| Shepaug Valley 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 536 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Mon., 8/29 | V Boys Soccer | New Fairfield (Scrim.) | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:00 p.m. | 2:25 PM | |
| Mon., 8/29 | JV Boys Soccer | New Fairfield (Scrim.) | Away - New Fairfield HS-Komlo Field [Directions] | 4:00 p.m. | 2:25 PM | |
| Tue., 8/30 | V Field Hockey | Danbury (Scrim.) | Away - Danbury HS-Stadium Turf Field [Directions] | 7:00 p.m. | 4:30 PM | |
| Tue., 8/30 | V Girls Soccer | North Branford/Hale Ray (Scrim.) | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 8/31 | V Football | Wilby (Scrim.) | Home - Nonnewaug HS-Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 8/31 | V Boys Soccer | Wolcott (Scrim.) | Away - Wolcott HS-Turf Field [Directions] | 4:00 p.m. | 2:25 PM | |
| Thu., 9/1 | V Field Hockey | Weston (Scrim.) | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | 4:30 p.m. | ||
| Thu., 9/1 | V Girls Soccer | Oxford (Scrim.) | Away - Oxford HS-OHS Wolverine Field (Turf) [Directions] | 6:00 p.m. | 4:30 PM | |
| Fri., 9/2 | V Girls Soccer | New Milford (Scrim.) | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 3:30 p.m. | 2:25 PM | |
| Sat., 9/3 | V Field Hockey | New Fairfield, Amity, Bethel, Brookfield, Masuk, New Milford, Newtown, Ridgefield, Weston | Away - New Fairfield HS-Marty Morgan Field | 9:00 a.m. | 7:30 AM | |
| Mon., 9/5 | Miscellaneous Events | Labor Day | Home - Shepaug Valley HS [Directions] | TBA | ||
| Tue., 9/6 | V Boys Cross Country | BL Cross Country Scrimmage | Away - Black Rock State Park | 4:00 p.m. | 2:25 PM | |
| Pending change awaiting acceptance by one or more parties involved: Date to 9/7 | ||||||
| Tue., 9/6 | V Girls Cross Country | BL Cross Country Scrimmage | Away - Black Rock State Park | 4:00 p.m. | 2:25 PM | |
| Pending change awaiting acceptance by one or more parties involved: Date to 9/7 | ||||||
| Wed., 9/7 | V Boys Golf | Housatonic Regional | Away - Canaan Country Club [Directions] | Shepaug: 174 Housatonic: 237 | 1:40 PM, Dismiss 1:30 PM | |
| Thu., 9/8 | V Boys Soccer | Litchfield | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | W 3-0 | ||
| Thu., 9/8 | V Field Hockey | Litchfield | Away - Plumb Hill Field Complex-Field Hockey Field [Directions] | W 3-1 | 2:25 PM | |
| Thu., 9/8 | JV Field Hockey | Litchfield | Away - Plumb Hill Field Complex-Field Hockey Field [Directions] | 5:00 p.m. | 2:25 PM | |
| Thu., 9/8 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | L 4-0 | 2:25 PM | |
| Fri., 9/9 | V Football | VGW Techs | Home - Nonnewaug HS-Turf Field [Directions] | W 52-16 | ||
| Sat., 9/10 | V Boys Cross Country | Washingtonville Wizards Invitational | Away - Washingtonville HS-Cross Country Course | 9:30 a.m. | ||
| Sat., 9/10 | V Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-JV Girls Soccer Field [Directions] | W 5-0 | 8:15 AM, Dismiss 1:50 PM | |
| Sat., 9/10 | JV Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | Cancelled | 8:15 AM | |
| Sat., 9/10 | V Girls Cross Country | Washingtonville Wizards Invitational | Away - Washingtonville HS-Cross Country Course | 10:10 a.m. | ||
| Sat., 9/10 | V Field Hockey | Watertown | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | L 0-2 | ||
| Sat., 9/10 | JV Field Hockey | Watertown | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | Cancelled | ||
| Sat., 9/10 | V Girls Soccer | Housatonic Regional | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | L 2-6 | ||
| Mon., 9/12 | JV Football | Wilcox/Kaynor | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | ||
| Mon., 9/12 | V Boys Soccer | Gilbert | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | W 15-0 | ||
| Mon., 9/12 | V Girls Soccer | Gilbert | Away - Walker Field [Directions] | L 5-2 | 2:00 PM, Dismiss 1:50 PM | |
| Tue., 9/13 | V Boys Cross Country | Thomaston, Housatonic Regional | Away - Black Rock State Park [Directions] | 4:00 p.m. | 2:25 PM | |
| Tue., 9/13 | V Girls Cross Country | Thomaston, Housatonic Regional | Away - Black Rock State Park [Directions] | 4:00 p.m. | 2:25 PM | |
| Thu., 9/15 | V Boys Golf | Nonnewaug | Home - Lake Waramaug Country Club [Directions] | Shepaug: 188 Nonnewaug: 210 | ||
| Thu., 9/15 | V Field Hockey | Brookfield | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | L 2-5 | ||
| Thu., 9/15 | JV Field Hockey | Brookfield | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | 5:30 p.m. | ||
| Fri., 9/16 | V Boys Soccer | Terryville | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | W 1-0 | ||
| Fri., 9/16 | V Field Hockey | Lewis Mills | Away - Lewis Mills HS-Field Hockey Field [Directions] | L 1-2 | 2:00 PM, Dismiss 1:50 PM | |
| Fri., 9/16 | JV Field Hockey | Lewis Mills | Away - Lewis Mills HS-Field Hockey Field [Directions] | 5:15 p.m. | 2:00 PM, Dismiss 1:50 PM | |
| Fri., 9/16 | V Girls Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | L 3-1 | 2:15 PM, Dismiss 2:05 PM | |
| Sat., 9/17 | JV Boys Soccer | Housatonic Regional | Home - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | JV Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | 10:00 a.m. | 8:15 AM | |
| Mon., 9/19 | JV Football | Gilbert/Northwestern/Housy | Away - Gilbert School-Football Field [Directions] | 4:00 p.m. | ||
| Mon., 9/19 | V Boys Soccer | Wamogo | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | W 5-0 | ||
| Mon., 9/19 | JV Boys Soccer | Wamogo | Home - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 9/19 | V Field Hockey | Wamogo | Away - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | L 2-1 | 2:25 PM | |
| Mon., 9/19 | JV Field Hockey | Wamogo | Away - Wamogo HS-Wamogo Varsity Field Hockey Field [Directions] | 5:00 p.m. | 2:25 PM | |
| Mon., 9/19 | V Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | W 4-1 | 2:25 PM | |
| Tue., 9/20 | V Boys Golf | Northwestern, Litchfield | Away - Northwestern Regional H.S.-Norfolk CC [Directions] | Shepaug: 176 Litchfield: 185 Northwestern: 230 | 1:40 PM, Dismiss 1:30 PM | |
| Wed., 9/21 | V Boys Soccer | Northwestern | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | W 6-1 | ||
| Wed., 9/21 | JV Boys Soccer | Northwestern | Home - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 9/21 | V Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | W 2-0 | 2:00 PM, Dismiss 2:00 AM | |
| Wed., 9/21 | JV Field Hockey | Northwestern | Away - Northwestern Regional H.S.-Field Hockey Field [Directions] | 5:00 p.m. | 2:00 PM, Dismiss 1:50 PM | |
| Wed., 9/21 | V Girls Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | L 3-0 | 2:00 PM, Dismiss 1:50 PM | |
| Wed., 9/21 | Miscellaneous Events | Early Dismissal | Home - Shepaug Valley HS [Directions] | 11:45 a.m. | ||
| Fri., 9/23 | V Football | Wilcox/Kaynor | Home - Nonnewaug HS-Turf Field [Directions] | W 22-6 | ||
| Fri., 9/23 | V Boys Soccer | Thomaston | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | W 3-1 | ||
| Fri., 9/23 | V Field Hockey | Thomaston | Away - Thomaston HS-Gym [Directions] | W 2-1 | 2:25 PM | |
| Fri., 9/23 | JV Field Hockey | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:00 p.m. | 2:25 PM | |
| Fri., 9/23 | V Girls Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | L 6-0 | 2:25 PM | |
| Sat., 9/24 | V Boys Cross Country | Winding Trails Invitational | Away - Winding Trails-Cross Country Course | 10:45 a.m. | 7:45 AM | |
| Sat., 9/24 | JV Boys Soccer | Thomaston | Home - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 9/24 | V Girls Cross Country | Winding Trails Invitational | Away - Winding Trails-Cross Country Course | 10:10 a.m. | 7:45 AM | |
