Pool [Directions] | 6:00 p.m. | $5 Adult and $3 Student Admission | |
| Wed., 1/24 | V Wrestling | Bunnell | Home - Auxiliary Gym [Directions] | Pomp 50 Bunnell 21 | ||
| Wed., 1/24 | V Girls Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | 2:15 pm | @ Danbury Dome |
| Wed., 1/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/24 | Miscellaneous Events | Middlebury Travel Bball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 1/25 | V Co-ed Alpine Skiing | Race Day | Away | 3:00 p.m. | 2:20 pm | |
| Thu., 1/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/25 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Thu., 1/25 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Fri., 1/26 | V Boys Basketball | Masuk | Home - PHS Main Gym [Directions] | W 70-54 | $5 Adult & $3 Student Admission | |
| Fri., 1/26 | JV Boys Basketball | Masuk | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | Masuk | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/26 | V Boys Ice Hockey | New Milford | Home - Taft-Mays Rink [Directions] | W 5-2 | ||
| Fri., 1/26 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | 2:15 | |
| Fri., 1/26 | JV Wrestling | JV Development Night | Home - Auxiliary Gym [Directions] | Cancelled | ||
| Fri., 1/26 | V Girls Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | W 59-42 | 4:00 | |
| Fri., 1/26 | JV Girls Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | ||
| Fri., 1/26 | FR Girls Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:30 p.m. | 2:15 | |
| Fri., 1/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/26 | Miscellaneous Events | Middlebury Park & Rec Travel Bball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 1/27 | V Wrestling | Fairfield Ludlow Duals | Away | 8:00 a.m. | 6:40 am | |
| Sat., 1/27 | JV Wrestling | Fairfield Ludlow Duals | Away | Cancelled | 6:00 am | |
| Sat., 1/27 | V Girls Basketball | Wilton | Home - PHS Main Gym [Directions] | L 48-53 | $5 Adult & $3 Student Admission | |
| Sat., 1/27 | JV Girls Basketball | Wilton | Home - PHS Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 1/27 | FR Girls Basketball | Wilton | Home - PHS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 11:30 a.m. | 11:30 - 2:00 pm | |
| Sat., 1/27 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sun., 1/28 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 1/28 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sun., 1/28 | Miscellaneous Events | PHS Parent Softball Association | - Auxiliary Gym | 2:00 p.m. | 2:00 - 4:00 pm | |
| Mon., 1/29 | FR Boys Basketball | St. Paul Catholic | Away [Directions] | Cancelled | 2:15 pm | |
| Mon., 1/29 | Miscellaneous Events | PHS Parent Softball Association | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 1/29 | Miscellaneous Events | Middlebury Park & Rec Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/30 | V Boys Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | W 67-54 | 4:00 pm share w/ JV | |
| Tue., 1/30 | JV Boys Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | 5:15 p.m. | ||
| Tue., 1/30 | V Boys Swimming and Diving | New Fairfield | Away [Directions] | 4:00 p.m. | 2:30 | |
| Tue., 1/30 | V Girls Basketball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | L 48-47 | $5 Adult & $3 Student Admission | |
| Tue., 1/30 | JV Girls Basketball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/30 | FR Girls Basketball | Holy Cross | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/30 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Wed., 1/31 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Taft-Mays Rink [Directions] | W 5-2 | ||
| Wed., 1/31 | V Wrestling | Joel Barlow | Away - JBHS Upper Gym [Directions] | 6:00 p.m. | 4:15 pm | |
| Wed., 1/31 | V Co-ed Alpine Skiing | Race Day | Away | 3:00 p.m. | 2:20 pm | @ Mt. Southington |
| Wed., 1/31 | Miscellaneous Events | Pomperaug Youth Baseball | - Auxiliary Gym | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 1/31 | Miscellaneous Events | Middlebury Travel Bball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 2/1 | V Girls Gymnastics | New Milford, Nonnewaug | Away - New Milford HS [Directions] | 135.55 | ||
| Thu., 2/1 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Thu., 2/1 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Fri., 2/2 | V Boys Basketball | Brookfield | Home - PHS Main Gym [Directions] | W 53-44 | $5 Adult & $3 Student Admission | |
| Fri., 2/2 | JV Boys Basketball | Brookfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/2 | FR Boys Basketball | Brookfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/2 | V Wrestling | Farmington, Branford, Maloney | Away - Farmington HS [Directions] | Pomperaug: 60 Stratford: 15 | 2:30 pm | |
| Fri., 2/2 | V Girls Basketball | Brookfield | Away - BHS Big Gym [Directions] | W 70-51 | 4:00 | |
| Fri., 2/2 | JV Girls Basketball | Brookfield | Away - BHS Big Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/2 | FR Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 3:45 p.m. | 2:30 | |
| Fri., 2/2 | Miscellaneous Events | Middlebury Park & Rec Travel Bball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 2/3 | V Boys Ice Hockey | Woodstock Academy | Home - Taft-Mays Rink [Directions] | W 5-3 | ||
| Sat., 2/3 | JV Wrestling | Farmington, Branford | Away [Directions] | Cancelled | 3:00 pm | |
| Sat., 2/3 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sun., 2/4 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 2/4 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sun., 2/4 | Miscellaneous Events | PHS Parent Softball Association | - Auxiliary Gym | 2:00 p.m. | 2:00 - 4:00 pm | |
| Mon., 2/5 | V Wrestling | Stratford | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Mon., 2/5 | JV Wrestling | Stratford | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Mon., 2/5 | Miscellaneous Events | PHS Parent Softball Association | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 2/5 | Miscellaneous Events | Middlebury Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/6 | V Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | W 60-52 | 3:30 pm share w/ JV | |
| Tue., 2/6 | JV Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/6 | FR Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 2/6 | V Boys Swimming and Diving | New Milford | Home - PHS Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Weston | Home - PHS Main Gym [Directions] | W 60-50 | $5 Adult & $3 Student Admission | |
