| Housatonic Regional 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 356 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 9/7 | V Boys Golf | Shepaug Valley | Home - Canaan Country Club [Directions] | 3:00 p.m. | Shepaug 174, Housatonic 237 | |
| Thu., 9/8 | V Boys Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:45 p.m. | L 1-2 | |
| Thu., 9/8 | JV Boys Soccer | Terryville | Away - Terryville HS-Baseball Field [Directions] | Postponed | ||
| Thu., 9/8 | V Girls Soccer | Terryville | Home - Housatonic Valley Regional High-JV Boys Soccer [Directions] | 3:45 p.m. | L 2-3 | |
| Fri., 9/9 | V Football | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 7:00 p.m. | L 6-21 | |
| Fri., 9/9 | V Girls Volleyball | Northwestern | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:00 p.m. | L 0-3 | |
| Fri., 9/9 | JV Girls Volleyball | Northwestern | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | L 1-2 | |
| Sat., 9/10 | JV Football | Naugatuck | Home - Gilbert School-Football Field [Directions] | 10:00 a.m. | ||
| Sat., 9/10 | V Boys Soccer | Shepaug Valley | Home - Housatonic Valley Regional High-JV Girls Soccer Field [Directions] | 10:00 a.m. | L 0-5 | |
| Sat., 9/10 | JV Boys Soccer | Shepaug Valley | Home - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | Canceled | Cancelled | |
| Sat., 9/10 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 10:00 a.m. | W 6-2 | |
| Mon., 9/12 | V Boys Golf | Litchfield, Wamogo | Home - Canaan Country Club [Directions] | 3:00 p.m. | Litchfield 163 Wamogo 228 Housatonic 234 | |
| Tue., 9/13 | V Boys Cross Country | Thomaston, Shepaug Valley | Away - Black Rock State Park [Directions] | 4:00 p.m. | H-T 38-21 H-S 32-26 | |
| Tue., 9/13 | V Boys Soccer | Northwestern | Home - Housatonic Valley Regional High-JV Girls Soccer Field [Directions] | 3:45 p.m. | L 4-6 | |
| Tue., 9/13 | V Girls Cross Country | Thomaston, Shepaug Valley | Away - Black Rock State Park [Directions] | 4:00 p.m. | H-T 15-50 H-S 28-28 (S wins) | |
| Wed., 9/14 | V Girls Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | T 3-3 | |
| Wed., 9/14 | JV Girls Soccer | Northwestern | Away - Northwestern Regional H.S.-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 9/15 | V Girls Volleyball | New Fairfield | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Thu., 9/15 | JV Girls Volleyball | New Fairfield | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 9/16 | V Boys Golf | Gilbert | Away - Green woods Country Club [Directions] | 3:00 p.m. | Gilbert 227, Housatonic 233 | |
| Fri., 9/16 | V Boys Soccer | Gilbert | Away - Walker Field [Directions] | 3:45 p.m. | W 7-2 | |
| Fri., 9/16 | V Girls Soccer | Gilbert | Home - Housatonic Valley Regional High-JV Boys Soccer [Directions] | 3:45 p.m. | W 9-4 | |
| Sat., 9/17 | V Football | Kennedy | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 10:00 a.m. | W 34-6 | |
| Sat., 9/17 | JV Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley JV & MS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | JV Girls Soccer | Shepaug Valley | Home - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | 10:00 a.m. | ||
| Mon., 9/19 | JV Football | Northwest United | Home - Gilbert School-Football Field [Directions] | 4:00 p.m. | ||
| Mon., 9/19 | V Boys Golf | Wamogo, Terryville | Away - Wamogo HS-Stoneybrook Golf Course [Directions] | 3:00 p.m. | Wamogo 227, Housatonic 235, Terryville forfeit | |
| Mon., 9/19 | V Boys Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | L 1-6 | |
| Mon., 9/19 | JV Boys Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Canceled | Cancelled | |
| Mon., 9/19 | V Girls Soccer | Thomaston | Home - Housatonic Valley Regional High-JV Boys Soccer [Directions] | 3:45 p.m. | L 1-4 | |
| Mon., 9/19 | JV Girls Soccer | Thomaston | Home - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | Postponed | ||
| Mon., 9/19 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 9/19 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | W 2-1 | |
| Wed., 9/21 | V Boys Golf | Northwestern | Home - Canaan Country Club [Directions] | 3:00 p.m. | Northwestern 222, Housatonic 226 | |
