| Wamogo 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 480 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Mon., 8/30 | V Boys Golf | Gilbert, Litchfield | Home - Wamogo HS-Stoneybrook Golf Course [Directions] | 3:00 p.m. | Gilbert 228 Litchfield 182 Wamogo 291 | |
| Tue., 8/31 | V Boys Soccer | WCA (Scrim.) | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 9/2 | V Football | Woodland (Scrim.) | Home - Nonnewaug HS-football field [Directions] | 6:00 p.m. | ||
| Thu., 9/2 | V Girls Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 3:45 p.m. | ||
| Fri., 9/3 | V Boys Soccer | Wolcott Tech (Scrim.) | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/3 | JV Boys Soccer | Wolcott Tech (Scrim.) | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | 3:45 p.m. | ||
| Sat., 9/4 | V Field Hockey | Field Hockey Pre-Season Play Day | Away - Farmington HS-Turf Field | 10:00 a.m. | ||
| Tue., 9/7 | V Boys Cross Country | BL Scrimmage | Away - Black Rock State Park | 4:00 p.m. | ||
| Tue., 9/7 | V Boys Golf | Terryville | Home - Wamogo HS-Stoneybrook Golf Course [Directions] | 3:00 p.m. | Terryville 281 wamogo 234 | |
| Tue., 9/7 | V Boys Soccer | St. Paul Catholic (Scrim.) | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/7 | JV Boys Soccer | St. Paul Catholic (Scrim.) | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/7 | V Girls Cross Country | BL Scrimmage | Away - Black Rock State Park | 4:00 p.m. | ||
| Wed., 9/8 | V Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 3:30 p.m. | ||
| Wed., 9/8 | JV Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 5:00 p.m. | ||
| Thu., 9/9 | V Boys Soccer | Nonnewaug | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-6 | |
| Thu., 9/9 | JV Boys Soccer | Nonnewaug | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Rainout | ||
| Thu., 9/9 | V Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 3:45 p.m. | W 2-1 | |
| Thu., 9/9 | JV Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | Canceled | Cancelled | |
| Thu., 9/9 | V Girls Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | L 0-10 | |
| Thu., 9/9 | V Girls Volleyball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 6:45 p.m. | L 0-3 | |
| Thu., 9/9 | JV Girls Volleyball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 9/10 | V Football | Platt Tech | Away - Foran Turf Field [Directions] | 7:00 p.m. | W 26-14 | |
| Sat., 9/11 | V Girls Volleyball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 12:00 p.m. | L 0-3 | |
| Sat., 9/11 | JV Girls Volleyball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 10:30 a.m. | ||
| Tue., 9/14 | V Boys Cross Country | Northwestern, Terryville | Away - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Boys Golf | Gilbert, Terryville | Home - Wamogo HS-Stoneybrook Golf Course [Directions] | Postponed | Terryville 242 Wamogo 212 | |
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/8, Time to 3:00 p.m. | ||||||
| Tue., 9/14 | V Boys Soccer | Northwestern | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | T 2-2 | |
| Tue., 9/14 | JV Boys Soccer | Northwestern | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/14 | V Girls Cross Country | Northwestern, Terryville | Away - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Field Hockey | Northwestern | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | W 4-1 | |
| Tue., 9/14 | V Girls Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-6 | |
| Tue., 9/14 | V Girls Volleyball | Gilbert | Home - Wamogo Regional HS-Large gym [Directions] | 3:45 p.m. | W 3-1 | |
| Tue., 9/14 | JV Girls Volleyball | Gilbert | Home - Wamogo Regional HS-Large Gym [Directions] | 5:00 p.m. | ||
| Thu., 9/16 | V Boys Soccer | Gilbert | Away - Walker Field [Directions] | 3:30 p.m. | W 8-0 | |
| Thu., 9/16 | V Field Hockey | Haddam-Killingworth | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | T 1-1 | |
| Thu., 9/16 | JV Field Hockey | Haddam-Killingworth | Home - Wamogo HS-Wamogo Large Gym [Directions] | Canceled | Cancelled | |
| Thu., 9/16 | V Girls Soccer | Gilbert | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-3 | |
| Fri., 9/17 | V Football | Cheney Tech | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | L 0-28 | |
| Sat., 9/18 | V Girls Volleyball | New Fairfield | Home - Wamogo Regional HS-Large gym [Directions] | 12:00 p.m. | L 0-3 | |
| Sat., 9/18 | JV Girls Volleyball | New Fairfield | Home - Wamogo Regional HS-Large Gym [Directions] | 10:30 a.m. | ||
| Mon., 9/20 | V Boys Cross Country | Shepaug Valley, Gilbert | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Cross Country Course [Directions] | 4:00 p.m. | ||
| Mon., 9/20 | V Boys Golf | Housatonic Regional | Home - Wamogo HS-Stoneybrook Golf Course [Directions] | 3:00 p.m. | Housatonic 215 Wamogo 242 | |
| Mon., 9/20 | V Boys Soccer | Shepaug Valley | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-3 | |
| Mon., 9/20 | JV Boys Soccer | Shepaug Valley | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 9/20 | V Girls Cross Country | Shepaug Valley, Gilbert | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Cross Country Course [Directions] | 4:00 p.m. | ||
| Mon., 9/20 | V Field Hockey | Shepaug Valley | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 4:00 p.m. | L 5-1 | |
| Mon., 9/20 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-11 | |
| Tue., 9/21 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 9/21 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/22 | V Boys Soccer | Thomaston | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | T 2-2 | |
| Wed., 9/22 | JV Boys Soccer | Thomaston | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 9/22 | V Field Hockey | Thomaston | Away - Thomaston HS-Field Hockey Field [Directions] | 3:45 p.m. | L 7-0 | |
| Wed., 9/22 | JV Field Hockey | Thomaston | Away - Thomaston HS-Field Hockey Field [Directions] | Canceled | Cancelled | |
| Wed., 9/22 | V Girls Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | L 0-10 | |
| Thu., 9/23 | V Girls Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:45 p.m. | L 0-8 | |
| Thu., 9/23 | V Girls Volleyball | Sheehan | Home - Wamogo Regional HS-Large gym [Directions] | 4:00 p.m. | L 0-3 | |
| Thu., 9/23 | JV Girls Volleyball | Sheehan | Home - Wamogo Regional HS-Large Gym [Directions] | 5:15 p.m. | ||