| Tue., 2/6 | JV Girls Basketball | Weston | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/6 | FR Girls Basketball | Weston | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/6 | V Girls Gymnastics | Daniel Hand, Stonington, Nonnewaug | Away - Polson Gymnastics Gym/DHHS Campus [Directions] | 121.8 | ||
| Tue., 2/6 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Wed., 2/7 | V Co-ed Alpine Skiing | Race Day | Away | 3:00 p.m. | 2:20 pm | @ Mt. Southington |
| Wed., 2/7 | Miscellaneous Events | Bowling Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 pm | |
| Wed., 2/7 | Miscellaneous Events | Pomperaug Youth Baseball | - Auxiliary Gym | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 2/7 | Miscellaneous Events | Middlebury Travel Bball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 2/8 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Thu., 2/8 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Fri., 2/9 | V Boys Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | W 67-59 | 4:15 pm share w/ JV | |
| Fri., 2/9 | JV Boys Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/9 | FR Boys Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 2/9 | V Boys Ice Hockey | Guilford | Home - Taft-Mays Rink [Directions] | L 1-2 | ||
| Fri., 2/9 | V Girls Basketball | Newtown | Home - PHS Main Gym [Directions] | L 25-61 | $5 Adult & $3 Student Admission | |
| Fri., 2/9 | JV Girls Basketball | Newtown | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/9 | FR Girls Basketball | Newtown | Home - PHS Main Gym [Directions] | Cancelled | ||
| Fri., 2/9 | Miscellaneous Events | Middlebury Park & Rec Travel Bball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 2/10 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sun., 2/11 | V Girls Basketball | New London | Away - Conway Gym [Directions] | L 33-72 | 11:00 am | |
| Sun., 2/11 | JV Girls Basketball | New London | Away - Conway Gym [Directions] | 2:00 p.m. | 11:00 am | |
| Sun., 2/11 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 2/11 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sun., 2/11 | Miscellaneous Events | PHS Parent Softball Association | - Auxiliary Gym | 2:00 p.m. | 2:00 - 4:00 pm | |
| Mon., 2/12 | Miscellaneous Events | PHS Parent Softball Association | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 2/12 | Miscellaneous Events | Middlebury Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/13 | V Boys Basketball | New Milford | Away - New Milford HS [Directions] | L 66-68 | 4:00 pm share w/ JV | |
| Tue., 2/13 | JV Boys Basketball | New Milford | Away - New Milford HS [Directions] | 5:15 p.m. | ||
| Tue., 2/13 | FR Boys Basketball | New Milford | Away - New Milford HS [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 2/13 | V Boys Swimming and Diving | Newtown | Home - PHS Pool [Directions] | 6:30 p.m. | $5 Adult and $3 Student Admission | |
| Tue., 2/13 | V Girls Basketball | New Milford | Home - PHS Main Gym [Directions] | W 57-31 | $5 Adult & $3 Student Admission | |
| Tue., 2/13 | JV Girls Basketball | New Milford | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/13 | FR Girls Basketball | New Milford | Home - PHS Main Gym [Directions] | Cancelled | ||
| Tue., 2/13 | Miscellaneous Events | Girls Basketball Senior Night | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 9:30 pm | |
| Tue., 2/13 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Wed., 2/14 | V Boys Ice Hockey | North Haven | Away - Northford Ice Pavilion [Directions] | W 4-3 | ||
| Wed., 2/14 | Miscellaneous Events | Pomperaug Youth Baseball | - Auxiliary Gym | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 2/14 | Miscellaneous Events | Middlebury Travel Bball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 2/15 | V Boys Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | L 53-85 | 3:45 pm share w/ JV | |
| Thu., 2/15 | JV Boys Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 5:15 p.m. | ||
| Thu., 2/15 | FR Boys Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | Cancelled | 2:15 pm | |
| Thu., 2/15 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Thu., 2/15 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Fri., 2/16 | V Girls Gymnastics | Newtown, Oxford, Nonnewaug, Fairfield Ludlowe | Home - Auxiliary Gym [Directions] | 129.65 | ||
| Fri., 2/16 | School Holidays and Closings | 1/2 Professional Development Day | ||||
| Fri., 2/16 | Unified Sports Basketball | Interscholastic Event | Away - Newtown Youth Academy | 3:00 p.m. | 2:15 pm | |
| Sat., 2/17 | FR Boys Basketball | St. Paul Catholic | Home - PHS Main Gym [Directions] | 10:00 a.m. | ||
| Sun., 2/18 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 2/18 | Miscellaneous Events | PHS Parent Softball Association | - Auxiliary Gym | 2:00 p.m. | 2:00 - 4:00 pm | |
| Mon., 2/19 | V Boys Ice Hockey | Woodstock Academy | Away - Jahn Hockey Rink - Pomfret School [Directions] | W 6-2 | ||
| Mon., 2/19 | JV Wrestling | Panther JV Tournament | Home - Auxiliary Gym [Directions] | 9:00 a.m. | ||
| Mon., 2/19 | V Girls Gymnastics | Newtown, Oxford, Nonnewaug | Home - Kinetic Kids [Directions] | 125.95 | ||
| Mon., 2/19 | Miscellaneous Events | JV Wrestling Tournament Refreshments | - Health Classroom - Room 201 | 6:00 a.m. | 6:00 am - 5:00 pm | |
| Mon., 2/19 | School Holidays and Closings | Presidents Day | ||||
| Tue., 2/20 | V Boys Basketball | Bethel | Home - PHS Main Gym [Directions] | W 71-39 | $5 Adult & $3 Student Admission | |
| Tue., 2/20 | JV Boys Basketball | Bethel | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/20 | FR Boys Basketball | Bethel | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/20 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Tue., 2/20 | School Holidays and Closings | February Break - No School | ||||
| Wed., 2/21 | V Boys Ice Hockey | New Fairfield | Home - Taft-Mays Rink [Directions] | L 2-4 | ||
| Wed., 2/21 | Miscellaneous Events | Pomperaug Youth Baseball | - Auxiliary Gym | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 2/21 | Miscellaneous Events | Middlebury Travel Bball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Fri., 2/23 | V Boys Swimming and Diving | Brookfield | Home - PHS Pool [Directions] | 5:30 p.m. | ||