| Wed., 9/21 | V Boys Soccer | Wamogo | Home - Housatonic Valley Regional High-JV Girls Soccer Field [Directions] | 3:45 p.m. | W 3-2 | |
| Wed., 9/21 | JV Boys Soccer | Wamogo | Home - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | Canceled | Cancelled | |
| Wed., 9/21 | V Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | W 7-4 | |
| Wed., 9/21 | JV Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Postponed | ||
| Wed., 9/21 | V Girls Volleyball | Holy Cross | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:15 p.m. | L 2-3 | |
| Wed., 9/21 | JV Girls Volleyball | Holy Cross | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | L 0-2 | |
| Thu., 9/22 | V Boys Golf | Litchfield | Home - Canaan Country Club [Directions] | 3:00 p.m. | ||
| Fri., 9/23 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-6 | |
| Fri., 9/23 | V Girls Soccer | Litchfield | Home - Housatonic Valley Regional High-JV Boys Soccer [Directions] | 3:45 p.m. | W 10-2 | |
| Fri., 9/23 | V Girls Volleyball | Dover (NY) | Away - Dover HS-Gym | 5:45 p.m. | L 0-3 | |
| Fri., 9/23 | JV Girls Volleyball | Dover (NY) | Away - Dover HS-Gym | 4:30 p.m. | L 0-2 | |
| Sat., 9/24 | V Football | Wilby | Home - Gilbert School-Football Field [Directions] | 1:00 p.m. | W 35-0 | |
| Sat., 9/24 | FM Football | Wilby | Away - Wilby HS-Football Field [Directions] | Postponed | ||
| Sat., 9/24 | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | Postponed | ||
| Sat., 9/24 | JV Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | Postponed | ||
| Tue., 9/27 | V Boys Golf | Terryville | Away - Pequabuck Golf Club-Golf Course, Front 9 [Directions] | 3:00 p.m. | Housatonic 209, Terryville 274 | |
| Tue., 9/27 | V Boys Soccer | Gilbert | Home - Housatonic Valley Regional High-JV Girls Soccer Field [Directions] | 3:45 p.m. | W 10-1 | |
| Tue., 9/27 | V Girls Volleyball | Wamogo | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:45 p.m. | W 3-1 | |
| Tue., 9/27 | JV Girls Volleyball | Wamogo | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | W 2-0 | |
| Wed., 9/28 | V Boys Cross Country | Northwestern, Wamogo | Away - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | H-NW 37-22 H-W 15-50 | |
| Wed., 9/28 | V Girls Cross Country | Northwestern, Wamogo | Away - Northwestern Regional H.S.-Track [Directions] | 4:00 p.m. | H-NW 24-33 H-W 15-50 | |
| Wed., 9/28 | V Girls Volleyball | Gilbert | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Wed., 9/28 | JV Girls Volleyball | Gilbert | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:30 p.m. | L 0-2 | |
| Thu., 9/29 | V Boys Golf | Shepaug Valley, Northwestern | Away - Washington Club Golf Course [Directions] | 3:00 p.m. | Shepaug 186, Northwestern 216, Housatonic 222 | |
| Thu., 9/29 | V Girls Soccer | Nonnewaug | Home - Housatonic Valley Regional High-JV Boys Soccer [Directions] | 3:45 p.m. | L 1-3 | |
| Thu., 9/29 | JV Girls Soccer | Nonnewaug | Home - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Housatonic Valley Regional High-JV Girls Soccer Field | ||||||
| Fri., 9/30 | V Football | Ansonia | Away - Nolan Field-Ansonia-Football Field [Directions] | 6:00 p.m. | L 20-30 | |
| Fri., 9/30 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | L 0-2 | |
| Fri., 9/30 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | Postponed | ||
| Sat., 10/1 | JV Boys Soccer | Northwestern | Home - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | Canceled | Cancelled | |
| Sat., 10/1 | JV Girls Soccer | Northwestern | Home - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | 10:00 a.m. | ||
| Mon., 10/3 | V Boys Golf | Gilbert | Home - Canaan Country Club [Directions] | 3:00 p.m. | Housatonic 208, Gilbert 214 | |
| Mon., 10/3 | V Girls Volleyball | Dover (NY) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:15 p.m. | L 2-3 | |
| Mon., 10/3 | JV Girls Volleyball | Dover (NY) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | L 0-2 | |
| Tue., 10/4 | V Boys Cross Country | Litchfield, Terryville | Home - Housatonic Valley Regional High-Cross Country Course [Directions] | 3:45 p.m. | H-T 15-50 H-L 34-25 | Senior Night |
| Tue., 10/4 | V Boys Soccer | Terryville | Home - Housatonic Valley Regional High-JV Girls Soccer Field [Directions] | 3:45 p.m. | L 1-4 | |
