| Wamogo 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 456 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/31 | V Boys Golf | Litchfield | Home - Wamogo HS-Stoneybrook Golf Course [Directions] | 3:00 p.m. | LITCHFIELD 170 WAMOGO 241 | |
| Wed., 9/7 | V Boys Golf | Litchfield, Gilbert | Away - Litchfield Country Club [Directions] | 3:00 p.m. | Litchfield 173 Gilbert 270 Wamogo 249 | |
| Pending change awaiting acceptance by one or more parties involved: Facility to Stonybrook Golf Course | ||||||
| Thu., 9/8 | V Field Hockey | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | L 3-2 | |
| Thu., 9/8 | JV Field Hockey | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | ||
| Fri., 9/9 | V Football | VGW Techs | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | W 52-16 | |
| Fri., 9/9 | V Girls Volleyball | Terryville | Home - Wamogo Regional HS-Large gym [Directions] | 5:00 p.m. | W 3-1 | |
| Fri., 9/9 | JV Girls Volleyball | Terryville | Home - Wamogo Regional HS-Large Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/10 | V Boys Soccer | Nonnewaug | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-3 | |
| Sat., 9/10 | JV Boys Soccer | Nonnewaug | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | 3:45 p.m. | ||
| Sat., 9/10 | V Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 10:30 a.m. | W 1-0 | |
| Sat., 9/10 | JV Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | Canceled | Cancelled | |
| Sat., 9/10 | V Girls Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 10:30 a.m. | L 0-7 | |
| Sat., 9/10 | JV Girls Soccer | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | 10:30 a.m. | ||
| Mon., 9/12 | JV Football | Wilcox/Kaynor | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | ||
| Mon., 9/12 | V Boys Golf | Housatonic Regional, Litchfield | Away - Canaan Country Club [Directions] | 3:00 p.m. | Housatonic Regional 234 Litchfield. 163 Wamogo 228 | |
| Mon., 9/12 | V Girls Volleyball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 5:15 p.m. | L 1-3 | |
| Mon., 9/12 | JV Girls Volleyball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 9/13 | V Boys Soccer | Thomaston | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 9/13 | JV Boys Soccer | Thomaston | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Postponed | ||
| Tue., 9/13 | V Field Hockey | Thomaston | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | W 4-2 | |
| Tue., 9/13 | JV Field Hockey | Thomaston | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 5:00 p.m. | ||
| Tue., 9/13 | JV Girls Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Postponed | ||
| Tue., 9/13 | V Girls Volleyball | Gilbert | Away - Gilbert School-Gym [Directions] | 7:15 p.m. | W 3-0 | |
| Tue., 9/13 | JV Girls Volleyball | Gilbert | Away - Gilbert School-Gym [Directions] | 5:45 p.m. | ||
| Wed., 9/14 | V Boys Cross Country | Litchfield, Nonnewaug | Home - Wamogo Regional HS-White Memorial Park [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | V Girls Cross Country | Litchfield, Nonnewaug | Home - Wamogo Regional HS-White Memorial Park [Directions] | 4:30 p.m. | ||
| Wed., 9/14 | V Girls Soccer | Gilbert | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 2-3 | |
| Thu., 9/15 | V Boys Golf | Northwestern | Away - Northwestern Regional H.S.-Norfolk CC [Directions] | 3:30 p.m. | Northwestern 206 Wamogo 220 | |
| Thu., 9/15 | V Girls Soccer | Thomaston | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 9/16 | V Girls Volleyball | New Fairfield | Home - Wamogo Regional HS-Large gym [Directions] | 5:15 p.m. | L 1-3 | |
| Fri., 9/16 | JV Girls Volleyball | New Fairfield | Home - Wamogo Regional HS-Large Gym [Directions] | 3:45 p.m. | ||
| Mon., 9/19 | JV Football | Gilbert/Northwestern/Housy | Away - Gilbert School-Football Field [Directions] | 4:00 p.m. | ||
| Mon., 9/19 | V Boys Golf | Housatonic Regional, Terryville | Home - Wamogo HS-Stoneybrook Golf Course [Directions] | 3:00 p.m. | Housatonic Regional 235 Terryville DNP FFT Wamogo 227 | |
| Mon., 9/19 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-5 | |
| Mon., 9/19 | JV Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 9/19 | V Field Hockey | Shepaug Valley | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | W 2-1 | |
| Mon., 9/19 | JV Field Hockey | Shepaug Valley | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 5:00 p.m. | ||
| Mon., 9/19 | V Girls Soccer | Shepaug Valley | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-4 | |
| Tue., 9/20 | V Girls Volleyball | Northwestern | Home - Wamogo Regional HS-Large gym [Directions] | 5:00 p.m. | L 0-3 | |
| Tue., 9/20 | JV Girls Volleyball | Northwestern | Home - Wamogo Regional HS-Large Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/21 | V Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-JV Girls Soccer Field [Directions] | 3:45 p.m. | L 2-3 | |
| Wed., 9/21 | JV Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | Canceled | Cancelled | |
| Wed., 9/21 | V Girls Soccer | Housatonic Regional | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 4-7 | |
| Wed., 9/21 | JV Girls Soccer | Housatonic Regional | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Postponed | ||
| Fri., 9/23 | V Football | Wilcox/Kaynor | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | W 22-6 | |
| Fri., 9/23 | V Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-2 | |
| Fri., 9/23 | JV Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/23 | V Field Hockey | Northwestern | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | W 2-0 | |
| Fri., 9/23 | JV Field Hockey | Northwestern | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 5:00 p.m. | ||
| Fri., 9/23 | V Girls Soccer | Northwestern | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-5 | |
| Mon., 9/26 | FR Football | Wilcox/Kaynor | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | ||
| Mon., 9/26 | V Field Hockey | New Fairfield | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | W 3-2 | |
| Mon., 9/26 | JV Field Hockey | New Fairfield | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 5:15 p.m. | ||
| Mon., 9/26 | JV Girls Soccer | Northwestern | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Postponed | ||