| Fri., 2/23 | Miscellaneous Events | Middlebury Park & Rec Travel Bball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Fri., 2/23 | Miscellaneous Events | State Gymnastic Set Up | - PHS Main Gym | 9:00 p.m. | 9:00 - 11:00 pm | |
| Sat., 2/24 | V Boys Ice Hockey | Amity | Away - Bennett Rink - West Haven [Directions] | W 6-1 | ||
| Sat., 2/24 | Miscellaneous Events | CIAC State Gymnastic Championships | - PHS Main Gym | 8:00 a.m. | 8:00 am - 7:00 pm | |
| Sat., 2/24 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sun., 2/25 | V Boys Ice Hockey | Daniel Hand | Away - Northford Ice Pavilion [Directions] | W 9-2 | ||
| Sun., 2/25 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 2/25 | Miscellaneous Events | CIAC State Gymnastic Championships | - PHS Main Gym | 8:00 a.m. | 8:00 am - 7:00 pm | |
| Sun., 2/25 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sun., 2/25 | Miscellaneous Events | PHS Parent Softball Association | - Auxiliary Gym | 2:00 p.m. | 2:00 - 4:00 pm | |
| Mon., 2/26 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavilion [Directions] | W 6-0 | ||
| Mon., 2/26 | V Co-ed Alpine Skiing | Ski Race | Away | 3:00 p.m. | 2:15 pm | @ Mt. Southington |
| Mon., 2/26 | Miscellaneous Events | PHS Parent Softball Association | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 2/26 | Miscellaneous Events | Middlebury Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/27 | Miscellaneous Events | Volleyball Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 pm | |
| Tue., 2/27 | Miscellaneous Events | CPR/First Aid class | - Health Classroom - Room 201 | 5:00 p.m. | ||
| Tue., 2/27 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Wed., 2/28 | V Co-ed Alpine Skiing | State Championships | Away | 1:15 | @ Mt. Southington | |
| Wed., 2/28 | Miscellaneous Events | Pomperaug Youth Baseball | - Auxiliary Gym | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 2/28 | Miscellaneous Events | Middlebury Travel Bball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 3/1 | Miscellaneous Events | Girls Lacrosse Meeting | - Health Classroom - Room 201 | 2:30 p.m. | 2:30 - 4:00 pm | |
| Thu., 3/1 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Thu., 3/1 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Fri., 3/2 | Miscellaneous Events | State Open Gymnastic Set-Up | - PHS Main Gym | 6:30 p.m. | 6:30 - 10:30 pm | |
| Fri., 3/2 | Miscellaneous Events | Middlebury Park & Rec Travel Bball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 3/3 | JV Boys Swimming and Diving | Naugatuck | Away [Directions] | Cancelled | 12;15 pm | |
| Sat., 3/3 | V Bowling | CIAC Tournament | Away - Bowl O Rama-Newington | 10:00 a.m. | 8:00 am | |
| Sat., 3/3 | Miscellaneous Events | Gymnastic State Open | - PHS Main Gym | 7:00 a.m. | 7:00 am - 3:00 pm | |
| Sat., 3/3 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sun., 3/4 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 3/4 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sun., 3/4 | Miscellaneous Events | PHS Parent Softball Association | - Auxiliary Gym | 2:00 p.m. | 2:00 - 4:00 pm | |
| Mon., 3/5 | JV Boys Swimming and Diving | Naugatuck | Away [Directions] | 5:00 p.m. | 3:00 | |
| Mon., 3/5 | Miscellaneous Events | PHS Parent Softball Association | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 3/5 | Miscellaneous Events | Middlebury Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/6 | Miscellaneous Events | Boys Lacrosse Meeting | - Health Classroom - Room 201 | 5:30 p.m. | 5:30 - 7:30 pm | |
| Tue., 3/6 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Thu., 3/8 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Thu., 3/8 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Thu., 3/8 | Unified Sports Basketball | Bunnell Unified Tournament | Away - Bunnell HS | 3:00 p.m. | 2:15 pm | |
| Fri., 3/9 | School Holidays and Closings | 1/2 Professional Development Day | ||||
| Sat., 3/10 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sun., 3/11 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 3/11 | Miscellaneous Events | Baseball Clinic-PHS Baseball | - Auxiliary Gym | 11:00-1:30 p.m. | ||
| Sun., 3/11 | Miscellaneous Events | Baseball Clinic- PHS Baseball | 11:00-1:30 p.m. | |||
| Sun., 3/11 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Mon., 3/12 | Miscellaneous Events | Middlebury Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/13 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Wed., 3/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 3/14 | Miscellaneous Events | Middlebury Park & Rec Travel Bball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 3/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 3/15 | Miscellaneous Events | Boys Lacrosse Conditioning | - Weight Room | 6:00 p.m. | 6:00 - 7:00 pm | |
| Thu., 3/15 | Unified Sports Basketball | Unified Basketball Tournament- Wilby High School | Away | 3:00 p.m. | 2:15 pm | |
| Fri., 3/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 3/16 | Miscellaneous Events | RMS-March Madness | Home - PHS Main Gym [Directions] | 6:30 p.m. | 5:00 - 9:30 pm | |
| Fri., 3/16 | Miscellaneous Events | Middlebury Park & Rec Travel Bball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Fri., 3/16 | Miscellaneous Events | Blood Drive | - Auxiliary Gym | 7:00-1:30 p.m. | ||
| Sun., 3/18 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Mon., 3/19 | Miscellaneous Events | Middlebury Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 3/21 | Miscellaneous Events | Middlebury Park & Rec Travel Bball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Fri., 3/23 | Miscellaneous Events | Gymnastics Set Up | - PHS Main Gym | 7:00 p.m. | 7:00 - 10:00 pm | |
| Fri., 3/23 | Miscellaneous Events | Middlebury Park & Rec Travel Bball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 3/24 | Miscellaneous Events | Kinetic Kids Gymnastics State Meet | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sun., 3/25 | Miscellaneous Events | Kinetic Kids Gymnastics State Meet | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sun., 3/25 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Mon., 3/26 | Miscellaneous Events | Middlebury Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:00 pm | |
| Wed., 3/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:00 pm | |
| Wed., 3/28 | Miscellaneous Events | Middlebury Park & Rec Travel Bball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 3/29 | Miscellaneous Events | Boys Soccer Meeting | - Health Classroom - Room 201 | 3:00 p.m. | ||