| Fri., 9/24 | JV Boys Soccer | Terryville | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Rainout | ||
| Fri., 9/24 | JV Field Hockey | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Postponed | ||
| Mon., 9/27 | V Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | 3:45 p.m. | W 4-1 | |
| Mon., 9/27 | JV Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | 3:45 p.m. | ||
| Mon., 9/27 | V Field Hockey | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | L 1-3 | |
| Mon., 9/27 | V Girls Soccer | Housatonic Regional | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 5:00 p.m. | L 1-9 | |
| Tue., 9/28 | V Boys Cross Country | Nonnewaug, Litchfield | Away - Nonnewaug HS-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | V Boys Golf | Housatonic Regional | Away - Canaan Country Club [Directions] | 3:00 p.m. | Housatonic Regional 174 Wamogo 248 | |
| Tue., 9/28 | V Girls Cross Country | Nonnewaug, Litchfield | Away - Nonnewaug HS-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | V Girls Volleyball | Housatonic Regional | Home - Wamogo Regional HS-Large gym [Directions] | 6:15 p.m. | L 0-3 | |
| Tue., 9/28 | JV Girls Volleyball | Housatonic Regional | Home - Wamogo Regional HS-Large Gym [Directions] | 5:00 p.m. | ||
| Thu., 9/30 | V Boys Golf | Shepaug Valley, Litchfield | Away - Lake Waramaug Country Club [Directions] | 3:00 p.m. | Wamogo 263 Litchfield 181 Shepaug 193 | |
| Thu., 9/30 | V Boys Soccer | Litchfield | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | 7:30 p.m. | L 5-0 | |
| Thu., 9/30 | V Girls Soccer | Litchfield | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 5:30 p.m. | L 2-9 | |
| Fri., 10/1 | V Boys Cross Country | Nonnewaug Invitational | Away - TBA-connell memorial rink | Canceled | Cancelled | |
| Fri., 10/1 | V Boys Cross Country | Nonnewaug Invitational | Away - Nonnewaug HS-XC Course | 4:00 p.m. | ||
| Fri., 10/1 | JV Boys Soccer | Litchfield | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | Canceled | Cancelled | |
| Fri., 10/1 | V Girls Cross Country | Nonnewaug Invitational | Away - TBA-connell memorial rink | Canceled | Cancelled | |
| Fri., 10/1 | V Girls Cross Country | Nonnewaug Invitational | Away - Nonnewaug HS-XC Course | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Fri., 10/1 | V Field Hockey | Litchfield | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 10/1 | JV Field Hockey | Litchfield | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | Canceled | Cancelled | |
| Fri., 10/1 | JV Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-JV Soccer Field [Directions] | Canceled | Cancelled | |
| Sat., 10/2 | V Football | Norwich Tech | Away - Norwich Technical HS-NTHS Outdoor Athletic Complex [Directions] | 3:00 p.m. | L 20-22 | |
| Sat., 10/2 | V Girls Volleyball | Plainville | Away - Plainville HS-Wood Gymnasium [Directions] | 11:00 a.m. | L 0-3 | |
| Sat., 10/2 | JV Girls Volleyball | Plainville | Away - Plainville HS-Wood Gymnasium [Directions] | 10:00 a.m. | ||
| Tue., 10/5 | V Boys Golf | Gilbert, Northwestern | Away - Green woods Country Club [Directions] | 3:00 p.m. | Wamogo 237 Gilbert 224 Northwestern 184 | |
| Tue., 10/5 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 3:45 p.m. | L 5-1 | |
| Tue., 10/5 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | 3:45 p.m. | ||
| Tue., 10/5 | JV Field Hockey | Nonnewaug | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | Canceled | Cancelled | |
| Tue., 10/5 | V Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 6:15 p.m. | L 0-3 | |
| Tue., 10/5 | JV Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 5:00 p.m. | ||
| Wed., 10/6 | V Boys Golf | Nonnewaug, Gilbert, Shepaug Valley | Away - Western Hills Golf Course (Wtby) [Directions] | 3:00 p.m. | Nonnewaug 195 Shepaug 186 Wamogo 240 | |
| Thu., 10/7 | V Boys Golf | Northwestern, Nonnewaug | Away - Northwestern Regional H.S.-Norfolk CC [Directions] | 3:30 p.m. | Northwestern 215 nonnewaug 224 wamogo 240 | |
| Thu., 10/7 | V Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | W 2-0 | |
| Thu., 10/7 | JV Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | Canceled | Cancelled | |
| Thu., 10/7 | V Girls Soccer | Northwestern | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-5 | |
| Thu., 10/7 | V Girls Volleyball | Plainville | Home - Wamogo Regional HS-Large gym [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 10/7 | JV Girls Volleyball | Plainville | Home - Wamogo Regional HS-Large Gym [Directions] | 3:45 p.m. | ||
| Fri., 10/8 | V Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-1 | |
| Fri., 10/8 | JV Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Sat., 10/9 | V Boys Cross Country | Wickham Park Invitational | Away - Wickham Park-Manchester, Ct | TBA | ||
| Sat., 10/9 | V Girls Cross Country | Wickham Park Invitational | Away - Wickham Park-Manchester, Ct | TBA | ||
| Mon., 10/11 | V Boys Soccer | Terryville | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 10:00 a.m. | T 0-0 | |
| Tue., 10/12 | V Boys Cross Country | Housatonic Regional, Thomaston | Home - Wamogo Regional HS-White Memorial Park [Directions] | 5:00 p.m. | ||
| Tue., 10/12 | V Boys Soccer | Gilbert | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | W 8-0 | |
| Tue., 10/12 | V Girls Cross Country | Housatonic Regional | Home - Wamogo Regional HS-White Memorial Park [Directions] | 5:00 p.m. | ||
| Tue., 10/12 | V Field Hockey | New Fairfield | Away - New Fairfield HS-Stadium Field [Directions] | 6:30 p.m. | L 7-1 | |
| Tue., 10/12 | MS Girls Soccer | Northwestern MS | Away - Northwestern Regional M.S.-MS Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | MS Field Hockey | Northwestern MS | Away - Northwestern Regional M.S.-Field Hockey Field [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | V Football | O'Brien Tech | Home - Nonnewaug HS-Turf Field [Directions] | 7:00 p.m. | W 44-8 | |
| Thu., 10/14 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-1 | |
| Thu., 10/14 | JV Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/14 | V Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | 3:45 p.m. | OT-L 2-1 | |
| Thu., 10/14 | JV Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | Canceled | Cancelled | |
| Thu., 10/14 | V Girls Soccer | Shepaug Valley | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-3 | |