| Mon., 9/26 | V Girls Volleyball | Wolcott Tech | Home - Wamogo Regional HS-Large gym [Directions] | 5:15 p.m. | L 0-3 | |
| Mon., 9/26 | JV Girls Volleyball | Wolcott Tech | Home - Wamogo Regional HS-Large Gym [Directions] | 3:45 p.m. | ||
| Tue., 9/27 | V Boys Golf | Nonnewaug | Away - Crestbrook Park-Crestbrook Park Golf [Directions] | 3:00 p.m. | Nonnewaug 190 Wamogo High school 230 | |
| Tue., 9/27 | V Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:45 p.m. | L 1-3 | |
| Tue., 9/27 | JV Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Wed., 9/28 | V Boys Cross Country | Northwestern, Housatonic Regional | Away - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Cross Country | Northwestern, Housatonic Regional | Away - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | V Boys Soccer | Terryville | Home - Trinity Health Stadium [Directions] | 6:30 p.m. | L 0-5 | |
| Fri., 9/30 | V Football | Cheney Tech | Away - Cheney Tech.-Football Field [Directions] | 6:00 p.m. | W 26-14 | |
| Fri., 9/30 | V Girls Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:45 p.m. | L 0-6 | |
| Fri., 9/30 | V Girls Volleyball | Nonnewaug | Home - Wamogo Regional HS-Large gym [Directions] | 5:00 p.m. | L 0-3 | |
| Fri., 9/30 | JV Girls Volleyball | Nonnewaug | Home - Wamogo Regional HS-Large Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/1 | JV Boys Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Postponed | ||
| Sat., 10/1 | V Field Hockey | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 3:00 p.m. | L 6-0 | |
| Sat., 10/1 | JV Field Hockey | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | Postponed | ||
| Sat., 10/1 | JV Girls Soccer | Thomaston | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Postponed | ||
| Sat., 10/1 | JV Girls Soccer | Litchfield | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Postponed | ||
| Mon., 10/3 | JV Football | Cheney Tech | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | ||
| Mon., 10/3 | V Boys Golf | Nonnewaug | Home - Wamogo HS-Stoneybrook Golf Course [Directions] | 3:00 p.m. | Nonnewaug 185 Wamogo 230 | |
| Tue., 10/4 | V Boys Cross Country | Thomaston, Gilbert | Away - Black Rock State Park [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Boys Soccer | Gilbert | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | W 8-4 | |
| Tue., 10/4 | V Girls Cross Country | Thomaston, Gilbert | Away - Thomaston HS-Black Rock State Park [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Girls Soccer | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 10/4 | V Girls Volleyball | Abbott Tech | Home - Wamogo Regional HS-Large gym [Directions] | 5:15 p.m. | L 2-3 | |
| Tue., 10/4 | JV Girls Volleyball | Abbott Tech | Home - Wamogo Regional HS-Large Gym [Directions] | 3:45 p.m. | ||
| Wed., 10/5 | V Boys Golf | Northwestern, Shepaug Valley | Away - Northwestern Regional H.S.-Norfolk CC [Directions] | 3:30 p.m. | Northwestern 206 | |
| Thu., 10/6 | V Boys Soccer | Litchfield | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 7:00 p.m. | L 0-5 | |
| Thu., 10/6 | JV Field Hockey | Litchfield | Away - Plumb Hill Field Complex-Field Hockey Field [Directions] | 4:15 p.m. | ||
| Thu., 10/6 | V Girls Soccer | Litchfield | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 5:00 p.m. | L 2-7 | |
| Thu., 10/6 | V Girls Volleyball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 7:00 p.m. | L 0-3 | |
| Thu., 10/6 | JV Girls Volleyball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 5:15 p.m. | ||
| Fri., 10/7 | V Boys Golf | Gilbert, Shepaug Valley | Away - Green woods Country Club [Directions] | 3:00 p.m. | Gilbert 202 Shepaug 175 Wamogo 220 | |
| Fri., 10/7 | V Field Hockey | Litchfield | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 7:00 p.m. | W 4-0 | |
| Sat., 10/8 | V Boys Cross Country | Wickham Invitational | Away - Wamogo Regional HS-White Memorial Park | TBA | ||
| Sat., 10/8 | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 10/8 | V Girls Cross Country | Wickham Invitational | Away - Wickham Park | TBA | ||
| Sat., 10/8 | JV Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | Postponed | ||
| Sun., 10/9 | V Football | O'Brien Tech | Away - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 10:30 a.m. | W 26-0 | |
| Tue., 10/11 | V Boys Cross Country | Shepaug Valley, Terryville | Home - Wamogo Regional HS-White Memorial Park [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Boys Golf | Shepaug Valley | Away - Washington Club Golf Course [Directions] | 3:00 p.m. | Shepaug 190 Wamogo 220 | |
| Tue., 10/11 | V Boys Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | L 8-1 | |
| Tue., 10/11 | JV Boys Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Canceled | Cancelled | |
| Tue., 10/11 | V Girls Cross Country | Shepaug Valley, Terryville | Home - Wamogo Regional HS-White Memorial Park [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Field Hockey | Thomaston | Away - Thomaston HS-Field Hockey Field [Directions] | 3:45 p.m. | T 0-0 | |
| Tue., 10/11 | JV Field Hockey | Thomaston | Away - Thomaston HS-Field Hockey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/11 | V Girls Soccer | Thomaston | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 10/11 | JV Girls Soccer | Thomaston | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Canceled | Cancelled | |
| Wed., 10/12 | MS Girls Soccer | Northwestern MS | Home - Wamogo Regional HS-Wamogo MS Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/12 | V Girls Volleyball | Gilbert | Home - Wamogo Regional HS-Large gym [Directions] | 5:00 p.m. | W 3-0 | |
| Wed., 10/12 | JV Girls Volleyball | Gilbert | Home - Wamogo Regional HS-Large Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | V Boys Golf | Terryville, Litchfield, Northwestern | Away - Pequabuck Golf Club-Golf Course, Front 9 [Directions] | 3:00 p.m. | Terryville x Northwestern 215 Wamogo 224 | |
| Thu., 10/13 | V Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Gym [Directions] | 5:45 p.m. | L 0-3 | |
| Thu., 10/13 | JV Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/14 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 7:00 p.m. | L 3-1 | |
| Fri., 10/14 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | 5:15 p.m. | ||
| Fri., 10/14 | V Girls Soccer | Nonnewaug | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-8 | |