| Sat., 9/24 | JV Girls Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 9:00 a.m. | 7:45 AM | |
| Mon., 9/26 | FR Football | Wilcox/Kaynor | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | ||
| Mon., 9/26 | V Boys Golf | Litchfield, Gilbert | Away - Litchfield Country Club [Directions] | Litchfield: 164 Shepaug: 185 Gilbert: 256 | 2:00 PM | |
| Mon., 9/26 | V Field Hockey | Joel Barlow | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | L 1-4 | ||
| Mon., 9/26 | JV Field Hockey | Joel Barlow | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | 5:30 p.m. | ||
| Tue., 9/27 | V Boys Cross Country | Litchfield, Gilbert | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | 2:25 PM | |
| Tue., 9/27 | V Boys Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | L 1-0 | 2:15 PM, Dismiss 2:05 PM | |
| Tue., 9/27 | V Girls Cross Country | Litchfield, Gilbert | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | 2:25 PM | |
| Tue., 9/27 | V Girls Soccer | Terryville | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | L 5-0 | ||
| Thu., 9/29 | V Boys Golf | Housatonic Regional, Northwestern | Home - Washington Club Golf Course [Directions] | Shepaug: 186 Northwestern: 216 Housatonic: 222 | ||
| Thu., 9/29 | JV Girls Soccer | New Fairfield | Away - New Fairfield HS-Komlo Field [Directions] | 5:15 p.m. | 4:00 PM | |
| Fri., 9/30 | V Football | Cheney Tech | Away - Cheney Tech.-Football Field [Directions] | W 26-14 | ||
| Mon., 10/3 | JV Football | Cheney Tech | Home - Nonnewaug HS-Turf Field [Directions] | 6:00 p.m. | ||
| Mon., 10/3 | V Boys Golf | Litchfield | Home - Washington Club Golf Course [Directions] | Litchfield:179 Shepaug:190 | ||
| Tue., 10/4 | V Boys Cross Country | Nonnewaug, Northwestern | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | L 2-0 | 2:25 PM | |
| Tue., 10/4 | V Girls Cross Country | Nonnewaug, Northwestern | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Field Hockey | Litchfield | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | W 5-0 | ||
| Tue., 10/4 | JV Field Hockey | Litchfield | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/4 | V Girls Soccer | Litchfield | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | L 3-1 | ||
| Wed., 10/5 | V Boys Golf | Northwestern, Wamogo | Away - Northwestern Regional H.S.-Norfolk CC [Directions] | Shepaug: 171 Northwestern: 206 | 2:00 PM | |
| Thu., 10/6 | V Boys Golf | Terryville | Home - Washington Club Golf Course [Directions] | Shepaug: 175 Terryville: 271 | ||
| Fri., 10/7 | V Boys Golf | Gilbert, Wamogo | Away - Green woods Country Club [Directions] | Shepaug: 175 Gilbert: 202 Wamogo: 220 | 1:40 PM | |
| Fri., 10/7 | Miscellaneous Events | No School, Professional Development | Home - Shepaug Valley HS [Directions] | TBA | ||
| Sat., 10/8 | V Boys Cross Country | Wickham Invitational | Away - Wickham Park | 3:45 p.m. | 1:00 PM | |
| Sat., 10/8 | V Boys Soccer | Nonnewaug | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | L 3-1 | ||
| Sat., 10/8 | JV Boys Soccer | Nonnewaug | Home - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 1:00 p.m. | ||
| Sat., 10/8 | V Girls Cross Country | Wickham Invitational | Away - Wickham Park | 3:15 p.m. | 1:00 PM | |
| Sat., 10/8 | V Field Hockey | Nonnewaug | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | W 3-0 | ||
| Sat., 10/8 | JV Field Hockey | Nonnewaug | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | 12:15 p.m. | ||
| Sat., 10/8 | V Girls Soccer | Nonnewaug | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | L 6-0 | ||
| Sun., 10/9 | V Football | O'Brien Tech | Away - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | W 26-0 | 8:25 AM | |
| Mon., 10/10 | Miscellaneous Events | Columbus Day | Home - Shepaug Valley HS [Directions] | TBA | ||
| Tue., 10/11 | V Boys Cross Country | Wamogo, Terryville | Away - Wamogo Regional HS-White Memorial Park [Directions] | 4:00 p.m. | 2:25 PM | |
| Tue., 10/11 | V Boys Golf | Wamogo | Home - Washington Club Golf Course [Directions] | Shepaug: 190 Wamogo: 220 | ||
| Tue., 10/11 | V Boys Soccer | Gilbert | Away - Walker Field [Directions] | W 6-0 | 2:00 PM, Dismiss 1:50 PM | |
| Tue., 10/11 | V Girls Cross Country | Wamogo, Terryville | Away - Wamogo Regional HS-White Memorial Park [Directions] | 4:00 p.m. | 2:25 PM | |
| Tue., 10/11 | V Field Hockey | Immaculate | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | L 0-4 | ||
| Tue., 10/11 | JV Field Hockey | Immaculate | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/11 | V Girls Soccer | Gilbert | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | L 3-1 | ||
| Wed., 10/12 | V Boys Golf | Terryville, Nonnewaug | Away - Pequabuck Golf Club-Golf Course, Front 9 [Directions] | Shepaug: 185 Nonnewaug: 202 Terryville: 270 | 1:40 PM | |
| Thu., 10/13 | V Boys Golf | Nonnewaug | Home - Washington Club Golf Course [Directions] | Shepaug:180 Nonnewaug: 192 | ||
| Thu., 10/13 | V Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-JV Boys Soccer [Directions] | L 7-1 | 2:00 PM, Dismiss 1:50 PM | |
| Fri., 10/14 | V Field Hockey | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | L 1-2 | 4:00 PM, Dismiss 2:05 PM | |
| Fri., 10/14 | JV Field Hockey | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | 4:00 PM, Dismiss 2:05 PM | |
| Sat., 10/15 | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | 9:00 a.m. | 7:45 AM | |
| Sat., 10/15 | JV Girls Soccer | Litchfield | Home - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 1:00 p.m. | ||
| Mon., 10/17 | FR Football | Wilcox/Kaynor | Away - Wilcox Tech-Football Field [Directions] | 3:30 p.m. | ||
| 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 | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | W 2-1 | 2:25 PM | |
| Tue., 10/18 | JV Boys Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Postponed | 2:25 PM | |
| Tue., 10/18 | V Field Hockey | Wamogo | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | L 1-2 | ||
| Tue., 10/18 | JV Field Hockey | Wamogo | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Tue., 10/18 | V Girls Soccer | Wamogo | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | L 2-4 | ||
| Thu., 10/20 | V Boys Cross Country | BL Championship | Away - Black Rock State Park | 3:30 p.m. | 12:45 PM, Dismiss 12:35 PM | |
| Thu., 10/20 | V Boys Soccer | Housatonic Regional | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | W 7-1 | ||
| Thu., 10/20 | V Girls Cross Country | BL XC Championship | Away - Black Rock State Park | 4:15 p.m. | 12:45 PM, Dismiss 12:35 PM | |
| Fri., 10/21 | V Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | L 2-1 | 2:00 PM, Dismiss 1:50 PM | |
| Fri., 10/21 | JV Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-JV Soccer Field [Directions] | 3:45 p.m. | 2:00 PM, Dismiss 1:50 PM | |
| Fri., 10/21 | V Field Hockey | Northwestern | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | W 3-0 | ||
| Fri., 10/21 | JV Field Hockey | Northwestern | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Fri., 10/21 | V Girls Soccer | Northwestern | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | L 6-0 | ||
| Sat., 10/22 | V Football | Wilcox/Kaynor | Away - Falcon Field (Meriden, CT)-Football Field [Directions] | W 14-10 | ||
| Sat., 10/22 | JV Boys Soccer | Litchfield | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | Cancelled | ||
| Sat., 10/22 | JV Field Hockey | Nonnewaug, Thomaston, Watertown | Away - Nonnewaug HS-Turf Field [Directions] | 10:00 a.m. | 9:00 AM | |
| Sat., 10/22 | JV Girls Soccer | Northwestern | Home - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 10:00 a.m. | ||