| Thu., 10/14 | V Girls Volleyball | Northwestern | Home - Wamogo Regional HS-Large gym [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 10/14 | JV Girls Volleyball | Northwestern | Home - Wamogo Regional HS-Large Gym [Directions] | 3:45 p.m. | ||
| Fri., 10/15 | JV Girls Soccer | Gilbert | Home - Wamogo Regional HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Sat., 10/16 | JV Football | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | ||
| Mon., 10/18 | V Boys Golf | CIAC Fall Division II Boys Golf Championship | Away - Silo Point GC | 8:30 a.m. | ||
| Mon., 10/18 | V Field Hockey | Nonnewaug | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | T 1-1 | |
| Mon., 10/18 | V Girls Soccer | Nonnewaug | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-8 | |
| Mon., 10/18 | V Girls Volleyball | Granby Memorial | Home - Wamogo Regional HS-Large gym [Directions] | 6:45 p.m. | L 0-3 | |
| Mon., 10/18 | JV Girls Volleyball | Granby Memorial | Home - Wamogo Regional HS-Large Gym [Directions] | 5:30 p.m. | ||
| Tue., 10/19 | V Boys Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | L 0-4 | |
| Tue., 10/19 | JV Boys Soccer | Thomaston | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Canceled | Cancelled | |
| Tue., 10/19 | V Field Hockey | Thomaston | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | L 7-2 | |
| Tue., 10/19 | JV Field Hockey | Thomaston | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | Canceled | Cancelled | |
| Tue., 10/19 | V Girls Soccer | Thomaston | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-8 | |
| Tue., 10/19 | V Girls Volleyball | Gilbert | Home - Wamogo Regional HS-Large gym [Directions] | 5:15 p.m. | L 2-3 | |
| Tue., 10/19 | JV Girls Volleyball | Gilbert | Home - Wamogo Regional HS-Large Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/20 | V Girls Volleyball | Abbott Tech | Away - Abbott V-T School-Daniel A. Garamella Memorial Gymnasium [Directions] | 5:15 p.m. | L 0-3 | |
| Wed., 10/20 | JV Girls Volleyball | Abbott Tech | Away - Abbott V-T School-Daniel A. Garamella Memorial Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 10/21 | V Boys Cross Country | Berkshire League Championship | Away - Black Rock State Park | 4:15 p.m. | ||
| Thu., 10/21 | V Girls Cross Country | Berkshire League Championship | Away - Black Rock State Park | 3:30 p.m. | ||
| Thu., 10/21 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 7:00 p.m. | L 0-8 | |
| Thu., 10/21 | V Girls Volleyball | Nonnewaug | Home - Wamogo Regional HS-Large gym [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 10/21 | JV Girls Volleyball | Nonnewaug | Home - Wamogo Regional HS-Large Gym [Directions] | 3:45 p.m. | ||
| Fri., 10/22 | V Football | Wilcox/Kaynor | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | W 50-6 | |
| Fri., 10/22 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 7:00 p.m. | L 0-3 | |
| Sat., 10/23 | JV Boys Soccer | Nonnewaug, Litchfield, Watertown | Away - Nonnewaug HS-JV Field [Directions] | 10:00 a.m. | ||
| Sat., 10/23 | V Field Hockey | Litchfield | Away - Plumb Hill Field Complex-Field Hockey Field [Directions] | 7:00 p.m. | W 3-0 | |
| Mon., 10/25 | V Boys Cross Country | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:30 p.m. | ||
| Mon., 10/25 | JV Football | Wilcox/Kaynor | Home - Nonnewaug HS-Turf Field [Directions] | 4:30 p.m. | ||
| Mon., 10/25 | V Girls Cross Country | Oxford | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 3:30 p.m. | ||
| Mon., 10/25 | V Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | L 2-0 | |
| Mon., 10/25 | JV Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | Canceled | Cancelled | |
| Thu., 10/28 | V Boys Soccer | Housatonic Regional | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | W 3-1 | |
| Thu., 10/28 | JV Boys Soccer | Housatonic Regional | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Canceled | Cancelled | |
| Thu., 10/28 | V Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | 3:45 p.m. | L 0-9 | |
| Thu., 10/28 | V Girls Volleyball | Terryville | Home - Wamogo Regional HS-Large gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/28 | JV Girls Volleyball | Terryville | Home - Wamogo Regional HS-Large Gym [Directions] | 4:45 p.m. | ||
| Fri., 10/29 | V Football | Quinebaug Valley | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | W 38-14 | |
| Fri., 10/29 | V Field Hockey | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | L 2-0 | |
| Sat., 10/30 | V Girls Volleyball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 11:30 a.m. | L 0-3 | |
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class S Championship | Away - Wickham Park | 2:05 p.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class S Championship | Away - Wickham Park | 2:35 p.m. | ||
| Tue., 11/2 | V Boys Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:15 p.m. | L 0-2 | |
| Tue., 11/2 | V Field Hockey | Watertown | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | L 4-2 | |
| Tue., 11/2 | JV Field Hockey | Watertown | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | Canceled | Cancelled | |
| Tue., 11/2 | V Girls Soccer | Terryville | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 11/3 | MS Field Hockey | Thomaston MS | Home - Wamogo MS-Middle school Field Hockey Field [Directions] | 3:30 p.m. | ||
| Wed., 11/3 | V Girls Soccer | Gilbert | Away - Walker Field [Directions] | 3:30 p.m. | ||
| Thu., 11/4 | V Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 11/4 | JV Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | VGW Techs | Away - Pat Kidney Field-Pat Kidney 1 [Directions] | 6:00 p.m. | W 45-0 | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | JV Football | Woodland | Home - Nonnewaug HS-football field [Directions] | 10:00 a.m. | ||
| Mon., 11/8 | V Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 2:00 p.m. | W 3-0 | |
| Tue., 11/9 | V Field Hockey | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 2:00 p.m. | ||
| Sat., 11/13 | V Football | Bullard/Kolbe | Away - Kennedy Stadium (Bridgeport) [Directions] | 12:00 p.m. | L 22-24 | |
| Mon., 11/15 | JV Football | Bullard/Kolbe | Home - Nonnewaug HS-Turf Field [Directions] | 4:30 p.m. | ||
| Fri., 11/19 | V Football | Prince Tech-Innovation | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | W 38-0 | |
| Thu., 11/25 | V Football | ATI | Away - Immaculate HS-Mustang Valley [Directions] | 10:00 a.m. | W 36-20 | |