| Fri., 10/14 | JV Girls Soccer | Nonnewaug | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Postponed | ||
| Fri., 10/14 | V Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 5:00 p.m. | W 3-2 | |
| Fri., 10/14 | JV Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | FR Football | Wilcox/Kaynor | Away - Wilcox Tech-Football Field [Directions] | 3:30 p.m. | ||
| Mon., 10/17 | V Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 3:45 p.m. | W 1-0 | |
| Mon., 10/17 | JV Field Hockey | Nonnewaug | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Nonnewaug HS-Turf Field | ||||||
| Tue., 10/18 | V Boys Golf | BL Golf All Star Tournament | Away - Fairfiew Farm Golf Course | 8:00 a.m. | ||
| Tue., 10/18 | V Boys Soccer | Shepaug Valley | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 2-1 OT | |
| Tue., 10/18 | JV Boys Soccer | Shepaug Valley | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Postponed | ||
| Tue., 10/18 | V Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | 3:45 p.m. | W 2-1 | |
| Tue., 10/18 | JV Field Hockey | Shepaug Valley | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/18 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | W 4-2 | |
| Tue., 10/18 | V Girls Volleyball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 6:30 p.m. | L 0-3 | |
| Tue., 10/18 | JV Girls Volleyball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/20 | V Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-JV Boys Soccer [Directions] | 3:45 p.m. | L 1-9 | |
| Thu., 10/20 | JV Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/21 | V Boys Cross Country | BL Cross Country Championships | Away - Black Rock State Park | TBA | ||
| Fri., 10/21 | V Boys Soccer | Housatonic Regional | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | W 4-3 | |
| Fri., 10/21 | JV Boys Soccer | Housatonic Regional | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Canceled | Cancelled | |
| Fri., 10/21 | V Girls Cross Country | BL Cross Country Championships | Away - Wamogo Regional HS-White Memorial Park | TBA | ||
| Sat., 10/22 | V Football | Wilcox/Kaynor | Away - Falcon Field (Meriden, CT)-Football Field [Directions] | 6:00 p.m. | W 14-10 | |
| Sat., 10/22 | JV Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | Canceled | Cancelled | |
| Sat., 10/22 | V Field Hockey | Immaculate | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 11:00 a.m. | L 1-0 | |
| Sat., 10/22 | JV Field Hockey | Immaculate | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 12:30 p.m. | ||
| Sat., 10/22 | JV Girls Soccer | Litchfield | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | 9:00 a.m. | ||
| Mon., 10/24 | V Girls Volleyball | Kaynor Tech | Home - Wamogo Regional HS-Large gym [Directions] | 5:15 p.m. | L 2-3 | |
| Mon., 10/24 | JV Girls Volleyball | Kaynor Tech | Home - Wamogo Regional HS-Large Gym [Directions] | 3:45 p.m. | ||
| Tue., 10/25 | JV Boys Soccer | Northwestern | Home - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Canceled | Cancelled | |
| Tue., 10/25 | V Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | 3:45 p.m. | W 3-0 | |
| Tue., 10/25 | JV Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/25 | V Girls Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-7 | |
| Tue., 10/25 | JV Girls Soccer | Northwestern | Away - Northwestern Regional H.S.-JV Soccer Field [Directions] | Postponed | ||
| Tue., 10/25 | V Girls Volleyball | Housatonic Regional | Home - Wamogo Regional HS-Large gym [Directions] | 5:00 p.m. | L 0-3 | |
| Tue., 10/25 | JV Girls Volleyball | Housatonic Regional | Home - Wamogo Regional HS-Large Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/26 | JV Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | 3:30 p.m. | ||
| Thu., 10/27 | V Football | Bullard/Kolbe | Home - Nonnewaug HS-Turf Field [Directions] | 7:00 p.m. | W 36-31 | |
| Thu., 10/27 | V Boys Soccer | Northwestern | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 4-1 | |
| Thu., 10/27 | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:30 p.m. | ||
| Thu., 10/27 | V Field Hockey | Litchfield | Away - Plumb Hill Field Complex-Field Hockey Field [Directions] | 7:00 p.m. | W 6-0 | |
| Fri., 10/28 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 6:00 p.m. | L 4-0 | |
| Fri., 10/28 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 7:45 p.m. | L 2-4 | |
| Sat., 10/29 | JV Football | Bullard/Kolbe | Away - Bullard Havens Tech-Football Field [Directions] | 10:30 a.m. | ||
| Mon., 10/31 | V Boys Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:15 p.m. | L 0-3 | |
| Mon., 10/31 | JV Boys Soccer | Terryville | Away - Terryville HS-Baseball Field [Directions] | Canceled | Cancelled | |
| Mon., 10/31 | V Field Hockey | Watertown | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 3:45 p.m. | L 1-0 | |
| Mon., 10/31 | JV Field Hockey | Watertown | Home - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 5:00 p.m. | ||
| Tue., 11/1 | V Girls Soccer | Terryville | Home - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-6 | |
| Wed., 11/2 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 11/2 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | ||
| Thu., 11/3 | V Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | L 0-1 | |
| Fri., 11/4 | V Football | Quinebaug Valley | Away - Ellis R V Tech School-Football Field [Directions] | 6:00 p.m. | W 54-8 | |
| Sat., 11/12 | V Football | Prince Tech-Innovation | Away - Cheney Tech [Directions] | 6:00 p.m. | W 40-18 | |
| Mon., 11/14 | JV Football | Prince Tech-Innovation | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | ||
| Fri., 11/18 | V Football | Platt Tech | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | W 36-14 | |
| Wed., 11/23 | V Football | ATI | Home - Nonnewaug HS-Turf Field [Directions] | 5:00 p.m. | W 20-0 | |
| Wed., 12/7 | Miscellaneous Events | Elementary Band/Choir Concert | Home - Wamogo HS [Directions] | 5:30 p.m. | ||
| Mon., 12/12 | V Boys Ice Hockey | JBWA | Home - South Kent School-Ice Rink [Directions] | 3:45 p.m. | L 2-4 | |
| Tue., 12/13 | V Girls Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 5:30 p.m. | W 30-15 | |