| Mon., 10/24 | V Boys Golf | CIAC Division II Championship | Away - Chippanee GC | 8:30 a.m. | ||
| Tue., 10/25 | V Boys Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | W 7-1 | 2:25 PM | |
| Tue., 10/25 | JV Boys Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Cancelled | 2:25 PM | |
| Wed., 10/26 | V Field Hockey | Thomaston | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | W 3-1 | ||
| Wed., 10/26 | JV Field Hockey | Thomaston | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | 5:00 p.m. | ||
| Wed., 10/26 | V Girls Soccer | Thomaston | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | L 0-9 | ||
| Thu., 10/27 | V Football | Bullard/Kolbe | Home - Nonnewaug HS-Turf Field [Directions] | W 36-31 | ||
| Thu., 10/27 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | W 3-2 | 2:25 PM | |
| Thu., 10/27 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | 3:15 p.m. | 2:00 PM, Dismiss 1:50 PM | |
| Thu., 10/27 | V Field Hockey | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | W 4-0 | 2:00 PM, Dismiss 1:50 PM | |
| Thu., 10/27 | JV Field Hockey | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 4:30 p.m. | 2:00 PM | |
| Thu., 10/27 | V Girls Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | L 9-0 | 2:00 PM, Dismiss 1:50 PM | |
| Sat., 10/29 | V Boys Cross Country | CIAC Class S Championship | Away - Wickham Park | 11:55 a.m. | 8:45 AM | |
| Sat., 10/29 | JV Football | Bullard/Kolbe | Away - Bullard Havens Tech-Football Field [Directions] | 10:30 a.m. | 12:00 PM | |
| Sat., 10/29 | V Girls Cross Country | CIAC Class S Championship | Away - Wickham Park | 11:20 a.m. | 8:45 AM | |
| Sat., 10/29 | JV Girls Soccer | Northwestern | Home - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 9:30 a.m. | ||
| Tue., 11/1 | JV Boys Soccer | Litchfield | Home - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 11/2 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:00 p.m. | 1:30 PM, Dismiss 1:20 PM | Berkshire League Boys Soccer Tournament Semifinals |
| Wed., 11/2 | V Field Hockey | New Milford (Scrim.) | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 3:30 p.m. | 2:25 PM | |
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | V Football | Quinebaug Valley | Away - Ellis R V Tech School-Football Field [Directions] | W 54-8 | ||
| Fri., 11/4 | V Boys Soccer | Litchfield | Away - Nonnewaug HS-Turf Field [Directions] | 7:00 p.m. | 5:30 PM | BL Tournament Championship - Admission $5.00 students, $10.00 Adults |
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/7 | V Boys Soccer | Notre Dame-Fairfield | Home - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 2:00 p.m. | First Round CIAC Tournament Game | |
| Mon., 11/7 | V Field Hockey | New Fairfield | Home - Shepaug Valley HS-Joan Gauthey Field [Directions] | 2:00 p.m. | CIAC Class S Qualifying Round Game | |
| Mon., 11/7 | Miscellaneous Events | Early Dismissal | Home - Shepaug Valley HS [Directions] | 11:45 a.m. | ||
| Tue., 11/8 | Miscellaneous Events | No School, Professional Development | Home - Shepaug Valley HS [Directions] | TBA | ||
| Wed., 11/9 | Miscellaneous Events | Early Dismissal | Home - Shepaug Valley HS [Directions] | 11:45 a.m. | ||
| Thu., 11/10 | Miscellaneous Events | Early Dismissal | Home - Shepaug Valley HS [Directions] | 11:45 a.m. | ||
| Fri., 11/11 | Miscellaneous Events | Veteran's Day | Home - Shepaug Valley HS [Directions] | TBA | ||
| Sat., 11/12 | V Football | Prince Tech-Innovation | Away - Cheney Tech [Directions] | 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] | W 36-14 | ||
| Wed., 11/23 | V Football | ATI | Home - Nonnewaug HS-Turf Field [Directions] | W 20-0 | ||
| Wed., 11/23 | Miscellaneous Events | Thanksgiving Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Thu., 11/24 | Miscellaneous Events | Thanksgiving Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Fri., 11/25 | Miscellaneous Events | Thanksgiving Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Mon., 12/5 | V Boys Basketball | New Milford (Scrim.) | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 6:00 p.m. | ||
| Tue., 12/6 | V Girls Basketball | Lewis Mills (Scrim.) | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 12/7 | V Boys Ice Hockey | Newtown/New Fairfield (Scrim.) | Away - Danbury Ice Arena-Patriot Rink [Directions] | 4:30 p.m. | 3:00 PM | |
| Wed., 12/7 | Miscellaneous Events | Early Dismissal | Home - Shepaug Valley HS [Directions] | 11:45 a.m. | ||
| Thu., 12/8 | Miscellaneous Events | Holiday Bazaar | Home - Shepaug Valley HS [Directions] | 6:00 p.m. | ||
| Fri., 12/9 | V Boys Basketball | New Fairfield (Scrim.) | Away - New Fairfield HS-High School Gym [Directions] | 4:00 p.m. | 2:25 PM | |
| Fri., 12/9 | JV Boys Basketball | New Fairfield (Scrim.) | Away - New Fairfield HS-High School Gym [Directions] | 5:15 p.m. | 2:25 PM | |
| Fri., 12/9 | V Girls Basketball | Derby (Scrim.) | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Mon., 12/12 | V Boys Basketball | Brookfield (Scrim.) | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 12/13 | V Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 46-30 | 4:00 PM | |
| Tue., 12/13 | JV Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Wed., 12/14 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | L 1-5 | 6:00 PM | |
| Thu., 12/15 | V Wrestling | New Milford | Home - Brookfield HS-BHS Big Gym [Directions] | 6:00 p.m. | ||
| Fri., 12/16 | V Boys Ice Hockey | Byram Hills (NY) | Home - The Frederick Gunn School-Ice Rink [Directions] | L 6-7(OT) | ||
| Fri., 12/16 | V Boys Indoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | 2:25 PM | |
| Fri., 12/16 | V Girls Basketball | Abbott Tech | Away - Abbott V-T School-Daniel A. Garamella Memorial Gymnasium [Directions] | W 37-33 | 2:45 PM | Tickets are Digital Only and No Cash will be accepted at the site. To purchase tickets, copy and paste the following link into your browser: https://gofan.co/app/events/817892?schoolId=CT71981 |
| Fri., 12/16 | JV Girls Basketball | Abbott Tech | Away - Abbott V-T School-Daniel A. Garamella Memorial Gymnasium [Directions] | 4:30 p.m. | 2:45 PM | Tickets are Digital Only and No Cash will be accepted at the site. To purchase tickets, copy and paste the following link into your browser: https://gofan.co/app/events/817892?schoolId=CT71981 |
| Fri., 12/16 | V Girls Indoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | 2:25 PM | |
| Sat., 12/17 | V Boys Indoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center-Field House | 10:00 a.m. | 8:00 AM | |
| Sat., 12/17 | V Wrestling | Berlin, Avon, Bristol Eastern, Conard, East Haven, Farmington, Jonathan Law, Foran, Middletown, Suffield/Windsor Locks | Away - Berlin HS-Jim Day Gymnasium | 9:00 a.m. | 7:00 AM | |
| Sat., 12/17 | V Girls Indoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center-Field House | 10:00 a.m. | 8:00 AM | |
| Tue., 12/20 | V Boys Basketball | Northwestern | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | L 55-67 | ||
| Tue., 12/20 | JV Boys Basketball | Northwestern | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 12/20 | V Boys Ice Hockey | Mt. Everett (MA) | Away - Berkshire School-NHL | W 4-0 | 4:45 PM | |
| Tue., 12/20 | V Boys Swimming and Diving | Wamogo | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 12/20 | V Wrestling | Weston | Home - Brookfield HS-BHS Small Gym [Directions] | 6:00 p.m. | ||
| Tue., 12/20 | V Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | L 16-55 | 4:00 PM | |
| Tue., 12/20 | JV Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Thu., 12/22 | V Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | L 43-52 | 3:15 PM | |