| Fri., 12/3 | V Girls Basketball | New Milford | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/8 | V Boys Ice Hockey | Shepaug Valley Ice Hockey (Scrim.) | Away - The Frederick Gunn School-Ice Rink [Directions] | 6:30 p.m. | ||
| Wed., 12/8 | V Girls Basketball | Wolcott Tech (Scrim.) | Away - Oliver Wolcott Technical HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 12/9 | V Boys Basketball | Granby Memorial | Home - Wamogo HS-Wamogo Large Gym [Directions] | 6:00 p.m. | ||
| Thu., 12/9 | JV Boys Basketball | Granby Memorial | Home - Wamogo HS-Wamogo Small Gym [Directions] | 6:00 p.m. | ||
| Sat., 12/11 | V Wrestling | Pre-season scrimmage | Away - Bristol Eastern HS-Gym | 1:00 p.m. | ||
| Mon., 12/13 | V Girls Basketball | Housatonic Regional | Home - Wamogo HS-Wamogo Large Gym [Directions] | 6:00 p.m. | L 25-46 | |
| Mon., 12/13 | JV Girls Basketball | Housatonic Regional | Home - Wamogo HS-Wamogo Large Gym [Directions] | Postponed | ||
| Tue., 12/14 | V Boys Basketball | WCA (Scrim.) | Away - Waterbury Career Academy-Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 12/14 | JV Boys Basketball | WCA (Scrim.) | Away - Waterbury Career Academy-Gymnasium [Directions] | Canceled | Cancelled | |
| Wed., 12/15 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 7:20 p.m. | L 5-6 | |
| Fri., 12/17 | V Boys Swimming and Diving | Litchfield | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Sat., 12/18 | V Boys Basketball | Somers | Home - Wamogo HS-Wamogo Large Gym [Directions] | 3:00 p.m. | L 55-56 | |
| Sat., 12/18 | JV Boys Basketball | Somers | Home - Wamogo HS-Wamogo Large Gym [Directions] | 1:30 p.m. | ||
| Sat., 12/18 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Home - South Kent School-Ice Rink [Directions] | 6:00 p.m. | L 5-9 | |
| Sat., 12/18 | V Wrestling | Pomperaug Quads | Away - Pomperaug HS-Auxiliary Gym | 10:00 a.m. | ||
| Mon., 12/20 | V Boys Ice Hockey | JBWA | Home - South Kent School-Ice Rink [Directions] | 4:00 p.m. | L 1-5 | |
| Tue., 12/21 | V Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | W 42-31 | |
| Tue., 12/21 | JV Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/21 | V Boys Swimming and Diving | Housatonic Regional | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Tue., 12/21 | V Girls Basketball | Northwestern | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | L 22-50 | |
| Wed., 12/22 | V Boys Ice Hockey | Eastern CT Eagles | Away - Norwich - Rose Garden-RoseGarden Arena [Directions] | 7:40 p.m. | L 0-7 | |
| Thu., 12/23 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | W 52-43 | |
| Thu., 12/23 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | Canceled | Cancelled | |
| Thu., 12/23 | V Girls Basketball | Nonnewaug | Home - Wamogo HS-Wamogo Large Gym [Directions] | 3:30 p.m. | L 22-63 | |
| Thu., 12/23 | JV Girls Basketball | Nonnewaug | Home - Wamogo HS-Wamogo Large Gym [Directions] | Postponed | ||
| Mon., 12/27 | JV Boys Basketball | Canton | Home - Wamogo HS-Wamogo Large Gym [Directions] | 3:00 p.m. | ||
| Mon., 12/27 | FR Boys Basketball | Canton | Home - Wamogo HS-Wamogo Large Gym [Directions] | 1:00 p.m. | ||
| Mon., 12/27 | JV Girls Basketball | Wolcott Tech | Home - Wamogo HS-Wamogo Large Gym [Directions] | 11:00 a.m. | ||
| Tue., 12/28 | V Boys Basketball | Suffield | Home - Wamogo HS-Wamogo Large Gym [Directions] | 2:00 p.m. | W 62-50 | |
| Wed., 12/29 | V Boys Basketball | Canton | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | L 30-53 | |
| Wed., 12/29 | JV Boys Basketball | Lewis Mills | Home - Wamogo HS-Wamogo Large Gym [Directions] | 3:00 p.m. | ||
| Wed., 12/29 | FR Boys Basketball | Litchfield | Home - Wamogo HS-Wamogo Small Gym [Directions] | 1:45 p.m. | ||
| Wed., 1/5 | V Boys Indoor Track | Wintergreen Meet SCSU | Away - Southern Connecticut State University | Canceled | Cancelled | |
| Wed., 1/5 | V Girls Indoor Track | Wintergreen Meet SCSU | Away - Southern Connecticut State University | Canceled | Cancelled | |
| Mon., 1/10 | V Boys Indoor Track | James Barber Invitational | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Mon., 1/10 | V Girls Indoor Track | James Barber Invitational | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Tue., 1/11 | V Boys Basketball | Terryville | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | L 55-39 | |
| Tue., 1/11 | JV Boys Basketball | Terryville | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/11 | V Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 6:00 p.m. | L 33-45 | |
| Wed., 1/12 | V Boys Basketball | Thomaston | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 49-46 | |
| Wed., 1/12 | JV Boys Basketball | Thomaston | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/12 | V Boys Ice Hockey | Tri-Town | Home - South Kent School-Gym [Directions] | 7:30 p.m. | L 3-6 | |
| Wed., 1/12 | V Boys Swimming and Diving | Northwestern | Away - Northwestern Regional H.S.-YMCA Swim [Directions] | 7:00 p.m. | ||
| Wed., 1/12 | V Wrestling | Derby/Oxford/Holy Cross | Away - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/12 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 6:00 p.m. | L 19-48 | |
| Thu., 1/13 | FR Boys Basketball | Shepaug Valley | Home - Wamogo HS-Wamogo Large Gym [Directions] | 6:00 p.m. | ||
| Fri., 1/14 | V Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 45-44 | |
| Fri., 1/14 | JV Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/14 | V Girls Basketball | Shepaug Valley | Home - Wamogo HS-Wamogo Large Gym [Directions] | 6:00 p.m. | L 29-52 | |
| Fri., 1/14 | JV Girls Basketball | Shepaug Valley | Home - Wamogo HS-Wamogo Large Gym [Directions] | Postponed | ||
| Sat., 1/15 | FR Boys Basketball | O'Brien Tech | Home - Wamogo HS-Wamogo Large Gym [Directions] | 12:00 p.m. | ||
| Sat., 1/15 | V Boys Ice Hockey | Tri-Town | Away - Enfield Twin Rinks-Rink 1 [Directions] | 4:20 p.m. | L 4-11 | |
| Sat., 1/15 | V Wrestling | Berlin, Avon, Bethel, Branford, Pomperaug, Portland | Away - Berlin HS-Jim Day Gymnasium | 10:00 a.m. | ||
| Sat., 1/15 | V Wrestling | Canton, Farmington, Northwestern, New Haven Wrestling | Away - Canton HS-Gym [Directions] | 10:00 a.m. | ||
| Tue., 1/18 | V Boys Basketball | Gilbert | Home - Wamogo HS-Wamogo Large Gym [Directions] | 6:00 p.m. | W 61-45 | |
| Tue., 1/18 | JV Boys Basketball | Gilbert | Home - Wamogo HS-Wamogo Large Gym [Directions] | Postponed | ||