| Tue., 12/13 | JV Girls Basketball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 12/14 | V Wrestling | St. Paul Catholic | Home - Terryville HS-Gym [Directions] | 6:00 p.m. | ||
| Mon., 12/19 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Home - South Kent School-Ice Rink [Directions] | 3:45 p.m. | L 3-4 | |
| Mon., 12/19 | Miscellaneous Events | High School Band Concert | Home - Wamogo HS-High School Auditorium [Directions] | 7:00 p.m. | Musicians report at 6 | |
| Tue., 12/20 | V Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 7:00 p.m. | W 57-43 | |
| Tue., 12/20 | JV Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/20 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 12/20 | V Girls Basketball | Thomaston | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | L 14-43 | |
| Tue., 12/20 | JV Girls Basketball | Thomaston | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/21 | V Boys Ice Hockey | Eastern CT Eagles | Away - Connecticut College-Dayton Arena [Directions] | 6:00 p.m. | L 2-11 | |
| Thu., 12/22 | V Boys Basketball | Housatonic Regional | Home - Wamogo HS-Wamogo Large Gym [Directions] | 6:00 p.m. | W 63-33 | |
| Thu., 12/22 | JV Boys Basketball | Housatonic Regional | Home - Wamogo HS-Wamogo Large Gym [Directions] | 4:30 p.m. | ||
| Thu., 12/22 | V Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:15 p.m. | W 42-37 | |
| Thu., 12/22 | JV Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:45 p.m. | ||
| Tue., 12/27 | V Boys Swimming and Diving | Litchfield | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Tue., 12/27 | V Girls Basketball | Bunnell | Home - Wamogo HS-Wamogo Large Gym [Directions] | 6:00 p.m. | L 40-43(OT) | |
| Tue., 12/27 | JV Girls Basketball | Bunnell | Home - Wamogo HS-Wamogo Large Gym [Directions] | 4:30 p.m. | ||
| Wed., 12/28 | V Boys Basketball | Canton | Away - Canton Holiday Tournament [Directions] | 7:00 p.m. | W 57-45 | |
| Wed., 12/28 | JV Boys Basketball | Canton | Away - Canton Holiday Tournament [Directions] | 3:00 p.m. | ||
| Wed., 12/28 | FR Boys Basketball | Canton | Away - Canton Holiday Tournament [Directions] | 1:00 p.m. | ||
| Wed., 12/28 | V Wrestling | Nonnewaug | Home - Terryville HS-Gym [Directions] | 1:00 p.m. | ||
| Thu., 12/29 | V Girls Basketball | Terryville | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | W 39-34 | |
| Thu., 12/29 | JV Girls Basketball | Terryville | Home - Wamogo HS-Wamogo Large Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/30 | V Boys Basketball | Lewis Mills | Away - Canton Holiday Tournament [Directions] | 7:00 p.m. | L 51-49 | |
| Fri., 12/30 | JV Boys Basketball | Suffield | Home - Canton Holiday Tournament [Directions] | 3:00 p.m. | ||
| Fri., 12/30 | FR Boys Basketball | Suffield | Home - Canton Holiday Tournament [Directions] | 1:00 p.m. | ||
| Fri., 12/30 | V Girls Basketball | Nonnewaug | Home - Wamogo HS-Wamogo Large Gym [Directions] | 3:30 p.m. | L 33-48 | |
| Fri., 12/30 | JV Girls Basketball | Nonnewaug | Home - Wamogo HS-Wamogo Large Gym [Directions] | 2:00 p.m. | ||
| Mon., 1/2 | V Boys Basketball | Housatonic Regional | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | ||
| Mon., 1/2 | JV Boys Basketball | Housatonic Regional | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | V Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | W 63-47 | |
| Tue., 1/3 | JV Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | V Girls Basketball | Northwestern | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | L 11-51 | |
| Tue., 1/3 | JV Girls Basketball | Northwestern | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/4 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | L 0-6 | |
| Wed., 1/4 | V Wrestling | Derby/Oxford/Holy Cross | Home - Terryville HS-Gym [Directions] | 6:30 p.m. | ||
| Fri., 1/6 | V Boys Basketball | Litchfield | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 63-59 | |
| Fri., 1/6 | JV Boys Basketball | Litchfield | Home - Wamogo HS-Wamogo Small Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | V Girls Basketball | Litchfield | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | W 31-20 | |
| Fri., 1/6 | JV Girls Basketball | Litchfield | Home - Wamogo HS-Wamogo Large Gym [Directions] | 3:45 p.m. | ||
| Sat., 1/7 | V Boys Ice Hockey | Woodstock Academy | Home - South Kent School-Ice Rink [Directions] | 7:30 p.m. | L 0-10 | |
| Sat., 1/7 | V Boys Indoor Track | Bethel 8 Team Meet | Away - Bethel HS-Bethel Track and Field Center | TBA | ||
| Sat., 1/7 | V Boys Indoor Track | Bethel 8 Team Meet | Away - Bethel HS Track & Field Training Center | TBA | ||
| Sat., 1/7 | V Boys Swimming and Diving | Northwestern | Away - Northwestern Regional H.S.-YMCA Swim [Directions] | 3:00 p.m. | ||
| Sat., 1/7 | V Wrestling | Warrior Invitational | Away - Canton HS-Gym | 9:30 a.m. | ||
| Sat., 1/7 | V Girls Indoor Track | Bethel 8 Team Meet | Away - Bethel HS-Bethel Track and Field Center | TBA | ||
| Mon., 1/9 | FR Boys Basketball | Shepaug Valley | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | ||
| Mon., 1/9 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | L 2-3 | |
| Tue., 1/10 | V Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 70-64 | |
| Tue., 1/10 | JV Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Shepaug Valley | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 41-35 | |
| Tue., 1/10 | JV Girls Basketball | Shepaug Valley | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/11 | V Boys Ice Hockey | Tri-Town | Away - Enfield Twin Rinks-Rink 1 [Directions] | 3:50 p.m. | W 4-3(OT) | |
| Wed., 1/11 | V Boys Indoor Track | James Barber Invitational | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Wed., 1/11 | V Boys Indoor Track | James Barber Invitational | Away - Southern CT State University-Moore Field House | TBA | ||
| Wed., 1/11 | V Girls Indoor Track | James Barber Invitational | Away - Southern Connecticut State University | 4:00 p.m. | ||
| Wed., 1/11 | Miscellaneous Events | High School Choir Concert | Home - Wamogo HS-High School Auditorium [Directions] | 7:00 p.m. | Choir reports at 6 | |
| Thu., 1/12 | V Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 6:30 p.m. | W 63-58(OT) | |
| Thu., 1/12 | JV Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 5:00 p.m. | ||