| Tue., 10/4 | JV Boys Soccer | Terryville | Home - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Housatonic Valley Regional High-JV Boys Soccer | ||||||
| Tue., 10/4 | V Girls Cross Country | Litchfield, Terryville | Home - Housatonic Valley Regional High-Cross Country Course [Directions] | 3:45 p.m. | H-T 15-50 H-L 15-50 | Senior Night |
| Tue., 10/4 | V Girls Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:45 p.m. | W 2-1 | |
| Tue., 10/4 | V Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Tue., 10/4 | JV Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 10/6 | V Boys Golf | Nonnewaug, Litchfield | Away - Crestbrook Park-Crestbrook Park Golf [Directions] | 3:00 p.m. | Litchfield 180,Housatonic 239; Nonnewaug 192, Housatonic 239 | |
| Thu., 10/6 | V Girls Volleyball | Mt. Everett (MA) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Thu., 10/6 | JV Girls Volleyball | Mt. Everett (MA) | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 10/7 | V Football | Oxford | Home - Gilbert School-Football Field [Directions] | 6:00 p.m. | W 41-7 | |
| Fri., 10/7 | JV Girls Soccer | Indian Mountain School | Away - Indian Mountain School-Indian Mtn School | 3:45 p.m. | ||
| Fri., 10/7 | V Girls Volleyball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:00 p.m. | L 0-3 | |
| Fri., 10/7 | JV Girls Volleyball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 4:00 p.m. | L 1-2 | |
| Mon., 10/10 | JV Football | Oxford | Away - Oxford HS-turf field [Directions] | 10:00 a.m. | ||
| Tue., 10/11 | V Boys Cross Country | Nonnewaug, Gilbert | Away - Nonnewaug HS-XC Course [Directions] | 3:45 p.m. | H-N 41-22 H-G 34-24 | |
| Tue., 10/11 | V Boys Golf | Nonnewaug, Northwestern | Home - Canaan Country Club [Directions] | 3:00 p.m. | Nonnewaug, 196 Northwestern, 205 Housatonic, 208 | Senior Night |
| Tue., 10/11 | V Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 3:45 p.m. | L 2-3 | |
| Tue., 10/11 | V Girls Cross Country | Nonnewaug, Gilbert | Away - Nonnewaug HS-XC Course [Directions] | 3:45 p.m. | H-N 26-30 H-G 15-50 | |
| Tue., 10/11 | V Girls Soccer | Northwestern | Home - Housatonic Valley Regional High-JV Boys Soccer [Directions] | 4:30 p.m. | L 1-2 | |
| Tue., 10/11 | JV Girls Soccer | Northwestern | Home - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | 4:30 p.m. | ||
| Wed., 10/12 | JV Boys Soccer | Indian Mountain School | Away - Indian Mountain School-Indian Mtn School | 3:30 p.m. | ||
| Wed., 10/12 | V Girls Volleyball | Terryville | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:45 p.m. | L 2-3 | |
| Wed., 10/12 | JV Girls Volleyball | Terryville | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Thu., 10/13 | V Girls Soccer | Shepaug Valley | Home - Housatonic Valley Regional High-JV Boys Soccer [Directions] | 3:45 p.m. | W 7-1 | |
| 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 | Thomaston | Home - Housatonic Valley Regional High-JV Girls Soccer Field [Directions] | 3:45 p.m. | L 2-4 | |
| Tue., 10/18 | V Girls Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | T 3-3 | |
| Tue., 10/18 | V Girls Volleyball | Nonnewaug | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 10/18 | JV Girls Volleyball | Nonnewaug | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:15 p.m. | ||
| Wed., 10/19 | V Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 10/19 | JV Girls Volleyball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 4:45 p.m. | L 0-2 | |
| Thu., 10/20 | FM Football | Crosby | Away - Crosby HS-CHS - Jimmy Lee Stadium (Turf) [Directions] | 3:30 p.m. | ||
| Thu., 10/20 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-7 | |
| Thu., 10/20 | V Girls Soccer | Wamogo | Home - Housatonic Valley Regional High-JV Boys Soccer [Directions] | 3:45 p.m. | W 9-1 | Senior Night |
| Thu., 10/20 | JV Girls Soccer | Wamogo | Home - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/21 | V Boys Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 3-4 | |
| Fri., 10/21 | JV Boys Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Canceled | Cancelled | |
| Fri., 10/21 | V Girls Volleyball | Wolcott Tech | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:45 p.m. | W 3-2 | |