| Tue., 1/18 | V Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 6:00 p.m. | L 34-49 | |
| Tue., 1/18 | JV Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | Postponed | ||
| Wed., 1/19 | V Boys Ice Hockey | Newington Coop | Away - Newington Ice Arena-Blue Rink [Directions] | 5:00 p.m. | L 4-8 | |
| Wed., 1/19 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Wed., 1/19 | MS Boys Swimming and Diving | West Side MS-Waterbury | Away - West Side MS [Directions] | Postponed | ||
| Thu., 1/20 | V Boys Swimming and Diving | Nonnewaug | Home - Shepaug Valley HS-Shepaug Valley School [Directions] | Postponed | ||
| Fri., 1/21 | V Boys Basketball | Housatonic Regional | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 59-37 | |
| Fri., 1/21 | JV Boys Basketball | Housatonic Regional | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/21 | V Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 6:00 p.m. | L 22-46 | |
| Fri., 1/21 | JV Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | Postponed | ||
| Sat., 1/22 | V Boys Basketball | Litchfield | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 46-45 | |
| Sat., 1/22 | JV Boys Basketball | Litchfield | Home - Wamogo HS-Wamogo Small Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/22 | FR Boys Basketball | Wolcott Tech | Home - Wamogo HS-Wamogo Large Gym [Directions] | 12:00 p.m. | ||
| Sat., 1/22 | V Wrestling | Cougar Duals | Away - Haddam Killingworth HS (HK)-Gym 1 | 9:00 a.m. | ||
| Sat., 1/22 | V Girls Basketball | Litchfield | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | L 36-43 | |
| Wed., 1/26 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - South Kent School-Ice Rink [Directions] | 6:00 p.m. | W 6-2 | |
| Wed., 1/26 | V Wrestling | Northwestern | Home - Terryville HS-Gym [Directions] | Postponed | ||
| Thu., 1/27 | MS Boys Swimming and Diving | North End MS | Away - North End MS-Main Campus [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:30 p.m. | ||||||
| Thu., 1/27 | V Girls Basketball | Abbott Tech | Away - Abbott V-T School-Daniel A. Garamella Memorial Gymnasium [Directions] | 6:00 p.m. | L 17-50 | |
| Thu., 1/27 | JV Girls Basketball | Abbott Tech | Away - Abbott V-T School-Daniel A. Garamella Memorial Gymnasium [Directions] | Canceled | Cancelled | |
| Fri., 1/28 | V Boys Basketball | Northwestern | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 48-46 | |
| Fri., 1/28 | JV Boys Basketball | Northwestern | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/28 | V Boys Indoor Track | Shoreline Coaches Invite | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | ||
| Fri., 1/28 | V Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 6:00 p.m. | L 27-57 | |
| Fri., 1/28 | V Girls Indoor Track | Shoreline Coaches Invite | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | ||
| Sat., 1/29 | FR Boys Basketball | Northwestern | Home - Wamogo HS-Wamogo Large Gym [Directions] | Postponed | ||
| Sat., 1/29 | V Boys Indoor Track | Frostbite Invitational | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | Canceled | Cancelled | |
| Sat., 1/29 | V Wrestling | Individuals Tourney | Away - Suffield HS | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 7:00 a.m. | ||||||
| Sat., 1/29 | V Wrestling | Portland, Avon, Cheshire, Coventry, Daniel Hand, East Haven, Gilbert, Glastonbury, Griswold/Wheeler, Morgan, TBA, TBA, New Britain, Nonnewaug, Plainville, Somers, St. Paul Catholic, Thomaston, New Haven Wrestling | Away - Portland HS-Portland HS | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sat., 1/29 | JV Girls Basketball | Northwestern | Home - Wamogo HS-Wamogo Small Gym [Directions] | Postponed | ||
| Sat., 1/29 | V Girls Indoor Track | Frostbite Invitational | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | Canceled | Cancelled | |
| Tue., 2/1 | V Boys Basketball | Nonnewaug | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 43-39 | |
| Tue., 2/1 | JV Boys Basketball | Nonnewaug | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/1 | V Boys Indoor Track | Bethel Last Chance Meet | Away - Bethel HS-Bethel Track and Field Center | 4:00 p.m. | ||
| Tue., 2/1 | V Boys Swimming and Diving | Shepaug Valley | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Tue., 2/1 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | L 28-47 | |
| Tue., 2/1 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | Postponed | ||
| Tue., 2/1 | V Girls Indoor Track | Bethel Last Chance Meet | Away - Bethel HS-Bethel Track and Field Center | 4:00 p.m. | ||
| Wed., 2/2 | FR Boys Basketball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/2 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 5:25 p.m. | W 5-3 | |
| Wed., 2/2 | V Wrestling | Gilbert/Torrington | Home - Terryville HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 2/3 | V Boys Swimming and Diving | Nonnewaug | Away - John F. Kennedy HS-JFK Pool [Directions] | 7:30 p.m. | ||
| Fri., 2/4 | JV Girls Basketball | Thomaston | Home - Wamogo HS-Wamogo Large Gym [Directions] | Postponed | ||
| Sat., 2/5 | JV Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/5 | V Boys Ice Hockey | Eastern CT Eagles | Home - South Kent School-Ice Rink [Directions] | 6:00 p.m. | L 2-8 | |
| Sat., 2/5 | V Wrestling | 2022 Bacon Academy Matt Bishel Bobcat Classic | Away - Bacon Academy-Gym | 9:00 a.m. | ||
| Sat., 2/5 | V Girls Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 2:30 p.m. | W 45-41 | |
| Mon., 2/7 | V Boys Swimming and Diving | Northwestern | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | Canceled | Cancelled | |
| Tue., 2/8 | V Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 7:00 p.m. | L 49-37 | |
| Tue., 2/8 | JV Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/8 | V Girls Basketball | Terryville | Home - Wamogo HS-Wamogo Large Gym [Directions] | 6:00 p.m. | W 37-30 | |
| Wed., 2/9 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - The Frederick Gunn School-Ice Rink [Directions] | 7:30 p.m. | W 5-4 | |
| Thu., 2/10 | V Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 65-43 | |
| Thu., 2/10 | JV Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/11 | V Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 38-36 | |
| Fri., 2/11 | JV Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/12 | V Boys Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/12 | V Boys Swimming and Diving | Northwestern | Away - Northwestern Regional H.S.-YMCA Swim [Directions] | 3:30 p.m. | ||