| Thu., 1/12 | V Boys Swimming and Diving | Northwestern | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Gilbert | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | L 31-47 | |
| Fri., 1/13 | JV Girls Basketball | Gilbert | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Mon., 1/16 | V Boys Indoor Track | BL Showcase | Away - Bethel HS Track & Field Training Center | 11:00 a.m. | ||
| Mon., 1/16 | V Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 1:30 p.m. | L 10-44 | |
| Mon., 1/16 | JV Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 12:00 p.m. | ||
| Tue., 1/17 | V Boys Swimming and Diving | Nonnewaug | Away - Wilby HS [Directions] | 7:00 p.m. | ||
| Wed., 1/18 | V Boys Ice Hockey | Mt. Everett (MA) | Home - South Kent School-Ice Rink [Directions] | 7:10 p.m. | W 8-5 | |
| Wed., 1/18 | MS Boys Swimming and Diving | Long River MS | Away - Woodland HS-pool [Directions] | Canceled | Cancelled | |
| Wed., 1/18 | V Wrestling | Northwestern | Away - Northwestern Regional H.S.-Small Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/18 | V Girls Basketball | Abbott Tech | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 36-18 | |
| Wed., 1/18 | JV Girls Basketball | Abbott Tech | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | V Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 7:00 p.m. | W 70-46 | |
| Fri., 1/20 | JV Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/21 | FR Boys Basketball | Watertown | Away - Watertown High-Robert B Cook Memorial Gym [Directions] | 12:30 p.m. | ||
| Sat., 1/21 | V Wrestling | New Milford Wrestling Tournament | Away - New Milford HS-Small Gym - NMHS | 8:00 a.m. | ||
| Mon., 1/23 | V Boys Indoor Track | Shoreline Coaches’ Meet | Away - Floyd Little Athletic Center-Field House | 4:00 p.m. | ||
| Mon., 1/23 | V Boys Indoor Track | Shoreline Coaches' Meet | Away - Floyd Little Athletic Center-Field House | TBA | ||
| Mon., 1/23 | V Girls Indoor Track | Shoreline Coaches’ Meet | Away - Floyd Little Athletic Center-Field House | 4:00 p.m. | ||
| Tue., 1/24 | V Boys Basketball | Nonnewaug | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 64-37 | |
| Tue., 1/24 | JV Boys Basketball | Nonnewaug | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | V Boys Swimming and Diving | Housatonic Regional | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:45 p.m. | L 32-68 | |
| Tue., 1/24 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/25 | V Wrestling | Gilbert/Torrington | Away - Gilbert School-Gym [Directions] | Postponed | ||
| Thu., 1/26 | V Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 7:00 p.m. | W 28-24 | |
| Thu., 1/26 | JV Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | V Boys Basketball | Thomaston | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 55-41 | |
| Fri., 1/27 | JV Boys Basketball | Thomaston | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | V Boys Swimming and Diving | Litchfield | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | Canceled | Cancelled | |
| Fri., 1/27 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 7:30 p.m. | L 18-63 | |
| Fri., 1/27 | JV Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/28 | V Wrestling | Portland, Avon, Bristol Eastern, Coventry, Daniel Hand, Griswold/Wheeler, Haddam-Killingworth, Old Lyme, Manchester, Morgan, TBA, New Britain, Nonnewaug, Plainville | Away - . | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Portland HS-PHS Gym | ||||||
| Sat., 1/28 | V Wrestling | Suffield/Windsor Locks, Hampden Charter (MA), Hampden Charter (MA), Ludlow (MA), TBA, TBA, Northwestern, Rockville, Sabis (MA), South Windsor, Stafford | Away - Suffield HS | 9:30 a.m. | ||
| Mon., 1/30 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | W 63-62 | |
| Mon., 1/30 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | ||
| Mon., 1/30 | V Boys Ice Hockey | Mt. Everett (MA) | Away - Berkshire School-NHL | 8:00 p.m. | L 2-3 (OT) | |
| Tue., 1/31 | V Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | W 72-40 | |
| Tue., 1/31 | JV Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Housatonic Regional | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 37-29 | |
| Tue., 1/31 | JV Girls Basketball | Housatonic Regional | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/1 | V Wrestling | Gilbert/Torrington, St. Paul Catholic | Away - Gilbert School-Gym [Directions] | 7:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 6:00 p.m. | ||||||
| Thu., 2/2 | V Boys Swimming and Diving | New Fairfield | Away - New Fairfield HS-Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/3 | V Boys Basketball | Northwestern | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 74-63 | |
| Fri., 2/3 | JV Boys Basketball | Northwestern | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/3 | V Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | L 17-63 | |
| Fri., 2/3 | JV Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 2/4 | V Boys Ice Hockey | Tri-Town | Home - South Kent School-Ice Rink [Directions] | 7:00 p.m. | L 2-5 | |
| Sat., 2/4 | V Wrestling | 2023 Bacon Academy Matt Bishel Bobcat Classic | Away - Bacon Academy | 9:00 a.m. | ||
| Mon., 2/6 | FR Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | ||
| Mon., 2/6 | V Boys Ice Hockey | Woodstock Academy | Away - Pomfret School-Jahn Rink [Directions] | 8:15 p.m. | L 1-9 | |
| Tue., 2/7 | V Boys Basketball | Shepaug Valley | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 60-58 (OT) | |
| Tue., 2/7 | JV Boys Basketball | Shepaug Valley | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | V Boys Swimming and Diving | Nonnewaug | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 6:00 p.m. | W 39-38 | |
| Tue., 2/7 | JV Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | Canceled | Cancelled | |
| Wed., 2/8 | FR Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 6:30 p.m. | ||
| Wed., 2/8 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | L 1-2 | |
| Fri., 2/10 | V Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 56-40 | |
| Fri., 2/10 | JV Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/10 | V Boys Swimming and Diving | Shepaug Valley | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Home - South Kent School-Ice Rink [Directions] | 3:15 p.m. | L 4-7 | |