| Fri., 10/21 | JV Girls Volleyball | Wolcott Tech | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Sat., 10/22 | V Football | Crosby | Home - Gilbert School-Football Field [Directions] | 1:00 p.m. | W 69-42 | |
| Sat., 10/22 | JV Boys Soccer | Wamogo | Home - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | Canceled | Cancelled | |
| Tue., 10/25 | V Boys Soccer | Litchfield | Home - Housatonic Valley Regional High-JV Girls Soccer Field [Directions] | 3:45 p.m. | L 3-6 | Senior Night |
| Tue., 10/25 | V Girls Soccer | Litchfield | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 3:45 p.m. | L 3-1 | |
| Tue., 10/25 | V Girls Volleyball | Wamogo | Away - Wamogo Regional HS-Large gym [Directions] | 5:00 p.m. | W 3-0 | |
| Tue., 10/25 | JV Girls Volleyball | Wamogo | Away - Wamogo Regional HS-Large Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 10/26 | JV Girls Soccer | Indian Mountain School | Home - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | 3:15 p.m. | ||
| Thu., 10/27 | V Girls Soccer | Gilbert | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 6:00 p.m. | W 6-1 | |
| Thu., 10/27 | V Girls Volleyball | Gilbert | Away - Gilbert School-Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Thu., 10/27 | JV Girls Volleyball | Gilbert | Away - Gilbert School-Gym [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 10/28 | V Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 7:00 p.m. | W 42-22 | |
| Fri., 10/28 | JV Boys Soccer | Thomaston | Home - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | Canceled | Cancelled | |
| Fri., 10/28 | JV Girls Soccer | Thomaston | Away - Thomaston Nystrom Park-Nystrom Park Field [Directions] | Canceled | Cancelled | |
| Fri., 10/28 | V Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 6:15 p.m. | L 0-3 | |
| Fri., 10/28 | JV Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 5:00 p.m. | ||
| Sat., 10/29 | JV Football | Torrington | Home - Gilbert School-Football Field [Directions] | 10:00 a.m. | ||
| Mon., 10/31 | V Boys Soccer | Nonnewaug | Home - Housatonic Valley Regional High-JV Girls Soccer Field [Directions] | 3:45 p.m. | L 4-5 | |
| Mon., 10/31 | JV Boys Soccer | Nonnewaug | Home - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Housatonic Valley Regional High-JV Boys Soccer | ||||||
| Mon., 10/31 | V Girls Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 2:45 p.m. | W 2-1 | |
| Mon., 10/31 | JV Girls Soccer | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | Postponed | ||
| Sat., 11/5 | V Football | Derby | Home - Gilbert School-Football Field [Directions] | 1:00 p.m. | W 75-28 | |
| Mon., 11/7 | JV Football | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 4:30 p.m. | ||
| Thu., 11/10 | V Football | WCA | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | W 55-6 | |
| Sat., 11/12 | JV Football | WCA | Home - Gilbert School-Football Field [Directions] | 11:00 a.m. | ||
| Fri., 11/18 | JV Football | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 4:30 p.m. | ||
| Mon., 11/21 | FM Football | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | Canceled | Cancelled | |
| Thu., 11/24 | V Football | St. Paul Catholic | Home - Gilbert School-Football Field [Directions] | 10:00 a.m. | W 56-6 | |
| 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 | Shepaug Valley | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | L 46-30 | |
| Tue., 12/13 | JV Girls Basketball | Shepaug Valley | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Sat., 12/17 | V Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 3:30 p.m. | L 18-71 | |
| Sat., 12/17 | JV Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 2:00 p.m. | ||
| Sat., 12/17 | V Girls Basketball | Northwestern | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 3:30 p.m. | L 29-58 | |
| Sat., 12/17 | JV Girls Basketball | Northwestern | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 2:00 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 | |
| Tue., 12/20 | V Boys Basketball | Litchfield | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | L 41 - 89 | |
| Tue., 12/20 | JV Boys Basketball | Litchfield | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/20 | V Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 37-30 | |
