| Shepaug Valley 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 529 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Lewis Mills | Away - Lewis Mills JV Baseball Field [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM |
| TBA | FR Boys Basketball | Immaculate | Home - Ted Alex Gymnasium [Directions] | TBA | ||
| TBA | JV Girls Soccer | Lewis Mills | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| TBA | V Softball | Canterbury (Scrim.) | Away | 2:00 p.m. | 12:45 PM | Bus Departs from Washington Primary School |
| TBA | JV Softball | Terryville | Away - New Terryville High School [Directions] | 3:45 p.m. | 2:15 PM | 2:05 PM Dismissal |
| TBA | V Girls Tennis | Immaculate | Home - Shepaug Valley High School Courts [Directions] | W 7-0 | ||
| Wed., 8/28 | V Girls Soccer | Bethel (Scrim.) | Away - @ Bethel High School [Directions] | 3:45 p.m. | 2:25 pm | |
| Thu., 8/29 | V Boys Soccer | South Kent (Scrim.) | Away | 3:45 p.m. | 2:25 PM | |
| Thu., 8/29 | V Field Hockey | New Milford (Scrim.) | Home - Joan Gauthey Field [Directions] | 3:45 p.m. | ||
| Sat., 8/31 | V Field Hockey | Brookfield Play Day | Away - Brookfield High School | 8:00 a.m. | No Bus | |
| Tue., 9/3 | V Football | Cheney Tech (Scrim.) | Away - Cheney Tech [Directions] | 6:00 p.m. | ||
| Wed., 9/4 | V Boys Soccer | Sacred Heart (Scrim.) | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 9/5 | V Boys Cross Country | Berkshire League Scrimmage | Away - Black Rock State Park | 4:15 p.m. | 2:25 PM | |
| Thu., 9/5 | V Girls Cross Country | Berkshire League Scrimmage | Away - Black Rock State Park | 4:15 p.m. | 2:25 pm | |
| Thu., 9/5 | V Girls Soccer | Sacred Heart (Scrim.) | Home - Shepaug Valley Varsity Soccer Field [Directions] | 3:30 p.m. | ||
| Sat., 9/7 | V Field Hockey | Farmington High School Play Day | Away - Farmington High School | 8:30 a.m. | 7:00 AM | |
| Tue., 9/10 | V Boys Cross Country | Terryville, Nonnewaug | Home - Shepaug Valley High School [Directions] | 4:15 p.m. | ||
| Tue., 9/10 | V Boys Soccer | Lewis Mills | Away - Nassahegan Field - Burlington [Directions] | L 3-0 | 3:15 PM | Boys and Girls Varsity Soccer Share Bus |
| Tue., 9/10 | JV Boys Soccer | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal; Boys and Girls JV Soccer Share Bus |
| Tue., 9/10 | V Girls Cross Country | Terryville, Nonnewaug | Home - Shepaug Valley High School [Directions] | 4:15 p.m. | ||
| Tue., 9/10 | V Field Hockey | Northwestern | Home - Joan Gauthey Field [Directions] | W 3-0 | ||
| Tue., 9/10 | JV Field Hockey | Northwestern | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Tue., 9/10 | V Girls Soccer | Lewis Mills | Away - Nassahegan Field - Burlington [Directions] | L 0-7 | 3:15 PM | Boys and Girls Varisty Soccer Share Bus |
| Tue., 9/10 | JV Girls Soccer | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | 2:00 PM | 1:50 Dismissal; Boys and Girls JV Soccer Share Bus |
| Thu., 9/12 | V Girls Soccer | Terryville | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 2-1 | ||
| Thu., 9/12 | JV Girls Soccer | Terryville | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/13 | V Boys Soccer | Northwestern | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 3-1 | ||
| Fri., 9/13 | JV Boys Soccer | Northwestern | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/13 | V Field Hockey | Litchfield | Away - Plumb Hill Field Complex [Directions] | W 7-2 | 2:25 PM | |
| Fri., 9/13 | JV Field Hockey | Litchfield | Away - Plumb Hill Field Complex [Directions] | 5:00 p.m. | 2:25 PM | |
| Mon., 9/16 | V Girls Soccer | Gilbert | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 3-1 | ||
| Tue., 9/17 | V Boys Cross Country | Lewis Mills, Gilbert | Away - Gilbert [Directions] | 4:15 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 9/17 | V Boys Soccer | Wamogo | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 6-0 | ||
| Tue., 9/17 | JV Boys Soccer | Wamogo | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/17 | V Girls Cross Country | Lewis Mills, Gilbert | Away [Directions] | 4:15 p.m. | 2:00 pm | 1:50 PM Dismissal |
| Tue., 9/17 | V Field Hockey | Lewis Mills | Home - Joan Gauthey Field [Directions] | L 3-2 | ||
| Tue., 9/17 | JV Field Hockey | Lewis Mills | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Thu., 9/19 | V Field Hockey | Wamogo | Away - Wamogo Varsity Field Hockey Field [Directions] | W 3-2 | 3:30 PM | |
| Thu., 9/19 | JV Field Hockey | Wamogo | Away - Wamogo Varsity Field Hockey Field [Directions] | 4:45 p.m. | 3:30 PM | |
| Thu., 9/19 | V Girls Soccer | Nonnewaug | Away - Nonnewaug High School [Directions] | L 3-0 | 2:25 PM | |
| Thu., 9/19 | JV Girls Soccer | Nonnewaug | Away - Nonnewaug HS JV Field [Directions] | 3:45 p.m. | 2:25 PM | |
| Fri., 9/20 | V Boys Soccer | Housatonic Regional | Away - High School Field [Directions] | L 2-1 | 2:00 PM | 1:50 PM Dismissal |
| Fri., 9/20 | JV Boys Soccer | Housatonic Regional | Away - High School Field [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Sat., 9/21 | V Boys Cross Country | Connecticut River Valley Championships | Away - Cromwell High School | 9:30 a.m. | 6:45 AM | |
| Sat., 9/21 | V Football | VGW Techs | Home - Oliver Wolcott Tech [Directions] | L 12-19 | ||
| Mon., 9/23 | JV Football | VGW Techs | Away - Vinal Tech Field [Directions] | 3:45 p.m. | ||
| Tue., 9/24 | V Boys Cross Country | Thomaston, Housatonic Regional, Litchfield | Away - Black Rock State Park [Directions] | 4:15 p.m. | 2:25 PM | |
| Tue., 9/24 | V Boys Soccer | Terryville | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 2-0 | ||
| Tue., 9/24 | JV Boys Soccer | Terryville | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/24 | V Girls Cross Country | Thomaston, Housatonic Regional, Litchfield | Away - Black Rock State Park [Directions] | 4:15 p.m. | 2:25 pm | |
| Tue., 9/24 | V Field Hockey | Thomaston | Away - Thomaston H.S. Field [Directions] | L 0-3 | 2:25 PM | |
| Tue., 9/24 | JV Field Hockey | Thomaston | Away - Thomaston H.S. Field [Directions] | 5:00 p.m. | 2:25 PM | |
| Tue., 9/24 | V Girls Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | W 5-1 | 2:25 PM | |
| Tue., 9/24 | JV Girls Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | 2:25 PM | |
| Fri., 9/27 | V Boys Soccer | Nonnewaug | Home - Shepaug Valley Varsity Soccer Field [Directions] | T 0-0 | ||
| Fri., 9/27 | JV Boys Soccer | Nonnewaug | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/27 | V Field Hockey | Nonnewaug | Home - Joan Gauthey Field [Directions] | L 1-3 | ||
| Fri., 9/27 | JV Field Hockey | Nonnewaug | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Sat., 9/28 | V Football | Capital/Achievement | Home - Wolcott Tech Football Field [Directions] | L 0-48 | ||
| Sat., 9/28 | V Girls Soccer | Northwestern | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 2-1 | ||
| Sat., 9/28 | JV Girls Soccer | Northwestern | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 9/30 | JV Football | Capital/Achievement | Away - Riverside Park [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Boys Cross Country | Thomaston, Northwestern, Wamogo | Away - Black Rock State Park [Directions] | 4:15 p.m. | 2:25 PM | |