| Sat., 2/12 | V Wrestling | Gilbert, Derby, Holy Cross, Berkshire League Tournament, Nonnewaug, Northwestern, Seymour, St. Paul Catholic, Thomaston | Away - Gilbert School-Gym | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Sat., 2/12 | V Girls Basketball | Amistad | Away - Amistad HS-Gym [Directions] | 1:00 p.m. | L 35-43 | |
| Sat., 2/12 | V Girls Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Mon., 2/14 | V Boys Ice Hockey | Brookfield | Home - South Kent School-Ice Rink [Directions] | 3:30 p.m. | L 3-6 | |
| Mon., 2/14 | V Girls Basketball | Thomaston | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:00 p.m. | L 23-57 | |
| Tue., 2/15 | V Boys Basketball | Shepaug Valley | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 70-45 | |
| Tue., 2/15 | JV Boys Basketball | Shepaug Valley | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/15 | V Boys Swimming and Diving | Housatonic Regional, Nonnewaug | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Tue., 2/15 | V Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 6:00 p.m. | L 26-53 | |
| Tue., 2/15 | JV Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | Postponed | ||
| Wed., 2/16 | FR Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 2/16 | V Boys Ice Hockey | Woodstock Academy | Away - Pomfret School-Jahn Rink [Directions] | 6:30 p.m. | L 4-12 | |
| Thu., 2/17 | V Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 7:00 p.m. | W 68-44 | |
| Thu., 2/17 | JV Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/17 | V Boys Ice Hockey | Brookfield | Away - Brewster Ice Rink-Ice Rink [Directions] | 7:15 p.m. | W 3-2 | |
| Thu., 2/17 | V Girls Basketball | Gilbert | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | L 30-50 | |
| Thu., 2/17 | JV Girls Basketball | Gilbert | Home - Wamogo HS-Wamogo Large Gym [Directions] | Postponed | ||
| Fri., 2/18 | V Wrestling | Class S Championship - Day 1 | Away - Killingly | 3:00 p.m. | ||
| Sat., 2/19 | V Boys Basketball | Classical Magnet | Away - Classical Magnet HS-gym [Directions] | 4:30 p.m. | L 45-35 | |
| Sat., 2/19 | JV Boys Basketball | Classical Magnet | Away - Classical Magnet HS-gym [Directions] | 3:00 p.m. | ||
| Sat., 2/19 | FR Boys Basketball | Thomaston | Home - Wamogo HS-Wamogo Large Gym [Directions] | 11:30 a.m. | ||
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class S Championship - Day 2 | Away - Killingly | 9:00 a.m. | ||
| Sat., 2/19 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 11:30 a.m. | ||
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | V Boys Ice Hockey | Woodstock Academy | Home - South Kent School-Ice Rink [Directions] | 4:00 p.m. | L 2-7 | Senior Day |
| Tue., 2/22 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Tue., 2/22 | V Girls Basketball | Amistad | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:05 p.m. | L 42-47 | |
| Wed., 2/23 | V Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 5:30 p.m. | W 60-44 | |
| Wed., 2/23 | JV Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/24 | V Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:00 p.m. | W 62-36 | |
| Thu., 2/24 | JV Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 3:30 p.m. | ||
| Thu., 2/24 | V Boys Ice Hockey | SCW Knights | Away - Newington Ice Arena-Blue Rink [Directions] | 5:30 p.m. | W 7-3 | |
| Sat., 2/26 | V Boys Basketball | Thomaston | Home - Nonnewaug HS-Gym [Directions] | 11:30 a.m. | ||
| Sat., 2/26 | V Boys Ice Hockey | New Milford | Home - Canterbury School-O'Neill Arena [Directions] | 10:00 a.m. | L 5-12 | |
| Sat., 2/26 | V Boys Swimming and Diving | TBA, Housatonic Regional, Litchfield, TBA, Nonnewaug, Northwestern, Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool | 11:00 a.m. | ||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/28 | FR Boys Basketball | Housatonic Regional | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/28 | FR Boys Basketball | Watertown | Home - Wamogo HS-Wamogo Small Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/28 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | L 4-6 | |
| Tue., 3/1 | V Boys Basketball | Northwestern | Home - Nonnewaug HS-Gym [Directions] | 5:15 p.m. | ||
| Tue., 3/1 | V Boys Basketball | Northwestern | Home - Nonnewaug HS-Nonnewaug [Directions] | 5:15 p.m. | ||
| Wed., 3/2 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Enfield Twin Rinks-Rink 2 [Directions] | 3:50 p.m. | L 1-8 | |
| Fri., 3/4 | V Boys Swimming and Diving | Berkshire League Dive Championship | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool | 5:30 p.m. | ||
| Sat., 3/5 | V Boys Swimming and Diving | Litchfield, Housatonic Regional, Nonnewaug, Northwestern, Shepaug Valley | Away - John F. Kennedy HS-JFK Pool | 4:30 p.m. | ||
| Sat., 3/5 | V Boys Swimming and Diving | TBA, Nonnewaug, Shepaug Valley | Away - TBA | TBA | ||
| Mon., 3/7 | V Boys Ice Hockey | E.O. Smith-Tolland | Away - UConn Storrs-Freitas Ice Forum [Directions] | 7:30 p.m. | ||
| Thu., 3/10 | V Boys Basketball | Canton | Home - Wamogo HS-Wamogo Large Gym [Directions] | 6:30 p.m. | ||
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 4:00 p.m. | ||
| Fri., 3/11 | V Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 3/11 | V Boys Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cornerstone Pool | 1:00 p.m. | ||
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class S Swimming Championships | Away - Cornerstone Pool | 6:30 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Thu., 3/31 | V Baseball | Crosby (Scrim.) | Away - Crosby HS-CHS Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 4/4 | V Softball | Terryville | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | W 19-3 | |
| Tue., 4/5 | V Baseball | Lewis Mills | Away - Lewis Mills HS-Baseball Field - Varsity [Directions] | 3:45 p.m. | L 17-3 | |
| Tue., 4/5 | JV Baseball | Lewis Mills | Away - Lewis Mills HS-Baseball Field - JV [Directions] | Postponed | ||
| Thu., 4/7 | JV Baseball | Crosby | Away - Crosby HS-CHS Baseball Field [Directions] | 10:00 a.m. | ||
| Fri., 4/8 | V Girls Tennis | Shepaug Valley | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Mon., 4/11 | V Boys Outdoor Track | Terryville Invitational | Away - Terryville HS-Default Facility | 4:00 p.m. | ||