| Mon., 2/13 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - South Kent School-Ice Rink [Directions] | 3:45 p.m. | L 1-2 | |
| Mon., 2/13 | V Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 31-25 | |
| Mon., 2/13 | JV Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/14 | V Boys Basketball | Gilbert | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 61-51 | |
| Tue., 2/14 | JV Boys Basketball | Gilbert | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/14 | V Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 7:00 p.m. | L 37-47 | |
| Wed., 2/15 | FR Boys Basketball | Litchfield | Home - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/15 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Home - South Kent School-Ice Rink [Directions] | 7:00 p.m. | L 3-4 | |
| Wed., 2/15 | V Boys Swimming and Diving | Housatonic Regional, Litchfield | Away - Hotchkiss School-Pool [Directions] | 6:00 p.m. | ||
| Sat., 2/18 | V Boys Basketball | Classical Magnet | Home - Wamogo HS-Wamogo Large Gym [Directions] | 3:00 p.m. | W 50-45 | |
| Sat., 2/18 | JV Boys Basketball | Classical Magnet | Home - Wamogo HS-Wamogo Large Gym [Directions] | 1:30 p.m. | ||
| Mon., 2/20 | V Boys Basketball | Somers | Home - Wamogo HS-Wamogo Large Gym [Directions] | 3:00 p.m. | W 63-51 | |
| Mon., 2/20 | JV Boys Basketball | Somers | Home - Wamogo HS-Wamogo Large Gym [Directions] | 1:30 p.m. | ||
| Tue., 2/21 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Wed., 2/22 | JV Boys Basketball | Terryville | Home - Wamogo HS-Wamogo Large Gym [Directions] | Canceled | Cancelled | |
| Thu., 2/23 | JV Boys Basketball | Terryville | Home - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 2/24, Time to 4:30 p.m. | ||||||
| Fri., 2/24 | V Boys Basketball | Terryville | Home - Wamogo HS-Wamogo Large Gym [Directions] | 6:00 p.m. | W 64-34 | |
| Fri., 2/24 | V Boys Ice Hockey | Simsbury | Away - Simsbury - ISCC-Olympic [Directions] | 7:10 p.m. | Cancelled | |
| Sat., 2/25 | FR Boys Basketball | Nonnewaug, Watertown | Away - Nonnewaug HS-Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/25 | V Boys Ice Hockey | Rocky Hill Coop | Home - South Kent School-Ice Rink [Directions] | 12:20 p.m. | L 4-7 | |
| Sun., 2/26 | V Boys Ice Hockey | Eastern CT Eagles | Home - South Kent School-Ice Rink [Directions] | 5:30 p.m. | L 1-6 | |
| Mon., 2/27 | V Boys Ice Hockey | New Milford | Away - South Kent School-Ice Rink [Directions] | 3:30 p.m. | L 1-7 | |
| Tue., 2/28 | FR Boys Basketball | Housatonic Regional | Home - Wamogo HS-Wamogo Large Gym [Directions] | Postponed | ||
| Wed., 3/1 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Simsbury - ISCC-Olympic [Directions] | 4:50 p.m. | L 2-3 | |
| Thu., 3/2 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 5:00 p.m. | L 4-8 | |
| Tue., 3/21 | Miscellaneous Events | Spring Band Concert | Home - Wamogo HS [Directions] | 7:00 p.m. | ||
| Sat., 4/1 | V Boys Lacrosse | Bristol Coop | Away - Bristol Eastern HS-Alumni Field-Turf [Directions] | 12:00 p.m. | L 4-8 | |
| Sat., 4/1 | V Girls Lacrosse | Rocky Hill | Away - Rocky Hill HS-Stadium [Directions] | 11:00 a.m. | L 3-13 | |
| Sat., 4/1 | JV Girls Lacrosse | Rocky Hill | Away - Rocky Hill HS-Stadium [Directions] | 12:30 p.m. | ||
| Mon., 4/3 | V Baseball | Terryville | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 11:00 a.m. | W 18-2 | |
| Mon., 4/3 | V Boys Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | L 0-5 [Detailed Results] | |
| Mon., 4/3 | V Softball | Terryville | Away - Terryville HS-Softball Field [Directions] | 3:45 p.m. | W 7-0 | |
| Mon., 4/3 | V Girls Tennis | Litchfield | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/4 | V Baseball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 4/4 | JV Baseball | Shepaug Valley | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 4/4 | V Boys Outdoor Track | Kangaroo Invitational | Away - Terryville HS-Track | 3:45 p.m. | ||
| Tue., 4/4 | V Girls Outdoor Track | Kangaroo Invitational | Away - Terryville HS-Track | 3:45 p.m. | ||
| Tue., 4/4 | V Softball | Thomaston | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | L 6-8 | |
| Wed., 4/5 | V Boys Lacrosse | Watertown | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 3-15 | |
| Wed., 4/5 | JV Boys Lacrosse | Watertown | Home - Plumb Hill Field Complex-Softball Field [Directions] | 5:15 p.m. | ||
| Wed., 4/5 | V Boys Tennis | Shepaug Valley | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 [Detailed Results] | |
| Wed., 4/5 | V Girls Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | L 8-12 | |
| Wed., 4/5 | JV Girls Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:30 p.m. | ||
| Wed., 4/5 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | L 0-4 | |
| Thu., 4/6 | V Baseball | Northwestern | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | L 11-0 | |
| Thu., 4/6 | JV Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 4/6 | V Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 3:45 p.m. | L 4-14 | |
| Thu., 4/6 | JV Softball | Northwestern | Away - Northwestern Regional H.S.-JV Softball Field [Directions] | 3:45 p.m. | ||
| Sat., 4/8 | V Boys Lacrosse | Ellington | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 11:00 a.m. | L 2-10 | |
| Sat., 4/8 | JV Boys Lacrosse | Ellington | Home - Plumb Hill Field Complex-Softball Field [Directions] | 12:15 p.m. | ||
| Sat., 4/8 | V Softball | Plainville | Away - Plainville HS-Plainville HS- Varsity Softball Field (Turf) [Directions] | 2:00 p.m. | L 0-15 | |
| Tue., 4/11 | JV Baseball | Crosby | Away - Crosby HS-CHS Baseball Field [Directions] | 11:00 a.m. | ||
| Tue., 4/11 | V Boys Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 4:00 p.m. | L 7-17 | |
| Tue., 4/11 | JV Boys Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 5:30 p.m. | ||
| Tue., 4/11 | JV Girls Lacrosse | St. Paul Catholic | Home - Plumb Hill Field Complex-Softball Field [Directions] | Canceled | Cancelled | |
| Tue., 4/11 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 4:45 p.m. | L 0-13 | |
| Wed., 4/12 | V Baseball | Litchfield | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | W 9-2 | |
| Thu., 4/13 | JV Baseball | Litchfield | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 11:00 a.m. | ||