| Thu., 12/22 | JV Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 4:30 p.m. | 3:15 PM | |
| Thu., 12/22 | V Girls Basketball | Terryville | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | W 33-27 | ||
| Thu., 12/22 | JV Girls Basketball | Terryville | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 12/22 | Miscellaneous Events | Early Dismissal | Home - Shepaug Valley HS [Directions] | 11:45 a.m. | ||
| Fri., 12/23 | Miscellaneous Events | Holiday Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Mon., 12/26 | Miscellaneous Events | Holiday Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Tue., 12/27 | V Boys Basketball | Coginchaug | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | W 65-64 | ||
| Tue., 12/27 | JV Boys Basketball | Coginchaug | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 12:00 p.m. | ||
| Tue., 12/27 | V Girls Basketball | Windsor Locks | Away - Windsor Locks HS-WLHS Gymnasium [Directions] | L 17-37 | 11:15 AM | |
| Tue., 12/27 | JV Girls Basketball | Windsor Locks | Away - Windsor Locks HS-WLHS Gymnasium [Directions] | 1:30 p.m. | 11:15 AM | |
| Tue., 12/27 | Miscellaneous Events | Holiday Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Wed., 12/28 | V Boys Basketball | North Branford | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | L 39-41 | ||
| Wed., 12/28 | JV Boys Basketball | North Branford | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 11:30 a.m. | ||
| Wed., 12/28 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | L 3-9 | 1:15 PM | |
| Wed., 12/28 | V Wrestling | Danbury, Bethel, Coventry (RI), Darien, Enfield, TBA, TBA, TBA, TBA, New Milford, Northfield Mt. Hampton (MA), Norwalk, Putnam Vo-Tech (MA), South Windsor, Staples, Wilton | Away - Danbury HS-Main Gym | 9:15 a.m. | ||
| Wed., 12/28 | Miscellaneous Events | Holiday Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Thu., 12/29 | Miscellaneous Events | Holiday Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Fri., 12/30 | V Boys Ice Hockey | Milford Coop | Home - The Frederick Gunn School-Ice Rink [Directions] | W 7-0 | ||
| Fri., 12/30 | V Girls Basketball | Canton | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | L 30-54 | ||
| Fri., 12/30 | JV Girls Basketball | Canton | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 12:00 p.m. | ||
| Fri., 12/30 | Miscellaneous Events | Holiday Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Mon., 1/2 | Miscellaneous Events | Holiday Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Tue., 1/3 | V Boys Basketball | Litchfield | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | W 56-45 | ||
| Tue., 1/3 | JV Boys Basketball | Litchfield | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | V Boys Swimming and Diving | Watertown | Away - Watertown HS-Pool [Directions] | 3:45 p.m. | 2:15 PM, Dismiss 2:05 PM | |
| Tue., 1/3 | V Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | W 31-23 | 4:30 PM | |
| Tue., 1/3 | JV Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | Postponed | 4:30 PM | |
| Wed., 1/4 | FR Boys Basketball | Litchfield | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 1/4 | V Boys Ice Hockey | Housatonic Coop | Home - The Frederick Gunn School-Ice Rink [Directions] | W 6-0 | ||
| Wed., 1/4 | V Wrestling | Pomperaug Coop | Away - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | 4:30 PM | |
| Thu., 1/5 | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 4:15 p.m. | 2:45 PM | |
| Thu., 1/5 | V Boys Indoor Track | Wintergreen Invitational | Away - Southern CT State University-Moore Field House | 4:00 p.m. | 2:00 PM, Dismiss 1:50 PM | |
| Thu., 1/5 | V Girls Indoor Track | Wintergreen Invitational | Away - Southern CT State University-Moore Field House | 4:00 p.m. | 2:00 PM, Dismiss 1:50 PM | |
| Fri., 1/6 | V Boys Basketball | Nonnewaug | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | W 74-27 | ||
| Fri., 1/6 | JV Boys Basketball | Nonnewaug | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 1/6 | V Boys Ice Hockey | Masuk | Home - The Frederick Gunn School-Ice Rink [Directions] | L 2-7 | ||
| Fri., 1/6 | V Girls Basketball | Nonnewaug | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | L 17-38 | ||
| Fri., 1/6 | JV Girls Basketball | Nonnewaug | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 3:00 p.m. | ||
| Sat., 1/7 | FR Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 12:30 p.m. | 11:30 AM | |
| Sat., 1/7 | JV Boys Ice Hockey | JBWA | Home - The Frederick Gunn School-Ice Rink [Directions] | 10:00 a.m. | ||
| Sat., 1/7 | V Wrestling | Warde Invitational | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | 6:45 AM | |
| Mon., 1/9 | FR Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | 6:00 PM | |
| Tue., 1/10 | V Boys Basketball | Wamogo | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | W 69-64 | ||
| Tue., 1/10 | JV Boys Basketball | Wamogo | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | L 35-41 | 4:30 PM | |
| Tue., 1/10 | JV Girls Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | 4:30 PM | |
| Wed., 1/11 | V Boys Ice Hockey | Pawling (NY) | Home - The Frederick Gunn School-Ice Rink [Directions] | L 2-6 | ||
| Wed., 1/11 | V Wrestling | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 6:00 p.m. | 4:30 PM | |
| Fri., 1/13 | V Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | W 78-47 | 4:30 PM | |
| Fri., 1/13 | JV Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | 4:30 PM | |
| Fri., 1/13 | V Boys Ice Hockey | Mt. Everett (MA) | Home - The Frederick Gunn School-Ice Rink [Directions] | W 6-0 | ||
| Fri., 1/13 | V Boys Indoor Track | Hillhouse Varsity Meet | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | 2:30 PM | |
| Fri., 1/13 | V Boys Swimming and Diving | Nonnewaug | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Thomaston | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | L 17-57 | ||
| Fri., 1/13 | JV Girls Basketball | Thomaston | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/13 | V Girls Indoor Track | Hillhouse Varsity Meet | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | 2:25 PM | |
| Sat., 1/14 | FR Boys Basketball | Housatonic Regional, Nonnewaug, Northwestern (Scrim.) | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 2:30 p.m. | 12:45 PM | |
| Sat., 1/14 | V Wrestling | John Chacho Dual Meet | Away - Staples HS-Staples Gym | 8:45 a.m. | 7:00 AM | |
| Mon., 1/16 | V Boys Indoor Track | Berkshire League Invitational | Away - Bethel HS-Indoor Track | 10:00 a.m. | 8:45 AM | |
| Mon., 1/16 | V Girls Indoor Track | Berkshire League Invitational | Away - Bethel HS-Indoor Track | 10:00 a.m. | 8:45 AM | |
| Mon., 1/16 | Miscellaneous Events | Martin Luther King Day | Home - Shepaug Valley HS [Directions] | TBA | ||
| Tue., 1/17 | V Boys Basketball | Gilbert | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | W 60-56 | ||
| Tue., 1/17 | JV Boys Basketball | Gilbert | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | L 15-40 | 4:45 PM | |
| Tue., 1/17 | JV Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | Postponed | 3:30 PM | |
| Tue., 1/17 | Unified Sports Basketball | Nonnewaug | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 2:30 p.m. | ||
| Wed., 1/18 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | W 2-1 OT | 4:45 PM | |
| Wed., 1/18 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss School-Pool [Directions] | 6:00 p.m. | 4:15 PM | |
| Wed., 1/18 | V Wrestling | Joel Barlow | Away - Joel Barlow High-Upper Gym [Directions] | 6:00 p.m. | 4:30 PM | |