| Tue., 10/1 | V Boys Soccer | Litchfield | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 5-0 | ||
| Tue., 10/1 | JV Boys Soccer | Litchfield | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/1 | V Girls Cross Country | Thomaston, Northwestern, Wamogo | Away - Black Rock State Park [Directions] | 4:15 p.m. | 2:25 pm | |
| Tue., 10/1 | V Field Hockey | Housatonic Regional | Home - Joan Gauthey Field [Directions] | W 3-2 | ||
| Tue., 10/1 | JV Field Hockey | Housatonic Regional | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/1 | V Girls Soccer | Housatonic Regional | Away - High School Field [Directions] | W 7-2 | 2:00 PM | 1:50 PM Dismissal |
| Tue., 10/1 | JV Girls Soccer | Housatonic Regional | Away - High School JV Field [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Fri., 10/4 | V Boys Cross Country | Nonnewaug Invitational | Away | 4:00 p.m. | 2:25 PM | |
| Fri., 10/4 | V Boys Soccer | Thomaston | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 2-1 | ||
| Fri., 10/4 | V Girls Cross Country | Nonnewaug Invitational | Away | 4:00 p.m. | 2:25 PM | |
| Fri., 10/4 | V Field Hockey | Northwestern | Away - NWR Varsity Field [Directions] | L 2-3 | 2:00 PM | 1:50 PM Dismissal |
| Fri., 10/4 | JV Field Hockey | Northwestern | Away - NWR Varsity Field [Directions] | 5:00 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Fri., 10/4 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | L 2-1 | 3:15 PM | |
| Fri., 10/4 | JV Girls Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | 4:30 p.m. | 3:15 PM | |
| Sat., 10/5 | V Football | Wilcox/Kaynor | Home - Wolcott Tech Football Field [Directions] | L 40-48 | ||
| Mon., 10/7 | JV Football | Wilcox/Kaynor | Away - Wilcox Tech Field [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Boys Cross Country | Nonnewaug | Away - Nonnewaug HS XC Course [Directions] | 4:00 p.m. | 2:25 PM | |
| Tue., 10/8 | V Boys Soccer | Gilbert | Away - Walker Field [Directions] | W 2-1 | 2:00 PM | 1:50 PM Dismissal |
| Tue., 10/8 | JV Boys Soccer | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 10/8 | V Girls Cross Country | Nonnewaug | Away - Nonnewaug HS XC Course [Directions] | 4:00 p.m. | 2:25 pm | |
| Tue., 10/8 | V Field Hockey | Litchfield | Home - Joan Gauthey Field [Directions] | W 6-0 | ||
| Tue., 10/8 | JV Field Hockey | Litchfield | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Wed., 10/9 | V Girls Soccer | Terryville | Away - New Terryville High School [Directions] | W 6-0 | 2:15 PM | 2:05 PM Dismissal |
| Wed., 10/9 | JV Girls Soccer | Terryville | Away - New Terryville High School [Directions] | 3:45 p.m. | 2:15 PM | 2:05 PM Dismissal |
| Thu., 10/10 | V Boys Soccer | Lewis Mills | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 0-1 | ||
| Thu., 10/10 | JV Boys Soccer | Lewis Mills | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Sat., 10/12 | V Boys Cross Country | Wickham Park Invitational | Away - Wickham Park, Manchester | 11:25 a.m. | 8:30 AM | JV at 11:25, Varsity at 1:50 |
| Sat., 10/12 | V Football | Whitney Tech | Away - O'Brien Tech Sports Complex [Directions] | W 34-0 | ||
| Sat., 10/12 | V Girls Cross Country | Wickham Park Invitational | Away - Wickham Park, Manchester | 10:50 a.m. | 8:30 AM | JV at 10:50, Varsity at 1:15 |
| Mon., 10/14 | JV Football | Lewis Mills | Away [Directions] | Cancelled | ||
| Mon., 10/14 | School Holidays and Closings | Columbus Day | ||||
| Tue., 10/15 | V Boys Soccer | Northwestern | Away - Northwestern Field [Directions] | L 2-1 | 2:00 PM | 1:50 PM Dismissal |
| Tue., 10/15 | JV Boys Soccer | Northwestern | Away - Northwestern Field [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 10/15 | V Field Hockey | Lewis Mills | Away - Lewis Mills Field Hockey Field [Directions] | L 4-0 | 2:00 PM | 1:50 PM Dismissal |
| Tue., 10/15 | JV Field Hockey | Lewis Mills | Away - Lewis Mills Field Hockey Field [Directions] | 5:00 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 10/15 | V Girls Soccer | Gilbert | Away - Walker Field [Directions] | W 2-1 | 2:00 PM | 1:50 PM Dismissal |
| Wed., 10/16 | V Girls Soccer | Lewis Mills | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 4-1 | ||
| Wed., 10/16 | School Holidays and Closings | Parent-Teacher Conferences | ||||
| Thu., 10/17 | V Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | L 0-7 | 3:45 PM | |
| Thu., 10/17 | JV Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 5:30 p.m. | 3:45 PM | |
| Thu., 10/17 | V Girls Soccer | Nonnewaug | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 2-0 | ||
| Thu., 10/17 | JV Girls Soccer | Nonnewaug | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/17 | School Holidays and Closings | Parent-Teacher Conferences | ||||
| Fri., 10/18 | V Boys Cross Country | BL Championship | Away - Black Rock State Park | 2:45 p.m. | 12:45 PM | JV 2:45; Varsity 4:15 |
| Fri., 10/18 | V Boys Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | L 3-5 | 2:25 PM | |
| Fri., 10/18 | JV Boys Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | 2:25 PM | |
| Fri., 10/18 | V Girls Cross Country | BL Championship | Away - Black Rock State Park | 3:30 p.m. | 12:45 pm | |
| Fri., 10/18 | V Field Hockey | Wamogo | Home - Joan Gauthey Field [Directions] | W 3-1 | ||
| Fri., 10/18 | JV Field Hockey | Wamogo | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Fri., 10/18 | School Holidays and Closings | Parent-Teacher Conferences | ||||
| Sat., 10/19 | V Boys Cross Country | BL Championship Rain Date | Away | 10:30 a.m. | TBA | JV 10:30; Varsity 12:00 |
| Sat., 10/19 | V Football | Prince Tech-Innovation | Home - Wolcott Tech Football Field [Directions] | L 18-45 | ||
| Sat., 10/19 | V Girls Cross Country | BL Championship Rain Date | Away | 11:15 a.m. | TBA | JV 10:30; Varsity 12:00 |
| Mon., 10/21 | JV Football | Prince Tech-Innovation | Away [Directions] | TBA | ||
| Mon., 10/21 | V Boys Soccer | Housatonic Regional | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 2-0 | ||
| Mon., 10/21 | JV Boys Soccer | Housatonic Regional | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/22 | V Field Hockey | Thomaston | Home - Joan Gauthey Field [Directions] | L 2-4 | ||
| Tue., 10/22 | JV Field Hockey | Thomaston | Home - Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/22 | V Girls Soccer | Wamogo | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 5-0 | ||
| Tue., 10/22 | JV Girls Soccer | Wamogo | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/23 | V Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | L 0-3 | 2:25 PM | |
| Wed., 10/23 | JV Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | 5:30 p.m. | 2:25 PM | |
| Fri., 10/25 | V Football | Putnam | Away - Ellis Tech Football Field [Directions] | L 0-48 | ||
| Fri., 10/25 | V Boys Soccer | Terryville | Away - New Terryville High School [Directions] | L 1-3 | 2:15 PM | 2:05 PM Dismissal |
| Fri., 10/25 | JV Boys Soccer | Terryville | Away - New Terryville High School [Directions] | 3:45 p.m. | 2:15 PM | 2:05 PM Dismissal |