| Mon., 4/11 | V Boys Tennis | Watertown | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-4 [Detailed Results] | |
| Mon., 4/11 | V Girls Outdoor Track | Terryville Invitational | Away - Terryville HS-Track | 4:00 p.m. | ||
| Mon., 4/11 | V Girls Tennis | Thomaston | Away - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 4/12 | JV Baseball | O'Brien Tech | Away - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 3:45 p.m. | ||
| Tue., 4/12 | V Softball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Athletic Complex [Directions] | 3:45 p.m. | L 4-10 | |
| Wed., 4/13 | V Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 3:45 p.m. | L 12-0 | |
| Wed., 4/13 | JV Baseball | Nonnewaug | Away - Woodbury MS [Directions] | 3:45 p.m. | ||
| Wed., 4/13 | V Boys Tennis | Thomaston | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Wed., 4/13 | V Softball | Nonnewaug | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | L 5-23 | |
| Wed., 4/13 | V Girls Tennis | Gilbert | Away - Gilbert School-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/14 | V Girls Tennis | Housatonic Regional | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Mon., 4/18 | V Baseball | Canton | Home - Litchfield HS-Gym [Directions] | 3:45 p.m. | L 4-2 | |
| Wed., 4/20 | V Baseball | Housatonic Regional | Home - Washington Ted Alex Field-Washington Depot [Directions] | 10:30 a.m. | L 2- | |
| Thu., 4/21 | JV Baseball | Crosby | Home - Wamogo Regional HS-Litchfield MS [Directions] | 10:30 a.m. | ||
| Thu., 4/21 | JV Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | ||
| Fri., 4/22 | V Baseball | Gilbert | Home - Fuessenich Park-Baseball Diamond [Directions] | 3:45 p.m. | W 21-11 | |
| Mon., 4/25 | V Baseball | Thomaston | Home - Fuessenich Park-Baseball Diamond [Directions] | 3:45 p.m. | W 13-5 | |
| Mon., 4/25 | V Boys Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-4 [Detailed Results] | |
| Mon., 4/25 | V Softball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | L 11-26 | |
| Mon., 4/25 | V Girls Tennis | Nonnewaug | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/26 | V Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 3:45 p.m. | L 0-16 | |
| Tue., 4/26 | JV Softball | Northwestern | Away - Northwestern Regional H.S.-JV Softball Field [Directions] | 3:45 p.m. | ||
| Wed., 4/27 | V Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | L 11-1 | |
| Wed., 4/27 | V Boys Tennis | Litchfield | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-4 [Detailed Results] | |
| Wed., 4/27 | V Softball | Shepaug Valley | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | L 0-20 | |
| Wed., 4/27 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 4/28 | V Baseball | Terryville | Away - Terryville HS-Baseball Field [Directions] | 3:45 p.m. | W 8-4 | |
| Thu., 4/28 | V Boys Outdoor Track | Northwestern, Terryville | Home - Wamogo Regional HS-Plumb Hill Field [Directions] | 5:00 p.m. | ||
| Thu., 4/28 | V Boys Tennis | Housatonic Regional | Away - Housatonic Valley Regional High-Tennis Courts [Directions] | 5:00 p.m. | L 2-3 [Detailed Results] | |
| Thu., 4/28 | V Girls Outdoor Track | Northwestern | Home - Wamogo Regional HS-Plumb Hill Field [Directions] | 5:00 p.m. | ||
| Fri., 4/29 | V Boys Tennis | Abbott Tech | Away - Abbott V-T School-Abbott Tech Tennis Complex [Directions] | 3:45 p.m. | W 4-1 [Detailed Results] | |
| Fri., 4/29 | V Girls Tennis | Gilbert | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Sat., 4/30 | V Baseball | Abbott Tech | Away - Abbott V-T School-Abbott Tech Baseball Field, School Campus [Directions] | 12:00 p.m. | L 20-10 | |
| Sat., 4/30 | JV Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 9:30 a.m. | ||
| Mon., 5/2 | V Baseball | Terryville | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | W 3-2 | |
| Mon., 5/2 | V Softball | Wolcott Tech | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | W 17-4 | |
| Tue., 5/3 | JV Baseball | Wolcott Tech | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 5/3 | V Boys Outdoor Track | Shepaug Valley, Gilbert | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Track [Directions] | 3:45 p.m. | ||
| Tue., 5/3 | V Boys Tennis | Housatonic Regional | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 2-3 [Detailed Results] | |
| Tue., 5/3 | V Girls Outdoor Track | Shepaug Valley, Gilbert | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Track [Directions] | 3:45 p.m. | ||
| Tue., 5/3 | V Softball | Terryville | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | W 25-0 | |
| Tue., 5/3 | JV Softball | Kaynor Tech | Home - Wamogo Regional HS-Plumb Hill Field [Directions] | 3:45 p.m. | ||
| Tue., 5/3 | V Girls Tennis | Housatonic Regional | Away - Housatonic Valley Regional High-Tennis Courts [Directions] | 5:00 p.m. | L 3-4 | |
| Wed., 5/4 | JV Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | Postponed | ||
| Thu., 5/5 | V Boys Tennis | Shepaug Valley | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 2-3 [Detailed Results] | |
| Thu., 5/5 | V Softball | Housatonic Regional | Away - Housatonic Valley Regional High-softball field [Directions] | 5:00 p.m. | L 7-8 | |
| Thu., 5/5 | JV Softball | Housatonic Regional | Away - Housatonic Valley Regional High-Softball Diamond [Directions] | 5:00 p.m. | ||
| Thu., 5/5 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 5/6 | JV Baseball | Wolcott Tech | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | Postponed | ||
| Fri., 5/6 | JV Softball | Northwestern | Home - Wamogo Regional HS-Plumb Hill Field [Directions] | Postponed | ||
| Sat., 5/7 | JV Baseball | Crosby | Away - Crosby HS-CHS Baseball Field [Directions] | Postponed | ||
| Mon., 5/9 | JV Baseball | Wilby | Away - Wilby HS-Wilby H.S. [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Mon., 5/9 | V Boys Tennis | Northwestern | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Mon., 5/9 | V Softball | Canton | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 4:00 p.m. | L 3-9 | |
| Mon., 5/9 | V Girls Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | 5:00 p.m. | L 0-7 | |
| Tue., 5/10 | JV Baseball | Northwestern | Home - Wamogo Regional HS-Softball Diamond [Directions] | 5:15 p.m. | ||
| Tue., 5/10 | V Boys Outdoor Track | Thomaston, Housatonic Regional | Away - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:45 p.m. | ||