| Thu., 3/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:00 pm | |
| Fri., 3/30 | School Holidays and Closings | Good Friday - No School | ||||
| Sat., 3/31 | V Baseball | Oxford | Home - PHS Baseball Field [Directions] | L 5-8 | Non-League | |
| Sat., 3/31 | JV Baseball | Oxford | Away - OHS Baseball Field [Directions] | 12:00 p.m. | 10:30 am | |
| Sat., 3/31 | V Boys Lacrosse | North Haven | Away - North Haven MS Turf Field [Directions] | L 15-3 | 9:00 am | Share bus w/JV |
| Sat., 3/31 | JV Boys Lacrosse | North Haven | Away - North Haven MS Turf Field [Directions] | 12:30 a.m. | 10:30 am | |
| Sat., 3/31 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | L 4-16 | 11:30 | Non-league |
| Sat., 3/31 | JV Softball | Trumbull | Away - JV Softball Field [Directions] | W 12 - 1 | 11:30 am | |
| Mon., 4/2 | Miscellaneous Events | Middlebury Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/3 | V Boys Lacrosse | Brookfield | Away - BHS Stadium Field [Directions] | L 8-7 | 2:15 pm | |
| Tue., 4/3 | JV Boys Lacrosse | Brookfield | Away - BHS Back Turf [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 4/3 | Miscellaneous Events | PAC Swim Practice | - PHS Main Gym | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 4/4 | JV Baseball | Oxford | Home - PHS Baseball Field [Directions] | Cancelled | ||
| Wed., 4/4 | V Girls Lacrosse | Brookfield | Home - Sports Complex & Track [Directions] | W 14-11 | ||
| Wed., 4/4 | JV Girls Lacrosse | Brookfield | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 4/5 | V Boys Golf | New Milford | Away - Candlewood Valley [Directions] | Pomperaug 187 New Milford 218 | 1:45-in front of bus line | Non-League |
| Thu., 4/5 | V Boys Lacrosse | New Milford | Home - Sports Complex & Track [Directions] | L 13-9 | ||
| Thu., 4/5 | JV Boys Lacrosse | New Milford | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 4/5 | V Boys Tennis | Newtown | Away - Newtown HS [Directions] | W 5-2 | 2:15 pm | Non-League |
| Thu., 4/5 | V Girls Lacrosse | New Milford | Away - New Milford HS [Directions] | W 17-7 | 4:00 pm | |
| Thu., 4/5 | JV Girls Lacrosse | New Milford | Away - New Milford HS [Directions] | 4:00 p.m. | 2:15 pm | |
| Thu., 4/5 | V Softball | Naugatuck | Home - Community Softball Field [Directions] | L 1-2 | 2:30 | Non-league |
| Thu., 4/5 | V Girls Tennis | New Fairfield | Home - PHS Tennis Courts [Directions] | W 4-3 | Non-League | |
| Thu., 4/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 4/6 | V Boys Lacrosse | Southington | Home - Sports Complex & Track [Directions] | L 11-9 | ||
| Fri., 4/6 | JV Boys Lacrosse | Southington | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Mon., 4/9 | FR Baseball | Naugatuck | Home - Community Baseball Field [Directions] | 4:00 p.m. | 2:15 pm | |
| Mon., 4/9 | V Boys Tennis | Immaculate | Away - Rogers Park [Directions] | W 7-0 | 2:15 pm | |
| Mon., 4/9 | V Girls Outdoor Track | Newtown, Notre Dame-Fairfield, New Fairfield | Away - Newtown HS [Directions] | Newtown 97 PHS 51 PHS 116 NFHS 21 PHS 128 Notre Dame 11 | 2:30- need 2 buses | Need 2 buses |
| Mon., 4/9 | V Softball | Joel Barlow | Home - PHS Softball Field [Directions] | L 4-10 | Non-League | |
| Mon., 4/9 | V Girls Tennis | Immaculate | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Mon., 4/9 | Miscellaneous Events | Middlebury Over 30 Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/10 | V Boys Golf | Bethel | Away - Redding Country Club [Directions] | Pomperaug 177 Bethel 238 | 1:45-in front of bus line | |
| Tue., 4/10 | V Boys Lacrosse | New Fairfield | Home - Sports Complex & Track [Directions] | L 18-1 | ||
| Tue., 4/10 | JV Boys Lacrosse | New Fairfield | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Tue., 4/10 | V Boys Outdoor Track | Newtown, Notre Dame-Fairfield, New Fairfield | Away [Directions] | Pomp:60.5 NEWT: 88.5
Pomp:112 ND:12
Pomp:127 NF:23 [Detailed Results] | 2:15 pm- 2 buses | At Newtown |
| Tue., 4/10 | V Girls Lacrosse | New Fairfield | Away - Rebel Turf [Directions] | W 11-8 | 5:00 pm | |
| Tue., 4/10 | JV Girls Lacrosse | New Fairfield | Away - Rebel Turf [Directions] | 5:00 p.m. | 3:45 pm- bus returns for varsity | |
| Tue., 4/10 | V Girls Tennis | Joel Barlow | Away - Tennis Courts [Directions] | L 2-5 | 2:15 pm | |
| Tue., 4/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 4/11 | V Baseball | Masuk | Away - John Giampaolo Baseball Field @ Masuk HS [Directions] | L 6-1 | 2:15-share w/ softball | Non-League |
| Wed., 4/11 | FR Baseball | Newtown | Home - PHS Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/11 | V Boys Golf | Immaculate | Away - Richter Park [Directions] | Pomperaug 185 Immaculate 180 | 1:45-in front of bus line | |
| Wed., 4/11 | V Softball | Masuk | Away - Masuk HS Softball Field [Directions] | L 0-13 | 2:15-share w/baseball- send another bus for pick-up | Non-League |
| Wed., 4/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 4/12 | V Baseball | Holy Cross | Away - Municipal Stadium-Waterbury [Directions] | L 7-1 | 2:45 | Non-League |
| Thu., 4/12 | JV Baseball | Masuk | Home - Community Baseball Field [Directions] | 4:15 p.m. | 2:15-share bus w/ softball | One way bus |
| Thu., 4/12 | V Boys Golf | Brookfield | Away [Directions] | Popmperaug 168 Brookfield 189 | 1:45-in front of bus line | Non-League |
| Thu., 4/12 | V Boys Lacrosse | Weston | Away - WHS Turf Field [Directions] | L 3-7 | 4:00 pm | |
| Thu., 4/12 | JV Boys Lacrosse | Weston | Away - WHS Turf Field [Directions] | 4:00 p.m. | 2:15 pm | |
| Thu., 4/12 | V Boys Tennis | Masuk | Away - Wolfe Park Tennis Courts [Directions] | W 4-3 | 2:15 pm | |
| Thu., 4/12 | V Girls Lacrosse | Weston | Home - Sports Complex & Track [Directions] | W 17-6 | ||
| Thu., 4/12 | JV Girls Lacrosse | Weston | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Thu., 4/12 | JV Softball | Masuk | Home - Community Softball Field [Directions] | L 11 -2 | 2:15 pm-share bus w/baseball | One way bus |
| Thu., 4/12 | V Girls Tennis | Masuk | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Thu., 4/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 4/13 | V Baseball | New Milford | Away - New Milford HS [Directions] | L 3-2 | 2:30 | Non-League |
| Fri., 4/13 | V Softball | Brookfield | Away - BHS Softball Field [Directions] | L 4-6 | 3:00 | Non-League |