| Fri., 10/25 | V Field Hockey | Nonnewaug | Away - Nonnewaug High School [Directions] | L 0-4 | 2:25 PM | |
| Fri., 10/25 | JV Field Hockey | Nonnewaug | Away - Nonnewaug High School [Directions] | 5:00 p.m. | 2:25 PM | |
| Fri., 10/25 | Miscellaneous Events | MS 6th Grade Social | 2:30-4:15 p.m. | |||
| Sat., 10/26 | V Boys Cross Country | CIAC Class S Championship | Away | TBA | 6:15 AM | |
| Sat., 10/26 | V Girls Cross Country | CIAC Class S Championship | Away | TBA | 6:15 AM | |
| Sat., 10/26 | V Girls Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | L 2-0 | 2:00 PM | 1:50 PM Dismissal |
| Sat., 10/26 | JV Girls Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Mon., 10/28 | V Boys Soccer | Thomaston | Away - Highwood Farms Field [Directions] | W 3-1 | 2:25 PM | |
| Mon., 10/28 | V Field Hockey | Housatonic Regional | Away - High School Field [Directions] | W 2-0 | 2:00 PM | 1:50 PM Dismissal |
| Mon., 10/28 | JV Field Hockey | Housatonic Regional | Away - High School Field [Directions] | 5:00 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Mon., 10/28 | V Girls Soccer | Housatonic Regional | Home - Shepaug Valley Varsity Soccer Field [Directions] | L 2-0 | ||
| Mon., 10/28 | JV Girls Soccer | Housatonic Regional | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/30 | V Boys Soccer | Nonnewaug | Away - Nonnewaug High School [Directions] | L 1-2 | 2:25 PM | |
| Wed., 10/30 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug High School [Directions] | 3:45 p.m. | 2:25 PM | |
| Wed., 10/30 | V Girls Soccer | Litchfield | Home - Shepaug Valley Varsity Soccer Field [Directions] | W 1-0 | ||
| Wed., 10/30 | JV Girls Soccer | Litchfield | Home - Shepaug Valley High School JV Soccer Field [Directions] | 3:45 p.m. | 2:25 PM | |
| Fri., 11/1 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park, Manchester | 3:30 p.m. | 12:30 PM | |
| Fri., 11/1 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park, Manchester | 4:15 p.m. | 12:30 PM | |
| Fri., 11/1 | School Holidays and Closings | No School - Professional Development | ||||
| Sat., 11/2 | V Football | Platt Tech | Away - foran [Directions] | L 21-64 | ||
| Mon., 11/4 | JV Football | Platt Tech | Home - tba [Directions] | Cancelled | ||
| Mon., 11/4 | V Field Hockey | Enfield | Home [Directions] | 2:00 p.m. | 12:50 PM Dismissal | |
| Mon., 11/4 | V Girls Soccer | Coventry | Away - Coventry High School [Directions] | L 3-0 | 1:00 PM | 12:50 PM Dismissal |
| Tue., 11/5 | V Field Hockey | Nonnewaug | Away [Directions] | 2:00 p.m. | 12:40 PM | 12:25 PM Dismissal |
| Sat., 11/9 | V Football | Bullard/Kolbe | Home - Wolcott Tech Football Field [Directions] | L 18-65 | ||
| Mon., 11/11 | School Holidays and Closings | Veteran's Day | ||||
| Tue., 11/12 | JV Football | Bullard/Kolbe | Away - Bullard Havens Field [Directions] | 3:00 p.m. | ||
| Sat., 11/16 | V Football | O'Brien Tech | Away - O'Brien Tech Athletic Complex [Directions] | L 12-28 | ||
| Mon., 11/18 | JV Football | Lewis Mills | Home - OWTS School Field [Directions] | 3:00 p.m. | ||
| Wed., 11/27 | School Holidays and Closings | Thanksgiving Recess | ||||
| Thu., 11/28 | V Football | ATI | Away - Stephen A. Kaplanis Field, Broadview MS [Directions] | L 34-44 | ||
| Thu., 11/28 | School Holidays and Closings | Thanksgiving Recess | ||||
| Fri., 11/29 | School Holidays and Closings | Thanksgiving Recess | ||||
| Sat., 11/30 | V Girls Basketball | Kennedy (Scrim.) | Home [Directions] | 10:00 a.m. | ||
| Sat., 12/7 | V Boys Basketball | O'Brien Tech (Scrim.) | Home - Ted Alex Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 12/7 | V Wrestling | Nonnewaug (Scrim.) | Away [Directions] | 10:00 a.m. | 8:00am | |
| Sat., 12/7 | V Girls Basketball | Brookfield (Scrim.) | Away [Directions] | 9:30 a.m. | 8:15 AM | |
| Sat., 12/7 | JV Girls Basketball | Brookfield (Scrim.) | Away [Directions] | 9:00 a.m. | 7:30 AM | |
| Wed., 12/11 | V Boys Ice Hockey | Shepaug Jamboree | Home - Gunnery Rink [Directions] | 7:15 p.m. | ||
| Wed., 12/11 | V Competitive Cheerleading | Wamogo | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Wed., 12/11 | V Girls Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | L 42-45 | ||
| Wed., 12/11 | JV Girls Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 12/12 | V Boys Basketball | Plainville (Scrim.) | Away - Wood Gymnasium [Directions] | 5:00 p.m. | 3:15 PM | |
| Fri., 12/13 | V Boys Basketball | Wolcott Tech (Scrim.) | Home - Ted Alex Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 12/13 | V Boys Swimming and Diving | Berkshire League Relays | Home - Shepaug Valley High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 12/13 | V Girls Basketball | Northwestern | Away - Northwestern Gym [Directions] | L 26-35 | 4:00 PM | |
| Fri., 12/13 | JV Girls Basketball | Northwestern | Away - Northwestern Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Fri., 12/13 | School Holidays and Closings | Early Release - Professional Development | ||||
| Wed., 12/18 | V Boys Basketball | Litchfield | Away - Litchfield High School [Directions] | L 37-69 | 4:30 PM | |
| Wed., 12/18 | JV Boys Basketball | Litchfield | Away - Litchfield High School [Directions] | 5:30 p.m. | 4:30 PM | |
| Wed., 12/18 | V Boys Ice Hockey | New Fairfield | Home - Rumsey Hall School Rink [Directions] | L 0-3 | ||
| Wed., 12/18 | V Boys Swimming and Diving | Watertown | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Wed., 12/18 | V Wrestling | Joel Barlow | Away - Upper Gym [Directions] | 6:00 p.m. | 4:00 P.M. | @ Barlow High School upper gym |
| Wed., 12/18 | V Competitive Cheerleading | Litchfield | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Wed., 12/18 | V Girls Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | W 32-31 | ||
| Wed., 12/18 | JV Girls Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/20 | V Boys Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | L 44-73 | ALUMNI NIGHT | |
| Fri., 12/20 | JV Boys Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/20 | FR Boys Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 12/20 | V Boys Swimming and Diving | Lewis Mills | Home - Shepaug Valley High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 12/20 | V Competitive Cheerleading | Gilbert | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Fri., 12/20 | V Girls Basketball | Gilbert | Away - Gilbert Gym [Directions] | W 24-22 | 4:00 PM | |
| Fri., 12/20 | JV Girls Basketball | Gilbert | Away - Gilbert Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Sat., 12/21 | V Boys Ice Hockey | Sheehan | Home - Rumsey Hall School Rink [Directions] | L 2-9 | ||
| Mon., 12/23 | V Wrestling | Nonnewaug tournament | Away - nonnewaug gym | 7:30 a.m. | 6:45 a.m. | |
| Mon., 12/23 | School Holidays and Closings | Holiday Recess | ||||
| Tue., 12/24 | School Holidays and Closings | Holiday Recess | ||||
| Wed., 12/25 | School Holidays and Closings | Holiday Recess | ||||
| Thu., 12/26 | School Holidays and Closings | Holiday Recess | ||||
| Fri., 12/27 | V Boys Basketball | Abbott Tech | Away - Daniel A. Garamella Memorial Gymnasium [Directions] | L 36-79 | 4:00 PM | |