| Thu., 1/19 | FR Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | 2:25 PM | |
| Fri., 1/20 | V Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | W 99-41 | 4:00 PM | |
| Fri., 1/20 | JV Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Fri., 1/20 | V Boys Ice Hockey | JBWA | Home - The Frederick Gunn School-Ice Rink [Directions] | L 1-4 | ||
| Fri., 1/20 | V Girls Basketball | Housatonic Regional | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | L 20-27 | ||
| Fri., 1/20 | JV Girls Basketball | Housatonic Regional | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 1/21 | V Wrestling | Colter Abely Wrestling Tournament | Away - Mercy HS-Gym | 8:00 a.m. | 6:15 AM | |
| Mon., 1/23 | FR Boys Basketball | Nonnewaug | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | ||
| Tue., 1/24 | V Wrestling | Fairfield Warde, Notre Dame-Fairfield | Home - Brookfield HS-BHS Small Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/25 | Miscellaneous Events | Early Dismissal | Home - Shepaug Valley HS [Directions] | 11:45 a.m. | ||
| Thu., 1/26 | V Girls Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | W 41-24 | 3:45 PM | |
| Thu., 1/26 | JV Girls Basketball | Wilby | Away - Wilby HS-George Tirado Floor @ The Reggie O'Brien Gymnasium [Directions] | 5:15 p.m. | 3:45 PM | |
| Fri., 1/27 | V Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | L 76-70 | 4:00 PM | |
| Fri., 1/27 | JV Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Fri., 1/27 | V Girls Basketball | Northwestern | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | L 17-47 | ||
| Fri., 1/27 | JV Girls Basketball | Northwestern | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 1/28 | V Boys Swimming and Diving | Northwestern | Away - Northwestern Regional H.S.-YMCA Swim [Directions] | 2:30 p.m. | 12:45 PM, Dismiss 2:05 PM | |
| Sat., 1/28 | V Wrestling | Brookfield Wrestling Tournament | Home - Brookfield HS-BHS Small Gym [Directions] | 9:30 a.m. | ||
| Mon., 1/30 | FR Boys Basketball | Northwestern | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | ||
| Mon., 1/30 | V Boys Ice Hockey | Pawling (NY) | Away - Trinity-Pawling School-Ice Rink | L 2-6 | 5:15 PM | |
| Tue., 1/31 | V Boys Basketball | Terryville | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | W 71-33 | ||
| Tue., 1/31 | JV Boys Basketball | Terryville | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | JV Boys Ice Hockey | Forman School | Away - Rumsey Hall School-Ice Rink | 7:15 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | W 35-22 | 4:15 PM | |
| Tue., 1/31 | JV Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | 4:15 PM | |
| Wed., 2/1 | V Wrestling | Bethel | Away - Bethel HS-BHS gym [Directions] | 6:15 p.m. | 4:45 PM | |
| Thu., 2/2 | FR Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 7:00 p.m. | 6:00 PM | |
| Thu., 2/2 | JV Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:15 p.m. | 6:30 PM | |
| Fri., 2/3 | V Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | W 72-60 | 4:30 PM | |
| Fri., 2/3 | JV Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:30 p.m. | 4:30 PM | |
| Fri., 2/3 | V Boys Swimming and Diving | Nonnewaug | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:30 p.m. | ||
| Fri., 2/3 | V Girls Basketball | Litchfield | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | W 24-22 | ||
| Fri., 2/3 | JV Girls Basketball | Litchfield | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | Cancelled | ||
| Fri., 2/3 | Miscellaneous Events | MS Social | Home - Shepaug Valley HS [Directions] | 2:30 p.m. | ||
| Mon., 2/6 | FR Boys Basketball | Wamogo | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | ||
| Mon., 2/6 | V Boys Indoor Track | Last Chance Meet | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | 2:25 PM | |
| Mon., 2/6 | V Wrestling | Masuk | Home - Brookfield HS-BHS Small Gym [Directions] | 6:00 p.m. | ||
| Mon., 2/6 | V Girls Indoor Track | Last Chance Meet | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | 2:25 PM | |
| Tue., 2/7 | V Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | L 58-60 | 4:30 PM | |
| Tue., 2/7 | JV Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | 4:30 PM | |
| Tue., 2/7 | V Boys Swimming and Diving | Housatonic Regional | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Wamogo | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | L 38-39 | ||
| Tue., 2/7 | JV Girls Basketball | Wamogo | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | Cancelled | ||
| Wed., 2/8 | V Boys Ice Hockey | SCW Knights | Away - Cromwell-Upper Rink [Directions] | L 3-4 OT | 2:00 PM, Dismiss 1:50 PM | |
| Thu., 2/9 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | 2:25 PM | |
| Thu., 2/9 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/10 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | W 65-56 | 4:30 PM | |
| Fri., 2/10 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | 2:00 PM | |
| Fri., 2/10 | JV Boys Ice Hockey | Newtown/New Fairfield | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | ||
| Fri., 2/10 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Fri., 2/10 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | L 22-59 | 4:30 PM | |
| Fri., 2/10 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 3:00 p.m. | 2:00 PM, Dismiss 1:50 PM | |
| Sat., 2/11 | V Wrestling | SWC Wrestling Championships | Away - Stratford HS-Gym | 8:30 a.m. | 6:15 AM | |
| Mon., 2/13 | V Boys Basketball | Ellington | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | L 44-52(2OT) | ||
| Mon., 2/13 | JV Boys Basketball | Ellington | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/13 | V Boys Ice Hockey | Housatonic Coop | Away - South Kent School-Ice Rink [Directions] | W 2-1 | 2:00 PM, Dismiss 1:50 PM | |
| Mon., 2/13 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | L 14-57 | 4:30 PM | |
| Mon., 2/13 | JV Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | 4:30 PM | |
| Tue., 2/14 | V Boys Basketball | Thomaston | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | W 53-52 | ||
| Tue., 2/14 | JV Boys Basketball | Thomaston | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/14 | V Boys Swimming and Diving | Northwestern | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/14 | Unified Sports Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 2:30 p.m. | 2:00 PM | |
| Wed., 2/15 | V Girls Basketball | Gilbert | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | L 21-38 | ||
| Wed., 2/15 | JV Girls Basketball | Gilbert | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | Cancelled | ||
| Thu., 2/16 | V Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | W 67-51 | 3:30 PM | |
| Thu., 2/16 | JV Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 5:00 p.m. | 3:30 PM | |
| Thu., 2/16 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | W 6-5 | 1:45 PM, Dismiss 1:35 PM | |
| Fri., 2/17 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Home - The Frederick Gunn School-Ice Rink [Directions] | W 3-2 | ||
| Fri., 2/17 | V Wrestling | CIAC M Championship | Away - Jonathan Law | 4:00 p.m. | 11:00 AM | |
| Fri., 2/17 | V Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:00 p.m. | 3:30 PM | |
| Sat., 2/18 | FR Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 1:00 p.m. | 12:00 PM | |
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Wrestling | CIAC M Championship | Away - Jonathan Law | 10:30 a.m. | ||
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/20 | Miscellaneous Events | President's Day | Home - Shepaug Valley HS [Directions] | TBA | ||
| Tue., 2/21 | V Boys Basketball | O'Brien Tech | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | W 74-33 | ||