| Tue., 5/10 | V Boys Tennis | Thomaston | Away - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 4:30 p.m. | W 5-0 [Detailed Results] | |
| Tue., 5/10 | V Girls Outdoor Track | Thomaston, Housatonic Regional | Away - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:45 p.m. | ||
| Tue., 5/10 | V Girls Tennis | Thomaston | Home - Wamogo Regional HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Wed., 5/11 | V Baseball | Nonnewaug | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | L 5-0 | |
| Wed., 5/11 | V Boys Tennis | Nonnewaug | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-4 [Detailed Results] | |
| Wed., 5/11 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 4:00 p.m. | L 0-15 | |
| Wed., 5/11 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Thu., 5/12 | V Baseball | Kaynor Tech | Away - Kaynor Technical School- Kaynor Baseball Diamond [Directions] | 5:15 p.m. | W 8-3 | |
| Thu., 5/12 | JV Baseball | Canton | Away - Bowdoin Field-Baseball Diamond [Directions] | 5:00 p.m. | ||
| Thu., 5/12 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 5:00 p.m. | W 3-2 [Detailed Results] | |
| Thu., 5/12 | V Softball | Kaynor Tech | Home - Plumb Hill Field Complex-Softball Field [Directions] | 3:45 p.m. | L 0-12 | |
| Fri., 5/13 | V Baseball | Litchfield | Away - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | W 7-1 | |
| Fri., 5/13 | V Boys Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | L 2-3 [Detailed Results] | |
| Fri., 5/13 | V Softball | Northwestern | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | L 0-15 | |
| Fri., 5/13 | V Girls Tennis | Litchfield | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 5/14 | V Baseball | Northwestern | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 10:00 p.m. | L 13-0 | |
| Sat., 5/14 | V Baseball | Northwestern | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 12:00 p.m. | L 10-0 | |
| Sat., 5/14 | JV Baseball | Litchfield | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | Canceled | Cancelled | |
| Tue., 5/17 | V Boys Outdoor Track | Litchfield, Nonnewaug | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Girls Outdoor Track | Litchfield, Nonnewaug | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Softball | Gilbert | Away - Winsted Rowley Field [Directions] | 4:00 p.m. | L 12-14 | |
| Tue., 5/17 | V Softball | Gilbert | Away - Winsted Rowley Field [Directions] | 5:30 p.m. | W 13-0 | |
| Wed., 5/18 | V Baseball | Litchfield | Home - Wamogo Regional HS-Dunkin Donuts Park [Directions] | 6:30 p.m. | W 5-4 | |
| Wed., 5/18 | V Girls Tennis | Berkshire League Girls Tennis Tournament | Away - Nonnewaug HS-Nonnewaug | 8:00 a.m. | ||
| Thu., 5/19 | V Baseball | Thomaston | Away - Washington Ted Alex Field-Washington Depot [Directions] | 5:30 p.m. | W 12-2 | |
| Thu., 5/19 | V Boys Tennis | Wolcott | Away - TBA [Directions] | 8:00 a.m. | W 4-1 | |
| Fri., 5/20 | V Softball | Thomaston | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | L 0-10 | |
| Sat., 5/21 | V Boys Outdoor Track | Berkshire League Track Championships | Away - Plumb Hill Field Complex-Plumb Hill Track | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Sat., 5/21 | V Girls Outdoor Track | Berkshire League Track Championships | Away - Plumb Hill Field Complex-Plumb Hill Track | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Mon., 5/23 | V Baseball | Shepaug Valley | Home - Fuessenich Park-Baseball Diamond [Directions] | 3:45 p.m. | L 6-5 | |
| Mon., 5/23 | V Boys Tennis | Berkshire League Boys Tennis Tournament Semi & Finals | Away - TBA | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:00 p.m. | ||||||
| Mon., 5/23 | V Softball | Shepaug Valley | Away - Washington Primary School-Dick Ayer Field [Directions] | 3:45 p.m. | L 0-10 | |
| Mon., 5/23 | V Girls Tennis | Berkshire League Girls Tennis Tournament Semi & Finals | Away - Nonnewaug HS-Nonnewaug | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:00 p.m. | ||||||
| Tue., 5/24 | V Baseball | Gilbert | Away - Walker Field [Directions] | 5:00 p.m. | W 12-0 | |
| Tue., 5/24 | JV Baseball | Lewis Mills | Away - Lewis Mills HS-Baseball Field - JV [Directions] | 5:00 p.m. | ||
| Tue., 5/24 | V Boys Outdoor Track | Berkshire League Festival Hammer Throw Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Away - Housatonic Valley Regional High-Track | 3:30 p.m. | ||
| Tue., 5/24 | V Girls Outdoor Track | Berkshire League Festival Hammer Throw Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Away - Housatonic Valley Regional High-Track | 3:30 p.m. | ||
| Tue., 5/24 | V Softball | Canton | Away - Canton HS-Softball Diamond [Directions] | 5:00 p.m. | L 2-7 | |
| Wed., 5/25 | V Boys Outdoor Track | Berkshire League Festival Hammer Throw Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Home - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 3:30 p.m. | ||
| Wed., 5/25 | V Boys Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Wed., 5/25 | V Girls Outdoor Track | Berkshire League Festival Hammer Throw Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Home - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 3:30 p.m. | ||
| Wed., 5/25 | V Softball | Housatonic Regional | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | L 2-5 | |
| Wed., 5/25 | V Girls Tennis | Northwestern | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 5/26 | V Baseball | Housatonic Regional | Away - Housatonic Valley Regional High-Varsity Baseball Diamond [Directions] | 5:00 p.m. | W 6-2 | |
| Thu., 5/26 | JV Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | Postponed | ||
| Fri., 5/27 | V Boys Tennis | Wolcott | Away - Wolcott HS-WHS Tennis Courts [Directions] | 10:00 a.m. | ||
| Tue., 5/31 | V Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 5/31 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/31 | V Boys Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 10:00 a.m. | ||
| Tue., 5/31 | V Girls Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/1 | JV Baseball | Litchfield | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | Rainout | ||
| Thu., 6/2 | JV Baseball | Litchfield | Away - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Golf | CIAC Division II Championship | Away - Timberlin GC | 8:30 a.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Girls Golf | CIAC Girls State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||