| Fri., 12/27 | JV Boys Basketball | Abbott Tech | Away - Daniel A. Garamella Memorial Gymnasium [Directions] | 5:30 p.m. | 4:00 PM | |
| Fri., 12/27 | FR Boys Basketball | Abbott Tech | Away - Daniel A. Garamella Memorial Gymnasium [Directions] | 4:00 p.m. | 2:00 PM | |
| Fri., 12/27 | V Boys Swimming and Diving | Sacred Heart | Away - Kennedy High School Pool | 4:00 p.m. | 2:10 PM | |
| Fri., 12/27 | V Competitive Cheerleading | Abbott Tech | Home - Ted Alex Gymnasium [Directions] | 2:30 p.m. | Girls Basketball Game | |
| Fri., 12/27 | V Girls Basketball | Abbott Tech | Home - Ted Alex Gymnasium [Directions] | W 45-23 | ||
| Fri., 12/27 | JV Girls Basketball | Abbott Tech | Home - Ted Alex Gymnasium [Directions] | 1:00 p.m. | ||
| Fri., 12/27 | School Holidays and Closings | Holiday Recess | ||||
| Mon., 12/30 | V Boys Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | L 41-47 | ||
| Mon., 12/30 | JV Boys Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 12/30 | V Boys Ice Hockey | Eastern CT Eagles | Away - Connecticut College [Directions] | W 9-1 | 12:25 PM | |
| Mon., 12/30 | V Competitive Cheerleading | Thomaston | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Mon., 12/30 | School Holidays and Closings | Holiday Recess | ||||
| Tue., 12/31 | V Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | L 26-62 | 11:45 AM | |
| Tue., 12/31 | JV Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 1:00 p.m. | 11:45 AM | |
| Tue., 12/31 | School Holidays and Closings | Holiday Recess | ||||
| Wed., 1/1 | School Holidays and Closings | Holiday Recess | ||||
| Sat., 1/4 | V Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | L 28-66 | 12:45 PM | |
| Sat., 1/4 | JV Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 2:30 p.m. | 12:45 PM | |
| Sat., 1/4 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Pool [Directions] | 2:00 p.m. | ||
| Sat., 1/4 | V Wrestling | Derby/Oxford/Holy Cross | Away [Directions] | 10:00 a.m. | 8:00 a.m. | |
| Sat., 1/4 | V Wrestling | Fairfield Warde Touranment | Away | Cancelled | 6:45 a.m. | |
| Tue., 1/7 | V Boys Basketball | Terryville | Home - Ted Alex Gymnasium [Directions] | L 39-79 | ||
| Tue., 1/7 | JV Boys Basketball | Terryville | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/7 | V Boys Swimming and Diving | Avon | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 1/7 | V Competitive Cheerleading | Terryville | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Tue., 1/7 | V Girls Basketball | Terryville | Away - New Terryville High School [Directions] | L 28-59 | 4:15 PM | |
| Tue., 1/7 | JV Girls Basketball | Terryville | Away - New Terryville High School [Directions] | 5:30 p.m. | 4:15 PM | |
| Wed., 1/8 | V Boys Ice Hockey | Housatonic Coop | Away - Hotchkiss [Directions] | L 0-2 | 5:00 PM | |
| Wed., 1/8 | V Wrestling | Oxford | Home - BHS Small Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/9 | V Competitive Cheerleading | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Thu., 1/9 | V Girls Basketball | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | L 23-46 | ||
| Thu., 1/9 | JV Girls Basketball | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/10 | V Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | L 36-70 | 4:00 PM | |
| Fri., 1/10 | JV Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Fri., 1/10 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Gunnery Rink [Directions] | L 3-10 | ||
| Fri., 1/10 | V Competitive Cheerleading | Northwestern | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Fri., 1/10 | V Girls Basketball | Northwestern | Home - Ted Alex Gymnasium [Directions] | L 17-30 | ||
| Fri., 1/10 | JV Girls Basketball | Northwestern | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 1/11 | FR Boys Basketball | Wamogo | Away - Wamogo Gym 2 (Small Gym) [Directions] | 10:30 a.m. | 9:30 AM | |
| Sat., 1/11 | V Boys Swimming and Diving | Gilbert | Away - Winsted YMCA [Directions] | 4:30 p.m. | 2:25 PM | |
| Sat., 1/11 | V Wrestling | East Haven Duals | Away | 7:45 a.m. | 6:30 a.m. | |
| Mon., 1/13 | FR Boys Basketball | Litchfield | Away - Litchfield High School [Directions] | 7:00 p.m. | 5:45 PM | |
| Mon., 1/13 | V Boys Ice Hockey | Mt. Everett (MA) | Home - Gunnery Rink [Directions] | W 8-3 | ||
| Mon., 1/13 | V Wrestling | Weston | Home - BHS Small Gym [Directions] | 5:00 p.m. | ||
| Tue., 1/14 | V Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | L 51-70 | 4:00 PM | |
| Tue., 1/14 | JV Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 5:30 p.m. | 4:00 PM | |
| Tue., 1/14 | V Boys Swimming and Diving | Wamogo | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 1/14 | V Competitive Cheerleading | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Tue., 1/14 | V Girls Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | L 37-66 | ||
| Tue., 1/14 | JV Girls Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/15 | V Boys Ice Hockey | Mt. Everett (MA) | Away - Berkshire School | W 5-4 | 4:15 PM | |
| Wed., 1/15 | V Wrestling | New Fairfield | Away - New Fairfield HS [Directions] | 6:00 p.m. | 4:30 p.m. | |
| Fri., 1/17 | V Boys Basketball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | L 27-84 | 4:30 PM | |
| Fri., 1/17 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | 5:30 p.m. | 4:30 PM | |
| Fri., 1/17 | V Wrestling | Harding/Bassick/Bridgeport Central | Away [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Fri., 1/17 | JV Wrestling | Tournament Game - Opponent Not Known | Away - pomperaug HS | 3:30 p.m. | 2:30 p.m. | |
| Fri., 1/17 | V Competitive Cheerleading | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Fri., 1/17 | V Girls Basketball | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | L 31-48 | ||
| Fri., 1/17 | JV Girls Basketball | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/17 | School Holidays and Closings | Early Release - Professional Development | ||||
| Sat., 1/18 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena [Directions] | W 4-3 | 2:35 PM | |
| Sat., 1/18 | V Boys Swimming and Diving | Lewis Mills | Away - Giamatti Center - Bristol [Directions] | 6:45 p.m. | 5:00 PM | |
| Mon., 1/20 | V Boys Ice Hockey | Eastern CT Eagles | Home - Gunnery Rink [Directions] | W 5-2 | ||
| Mon., 1/20 | School Holidays and Closings | Martin Luther King Day | ||||
| Wed., 1/22 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall [Directions] | L 4-9 | 4:30 PM | |
| Wed., 1/22 | V Wrestling | Bethel | Away - Bethel High School [Directions] | 6:00 p.m. | 4:00 P.M. | |
| Thu., 1/23 | V Boys Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | W 47-35 | ||
| Thu., 1/23 | JV Boys Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 1/23 | V Boys Ice Hockey | Forman School (Scrim.) | Home - Rumsey Hall Rink [Directions] | 7:15 p.m. | ||
| Thu., 1/23 | V Competitive Cheerleading | Wamogo | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Thu., 1/23 | V Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | L 32-46 | 4:30 PM | |
| Thu., 1/23 | JV Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | 4:30 PM | |