| Tue., 2/21 | JV Boys Basketball | O'Brien Tech | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/21 | V Boys Ice Hockey | New Milford | Home - The Frederick Gunn School-Ice Rink [Directions] | L 1-7 | ||
| Tue., 2/21 | JV Boys Ice Hockey | New Milford | Home - The Frederick Gunn School-Ice Rink [Directions] | Cancelled | ||
| Tue., 2/21 | Miscellaneous Events | No School, Professional Development | Home - Shepaug Valley HS [Directions] | TBA | ||
| Thu., 2/23 | JV Boys Ice Hockey | Forman School | Home - The Frederick Gunn School-Ice Rink [Directions] | 8:15 p.m. | ||
| Fri., 2/24 | V Boys Basketball | Housatonic Regional | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | W 84-43 | ||
| Fri., 2/24 | JV Boys Basketball | Housatonic Regional | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/24 | FR Boys Basketball | Housatonic Regional | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | Postponed | ||
| Fri., 2/24 | V Boys Ice Hockey | Newtown/New Fairfield | Home - The Frederick Gunn School-Ice Rink [Directions] | W 3-0 | ||
| Fri., 2/24 | V Boys Swimming and Diving | Litchfield | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Fri., 2/24 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/25 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 4-2 | 3:45 PM | |
| Sat., 2/25 | V Boys Swimming and Diving | Girls "Splash Classic" Meet | Away - Cornerstone Aquatics Center-Pool | 5:15 p.m. | 11:30 AM | DIVING: Warm-up 1:00 pm – 2:00 pm and Competition 2:00 pm -4:00 pm; SWIMMING: Warm-up 4:00 pm – 5:10 pm and Competition 5:15pm - 8:15 pm |
| Sat., 2/25 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/27 | V Boys Basketball | Litchfield | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/28 | JV Boys Ice Hockey | JBWA | Home - The Frederick Gunn School-Ice Rink [Directions] | Cancelled | ||
| Wed., 3/1 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | L 1-8 | 2:45 PM | |
| Wed., 3/1 | V Girls Basketball | Windham Tech | Away - Windham Technical HS-Gym [Directions] | 6:30 p.m. | 3:30 PM | |
| Thu., 3/2 | V Boys Basketball | Brookfield (Scrim.) | Away - Brookfield HS-BHS Big Gym [Directions] | 5:00 p.m. | ||
| Thu., 3/2 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | W 4-0 | 6:45 PM | |
| Thu., 3/2 | V Boys Swimming and Diving | Northwestern, Housatonic Regional, Litchfield, Nonnewaug, Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool | 6:00 p.m. | ||
| Sat., 3/4 | V Boys Swimming and Diving | Housatonic Regional, Litchfield, Nonnewaug, Northwestern, Wamogo | Away - Kennedy HS (Waterbury)-Pool | 4:00 p.m. | 1:15 PM | |
| Mon., 3/6 | V Boys Ice Hockey | Hall | Home - The Frederick Gunn School-Ice Rink [Directions] | L 3-6 | ||
| Wed., 3/8 | V Boys Basketball | Classical Magnet | Home - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | W 59-50 | ||
| Wed., 3/8 | V Boys Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan HS-Sheehan HS Pool | 5:30 p.m. | Warm Up 4:00 PM | |
| Wed., 3/8 | V Boys Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Fri., 3/10 | V Boys Basketball | Innovation | Away - Goodwin Tech [Directions] | 6:00 p.m. | 3:30 PM | |
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class S Swimming Trials | Away - East Hartford HS-East Hartford Pool | 4:30 p.m. | 12:30 PM | Warm Up 2:45 PM |
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class S Trials | Away - East Hartford | 4:30 p.m. | ||
| Wed., 3/15 | V Boys Basketball | Lyman Memorial | Home - Maloney HS-Gym [Directions] | 7:00 p.m. | 4:30 PM | Official CIAC Live Stream Link: https://www.nfhsnetwork.com/events/ciac/gam857f91df2e |
| Wed., 3/15 | V Boys Swimming and Diving | CIAC Class S Swimming Finals | Away - Southern CT State University-pool | 1:00 p.m. | 10:15 AM | Warm Up 12:00 PM |
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Class S Finals | Away - SCSU | 1:00 p.m. | ||
| Thu., 3/16 | Miscellaneous Events | Early Dismissal | Home - Shepaug Valley HS [Directions] | 11:45 a.m. | ||
| Fri., 3/17 | V Boys Swimming and Diving | CIAC Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 3/17 | Miscellaneous Events | Early Dismissal | Home - Shepaug Valley HS [Directions] | 11:45 a.m. | ||
| Sat., 3/18 | V Boys Basketball | Windsor Locks | Away - Mohegan Sun Arena-Arena [Directions] | 12:30 p.m. | 8:15 AM | NFHS Network Live Video Stream: https://www.nfhsnetwork.com/events/ciac/gam9d31de8b93 |
| Sat., 3/18 | V Boys Swimming and Diving | CIAC State Open Championship | Away - Yale | 1:00 p.m. | ||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC State Open | Away - Yale University-Kiphuth Exhibition Pool | 1:00 p.m. | Warm Up 11:00 AM | |
| Fri., 3/24 | V Baseball | Brookfield (Scrim.) | Away - Brookfield HS-Baseball Field [Directions] | 3:45 p.m. | 2:25 PM | |
| Sat., 3/25 | V Baseball | Haddam-Killingworth (Scrim.) | Home - Washington Primary School-Ted Alex Field [Directions] | Cancelled | ||
| Mon., 3/27 | V Baseball | Gunnery (Scrim.) | Away - The Frederick Gunn School-Baseball Diamond | 4:30 p.m. | ||
| Wed., 3/29 | V Baseball | Torrington (Scrim.) | Home - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | ||
| Wed., 3/29 | V Girls Tennis | Gunnery (Scrim.) | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | W 4-3 | ||
| Sat., 4/1 | JV Baseball | Thomaston | Home - Shepaug Valley HS-Shepaug Valley JV & MS Baseball Field [Directions] | Cancelled | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:00 p.m. | ||||||
| Mon., 4/3 | V Baseball | Thomaston | Home - Washington Primary School-Ted Alex Field [Directions] | W 12-2 | ||
| Mon., 4/3 | V Boys Tennis | Thomaston | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | W 5-0 [Detailed Results] | ||
| Mon., 4/3 | V Softball | Thomaston | Away - Thomaston HS-Softball Field [Directions] | W 8-0 | 2:25 PM | |
| Mon., 4/3 | V Girls Tennis | Thomaston | Away - Thomaston Nystrom Park-Nystroms Park courts [Directions] | W 6-1 [Detailed Results] | 2:25 PM | |
| Tue., 4/4 | V Baseball | Litchfield | Away - Litchfield HS-Litchfield High School Baseball Field [Directions] | W 6-2 | 2:25 PM | |
| Tue., 4/4 | JV Baseball | Wamogo | Away - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | 2:25 PM | |
| Wed., 4/5 | V Boys Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | W 5-0 [Detailed Results] | 2:25 PM | |
| Wed., 4/5 | JV Softball | Housatonic Regional | Away - Housatonic Valley Regional High-Softball Diamond [Directions] | 4:15 p.m. | 2:25 PM | |
| Wed., 4/5 | V Girls Tennis | Wamogo | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | W 4-0 [Detailed Results] | ||
| Thu., 4/6 | V Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | L 10-0 | 2:25 PM | |
| Thu., 4/6 | JV Baseball | Nonnewaug | Away - Woodbury MS [Directions] | 3:45 p.m. | 2:25 PM | |
| Thu., 4/6 | V Softball | Nonnewaug | Home - Washington Primary School-Dick Ayer Field [Directions] | W 1-0 | ||
| Fri., 4/7 | Miscellaneous Events | Good Friday | Home - Shepaug Valley HS [Directions] | TBA | ||
| Mon., 4/10 | V Baseball | Northwestern | Home - Washington Primary School-Ted Alex Field [Directions] | W 6-4 | ||
| Mon., 4/10 | V Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | W 5-1 | 2:00 PM, Dismiss 1:50 PM | Bus departs from and will return players to Washington Primary School |
| Mon., 4/10 | Miscellaneous Events | Spring Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Tue., 4/11 | Miscellaneous Events | Spring Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Wed., 4/12 | Miscellaneous Events | Spring Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Thu., 4/13 | V Baseball | Platt | Home - Washington Primary School-Ted Alex Field [Directions] | W 12-7 | Batting Practice 2:30 PM | |