| Thu., 4/13 | V Boys Lacrosse | Waterford | Away - Waterford HS-Alumni Turf Field/Track [Directions] | 2:00 p.m. | L 4-9 | |
| Thu., 4/13 | JV Boys Lacrosse | Waterford | Away - Waterford HS-Alumni Turf Field/Track [Directions] | 3:45 p.m. | ||
| Fri., 4/14 | V Baseball | Kaynor Tech | Away - Kaynor Technical School- Kaynor Baseball Diamond [Directions] | 11:00 a.m. | L 12-2(5) | |
| Sat., 4/15 | V Baseball | Nonnewaug | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 10:00 a.m. | L 15-4(5) | |
| Sat., 4/15 | JV Baseball | Abbott Tech | Away - Abbott V-T School-Abbott Tech Baseball Field, School Campus [Directions] | 10:30 a.m. | ||
| Mon., 4/17 | V Baseball | Gilbert | Away - Eastern CT State University-McCarthy Field (turf) [Directions] | 5:30 p.m. | W 12-3 | |
| Mon., 4/17 | V Boys Lacrosse | Capital Prep | Home - Nonnewaug HS-Turf Field [Directions] | 5:00 p.m. | W 15-1 | |
| Mon., 4/17 | JV Boys Lacrosse | Capital Prep | Home - Plumb Hill Field Complex-Softball Field [Directions] | Canceled | Cancelled | |
| Tue., 4/18 | V Boys Tennis | Gilbert | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-0 | |
| Tue., 4/18 | V Softball | WCA | Away - Huntingdon Park #3 [Directions] | 3:45 p.m. | W 16-14 | |
| Tue., 4/18 | V Girls Tennis | Gilbert | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-0 | |
| Wed., 4/19 | V Baseball | Wolcott | Away - Wolcott HS Baseball Field [Directions] | 4:00 p.m. | L 16-9 | |
| Wed., 4/19 | V Boys Lacrosse | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 3-18 | |
| Wed., 4/19 | V Girls Tennis | Housatonic Regional | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Thu., 4/20 | V Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | L 4-3 | |
| Thu., 4/20 | V Boys Tennis | Housatonic Regional | Away - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | W 4-1 [Detailed Results] | |
| Thu., 4/20 | V Softball | Shepaug Valley | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | L 0-12 | |
| Thu., 4/20 | JV Softball | Shepaug Valley | Home - Wamogo Regional HS-Wamogo Regional School JV Girls Softball [Directions] | 3:45 p.m. | ||
| Fri., 4/21 | JV Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | ||
| Fri., 4/21 | V Boys Tennis | Thomaston | Away - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 3:45 p.m. | W 4-1 [Detailed Results] | |
| Fri., 4/21 | V Girls Lacrosse | Housatonic Regional | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | W 9-6 | |
| Fri., 4/21 | JV Girls Lacrosse | Housatonic Regional | Home - Plumb Hill Field Complex-Softball Field [Directions] | Postponed | ||
| Fri., 4/21 | V Girls Tennis | Thomaston | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 3-2 | |
| Sat., 4/22 | V Girls Lacrosse | St. Paul Catholic | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 4:30 p.m. | L 6-7 (OT) | |
| Mon., 4/24 | V Baseball | Canton | Away - Bowdoin Field-Baseball Diamond [Directions] | 3:45 p.m. | L 10-0 | |
| Mon., 4/24 | JV Baseball | Canton | Away - Mills Pond Park - Canton-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Mon., 4/24 | V Boys Lacrosse | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 5:30 p.m. | W 17-10 | |
| Mon., 4/24 | V Boys Tennis | Nonnewaug | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 [Detailed Results] | |
| Mon., 4/24 | V Girls Lacrosse | Wolcott | Home - Nonnewaug HS-Turf Field [Directions] | 5:00 p.m. | L 7-9 | |
| Mon., 4/24 | JV Girls Lacrosse | Wolcott | Home - Nonnewaug HS-Turf Field [Directions] | 6:30 p.m. | ||
| Mon., 4/24 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Tue., 4/25 | V Boys Outdoor Track | Thomaston, Housatonic Regional | Away - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:00 p.m. | ||
| Wed., 4/26 | V Baseball | Housatonic Regional | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | W 10-5 | |
| Wed., 4/26 | V Softball | Housatonic Regional | Away - Housatonic Valley Regional High-softball field [Directions] | 4:15 p.m. | L 4-9 | |
| Thu., 4/27 | V Girls Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 4/28 | V Baseball | Terryville | Away - Terryville HS-Baseball Field [Directions] | 3:45 p.m. | W 15-2 | |
| Fri., 4/28 | V Boys Tennis | Litchfield | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-4 [Detailed Results] | |
| Fri., 4/28 | V Softball | Terryville | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | W 7-5 | |
| Fri., 4/28 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Mon., 5/1 | V Baseball | Thomaston | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | W 13-3 | |
| Mon., 5/1 | V Boys Lacrosse | Tolland | Home - Nonnewaug HS-Turf Field [Directions] | 5:30 p.m. | L 6-7 | |
| Mon., 5/1 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | L 0-5 [Detailed Results] | |
| Mon., 5/1 | V Girls Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 5:45 p.m. | L 4-13 | |
| Mon., 5/1 | V Softball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 4:20 p.m. | L 2-4 | |
| Mon., 5/1 | V Girls Tennis | Shepaug Valley | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 5/3 | JV Baseball | Northwestern | Home - Wamogo Regional HS-Softball Diamond [Directions] | 3:45 p.m. | ||
| Wed., 5/3 | V Boys Tennis | Gilbert | Away - Gilbert School-PineWoods Racquet Club [Directions] | 3:45 p.m. | W 1-0 [Detailed Results] | |
| Wed., 5/3 | V Girls Lacrosse | Rocky Hill | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | L 3-8 | |
| Wed., 5/3 | JV Girls Lacrosse | Rocky Hill | Home - Nonnewaug HS-Turf Field [Directions] | Canceled | Cancelled | |
| Wed., 5/3 | V Girls Tennis | Gilbert | Away - Gilbert School-PineWoods Racquet Club [Directions] | 3:45 p.m. | W 4-1 | |
| Thu., 5/4 | V Girls Tennis | Housatonic Regional | Away - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | L 5-0 | |
| Fri., 5/5 | V Baseball | Abbott Tech | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | L 3-1 | |
| Fri., 5/5 | V Boys Outdoor Track | Gilbert, Shepaug Valley | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | V Girls Outdoor Track | Gilbert, Shepaug Valley | Home - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Sat., 5/6 | V Boys Lacrosse | St. Paul Catholic | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 11-12 | |
| Sat., 5/6 | JV Boys Lacrosse | St. Paul Catholic | Home - Plumb Hill Field Complex-Softball Field [Directions] | 5:15 p.m. | ||