| Fri., 1/24 | V Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | L 32-73 | 4:00 PM | |
| Fri., 1/24 | JV Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Fri., 1/24 | FR Boys Basketball | Gilbert | Away - Gilbert Gym [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Fri., 1/24 | V Competitive Cheerleading | Gilbert | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Fri., 1/24 | V Girls Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | W 34-23 | SBA Night-Girls 3rd & 4th | |
| Fri., 1/24 | JV Girls Basketball | Gilbert | Home - Ted Alex Gymnasium [Directions] | Cancelled | ||
| Sat., 1/25 | FR Boys Basketball | O'Brien Tech | Home - Ted Alex Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 1/25 | V Boys Swimming and Diving | Northwestern | Away - Winsted YMCA [Directions] | 4:30 p.m. | 2:25 PM | |
| Mon., 1/27 | V Boys Ice Hockey | JBWA | Home - Gunnery Rink [Directions] | L 2-3 | ||
| Tue., 1/28 | V Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | L 40-57 | 4:15 PM | |
| Tue., 1/28 | JV Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | 4:15 PM | |
| Tue., 1/28 | V Boys Swimming and Diving | Wamogo | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 1/28 | V Competitive Cheerleading | Thomaston | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Tue., 1/28 | V Girls Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | L 28-59 | SBA Night-Girls 5th & 6th | |
| Tue., 1/28 | JV Girls Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/29 | FR Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 7:00 p.m. | 5:30 PM | |
| Wed., 1/29 | V Wrestling | Masuk | Home - BHS Small Gym [Directions] | Cancelled | ||
| Fri., 1/31 | V Boys Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | L 57-62 | SBA Night-Heat vs Spurs | |
| Fri., 1/31 | JV Boys Basketball | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/31 | V Boys Swimming and Diving | Oxford | Home - Shepaug Valley High School Pool [Directions] | Cancelled | ||
| Fri., 1/31 | V Competitive Cheerleading | Housatonic Regional | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Fri., 1/31 | V Girls Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | L 23-48 | 4:00 PM | |
| Fri., 1/31 | JV Girls Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 5:30 p.m. | 4:00 PM | |
| Sat., 2/1 | V Boys Ice Hockey | E.O. Smith-Tolland | Away - UConn Hockey Arena [Directions] | L 3-4 | 12:45 PM | |
| Sat., 2/1 | V Wrestling | Pomperaug Tournament | Away - PHS Main Gym | 10:00 a.m. | 8:30 a.m. | |
| Tue., 2/4 | V Boys Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | L 32-79 | SBA Night-Knicks vs Celtics | |
| Tue., 2/4 | JV Boys Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/4 | V Boys Swimming and Diving | Housatonic Regional | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/4 | V Competitive Cheerleading | Litchfield | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Tue., 2/4 | V Girls Basketball | Litchfield | Away - Litchfield High School [Directions] | W 33-30 (OT) | 4:30 PM | |
| Tue., 2/4 | JV Girls Basketball | Litchfield | Away - Litchfield High School [Directions] | 5:30 p.m. | 4:30 PM | |
| Wed., 2/5 | V Wrestling | Bunnell | Away - Bunnell [Directions] | Cancelled | 4:30 p.m. | |
| Thu., 2/6 | FR Boys Basketball | Thomaston | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | ||
| Thu., 2/6 | V Boys Ice Hockey | New Milford | Away - Canterbury School [Directions] | L 2-9 | 6:30 PM | |
| Fri., 2/7 | V Boys Swimming and Diving | Gilbert | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Sat., 2/8 | V Boys Ice Hockey | Danbury | Away - Danbury Ice Arena [Directions] | L 4-5 | 9:40 AM | |
| Sat., 2/8 | V Boys Swimming and Diving | Girls Sprint Meet | Home - Shepaug Valley High School Pool [Directions] | 11:00 a.m. | ||
| Mon., 2/10 | FR Boys Basketball | Immaculate | Away - Immaculate High School [Directions] | 7:00 p.m. | 5:15 PM | |
| Mon., 2/10 | V Boys Ice Hockey | Masuk | Home - Gunnery Rink [Directions] | L 3-6 | ||
| Tue., 2/11 | V Boys Basketball | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | L 36-81 | SBA Night-Thunder vs Lakers | |
| Tue., 2/11 | JV Boys Basketball | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/11 | V Competitive Cheerleading | Lewis Mills | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Tue., 2/11 | V Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | L 14-39 | 4:00 PM | |
| Tue., 2/11 | JV Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Wed., 2/12 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Gunnery Rink [Directions] | L 2-3 (OT) | ||
| Wed., 2/12 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss Pool [Directions] | 5:00 p.m. | 3:00 PM | |
| Wed., 2/12 | V Wrestling | New Milford | Home - BHS Big Gym [Directions] | Cancelled | ||
| Thu., 2/13 | FR Boys Basketball | Abbott Tech | Home - Ted Alex Gymnasium [Directions] | Cancelled | ||
| Fri., 2/14 | V Boys Basketball | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | L 48-64 | SBA Night-Bulls vs Lakers | |
| Fri., 2/14 | JV Boys Basketball | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | Cancelled | ||
| Fri., 2/14 | V Competitive Cheerleading | Nonnewaug | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | Boys Basketball Game | |
| Fri., 2/14 | V Girls Basketball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | L 20-40 | 4:15 PM | |
| Fri., 2/14 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | Cancelled | 2:25 PM | |
| Fri., 2/14 | Miscellaneous Events | MS 6th Grade Social | 2:30-4:15 p.m. | |||
| Sat., 2/15 | V Wrestling | SWC Championship | Away | Cancelled | SWC championship at Pomperaug | |
| Mon., 2/17 | School Holidays and Closings | President's Day | ||||
| Tue., 2/18 | School Holidays and Closings | No School - Professional Development | ||||
| Wed., 2/19 | FR Boys Basketball | Wamogo | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 2/19 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | L 1-4 | 5:00 PM | |
| Wed., 2/19 | V Boys Swimming and Diving | Northwestern | Home - Shepaug Valley High School Pool [Directions] | 5:00 p.m. | ||
| Thu., 2/20 | V Boys Ice Hockey | Forman School (Scrim.) | Home - Gunnery Rink [Directions] | 7:15 p.m. | ||
| Thu., 2/20 | V Girls Basketball | Abbott Tech | Away - Daniel A. Garamella Memorial Gymnasium [Directions] | W 59-21 | 3:00 PM | |
| Thu., 2/20 | JV Girls Basketball | Abbott Tech | Away - Daniel A. Garamella Memorial Gymnasium [Directions] | 4:30 p.m. | 3:00 PM | |
| Fri., 2/21 | V Boys Basketball | Canton | Home - Ted Alex Gymnasium [Directions] | L 54-78 | ||
| Fri., 2/21 | JV Boys Basketball | Canton | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/21 | V Competitive Cheerleading | Canton | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Sat., 2/22 | V Boys Basketball | Terryville | Away - New Terryville High School [Directions] | L 44-86 | 4:15 PM | |
| Sat., 2/22 | JV Boys Basketball | Terryville | Away - New Terryville High School [Directions] | 5:30 p.m. | 4:15 PM | |
| Sat., 2/22 | FR Boys Basketball | O'Brien Tech | Home - Ted Alex Gymnasium [Directions] | 12:00 p.m. | ||