| Thu., 4/13 | Miscellaneous Events | Spring Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Fri., 4/14 | V Baseball | Gilbert | Home - Washington Primary School-Ted Alex Field [Directions] | W 14-1 | Batting Practice 2:30 PM | |
| Fri., 4/14 | JV Baseball | Gilbert | Home - Shepaug Valley HS-Shepaug Valley JV & MS Baseball Field [Directions] | Postponed | ||
| Fri., 4/14 | V Softball | Gilbert | Away - Winsted Rowley Field [Directions] | W 26-2 | 2:00 PM | Bus departs from and will return players to Washington Primary School |
| Fri., 4/14 | Miscellaneous Events | Spring Recess | Home - Shepaug Valley HS [Directions] | TBA | ||
| Mon., 4/17 | V Baseball | Housatonic Regional | Away - Housatonic Valley Regional High-Ed Kirby Field [Directions] | W 15-3 | 2:00 PM, Dismiss 1:50 PM | |
| Mon., 4/17 | V Softball | Housatonic Regional | Home - Washington Primary School-Dick Ayer Field [Directions] | W 11-0 | ||
| Tue., 4/18 | V Boys Tennis | Housatonic Regional | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | W 4-1 [Detailed Results] | ||
| Tue., 4/18 | V Girls Tennis | Housatonic Regional | Away - Housatonic Valley Regional High-Tennis Courts [Directions] | W 7-0 | 2:00 PM, Dismiss 1:50 PM | |
| Wed., 4/19 | V Baseball | Abbott Tech | Away - Abbott V-T School-Abbott Tech Baseball Field, School Campus [Directions] | W 3-0 | 2:00 PM, Dismiss 1:50 PM | |
| Wed., 4/19 | V Boys Tennis | Gilbert | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | W 5-0 [Detailed Results] | ||
| Wed., 4/19 | V Softball | Abbott Tech | Home - Washington Primary School-Dick Ayer Field [Directions] | W 9-0 | ||
| Wed., 4/19 | V Girls Tennis | Gilbert | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | W 6-0 | ||
| Thu., 4/20 | V Baseball | Wamogo | Home - Washington Primary School-Ted Alex Field [Directions] | W 4-3 | ||
| Thu., 4/20 | V Boys Tennis | Northwestern | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | W 5-0 [Detailed Results] | ||
| Thu., 4/20 | V Softball | Wamogo/Litchfield | Away - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | W 12-0 | 2:25 PM | |
| Thu., 4/20 | JV Softball | Wamogo/Litchfield | Away - Wamogo Regional HS-Wamogo Regional School JV Girls Softball [Directions] | 3:45 p.m. | 2:25 PM | Game will be played at Plumb Hill Field Complex, 35 Plumb HIll Road, Litchfield |
| Thu., 4/20 | V Girls Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | W 4-3 | 2:00 PM, Dismiss 1:50 PM | |
| Fri., 4/21 | JV Baseball | Wamogo | Home - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | ||
| Fri., 4/21 | Miscellaneous Events | Shepaug Senior Trip | Home - TBA [Directions] | 8:00 a.m. | ||
| Sat., 4/22 | Miscellaneous Events | Shepaug Senior Trip | Home - TBA [Directions] | 8:00 a.m. | ||
| Sun., 4/23 | Miscellaneous Events | Shepaug Senior Trip | Home - TBA [Directions] | 8:00 a.m. | ||
| Mon., 4/24 | V Baseball | Terryville | Away - Terryville HS-Baseball Field [Directions] | W 17-4 | 2:15 PM, Dismiss 2:00 PM | |
| Mon., 4/24 | V Boys Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | W 5-0 [Detailed Results] | 2:25 PM | |
| Mon., 4/24 | V Softball | Terryville | Home - Washington Primary School-Dick Ayer Field [Directions] | W 8-0 | ||
| Mon., 4/24 | V Girls Tennis | Litchfield | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | L 3-4 | ||
| Tue., 4/25 | JV Baseball | Abbott Tech | Home - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | ||
| Tue., 4/25 | V Boys Outdoor Track | Northwestern, Litchfield | Away - Northwestern Regional H.S.-Track [Directions] | 3:45 p.m. | 2:00 PM, Dismiss 1:50 PM | |
| Tue., 4/25 | V Girls Outdoor Track | Northwestern, Litchfield | Away - Northwestern Regional H.S.-Track [Directions] | Shepaug 81 Litchfield 50 Shepaug 38 Northwestern 112 | 2:00 PM, Dismiss 1:50 PM | |
| Tue., 4/25 | JV Softball | Housatonic Regional | Home - Washington Primary School-Washington Primary School Softball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/26 | V Girls Tennis | Nonnewaug | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | L 2-5 | ||
| Thu., 4/27 | V Boys Tennis | Nonnewaug | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | W 3-2 [Detailed Results] | 2:25 PM | |
| Fri., 4/28 | V Baseball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | W 15-1 | 2:25 PM | |
| Fri., 4/28 | JV Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | 2:00 PM, Dismiss 1:50 PM | |
| Fri., 4/28 | V Boys Tennis | Thomaston | Away - Thomaston Nystrom Park-Nystroms Park courts [Directions] | W 5-0 [Detailed Results] | 2:25 PM | |
| Fri., 4/28 | V Softball | Thomaston | Home - Washington Primary School-Dick Ayer Field [Directions] | W 5-3 (8) | ||
| Fri., 4/28 | V Girls Tennis | Thomaston | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | W 7-0 | ||
| Sat., 4/29 | JV Softball | Northwestern | Away - Northwestern Regional H.S.-JV Softball Field [Directions] | Cancelled | 8:00 AM | Bus will depart from Shepaug |
| Mon., 5/1 | V Baseball | Litchfield | Home - Washington Primary School-Ted Alex Field [Directions] | W 6-1 | ||
| Mon., 5/1 | JV Baseball | Litchfield | Home - Shepaug Valley HS-Shepaug Valley JV & MS Baseball Field [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Mon., 5/1 | V Boys Tennis | Wamogo | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | W 5-0 [Detailed Results] | ||
| Mon., 5/1 | V Girls Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | W 6-0 | 2:25 PM | |
| Tue., 5/2 | JV Softball | Northwestern | Away - Northwestern Regional H.S.-JV Softball Field [Directions] | Postponed | 2:00 PM | |
| Wed., 5/3 | V Baseball | Nonnewaug | Home - Washington Primary School-Ted Alex Field [Directions] | L 11-0 | ||
| Wed., 5/3 | JV Baseball | Nonnewaug | Home - Shepaug Valley HS-Shepaug Valley JV & MS Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/3 | V Boys Tennis | Housatonic Regional | Away - Housatonic Valley Regional High-Tennis Courts [Directions] | W 5-0 [Detailed Results] | 2:00 PM, Dismiss 1:50 PM | |
| Wed., 5/3 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | L 3-4 | 2:25 PM | |
| Wed., 5/3 | V Girls Tennis | Housatonic Regional | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | W 5-0 | ||
| Fri., 5/5 | JV Baseball | Northwestern | Home - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | ||
| Fri., 5/5 | V Boys Outdoor Track | Wamogo, Gilbert | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | 2:25 PM | |
| Fri., 5/5 | V Boys Tennis | Gilbert | Away - Gilbert School-PineWoods Racquet Club [Directions] | W 5-0 [Detailed Results] | 2:00 PM, Dismiss 1:50 PM | There will be one singles match - player will travel with the girls team. |
| Fri., 5/5 | V Girls Outdoor Track | Wamogo, Gilbert | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | Shepaug98-Wamogo32 Shepaug 95 -Gilbert 41 | 2:25 PM | |
| Fri., 5/5 | V Softball | Northwestern | Home - Washington Primary School-Dick Ayer Field [Directions] | W 4-2 | ||
| Fri., 5/5 | JV Softball | Northwestern | Home - Washington Primary School-Washington Primary School Softball Field [Directions] | Postponed | ||
| Fri., 5/5 | V Girls Tennis | Gilbert | Away - Gilbert School-PineWoods Racquet Club [Directions] | W 3-0 | 2:00 PM, Dismiss 1:50 PM | |
| Sat., 5/6 | V Softball | Newtown | Away - Newtown HS-Lindell A. Hertberg Softball Field [Directions] | L 0-1 | 12:15 PM | Bus departs from and will return players to Washington Primary School |
| Sat., 5/6 | Miscellaneous Events | Frederick Gunn School using Ted Alex Field | Home - Washington Primary School-Ted Alex Field [Directions] | 2:30 p.m. | ||