| Tue., 12/20 | JV Girls Basketball | Litchfield | Away - Litchfield HS-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 | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 6:00 p.m. | L 33-63 | |
| Thu., 12/22 | JV Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 4:30 p.m. | ||
| Thu., 12/22 | V Girls Basketball | Wamogo | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:15 p.m. | L 42-37 | |
| Thu., 12/22 | JV Girls Basketball | Wamogo | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:45 p.m. | ||
| Tue., 12/27 | V Boys Basketball | Gilbert | Home - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 4:30 p.m. | L 33-74 | Part of the OWTS Winter Tournament |
| Thu., 12/29 | V Boys Basketball | O'Brien Tech | Away - Emmett O' Brien Reg Voc Tech School-Gym [Directions] | 4:30 p.m. | L 29-56 | |
| Mon., 1/2 | V Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | ||
| Mon., 1/2 | JV Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | V Boys Basketball | Gilbert | Home - Housatonic Valley Regional High-Gym [Directions] | 7:00 p.m. | Cancelled | |
| Tue., 1/3 | V Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 7:00 p.m. | L 31-60 | |
| Tue., 1/3 | JV Girls Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/4 | JV Boys Basketball | Gilbert | Home - Housatonic Valley Regional High-Gym [Directions] | Postponed | ||
| 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 | |
| Thu., 1/5 | V Girls Basketball | Lewis Mills | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:00 p.m. | L 53-18 | |
| Thu., 1/5 | JV Girls Basketball | Lewis Mills | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/6 | V Boys Basketball | East Windsor | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:00 p.m. | L 46-52 | |
| Fri., 1/6 | JV Boys Basketball | East Windsor | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/6 | V Boys Swimming and Diving | Northwestern | Away - Northwestern Regional H.S.-YMCA Swim [Directions] | 7:00 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 | |
| Mon., 1/9 | V Boys Basketball | O'Brien Tech | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | L 38 - 55 | |
| Mon., 1/9 | JV Boys Basketball | O'Brien Tech | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 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 | Terryville | Away - Terryville HS-Gym [Directions] | 7:00 p.m. | L 27-66 | |
| Tue., 1/10 | JV Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Terryville | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | W 41-23 | |
| Tue., 1/10 | JV Girls Basketball | Terryville | Home - Housatonic Valley Regional High-Edward S. Tyburski 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 Swimming and Diving | Nonnewaug | Home - Hotchkiss School-Pool [Directions] | 6:00 p.m. | ||
| Thu., 1/12 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | L 26-50 | |
| Thu., 1/12 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/13 | V Boys Basketball | Nonnewaug | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:00 p.m. | L 37-78 | |
| Fri., 1/13 | JV Boys Basketball | Nonnewaug | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/17 | V Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 7:00 p.m. | L 25-62 | |
| Tue., 1/17 | JV Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Thomaston | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | L 67-26 | |
| Tue., 1/17 | JV Girls Basketball | Thomaston | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 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 | V Boys Swimming and Diving | Shepaug Valley | Home - Hotchkiss School-Pool [Directions] | 6:00 p.m. | ||
| Thu., 1/19 | FR Boys Basketball | Shepaug Valley | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Boys Basketball | Shepaug Valley | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | L 41-99 | |
| Fri., 1/20 | JV Boys Basketball | Shepaug Valley | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | V Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 27-20 | |
| Fri., 1/20 | JV Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | V Boys Basketball | Northwestern | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | L 40-67 | |