| Sat., 2/22 | V Boys Swimming and Diving | Girls Splash Classic | Away - Plainville High School | 2:00 p.m. | 11:00 AM | |
| Mon., 2/24 | V Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | L 47-58 | 4:30 PM | |
| Mon., 2/24 | JV Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | 4:30 PM | |
| Mon., 2/24 | V Boys Ice Hockey | Housatonic Coop | Home - Gunnery Rink [Directions] | L 0-1 | Senior Night | |
| Mon., 2/24 | V Competitive Cheerleading | Terryville | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Girls Basketball Game | |
| Mon., 2/24 | V Girls Basketball | Terryville | Home - Ted Alex Gymnasium [Directions] | L 33-38 | ||
| Mon., 2/24 | JV Girls Basketball | Terryville | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/25 | FR Boys Basketball | Litchfield | Home - Ted Alex Gymnasium [Directions] | Cancelled | ||
| Tue., 2/25 | V Boys Swimming and Diving | Litchfield | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Wed., 2/26 | V Boys Basketball | Northwestern | Home - Ted Alex Gymnasium [Directions] | L 48-75 | ||
| Wed., 2/26 | JV Boys Basketball | Northwestern | Home - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/26 | V Competitive Cheerleading | Northwestern | Home - Ted Alex Gymnasium [Directions] | 7:00 p.m. | Boys Basketball Game | |
| Fri., 2/28 | V Boys Ice Hockey | New Fairfield | Away - Danbury Ice Arena [Directions] | L 1-7 | 3:30 PM | |
| Fri., 2/28 | V Boys Swimming and Diving | Holy Cross | Home - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Sat., 3/1 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavillion [Directions] | L 0-6 | 5:00 PM | |
| Fri., 3/7 | V Boys Swimming and Diving | Berkshire League Diving Championships | Home - Shepaug Valley High School Pool [Directions] | 6:00 p.m. | ||
| Sat., 3/8 | V Boys Swimming and Diving | Berkshire League Swimming Championship | Away - Hotchkiss School | 1:00 p.m. | 9:45 AM | |
| Mon., 3/10 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall [Directions] | 7:00 p.m. | 4:15 PM | |
| Wed., 3/12 | V Boys Swimming and Diving | Class S Diving | Away - Plainville High School | 5:30 p.m. | TBA | |
| Thu., 3/13 | School Holidays and Closings | Early Release - Professional Development | ||||
| Sat., 3/15 | V Boys Swimming and Diving | Class S Trials | Away - Plainville High School | 3:30 p.m. | 12:00 PM | |
| Tue., 3/18 | V Boys Swimming and Diving | Class S Finals | Away - Freeman Center - Wesleyan University, Middletown CT | 7:15 p.m. | 4:30 PM | |
| Thu., 3/20 | V Boys Swimming and Diving | Open Diving Championships | Away - Middletown High School | 5:30 p.m. | ||
| Sat., 3/22 | V Boys Swimming and Diving | CIAC Open | Away - Yale University | 2:30 p.m. | ||
| Fri., 3/28 | School Holidays and Closings | Early Release - Professional Development | ||||
| Wed., 4/2 | V Baseball | Torrington (Scrim.) | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Wed., 4/2 | V Softball | New Milford (Scrim.) | Away - New Milford High School [Directions] | 3:45 p.m. | 2:25 PM | |
| Thu., 4/3 | V Baseball | New Milford (Scrim.) | Away - New Milford High School [Directions] | 3:45 p.m. | 2:25 PM | |
| Thu., 4/3 | V Boys Tennis | Bethel (Scrim.) | Home - Shepaug Valley High School Courts [Directions] | 3:45 p.m. | ||
| Thu., 4/3 | V Girls Tennis | Bethel (Scrim.) | Away - Bethel High School [Directions] | 3:45 p.m. | 2:25 PM | |
| Thu., 4/3 | School Holidays and Closings | Early Release - Professional Development | ||||
| Sat., 4/5 | V Baseball | Haddam-Killingworth (Scrim.) | Home - Ted Alex Field [Directions] | 11:00 a.m. | ||
| Sat., 4/5 | V Softball | Weston (Scrim.) | Home - Dick Ayer Field [Directions] | 12:00 p.m. | ||
| Wed., 4/9 | V Baseball | Lewis Mills | Away - Lewis Mills Baseball Field [Directions] | L 10-9 | 2:00 PM | 1:50 PM Dismissal |
| Wed., 4/9 | V Boys Outdoor Track | Lewis Mills, Wamogo | Home - Shepaug Valley High School Track [Directions] | 3:45 p.m. | ||
| Wed., 4/9 | V Boys Tennis | Thomaston | Away - Thomaston Center School [Directions] | L 1-4 | 2:45 PM | |
| Wed., 4/9 | V Girls Outdoor Track | Lewis Mills, Wamogo | Home - Shepaug Valley High School Track [Directions] | 3:45 p.m. | ||
| Wed., 4/9 | V Softball | Lewis Mills | Home - Dick Ayer Field [Directions] | L 12-7 | ||
| Wed., 4/9 | V Girls Tennis | Thomaston | Home - Shepaug Valley High School Courts [Directions] | L 3-4 | ||
| Thu., 4/10 | JV Softball | Litchfield | Home - Dick Ayer Field [Directions] | 4:00 p.m. | ||
| Fri., 4/11 | V Baseball | Northwestern | Away - NWR Varsity Field [Directions] | L 5-6 | 2:00 PM | 1:50 PM Dismissal |
| Fri., 4/11 | V Softball | Northwestern | Home - Dick Ayer Field [Directions] | L 1-10 | ||
| Mon., 4/14 | V Baseball | Litchfield | Home - Ted Alex Field [Directions] | L 7-13 | ||
| Mon., 4/14 | V Boys Tennis | Litchfield | Away - Litchfield High School [Directions] | W 5-0 | 9:15 AM | |
| Mon., 4/14 | V Softball | Litchfield | Away - Plumb Hill Field Complex [Directions] | W 22-1 | 2:25 PM | Bus Departs from Washington Primary School |
| Mon., 4/14 | V Girls Tennis | Litchfield | Home - Shepaug Valley High School Courts [Directions] | L 1-6 | ||
| Mon., 4/14 | School Holidays and Closings | Spring Vacation | ||||
| Tue., 4/15 | School Holidays and Closings | Spring Vacation | ||||
| Wed., 4/16 | V Baseball | New Milford | Home - Ted Alex Field [Directions] | L 2-14 | ||
| Wed., 4/16 | School Holidays and Closings | Spring Vacation | ||||
| Thu., 4/17 | V Baseball | Wamogo | Home - Ted Alex Field [Directions] | W 6-0 | ||
| Thu., 4/17 | JV Baseball | Wamogo | Home - Ted Alex Field [Directions] | Cancelled | Bus Departs from Washington Primary School | |
| Thu., 4/17 | V Boys Outdoor Track | Gilbert, Housatonic Regional | Home - Shepaug Valley High School Track [Directions] | 12:00 p.m. | ||
| Thu., 4/17 | V Boys Tennis | Gilbert | Away - Gilbert [Directions] | W 4-1 | 2:00 PM | |
| Thu., 4/17 | V Girls Outdoor Track | Gilbert, Housatonic Regional | Home - Shepaug Valley High School Track [Directions] | 12:00 p.m. | ||
| Thu., 4/17 | V Softball | Wamogo/Litchfield | Home - Dick Ayer Field [Directions] | W 13-4 | ||
| Thu., 4/17 | School Holidays and Closings | Spring Vacation | ||||
| Fri., 4/18 | School Holidays and Closings | Spring Vacation | ||||
| Mon., 4/21 | V Baseball | Terryville | Home - Ted Alex Field [Directions] | W 8-7 | ||
| Mon., 4/21 | JV Baseball | Terryville | Home - Shepaug Valley High School JV Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 4/21 | V Boys Golf | Nonnewaug, Litchfield | Home - Washington Club [Directions] | Litchfield 177, Shepaug 183, Nonnewaug 200 | ||
| Mon., 4/21 | V Boys Tennis | Wamogo | Home - Shepaug Valley High School Courts [Directions] | W 3-2 | ||
| Mon., 4/21 | V Softball | Terryville | Away - New Terryville High School [Directions] | W 19-1 | 2:15 PM | 2:05 PM Dismissal |
| Mon., 4/21 | V Girls Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | W 7-0 | 2:25 PM | |
| Tue., 4/22 | V Boys Outdoor Track | Nonnewaug, Gilbert | Away - Nonnewaug High School [Directions] | 3:45 p.m. | 2:25 PM | |