| Sat., 4/14 | V Baseball | Danbury | Home - PHS Baseball Field [Directions] | W 8-6 | Non-League | |
| Sat., 4/14 | JV Baseball | New Milford | Home - Community Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/14 | V Girls Lacrosse | Branford | Away - Branford HS-Turf Field [Directions] | L 13-8 | 11:00 am-share bus w/JV | |
| Sat., 4/14 | JV Girls Lacrosse | Branford | Away - Branford HS-Turf Field [Directions] | 1:00 p.m. | 11:00 am-share bus w/varsity | |
| Sat., 4/14 | V Softball | Holy Cross | Home - PHS Softball Field [Directions] | L 2-5 | Non-league | |
| Sat., 4/14 | JV Softball | Brookfield | Home - PHS Softball Field [Directions] | L 4 - 3 | ||
| Mon., 4/16 | V Boys Lacrosse | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | L 10-4 | 5:15 pm | |
| Mon., 4/16 | JV Boys Lacrosse | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | Cancelled | 3:45- return for varsity pick up | |
| Mon., 4/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 9:00 a.m. | 9:00 - 10:30 am | |
| Mon., 4/16 | School Holidays and Closings | Spring Vacation | ||||
| Tue., 4/17 | V Boys Tennis | New Milford | Away - New Milford HS [Directions] | W 7-0 | 9:30 am | |
| Tue., 4/17 | V Boys Tennis | Bunnell | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/17 | V Girls Lacrosse | Masuk | Home - Sports Complex & Track [Directions] | W 18-8 | ||
| Tue., 4/17 | JV Girls Lacrosse | Masuk | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Tue., 4/17 | V Girls Tennis | Brookfield | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Tue., 4/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 9:00 a.m. | 9:00 - 10:30 am | |
| Tue., 4/17 | School Holidays and Closings | Spring Vacation | ||||
| Wed., 4/18 | FR Baseball | New Fairfield | Home - PHS Baseball Field [Directions] | 11:00 a.m. | ||
| Wed., 4/18 | V Boys Golf | Brookfield | Home - Heritage Village C.C. [Directions] | Pomperaug 174 Brookfield 214 | ||
| Wed., 4/18 | V Softball | New Fairfield | Away - NFHS Softball Field [Directions] | W 8-2 | 2:45 | |
| Wed., 4/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 9:00 a.m. | 9:00 - 10:30 am | |
| Wed., 4/18 | Miscellaneous Events | Mdby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 3:15 pm | |
| Wed., 4/18 | School Holidays and Closings | Spring Vacation | ||||
| Thu., 4/19 | V Boys Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | L 5-17 | 5:30 pm | |
| Thu., 4/19 | JV Boys Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | 5:15 p.m. | 4:00-return for varsity pick up | |
| Thu., 4/19 | V Girls Lacrosse | Newtown | Home - Sports Complex & Track [Directions] | W 9-8 OT | ||
| Thu., 4/19 | JV Girls Lacrosse | Newtown | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Thu., 4/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Thu., 4/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 9:00 a.m. | 9:00 - 10:30 am | |
| Thu., 4/19 | School Holidays and Closings | Spring Vacation | ||||
| Fri., 4/20 | V Baseball | Joel Barlow | Away - Field G (Baseball) [Directions] | W 7-0 | 2:30 | |
| Fri., 4/20 | FR Baseball | New Fairfield | Home - Community Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/20 | V Girls Outdoor Track | Wilton, Stamford | Away [Directions] | No team score | 2:00 pm | |
| Fri., 4/20 | V Girls Outdoor Track | Connecticut Distance Festival | Away - Xavier HS-Middletown | 6:00 p.m. | 4:00 pm | |
| Fri., 4/20 | V Softball | Joel Barlow | Away - Field E (Softball) [Directions] | W 3-1 | 2:30 | |
| Fri., 4/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 9:00 a.m. | 9:00 - 10:30 am | |
| Fri., 4/20 | School Holidays and Closings | Spring Vacation | ||||
| Sat., 4/21 | V Baseball | Seymour | Away - French Park [Directions] | L 17-4 | 9:00 am | Non-League |
| Sat., 4/21 | JV Baseball | Joel Barlow | Home - PHS Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/21 | V Boys Lacrosse | Watertown | Home - Sports Complex & Track [Directions] | W 13-5 | ||
| Sat., 4/21 | JV Boys Lacrosse | Watertown | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Sat., 4/21 | V Girls Lacrosse | Conard | Home - Sports Complex & Track [Directions] | W 13-8 | ||
| Sat., 4/21 | JV Girls Lacrosse | Conard | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 4/21 | V Softball | Newtown | Home - PHS Softball Field [Directions] | L 3-13 | Non-League | |
| Sat., 4/21 | V Girls Tennis | Bunnell | Away - Bunnell Tennis Courts [Directions] | W 7-0 | 9:45 am | |
| Sun., 4/22 | V Baseball | Newtown | Home - PHS Baseball Field [Directions] | W 8-7 | Non-League | |
| Mon., 4/23 | V Baseball | New Milford | Home - PHS Baseball Field [Directions] | L 6-5 | ||
| Mon., 4/23 | FR Baseball | New Milford | Home - Community Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/23 | V Boys Golf | Joel Barlow | Home [Directions] | Pomperaug 170 Joel Barlow 185 | ||
| Mon., 4/23 | V Boys Tennis | Weston | Away - WHS Tennis Courts [Directions] | L 0-7 | 2:15 pm | |
| Mon., 4/23 | V Girls Outdoor Track | Weston, Joel Barlow, New Milford | Away - WHS Track [Directions] | PHS 92 JBHS 54 PHS 75 NMHS 70 Weston 80 PHS 70 | 2:15- 2 buses | at Weston |
| Mon., 4/23 | V Softball | New Milford | Home - PHS Softball Field [Directions] | L 5-7 | ||
| Mon., 4/23 | V Girls Tennis | Weston | Home - PHS Tennis Courts [Directions] | L 1-6 | ||
| Mon., 4/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:30 p.m. | 3:30 - 8:30 pm | |
| Tue., 4/24 | V Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | W 10-0 | 2:30 | |
| Tue., 4/24 | JV Baseball | New Milford | Away - New Milford HS [Directions] | 4:15 p.m. | 2:15- share bus w/softball | |
| Tue., 4/24 | V Boys Golf | Newtown | Home - Heritage Golf Course [Directions] | Pomperaug 173 Newtown 179 | Yes | |
| Tue., 4/24 | V Boys Lacrosse | Stratford | Away - Penders Field [Directions] | W 7-6 | 5:00 pm | |
| Tue., 4/24 | JV Boys Lacrosse | Stratford | Away - Penders Field [Directions] | Cancelled | 3:45- return for varsity pick up | |
| Tue., 4/24 | V Boys Outdoor Track | Weston, Joel Barlow, New Milford | Home - Sports Complex & Track [Directions] | Pomp:69 Weston:81 Pomp:104.5 JB:33.5 Pomp:70 NM:76 | ||
| Tue., 4/24 | JV Softball | New Milford | Away - New Milford HS [Directions] | W 15 - 6 | 2:15 pm- share bus w/baseball | |
| Tue., 4/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:30 p.m. | 3:30 - 8:30 pm | |
| Wed., 4/25 | V Girls Lacrosse | Stratford/Bunnell | Home - Sports Complex & Track [Directions] | W 17-5 | ||