| Mon., 5/8 | V Boys Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | W 5-0 [Detailed Results] | 2:00 PM, Dismiss 1:50 PM | |
| Mon., 5/8 | V Softball | Gilbert | Home - Washington Primary School-Dick Ayer Field [Directions] | W 22-0 | ||
| Mon., 5/8 | V Girls Tennis | Northwestern | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | W 5-2 | ||
| Tue., 5/9 | JV Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 3:45 p.m. | 2:25 PM | |
| Tue., 5/9 | V Boys Outdoor Track | Terryville, Thomaston | Away - Terryville HS-Track [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:50 PM | |
| Tue., 5/9 | V Girls Outdoor Track | Terryville, Thomaston | Away - Terryville HS-Track [Directions] | Shepaug 115 Terryville 26 Shepaug 68 Thomsaston 73 | 2:00 PM, Dismiss 1:50 PM | |
| Wed., 5/10 | V Baseball | Gilbert | Away - Walker Field [Directions] | W 10-0 | 2:00 PM | |
| Wed., 5/10 | V Boys Tennis | Litchfield | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | W 3-2 [Detailed Results] | ||
| Wed., 5/10 | V Softball | Housatonic Regional | Away - Housatonic Valley Regional High-softball field [Directions] | W 20-10 | 2:25 PM | |
| Wed., 5/10 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | W 4-3 | 2:25 PM | |
| Fri., 5/12 | V Baseball | Housatonic Regional | Home - Washington Primary School-Ted Alex Field [Directions] | W 10-0 | ||
| Fri., 5/12 | V Boys Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | L 1-4 [Detailed Results] | 2:25 PM | |
| Fri., 5/12 | V Softball | New Milford | Away - New Milford HS-Softball Varsity Field - NMHS [Directions] | W 6-2 | 2:25 PM | |
| Fri., 5/12 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | L 3-4 | 2:25 PM | |
| Mon., 5/15 | V Boys Outdoor Track | Housatonic Regional, Nonnewaug | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Track [Directions] | 3:45 p.m. | ||
| Mon., 5/15 | V Girls Outdoor Track | Housatonic Regional, Nonnewaug | Home - Shepaug Valley HS-Shepaug Valley Middle & High School Track [Directions] | 3:45 p.m. | ||
| Mon., 5/15 | V Softball | Coginchaug | Home - Washington Primary School-Dick Ayer Field [Directions] | W 2-0 | ||
| Mon., 5/15 | JV Softball | Coginchaug | Home - Washington Primary School-Dick Ayer Field [Directions] | Postponed | ||
| Tue., 5/16 | V Baseball | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | L 7-3 | 4:15 PM | Bus departs from Washington Primary School |
| Tue., 5/16 | JV Baseball | Northwestern | Home - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | ||
| Tue., 5/16 | JV Softball | Wamogo/Litchfield | Home - Washington Primary School-Washington Primary School Softball Field [Directions] | 3:45 p.m. | ||
| Tue., 5/16 | V Girls Tennis | Berkshire League Girls Tennis Tournament | Away - TBA | 8:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Wed., 5/17 | V Baseball | Wamogo | Away - Wamogo Regional HS-Varsity Baseball Field [Directions] | W 13-2 | 2:25 PM | |
| Wed., 5/17 | JV Baseball | Wamogo | Home - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | ||
| Wed., 5/17 | V Boys Tennis | Berkshire League Boys Tennis Tournament | Away - TBA | 8:00 a.m. | 7:20 AM, Dismiss TBA | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Wed., 5/17 | V Softball | Wamogo/Litchfield | Home - Washington Primary School-Dick Ayer Field [Directions] | W 12-0 | ||
| Fri., 5/19 | V Baseball | Terryville | Home - Washington Primary School-Ted Alex Field [Directions] | W 7-0 | ||
| Fri., 5/19 | V Softball | Terryville | Away - Terryville HS-Softball Field [Directions] | W 18-0 | 2:15 PM, Dismiss 2:00 PM | |
| Sat., 5/20 | V Boys Outdoor Track | Berkshire League Track Championships | Away - Plumb Hill Field Complex-Plumb Hill Track | 9:00 a.m. | 6:30 AM | |
| 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. | 6:30 AM | |
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Mon., 5/22 | V Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | L 5-0 | 2:00 PM, Dismiss 1:50 PM | |
| Mon., 5/22 | V Boys Tennis | Berkshire League Boys Tennis Tournament Semi & Finals | Away - TBA | 1:00 p.m. | 11:30 AM, Dismiss 11:20 AM | 479-423 Hickory Hill Rd, Thomaston, CT 06787 |
| Mon., 5/22 | V Girls Tennis | Berkshire League Girls Tennis Tournament Semi & Finals | Away - TBA | TBA | TBA | |
| Pending change awaiting acceptance by one or more parties involved: Time to 1:00 p.m. | ||||||
| Tue., 5/23 | V Baseball | Lewis Mills | Home - Washington Primary School-Ted Alex Field [Directions] | L 4-0 | ||
| Tue., 5/23 | JV Baseball | Lewis Mills | Home - Shepaug Valley HS-Shepaug Valley JV & MS Baseball Field [Directions] | 3:45 p.m. | ||
| 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. | TBA | |
| 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. | TBA | |
| Tue., 5/23 | Unified Sports Volleyball | Nonnewaug | Away - Nonnewaug HS-Nonnewaug Gymnasium [Directions] | 2:30 p.m. | 2:00 PM, Dismiss 1:50 PM | |
| 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. | TBA | |
| 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. | TBA | |
| Wed., 5/24 | JV Softball | Wamogo/Litchfield | Away - Wamogo Regional HS-Wamogo Regional School JV Girls Softball [Directions] | 3:45 p.m. | 2:25 PM | |
| Fri., 5/26 | V Baseball | Torrington (Scrim.) | Away - Fuessenich Park-Baseball Diamond [Directions] | 3:45 p.m. | 2:25 PM | |
| Fri., 5/26 | V Girls Tennis | Morgan | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 10:00 a.m. | CIAC TOURNAMENT | |
| Sat., 5/27 | V Boys Tennis | Cromwell | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 9:00 a.m. | ||
| Mon., 5/29 | Miscellaneous Events | Memorial Day | Home - Shepaug Valley HS [Directions] | TBA | ||
| Tue., 5/30 | V Baseball | Derby | Home - Washington Primary School-Ted Alex Field [Directions] | L 8-5 | ||
| Tue., 5/30 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/30 | V Boys Outdoor Track | CIAC Class S Championship | Away - Veteran's Stadium-Willow Brook Park-Veterans Stadium Irv Black track | 4:00 p.m. | 1:45 PM, Dismiss 1:35 PM | |
| Tue., 5/30 | V Boys Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:00 p.m. | 1:45 PM, Dismiss 1:35 PM | |
| Tue., 5/30 | V Girls Outdoor Track | CIAC Class S Championship | Away - Veteran's Stadium-Willow Brook Park-Veterans Stadium Irv Black track | 4:00 p.m. | 1:45 PM, Dismiss 1:35 PM | |
| Tue., 5/30 | V Girls Outdoor Track | CIAC Class S Championships | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/30 | V Girls Tennis | East Catholic | Home - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 5/31 | V Softball | Thomaston | Home - Washington Primary School-Dick Ayer Field [Directions] | 4:00 p.m. | ||
| Wed., 5/31 | V Girls Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:00 p.m. | 11:45 AM, Dismiss 11:15 AM | |
| Fri., 6/2 | V Softball | Canton | Home - Washington Primary School-Dick Ayer Field [Directions] | 3:00 p.m. | ||
| Sat., 6/3 | V Softball | Canton | Home - Washington Primary School-Dick Ayer Field [Directions] | 4:00 p.m. | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Softball | Coventry | Away - Dunn Sports Complex [Directions] | 7:00 p.m. | 4:30 PM | Bus departs from Washington Primary School |
| Mon., 6/5 | V Girls Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Boys Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Girls Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Girls Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Mon., 6/12 | V Boys Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 2:00 p.m. | ||
| Mon., 6/12 | V Girls Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||