| Tue., 4/22 | V Girls Outdoor Track | Nonnewaug, Gilbert | Away - Paul Burns Memorial Track [Directions] | 3:45 p.m. | 2:25 PM | |
| Wed., 4/23 | V Baseball | Thomaston | Home - Ted Alex Field [Directions] | L 4-1 | ||
| Wed., 4/23 | JV Baseball | Thomaston | Home - Shepaug Valley High School JV Baseball Field [Directions] | Cancelled | ||
| Wed., 4/23 | V Boys Golf | Terryville, Northwestern | Away - Pequabuck Golf Course, Bristol [Directions] | Shepaug 191, Northwestern 200, Terryville 228 | 2:00 PM | 1:50 PM Dismissal |
| Wed., 4/23 | V Boys Tennis | Northwestern | Away - Northwestern [Directions] | L 0-5 | 2:45 PM | |
| Wed., 4/23 | V Softball | Thomaston | Away - Bev Lowden Softball Field (T.H.S.) [Directions] | L 2-17(5) | 2:25 PM | |
| Wed., 4/23 | V Girls Tennis | Northwestern | Home - Shepaug Valley High School Courts [Directions] | L 3-4 | ||
| Thu., 4/24 | V Boys Golf | Lewis Mills, Thomaston | Away - Fairview Farm Golf Course [Directions] | Thomaston/Wamogo 181, Lweis Mills 195, Shepaug 210 | 1:50 PM | 1:40 PM Dismissal |
| Thu., 4/24 | V Boys Tennis | Nonnewaug | Home - Shepaug Valley High School Courts [Directions] | L 0-5 | ||
| Thu., 4/24 | V Girls Tennis | Nonnewaug | Away - Edgewood Bath and Tennis [Directions] | W 6-1 | 2:25 AM | |
| Fri., 4/25 | V Baseball | Terryville | Away - New Terryville High School [Directions] | L 3-10 | 2:15 PM | 2:05 PM Dismissal |
| Fri., 4/25 | JV Baseball | Terryville | Away - Lower Fisher Elementary [Directions] | Cancelled | 2:15 PM | 2:05 PM Dismissal |
| Fri., 4/25 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury High School | 6:00 p.m. | 3:30 PM | |
| Fri., 4/25 | V Boys Tennis | New Fairfield | Away - New Fairfield HS [Directions] | L 1-6 | 2:45 PM | |
| Fri., 4/25 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury High School | 6:00 p.m. | 4:00 PM | |
| Fri., 4/25 | V Softball | Terryville | Home - Dick Ayer Field [Directions] | W 19-4 | ||
| Sat., 4/26 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury High School | 9:00 a.m. | 7:00 AM | |
| Sat., 4/26 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury High School | 9:00 a.m. | 7:00 AM | |
| Mon., 4/28 | V Baseball | Gilbert | Home - Ted Alex Field [Directions] | W 6-2 | ||
| Mon., 4/28 | V Boys Golf | North Branford | Away - Tradition Golf Course - Wallingford [Directions] | Shepaug 181 North Branford 199 | 1:00 PM | 12:50 PM Dismissal |
| Mon., 4/28 | V Boys Tennis | Lewis Mills | Home - Shepaug Valley High School Courts [Directions] | L 0-5 | ||
| Mon., 4/28 | V Softball | Gilbert | Away - Walker Field [Directions] | W 17-6 | 2:00 PM | 1:50 PM Dismissal |
| Mon., 4/28 | V Girls Tennis | Lewis Mills | Away - Lewis Mills H.S. [Directions] | W 4-3 | 2:00 PM | 1:50 PM Dismissal |
| Tue., 4/29 | JV Baseball | Thomaston | Home - Ted Alex Field [Directions] | 3:45 p.m. | 2:25 PM | |
| Tue., 4/29 | V Boys Golf | Housatonic Regional | Away - Canaan Country Club [Directions] | Shepaug 171, Housatonic 209 | 1:15 PM | 1:05 PM Dismissal |
| Tue., 4/29 | V Boys Outdoor Track | Thomaston, Housatonic Regional | Home - Shepaug Valley High School Track [Directions] | 3:45 p.m. | ||
| Tue., 4/29 | V Girls Outdoor Track | Thomaston, Housatonic Regional | Home [Directions] | 3:45 p.m. | ||
| Tue., 4/29 | V Girls Tennis | Gilbert | Home - Shepaug Valley High School Courts [Directions] | W 7-0 | ||
| Wed., 4/30 | JV Baseball | Housatonic Regional | Away - High School Field [Directions] | Cancelled | 2:00 PM | 1:50 PM Dismissal |
| Thu., 5/1 | V Baseball | Nonnewaug | Home - Ted Alex Field [Directions] | W 10-6 | ||
| Thu., 5/1 | V Boys Golf | Woodland Hawk Invitational | Away - Oxford Greens | Cancelled | Coach Driving | |
| Thu., 5/1 | V Boys Tennis | Thomaston | Home - Shepaug Valley High School Courts [Directions] | L 1-4 | ||
| Thu., 5/1 | V Softball | Nonnewaug | Home - Dick Ayer Field [Directions] | L 3-8 | ||
| Thu., 5/1 | V Girls Tennis | Thomaston | Away - Thomaston Center School [Directions] | L 1-6 | 2:25 PM | |
| Fri., 5/2 | JV Baseball | Nonnewaug | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Fri., 5/2 | JV Softball | Nonnewaug | Home - Dick Ayer Field [Directions] | 3:45 p.m. | ||
| Fri., 5/2 | Miscellaneous Events | MS 6th Grade Social | 2:30-4:15 p.m. | |||
| Mon., 5/5 | V Baseball | Lewis Mills | Home - Ted Alex Field [Directions] | W 12-5 | ||
| Mon., 5/5 | JV Baseball | Lewis Mills | Home - Shepaug Valley High School JV Baseball Field [Directions] | Cancelled | ||
| Mon., 5/5 | V Boys Golf | Avon Invitational | Away - Blue Fox Run | Shepaug 189 | 10:30 AM | 10:20 AM Dismissal |
| Mon., 5/5 | V Boys Tennis | Gilbert | Home - Shepaug Valley High School Courts [Directions] | W 3-2 | ||
| Mon., 5/5 | V Softball | Lewis Mills | Away - Lewis Mills H.S. [Directions] | L 3-18 | 2:00 PM | 1:50 PM Dismissal |
| Mon., 5/5 | V Girls Tennis | Gilbert | Away - Gilbert [Directions] | W 7-0 | 2:00 PM | 1:50 PM Dismissal |
| Tue., 5/6 | V Baseball | Housatonic Regional | Away - High School Field [Directions] | L 3-7 | 2:00 PM | 1:50 PM Dismissal |
| Tue., 5/6 | V Boys Golf | New Milford | Home - Lake Waramaug Country Club [Directions] | New Milford 167, Shepaug 172 | ||
| Tue., 5/6 | V Boys Outdoor Track | Northwestern, Terryville, Gilbert | Away - Northwestern [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 5/6 | V Boys Tennis | Housatonic Regional | Away - High School Courts [Directions] | L 2-3 | 2:45 PM | |
| Tue., 5/6 | V Girls Outdoor Track | Northwestern, Terryville, Gilbert | Away - Northwestern [Directions] | 3:45 p.m. | 2:00 PM | 1:50 PM Dismissal |
| Tue., 5/6 | V Softball | Housatonic Regional | Home - Dick Ayer Field [Directions] | W 2-1 | ||
| Tue., 5/6 | JV Softball | Lewis Mills | Home - Dick Ayer Field [Directions] | Cancelled | ||
| Tue., 5/6 | V Girls Tennis | Housatonic Regional | Home - Shepaug Valley High School Courts [Directions] | W 7-0 | ||
| Wed., 5/7 | V Baseball | Northwestern | Home - Ted Alex Field [Directions] | L 1-15 | ||
| Wed., 5/7 | JV Baseball | Northwestern | Away - NWR Varsity Field [Directions] | Cancelled | 2:00 PM | 1:50 PM Dismissal |
| Wed., 5/7 | V Boys Golf | Stigberg Invitational | Away - Farmingbury Hills Golf Course | Cancelled | Coach Driving | |
| Wed., 5/7 | V Boys Tennis | Litchfield | Home - Shepaug Valley High School Courts [Directions] | W 3-2 | ||
| Wed., 5/7 | V Softball | Northwestern | Away - Northwestern Field [Directions] | L 1-21 | 2:00 PM | 1:50 PM Dismissal |
| Wed., 5/7 | V Girls Tennis | Litchfield | Away - Litchfield High School [Directions] | L 1-6 | 2:25 PM | |
| Thu., 5/8 | JV Baseball | Litchfield | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Thu., 5/8 | V Boys Golf | Thomaston, Northwestern | Home - Washington Club [Directions] | Thomaston/Wamogo 170, Shepaug 183, Northwestern 196 | ||
| Fri., 5/9 | V Baseball | Litchfield | Home - Ted Alex Field [Directions] | L 1-4 | 2:25 PM | |
| Fri., 5/9 | V Softball | Litchfield | Home - Dick Ayer Field [Directions] | W 17-3 | ||
| Sat., 5/10 | V Boys Outdoor Track | Spartan Invitational | Home [Directions] | 9:30 a.m. | ||
| Sat., 5/10 | V Girls Outdoor Track | Spartan Invitational | Home [Directions] | 9:30 a.m. | ||