| Wed., 4/25 | JV Girls Lacrosse | Stratford/Bunnell | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Wed., 4/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:30 p.m. | 3:30 - 8:30 pm | |
| Thu., 4/26 | V Baseball | Brookfield | Home - Community Baseball Field [Directions] | L 9-2 | ||
| Thu., 4/26 | FR Baseball | Masuk | Away - Wolfe Park [Directions] | 4:15 p.m. | 2:30 | |
| Thu., 4/26 | V Boys Golf | New Milford | Home - Heritage Village C.C. [Directions] | Pomperaug 178 New Milford 200 | ||
| Thu., 4/26 | V Boys Lacrosse | Amity | Away - Amity HS - Field # 3 [Directions] | L 7-8 | 2:15 | |
| Thu., 4/26 | JV Boys Lacrosse | Amity | Away - Amity HS - Field # 3 [Directions] | 5:30 p.m. | 4:15 | |
| Thu., 4/26 | V Boys Tennis | Bethel | Away - Bethel HS [Directions] | L 3-4 | 2:15 pm | |
| Thu., 4/26 | V Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | L 12-6 | 2:15 | |
| Thu., 4/26 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:30 p.m. | 2:15-share bus w/varsity | |
| Thu., 4/26 | V Softball | Brookfield | Home - Community Softball Field [Directions] | L 3-5 | ||
| Thu., 4/26 | V Girls Tennis | Bethel | Home - PHS Tennis Courts [Directions] | W 6-1 | ||
| Thu., 4/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Thu., 4/26 | Miscellaneous Events | Art Show Set Up | - PHS Main Gym | 7:30 a.m. | 7:30 am - 7:00 pm | |
| Thu., 4/26 | Miscellaneous Events | Art Show Set Up | - Health Classroom - Room 201 | 7:30 a.m. | 7:30 am - 7:00 pm | |
| Thu., 4/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:30 p.m. | 3:30 - 8:30 pm | |
| Thu., 4/26 | Miscellaneous Events | Art Show Set Up | - PHS Main Gym | 6:00 p.m. | ||
| Fri., 4/27 | Miscellaneous Events | Art Show Set Up & Art Show | - Health Classroom - Room 201 | 7:30 a.m. | 7:30 am - 9:00 pm | |
| Fri., 4/27 | Miscellaneous Events | Art Show Set Up & Art Show | - PHS Main Gym | 7:30 a.m. | 7:30 am - 9:00 pm | |
| Fri., 4/27 | Miscellaneous Events | Art Show | - PHS Main Gym | 7:30 a.m. | 7:30 am - 9:00 pm | |
| Fri., 4/27 | Miscellaneous Events | Art Show | - Health Classroom - Room 201 | 7:30 a.m. | 7:30 am - 9:00 pm | |
| Fri., 4/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:30 p.m. | 3:30 - 8:30 pm | |
| Sat., 4/28 | V Boys Outdoor Track | O'Grady Relays | Away | 9:00 a.m. | 7:00 am- 2 buses | @ Danbury HS |
| Sat., 4/28 | V Girls Lacrosse | Farmington | Home - Sports Complex & Track [Directions] | W 17-5 | ||
| Sat., 4/28 | JV Girls Lacrosse | Farmington | Home - Sports Complex & Track [Directions] | 12:30 p.m. | ||
| Sat., 4/28 | V Girls Outdoor Track | O'Grady Relays | Away | 9:00 a.m. | 7:00 am | @ Danbury HS |
| Sat., 4/28 | Miscellaneous Events | Region 15 Art Show | - PHS Main Gym | 9:00 a.m. | 9:00 am - 3:00 pm | |
| Sat., 4/28 | Miscellaneous Events | Art Show | - Health Classroom - Room 201 | 9:00 a.m. | 9:00 am - 6:00 pm | |
| Sat., 4/28 | Miscellaneous Events | Art Show | - Health Classroom - Room 201 | 9:00 a.m. | 9:00 am - 6:00 pm | |
| Mon., 4/30 | V Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | L 4-8 | 2:30 | |
| Mon., 4/30 | JV Baseball | Brookfield | Away - H.H.E.S. Baseball Field [Directions] | 4:00 p.m. | 8:30 | |
| Mon., 4/30 | V Boys Golf | Weston | Away - Aspetuck Valley Country Club [Directions] | Pomperaug 185 Weston 185 | 1:45- in front of bus line | Non-League |
| Mon., 4/30 | V Boys Tennis | Stratford | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/30 | V Girls Outdoor Track | Brookfield, Masuk, Kolbe Cathedral | Home - Sports Complex & Track [Directions] | PHS 122 Kolbe 12 PHS 103 Masuk 47 PHS 102 Brookfield 47 | ||
| Mon., 4/30 | V Softball | Bunnell | Away - Bunnell Softball Field [Directions] | W 14-2 | 2:30 | |
| Mon., 4/30 | V Girls Tennis | Stratford | Away - Flood M.S. Tennis Courts [Directions] | W 7-0 | 2:15 pm | |
| Tue., 5/1 | V Baseball | Masuk | Home - PHS Baseball Field [Directions] | L 7-5 | ||
| Tue., 5/1 | JV Baseball | Bunnell | Home - Community Baseball Field [Directions] | 4:15 p.m. | 2:15-share bus w/softball | One way bus |
| Tue., 5/1 | V Boys Golf | Weston | Home [Directions] | Pomperaug 184 Weston 178 | ||
| Tue., 5/1 | V Boys Lacrosse | Bethel | Home - Sports Complex & Track [Directions] | L 10-15 | ||
| Tue., 5/1 | JV Boys Lacrosse | Bethel | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Tue., 5/1 | V Boys Outdoor Track | Brookfield, Masuk, Kolbe Cathedral | Away - BHS Track [Directions] | 4:00 p.m. | 2:45 pm | at Brookfield |
| Tue., 5/1 | V Boys Tennis | Brookfield | Home - PHS Tennis Courts [Directions] | W 4-3 | ||
| Tue., 5/1 | V Girls Lacrosse | Bethel | Away - Rockwell Field [Directions] | W 22-14 | 2:30 pm-return for JV's | |
| Tue., 5/1 | JV Girls Lacrosse | Bethel | Away - Rockwell Field [Directions] | 5:30 p.m. | 4:15 | |
| Tue., 5/1 | V Softball | Masuk | Home - PHS Softball Field [Directions] | L 0-14 | ||
| Tue., 5/1 | JV Softball | Bunnell | Home - Community Softball Field [Directions] | W 20 - 3 | 2:15 pm-share bus w/baseball | One way bus |
| Tue., 5/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Tue., 5/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:00 pm | |
| Wed., 5/2 | V Baseball | Weston | Home - PHS Baseball Field [Directions] | W 9-2 | ||
| Wed., 5/2 | FR Baseball | Weston | Away - Revson Field, Weston [Directions] | 4:15 p.m. | 2:30 | |
| Wed., 5/2 | V Boys Tennis | Newtown | Home - PHS Tennis Courts [Directions] | W 5-2 | ||
| Wed., 5/2 | V Softball | Weston | Home - PHS Softball Field [Directions] | W 14-0 | ||
| Wed., 5/2 | V Girls Tennis | Newtown | Away - Newtown HS [Directions] | W 5-2 | 2:45 pm | |
| Wed., 5/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:00 pm | |
| Thu., 5/3 | JV Baseball | Weston | Away - Revson Field, Weston [Directions] | 4:15 p.m. | 2:30-share bus w/softball | |
| Thu., 5/3 | V Boys Golf | Woodland Hawks Invitational | Away - Oxford Greens | 176 | 7:00 am | |
| Thu., 5/3 | JV Softball | Weston | Away - Weston MS [Directions] | W 15-1 | 2:15 pm-share bus w/baseball | |
| Thu., 5/3 | V Girls Tennis | Notre Dame-Fairfield | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 5/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:00 pm | |
| Fri., 5/4 | V Baseball | Kolbe Cathedral | Away - Veterans Park [Directions] | W 3-1 | 2:30 | |
| Fri., 5/4 | FR Baseball | Weston | Home - PHS Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 5/4 | V Boys Lacrosse | Immaculate | Home - Sports Complex & Track [Directions] | W 12-4 | ||