| Mon., 5/8 | V Baseball | Litchfield | Away - Dunkin' Donuts Park-Yard Goats [Directions] | 6:30 p.m. | L 8-5 | |
| Mon., 5/8 | V Boys Lacrosse | Holy Cross | Home - Nonnewaug HS-Turf Field [Directions] | 5:00 p.m. | L 6-15 | |
| Mon., 5/8 | JV Boys Lacrosse | Holy Cross | Home - Plumb Hill Field Complex-Softball Field [Directions] | Canceled | Cancelled | |
| Mon., 5/8 | V Boys Tennis | Thomaston | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-1 [Detailed Results] | |
| Mon., 5/8 | V Softball | Coginchaug | Away - Coginchaug Regional HS-Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 4:30 p.m. | L 0-19 | |
| Mon., 5/8 | V Girls Tennis | Thomaston | Away - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 4:00 p.m. | L 4-1 | |
| Tue., 5/9 | V Boys Outdoor Track | Nonnewaug, Litchfield | Away - Nonnewaug HS-Paul Burns Memorial Track [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Girls Lacrosse | Housatonic Regional | Away - Housatonic Valley Regional High-football field [Directions] | 6:15 p.m. | W 9-6 | |
| Tue., 5/9 | V Girls Outdoor Track | Nonnewaug, Litchfield | Away - Nonnewaug HS-Paul Burns Memorial Track [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Softball | Gilbert | Away - Winsted Rowley Field [Directions] | 3:45 p.m. | L 14-15 | |
| Wed., 5/10 | V Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 3:45 p.m. | L 17-7 | |
| Wed., 5/10 | JV Baseball | Nonnewaug | Away - Woodbury MS [Directions] | 3:45 p.m. | ||
| Wed., 5/10 | V Boys Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 5/10 | V Softball | Nonnewaug | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | L 4-19 | |
| Wed., 5/10 | V Girls Tennis | Nonnewaug | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 5-0 | |
| Thu., 5/11 | V Baseball | Gilbert | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | L 7-2 | |
| Thu., 5/11 | V Boys Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:30 p.m. | L 4-18 | |
| Thu., 5/11 | V Girls Lacrosse | Watertown | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 5:00 p.m. | L 4-15 | |
| Thu., 5/11 | JV Girls Lacrosse | Watertown | Home - Plumb Hill Field Complex-Softball Field [Directions] | Postponed | ||
| Fri., 5/12 | V Boys Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | W 4-1 [Detailed Results] | |
| Fri., 5/12 | V Girls Tennis | Northwestern | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-4 | |
| Sat., 5/13 | JV Baseball | Watertown | Away - Deland Field-Deland field [Directions] | Canceled | Cancelled | |
| Sat., 5/13 | JV Baseball | Northwestern | Home - Wamogo Regional HS-Softball Diamond [Directions] | 9:45 a.m. | ||
| Sat., 5/13 | JV Baseball | Wilby | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 12:00 p.m. | ||
| Mon., 5/15 | V Boys Outdoor Track | Northwestern, Terryville | Away - Northwestern Regional H.S.-Track [Directions] | 3:45 p.m. | ||
| Mon., 5/15 | V Boys Tennis | Northwestern | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 3-2 [Detailed Results] | |
| Mon., 5/15 | V Girls Outdoor Track | Northwestern, Terryville | Away - Northwestern Regional H.S.-Track [Directions] | 3:45 p.m. | ||
| Tue., 5/16 | V Boys Tennis | Housatonic Regional | Home - Wamogo Regional HS-Tennis Courts [Directions] | 3:15 p.m. | L 1-4 [Detailed Results] | |
| Tue., 5/16 | V Girls Lacrosse | Sacred Heart Academy | Away - Sacred Heart Academy-Lacrosse Field [Directions] | 5:15 p.m. | L 4-19 | |
| Tue., 5/16 | JV Girls Lacrosse | Sacred Heart Academy | Away - Sacred Heart Academy-Lacrosse Field [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | JV Softball | Shepaug Valley | Away - Washington Primary School-Washington Primary School Softball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/17 | V Baseball | Shepaug Valley | Home - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | L 13-2 | |
| Wed., 5/17 | JV Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | ||
| Wed., 5/17 | V Boys Lacrosse | Wolcott | Home - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 5:30 p.m. | W 17-7 | |
| Wed., 5/17 | JV Boys Lacrosse | Wolcott | Home - Plumb Hill Field Complex-Softball Field [Directions] | Canceled | Cancelled | |
| Wed., 5/17 | V Girls Lacrosse | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 6:00 p.m. | L 9-10 | |
| Wed., 5/17 | V Softball | Shepaug Valley | Away - Washington Primary School-Dick Ayer Field [Directions] | 3:45 p.m. | L 12-0 | |
| Thu., 5/18 | JV Baseball | Abbott Tech | Away - Abbott V-T School-Abbott Tech Baseball Field, School Campus [Directions] | 3:45 p.m. | ||
| Thu., 5/18 | V Softball | Northwestern | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:00 p.m. | W 13-10 | |
| Thu., 5/18 | Miscellaneous Events | Creation Celebration | Home - Wamogo Regional HS-Auditorium [Directions] | 12:00 p.m. | ||
| Sat., 5/20 | 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., 5/20 | 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., 5/22 | V Baseball | Housatonic Regional | Away - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | W 10-5 | |
| Mon., 5/22 | V Softball | Housatonic Regional | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 5:15 p.m. | L 2-12 | |
| Tue., 5/23 | V Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | L 13-1 | |
| Tue., 5/23 | V Boys Outdoor Track | Berkshire League Festival Steeplechase Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Away - Thomaston HS-Nystrom Park | 3:30 p.m. | ||
| Tue., 5/23 | V Girls Outdoor Track | Berkshire League Festival Steeplechase Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Away - Thomaston Nystrom Park-Nystroms Park Track | 3:30 p.m. | ||
| Tue., 5/23 | V Softball | Gilbert | Home - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 3:45 p.m. | W 18-3 | |
| Wed., 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. | ||
| Wed., 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. | ||
| Wed., 5/24 | JV Softball | Shepaug Valley | Home - Wamogo Regional HS-Wamogo Regional School JV Girls Softball [Directions] | 3:45 p.m. | ||
| Thu., 5/25 | JV Baseball | Litchfield | Away - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/31 | Miscellaneous Events | High School Choir Concert | Home - Wamogo HS [Directions] | 7:00 p.m. | ||