| Mon., 5/12 | V Boys Golf | Gilbert, Terryville | Away - Greenwood Country Club [Directions] | Shepaug 186, Terryville 215, Gilbert 257 | 1:35 PM | 1:25 PM Dismissal |
| Mon., 5/12 | V Boys Outdoor Track | Wamogo, Northwestern, Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | 2:25 PM | |
| Mon., 5/12 | V Boys Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | L 2-3 | 2:45 PM | |
| Mon., 5/12 | V Girls Outdoor Track | Wamogo, Northwestern, Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | 2:25 PM | |
| Mon., 5/12 | V Softball | O'Brien Tech | Home - Dick Ayer Field [Directions] | W 22-0 | ||
| Mon., 5/12 | V Girls Tennis | Wamogo | Home - Shepaug Valley High School Courts [Directions] | W 7-0 | ||
| Tue., 5/13 | V Boys Golf | Nonnewaug | Away - Heitage Village CC [Directions] | Shepaug 185, Nonnewaug 179 | 2:15 PM | 2:05 PM Dismissal |
| Tue., 5/13 | JV Softball | Housatonic Regional | Away - Housatonic [Directions] | 4:00 p.m. | 2:25 PM | |
| Tue., 5/13 | V Girls Tennis | Northwestern | Away - Northwestern [Directions] | W 6-1 | 2:00 PM | 1:50 PM Dismissal |
| Wed., 5/14 | V Baseball | Wamogo | Away - Wamogo High School [Directions] | W 2-0 | ||
| Wed., 5/14 | V Boys Golf | Litchfield, Gilbert | Away - Litchfield CC [Directions] | Litchfield 162, Shepaug 167, Gilbert 267 | 2:15 PM | 2:05 PM Dismissal |
| Wed., 5/14 | V Boys Tennis | Northwestern | Home - Shepaug Valley High School Courts [Directions] | L 0-5 | ||
| Wed., 5/14 | V Softball | Wamogo/Litchfield | Away - Wamogo Varsity Softball Field [Directions] | L 2-4 | 2:25 PM | |
| Thu., 5/15 | JV Baseball | Wamogo | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Fri., 5/16 | JV Softball | Northwestern | Away - Northwestern Field [Directions] | Cancelled | 2:00 PM | 1:50 PM Dismissal |
| Sat., 5/17 | V Boys Outdoor Track | BL Championships | Away - Plumb Hill Complex, Litchfield | 9:00 a.m. | 7:15 AM | |
| Sat., 5/17 | V Boys Tennis | Berkshire League All-Star Tournament | Away - Litchfield High School | 12:00 p.m. | ||
| Sat., 5/17 | V Girls Outdoor Track | BL Championships | Away - Plumb Hill Complex, Litchfield | 9:00 a.m. | 7:15 AM | |
| Sat., 5/17 | V Girls Tennis | Berkshire League All-Star Tournament | Away - Wamogo High School | 12:00 p.m. | ||
| Sun., 5/18 | V Boys Outdoor Track | BL Championships Rain Date | Away - Plumb Hill Complex, Litchfield | 9:00 a.m. | 7:15 AM | |
| Sun., 5/18 | V Girls Outdoor Track | BL Championships Rain Date | Away - Plumb Hill Complex, Litchfield | 9:00 a.m. | 7:15 AM | |
| Mon., 5/19 | V Baseball | Thomaston | Away - Thomaston H.S. Field [Directions] | L 6-4 | 2:25 PM | |
| Mon., 5/19 | V Boys Golf | North Branford | Home - Lake Waramaug Country Club [Directions] | Shepaug 187, North Branford 193 | ||
| Mon., 5/19 | V Boys Tennis | Lewis Mills | Away - Lewis Mills H.S. [Directions] | L 2-3 | 3:30 PM | |
| Mon., 5/19 | V Softball | Thomaston | Home - Dick Ayer Field [Directions] | L 2-10 | ||
| Mon., 5/19 | V Girls Tennis | Lewis Mills | Home - Shepaug Valley High School Courts [Directions] | W 7-0 | ||
| Tue., 5/20 | JV Baseball | Litchfield | Home - Ted Alex Field [Directions] | 3:45 p.m. | ||
| Tue., 5/20 | V Boys Golf | Housatonic Regional, Lewis Mills | Home - Washington Club [Directions] | Lewis Mills 183, Shepaug 207, Housatonic 228 | ||
| Tue., 5/20 | V Boys Tennis | BL All-Star Tournament | Away | 11:00 a.m. | 10:00 AM | |
| Tue., 5/20 | V Softball | O'Brien Tech | Away - O'Brien Tech Athletic Complex [Directions] | W 22-4 | 2:00 PM | 1:50 PM Dismissal |
| Tue., 5/20 | V Girls Tennis | BL All-Star Tournament | Away - Wamogo High School | 11:00 a.m. | ||
| Wed., 5/21 | V Boys Tennis | Housatonic Regional | Home - Shepaug Valley High School Courts [Directions] | L 1-4 | ||
| Wed., 5/21 | JV Softball | Rumsey Hall | Home - Dick Ayer Field [Directions] | 4:00 p.m. | ||
| Wed., 5/21 | V Girls Tennis | Housatonic Regional | Away [Directions] | W 7-0 | 2:00 PM | 1:50 PM Dismissal |
| Wed., 5/21 | Unified Sports Track | Unified Track Meet | Away - Newington High School | 3:00 p.m. | 1:30 PM | 1:20 Dismissal |
| Thu., 5/22 | V Boys Golf | Chappa Invitational | Away - Longshore Country Club | TBA | Coach Driving | |
| Thu., 5/22 | V Boys Tennis | Nonnewaug | Away - Edgewood Bath and Tennis [Directions] | L 0-5 | 2:45 PM | |
| Fri., 5/23 | V Softball | Gilbert | Home - Dick Ayer Field [Directions] | W 7-5 | ||
| Fri., 5/23 | School Holidays and Closings | Early Release - Professional Development | ||||
| Mon., 5/26 | V Baseball | Gilbert | Away - Walker Field [Directions] | L 7-6 | 1:30 PM | |
| Mon., 5/26 | School Holidays and Closings | Memorial Day | ||||
| Tue., 5/27 | V Baseball | Kennedy | Home - Ted Alex Field [Directions] | W 4-1 | ||
| Tue., 5/27 | V Baseball | Housatonic Regional | Home - Ted Alex Field [Directions] | W 12-1 | ||
| Tue., 5/27 | JV Baseball | Housatonic Regional | Home - Shepaug Valley High School JV Baseball Field [Directions] | Cancelled | ||
| Tue., 5/27 | V Boys Golf | Berkshire League All Star Tourney | Away - Fairview Farm Golf Course | 7:30 a.m. | Coach Driving | |
| Tue., 5/27 | V Boys Tennis | Abbott Tech | Home - Shepaug Valley High School Courts [Directions] | W 7-0 | ||
| Tue., 5/27 | V Softball | Housatonic Regional | Away - High School Field [Directions] | W 7-0 | 2:00 PM | 1:50 PM |
| Wed., 5/28 | V Baseball | Nonnewaug | Home - Ted Alex Field [Directions] | W 6-3 | 2:25 PM | |
| Wed., 5/28 | JV Baseball | Nonnewaug | Home - Shepaug Valley High School JV Baseball Field [Directions] | Cancelled | ||
| Wed., 5/28 | V Softball | Nonnewaug | Away - Nonnewaug High School [Directions] | L 18-9 | 2:25 PM | |
| Wed., 5/28 | V Girls Tennis | Nonnewaug | Home - Shepaug Valley High School Courts [Directions] | W 5-2 | ||
| Sat., 5/31 | V Boys Tennis | CIAC Class S | Away - Conard High School, West Hartford | 8:30 a.m. | TBA | |
| Mon., 6/2 | V Baseball | Westbrook | Away [Directions] | 3:30 p.m. | 12:45 PM | 12:30 Dismissal |
| Mon., 6/2 | V Softball | St. Bernard | Away [Directions] | L 7-5 | 1:00 PM | 12:50 Dismissal |
| Mon., 6/2 | V Girls Tennis | Litchfield | Away [Directions] | 3:00 p.m. | 1:30 PM | 1:20 Dismissal |
| Wed., 6/4 | V Boys Outdoor Track | CIAC Class S Championship | Away - Danbury High School | 2:30 p.m. | 12:15 PM | 12:00 PM Dismissal |
| Wed., 6/4 | V Girls Outdoor Track | CIAC Class S Championship | Away - Danbury High School | 2:30 p.m. | 12:15 PM | 12:00 Dismissal |
| Fri., 6/6 | Miscellaneous Events | Shepaug Athletic Awards Night | Home - Shepaug Valley Auditorium [Directions] | 7:00 p.m. | ||
| Sat., 6/7 | V Girls Tennis | CIAC Individual Tournament | Away - Singles - Conard HS, Doubles - Hall HS, West Hartford | 1:00 p.m. | TBA | |
| Mon., 6/9 | V Boys Outdoor Track | CIAC Open Championship | Away - Middletown High School | 1:30 p.m. | 11:15 AM | 11:05 AM Dismissal |
| Mon., 6/9 | V Girls Outdoor Track | CIAC Open Championship | Away | 1:30 p.m. | 11:15 AM | 11:05 Dismissal |
| Wed., 6/11 | V Boys Golf | CIAC Class S Tournament | Away - Timberlin Golf Course, Berlin CT | 8:40 a.m. | 6:30 AM | |