| Fri., 5/4 | V Boys Tennis | Joel Barlow | Away - Tennis Courts [Directions] | L 2-5 | 2:15 pm | |
| Fri., 5/4 | V Girls Lacrosse | Immaculate | Away - Mustang Valley [Directions] | W 15-5 | 2:15-return for JV's | |
| Fri., 5/4 | V Softball | Kolbe Cathedral | Away - Cal Ripken Field at Longfellow Park [Directions] | W 14-4 | 2:45 | |
| Fri., 5/4 | V Girls Tennis | New Milford | Home - PHS Tennis Courts [Directions] | W 6-1 | ||
| Fri., 5/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:00 pm | |
| Fri., 5/4 | Miscellaneous Events | Kinetic Kids Gymnastics Set Up and Rehearsal | - PHS Main Gym | 2:30 p.m. | 2:30 - 7:00 pm | |
| Sat., 5/5 | JV Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 1:00 p.m. | 11:30 | |
| Sat., 5/5 | FR Baseball | New Milford | Away - New Milford HS [Directions] | 12:00 p.m. | 10:15 am | |
| Sat., 5/5 | V Boys Outdoor Track | Middletown Invitational | Away | 1:00 p.m. | 11:00 am-share bus w/girls track | |
| Sat., 5/5 | V Girls Outdoor Track | Middletown Invitational | Away | 1:00 p.m. | 11:00 am-share bus w/boys track | |
| Sat., 5/5 | Miscellaneous Events | Kinetic Kids Gymnastics State Meet | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sun., 5/6 | Miscellaneous Events | Kinetic Kids Gymnastics State Meet | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Mon., 5/7 | V Baseball | Bethel | Home - PHS Baseball Field [Directions] | L 2-7 | ||
| Mon., 5/7 | V Boys Golf | Bunnell | Home [Directions] | Pomperaug 167 Bunnell no score | ||
| Mon., 5/7 | V Girls Outdoor Track | Bunnell, Immaculate, Stratford | Away - Bunnell Track [Directions] | PHS 95 Stratford 53 PHS 88 Immaculate 49 Bunnell 76.5 PHS 73.5 | 3:00 pm- 2 buses | at Bunnell |
| Mon., 5/7 | V Softball | Bethel | Home - PHS Softball Field [Directions] | W 13-1 | ||
| Mon., 5/7 | V Girls Tennis | New Fairfield | Away [Directions] | W 5-2 | 3:00 pm | |
| Mon., 5/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Mon., 5/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Tue., 5/8 | V Boys Lacrosse | Bunnell-Stratford | Home - Sports Complex & Track [Directions] | W 11-4 | ||
| Tue., 5/8 | JV Boys Lacrosse | Bunnell-Stratford | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Tue., 5/8 | V Boys Outdoor Track | Bunnell, Immaculate, Stratford | Away - Bunnell Track [Directions] | 4:00 p.m. | 2:15 pm- 2 buses | at Bunnell |
| Tue., 5/8 | V Girls Lacrosse | Bunnell | Away - Bunnell Turf Field [Directions] | W 14-4 | 5:15 | |
| Tue., 5/8 | JV Girls Lacrosse | Bunnell | Away - Bunnell Turf Field [Directions] | Cancelled | 3:30-bus returns for varsity pick up | |
| Tue., 5/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Tue., 5/8 | Unified Sports Volleyball | Newtown | Home - Auxiliary Gym [Directions] | 3:00 p.m. | ||
| Wed., 5/9 | V Baseball | Stratford | Away - Penders Field [Directions] | W 6-5 | 4:15 | |
| Wed., 5/9 | JV Baseball | Masuk | Away - John Giampaolo Baseball Field @ Masuk HS [Directions] | 4:00 p.m. | 2:30 | |
| Wed., 5/9 | FR Baseball | Stratford | Home - PHS Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/9 | V Boys Tennis | New Fairfield | Home - PHS Tennis Courts [Directions] | W 5-2 | ||
| Wed., 5/9 | JV Girls Lacrosse | New Milford | Home - Sports Complex & Track [Directions] | 6:45 p.m. | ||
| Wed., 5/9 | V Softball | Stratford | Away - DeLuca Field [Directions] | W 6-0 | 4:15 | |
| Wed., 5/9 | V Girls Tennis | Bethel | Away - Bethel HS [Directions] | W 5-2 | 2:15 pm | Non-League |
| Wed., 5/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Thu., 5/10 | V Baseball | Newtown | Away - Baseball Field at Fairfield Hills Complex [Directions] | L 5-0 | 4:15 pm | |
| Thu., 5/10 | JV Baseball | Stratford | Home - Community Baseball Field [Directions] | 4:15 p.m. | 2:15-share bus w/softball | |
| Thu., 5/10 | V Boys Lacrosse | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | W 18-4 | ||
| Thu., 5/10 | JV Boys Lacrosse | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | Cancelled | ||
| Thu., 5/10 | V Boys Tennis | Holy Cross | Home - PHS Tennis Courts [Directions] | W 6-1 | Non-league | |
| Thu., 5/10 | V Girls Lacrosse | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | W 17-6 | 3:15 pm | |
| Thu., 5/10 | JV Girls Lacrosse | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | Cancelled | 4:00 | |
| Thu., 5/10 | JV Softball | Stratford | Home - Community Softball Field [Directions] | W 9 - 4 | 2:15 pm-share bus w/baseball | |
| Thu., 5/10 | V Girls Tennis | Newtown | Home - Edgewood Bath and Tennis [Directions] | L 3-4 | 3:00 | Non-League |
| Thu., 5/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Fri., 5/11 | V Softball | Newtown | Away - Treadwell Town Park [Directions] | L 0-2 | 5:30 pm | |
| Fri., 5/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Fri., 5/11 | School Holidays and Closings | 1/2 Professional Development Day | ||||
| Sat., 5/12 | Miscellaneous Events | Weightlifting Competition | Home - Auxiliary Gym [Directions] | 10:00 a.m. | ||
| Mon., 5/14 | V Baseball | Notre Dame-Fairfield | Home - PHS Baseball Field [Directions] | L 5-0 | ||
| Mon., 5/14 | V Boys Golf | Notre Dame-Fairfield | Home - Heritage Village CC [Directions] | Pomperaug 177 ND . no score | ||
| Mon., 5/14 | V Boys Outdoor Track | Bethel | Away - Bethel HS [Directions] | Pomp: 82 Bethel: 68 | 2:15-2 buses | |
| Mon., 5/14 | V Girls Outdoor Track | Bethel | Away - Bethel HS [Directions] | PHS 121 Bethel 28 | 2:15 | |
| Mon., 5/14 | V Softball | Notre Dame-Fairfield | Home - PHS Softball Field [Directions] | W 1-0 | ||
| Mon., 5/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Tue., 5/15 | V Boys Golf | New Fairfield | Away [Directions] | Pmperaug 165 New Fairfield 198 | 10:45-in front of bus line | |
| Tue., 5/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Tue., 5/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Thu., 5/17 | JV Girls Lacrosse | Brookfield | Home - Sports Complex & Track [Directions] | Cancelled | ||
| Mon., 5/21 | V Baseball | Immaculate | Home - PHS Baseball Field [Directions] | L 3-4 | ||
| Mon., 5/21 | V Boys Golf | Masuk | Home [Directions] | Pomperuag 162 Masuk 163 | ||
| Mon., 5/21 | V Boys Lacrosse | Joel Barlow | Away - Field I (Stadium) [Directions] | L 17-3 | 5:00 | |
| Mon., 5/21 | JV Boys Lacrosse | Joel Barlow | Away - Field I (Stadium) [Directions] | 5:00 p.m. | 3:00 | |
| Mon., 5/21 | V Girls Lacrosse | Joel Barlow | Home - Sports Complex & Track [Directions] | W 13-5 | ||
| Mon., 5/21 | JV Girls Lacrosse | Joel Barlow | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Mon., 5/21 | V Softball | Immaculate | Home - PHS Softball Field [Directions] | W 12-5 | ||
| Mon., 5/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Mon., 5/21 | Miscellaneous Events | Mdby Park & Rec Lifeguard Recert Class | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 9:30 pm | |
| Mon., 5/21 | Miscellaneous Events | Mdby Park & Rec Swim Test | - PHS Pool | 5:45 p.m. | One Lane, 6:00 - 7:00 pm | |
| Mon., 5/21 | Miscellaneous Events | Mdby Park & Rec Lifeguard Recert Class | - PHS Pool | 7:00 p.m. | 7:00 - 9:30 pm | |
| Tue., 5/22 | JV Baseball | Newtown | Away - Baseball Field at Fairfield Hills Complex [Directions] | 3:45 p.m. | 2:30 | |
| Tue., 5/22 | V Boys Golf | Stratford, Stratford | Away - River Oaks- New Fairfield [Directions] | Pomperaug 177 Stratford no score | 1:45-in front of bus line | |
| Tue., 5/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Tue., 5/22 | Miscellaneous Events | Mdby Park & Rec Lifeguard Recert Class | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 9:30 pm | |
| Tue., 5/22 | Miscellaneous Events | Mdby Park & Rec Lifeguard Recert Class | - PHS Pool | 7:00 p.m. | 7:00 - 9:30 pm | |
| Wed., 5/23 | V Boys Outdoor Track | Freshmen Meet | Away | Cancelled | @ Bethel HS | |
| Wed., 5/23 | V Girls Outdoor Track | Freshmen Meet | Away | Cancelled | @ Bethel HS | |
| Wed., 5/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Wed., 5/23 | Miscellaneous Events | Mdby Park & Rec Lifeguard Recert Class | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 9:30 pm | |
| Wed., 5/23 | Miscellaneous Events | Mdby Park & Rec Lifeguard Recert Class | - PHS Pool | 7:00 p.m. | 7:00 - 9:30 pm | |
| Thu., 5/24 | FR Baseball | Bethel | Away - Parloa Field [Directions] | 4:15 p.m. | 2:45 | |
| Thu., 5/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Thu., 5/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Fri., 5/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Mon., 5/28 | School Holidays and Closings | Memorial Day - No School | ||||
| Tue., 5/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Tue., 5/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Wed., 5/30 | Miscellaneous Events | Guidance Event | - Auxiliary Gym | 9:45-10:10 a.m. | ||
| Wed., 5/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Thu., 5/31 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Thu., 5/31 | Miscellaneous Events | Senior Awards Night | 6:00 p.m. | |||
| Fri., 6/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Sun., 6/3 | Miscellaneous Events | Kinetic Kids Gymnastics Exhibition | - PHS Main Gym | 7:00 a.m. | 12:00 - 7:00 pm | |
| Sun., 6/3 | Miscellaneous Events | Prom Night | 6:00 p.m. | |||
| Mon., 6/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Mon., 6/4 | Miscellaneous Events | Cheerleading Tryouts | - Auxiliary Gym | 5:00-9:00 p.m. | ||
| Tue., 6/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Tue., 6/5 | Miscellaneous Events | Cheerleading Tryouts | - Auxiliary Gym | 5:00-9:00 p.m. | ||
| Tue., 6/5 | Miscellaneous Events | Pomperaug Youth Baseball/American Legion | - PHS Baseball Field | 5:30 p.m. | ||
| Wed., 6/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Wed., 6/6 | Miscellaneous Events | Cheerleading Tryouts | - Auxiliary Gym | 5:00-9:00 p.m. | ||
| Wed., 6/6 | Miscellaneous Events | Pomperaug Youth Baseball/American Legion | - PHS Baseball Field | 5:30 p.m. | ||
| Thu., 6/7 | Miscellaneous Events | Pomperaug Youth Baseball/American Legion | - PHS Baseball Field | 5:30 p.m. | ||
| Sun., 6/10 | Miscellaneous Events | Pomperaug Youth Baseball/American Legion | - PHS Baseball Field | 12:00 p.m. | ||
| Mon., 6/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Tue., 6/12 | Miscellaneous Events | Field Hockey Preseason Meeting | - Health Classroom - Room 201 | 2:30 p.m. | 2:30 - 3:30 pm | |
| Tue., 6/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Tue., 6/12 | Miscellaneous Events | Pomperaug Youth Baseball/American Legion | - PHS Baseball Field | 5:30 p.m. | ||
| Tue., 6/12 | Miscellaneous Events | PHS Cross Country Pre-Season Organizational Meeting | - PHS Main Gym | 6:30 p.m. | ||
| Wed., 6/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Thu., 6/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Fri., 6/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Fri., 6/15 | Miscellaneous Events | Girls Soccer meeting | - PHS Health Room | 3:30 p.m. | ||
| Mon., 6/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Tue., 6/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Tue., 6/19 | Miscellaneous Events | Pomperaug Youth Baseball/American Legion | - PHS Baseball Field | 5:30 p.m. | ||
| Wed., 6/20 | Miscellaneous Events | RMS 8th Grade Graduation Rehearsal | - PHS Main Gym | 9:30-11:30 a.m. | ||
| Wed., 6/20 | Miscellaneous Events | Rochambeau Graduation | - PHS Main Gym | 4:00-7:00 p.m. | ||
| Wed., 6/20 | Miscellaneous Events | Pomperaug Youth Baseball/American Legion | - PHS Baseball Field | 5:30 p.m. | ||
| Thu., 6/21 | Miscellaneous Events | Pomperaug Youth Baseball/American Legion | - PHS Baseball Field | 5:30 p.m. | ||
| Mon., 6/25 | Miscellaneous Events | Stby Park & Rec Field Hockey Camp | - Field Hockey Field | 3:00 p.m. | 3:00 - 5:00 pm | |
| Tue., 6/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Tue., 6/26 | Miscellaneous Events | Stby Park & Rec Field Hockey Camp | - Field Hockey Field | 3:00 p.m. | 3:00 - 5:00 pm | |
| Tue., 6/26 | Miscellaneous Events | Southbury Park & Rec Track Mile Run | - Sports Complex & Track | 5:00 p.m. | 5:00 - 8:00 pm | |
| Wed., 6/27 | Miscellaneous Events | Southbury Park & Rec Track Mile Run | - Sports Complex & Track | 5:00 p.m. | 5:00 - 8:00 pm | |
| Thu., 6/28 | Miscellaneous Events | Stby Park & Rec Field Hockey Camp | - Field Hockey Field | 9:00 a.m. | 9:00 am - 12:00 pm | |
| Fri., 6/29 | Miscellaneous Events | Stby Park & Rec Field Hockey Camp | - Field Hockey Field | 9:00 a.m. | 9:00 am - 12:00 pm | |
| Sun., 7/8 | Miscellaneous Events | Wade Prajer Ceremonial Walk | - Sports Complex & Track | 3:30 p.m. | ||
| Wed., 12/12 | Miscellaneous Events | PHS Softball Team Meeting | - Health Classroom - Room 201 | 3:00 p.m. | 3:00 - 3:30 pm | |