| Tue., 1/24 | JV Boys Basketball | Northwestern | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | L 52-16 | |
| Tue., 1/24 | JV Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/25 | V Boys Swimming and Diving | Litchfield | Home - Hotchkiss School-Pool [Directions] | Canceled | Cancelled | |
| Thu., 1/26 | V Girls Basketball | Wolcott Tech | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | W 58-21 | |
| Thu., 1/26 | JV Girls Basketball | Wolcott Tech | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:45 p.m. | JV game will be immediately following varsity finish and will be running time. | |
| Fri., 1/27 | V Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 7:00 p.m. | L 44-96 | |
| Fri., 1/27 | JV Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | V Girls Basketball | Litchfield | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:00 p.m. | W 49-29 | |
| Fri., 1/27 | JV Girls Basketball | Litchfield | Home - Housatonic Valley Regional High-Gym [Directions] | Canceled | Cancelled | |
| 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 | Wamogo | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | L 40-72 | |
| Tue., 1/31 | JV Boys Basketball | Wamogo | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | L 37-29 | |
| Tue., 1/31 | JV Girls Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/1 | JV Girls Basketball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Gym [Directions] | Canceled | Cancelled | |
| Fri., 2/3 | V Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 6:30 p.m. | L 35-75 | |
| Fri., 2/3 | JV Boys Basketball | Gilbert | Away - Gilbert School-Gym [Directions] | 5:00 p.m. | ||
| Fri., 2/3 | V Girls Basketball | Gilbert | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | L 45-33 | |
| Fri., 2/3 | JV Girls Basketball | Gilbert | Home - Housatonic Valley Regional High-Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/4 | V Boys Ice Hockey | Tri-Town | Home - South Kent School-Ice Rink [Directions] | 7:00 p.m. | L 2-5 | |
| Mon., 2/6 | FR Boys Basketball | Litchfield | Away - Litchfield HS-Gym [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 | Terryville | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | L 47 - 72 | |
| Tue., 2/7 | JV Boys Basketball | Terryville | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 7:00 p.m. | W 36-29 | |
| Tue., 2/7 | JV Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/8 | FR Boys Basketball | Indian Mountain School | Away - Indian Mountain School-#4 | 3:30 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 | |
| Wed., 2/8 | V Boys Swimming and Diving | Northwestern | Home - Hotchkiss School-Pool [Directions] | 6:00 p.m. | ||
| Thu., 2/9 | V Boys Swimming and Diving | Nonnewaug | Away - Wilby HS [Directions] | 7:30 p.m. | ||
| Thu., 2/9 | V Girls Basketball | Lewis Mills | Away - Lewis Mills HS-Gymnasium [Directions] | 6:00 p.m. | W 31-27 | |
| Thu., 2/9 | JV Girls Basketball | Lewis Mills | Away - Lewis Mills HS-Gymnasium [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 Boys Swimming and Diving | Litchfield | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Tue., 2/14 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | L 46-86 | |
| Tue., 2/14 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 2/14 | V Girls Basketball | Nonnewaug | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:00 p.m. | L 67-32 | Senior Night |
| Tue., 2/14 | JV Girls Basketball | Nonnewaug | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:30 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 | Litchfield, Wamogo | Home - Hotchkiss School-Pool [Directions] | 6:00 p.m. | Senior Night | |
| Wed., 2/15 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 7:00 p.m. | L 15-60 | |
| Wed., 2/15 | JV Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/16 | V Boys Basketball | Thomaston | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 7:00 p.m. | L 49-76 | |
| Thu., 2/16 | JV Boys Basketball | Thomaston | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/20 | V Boys Basketball | Wolcott Tech | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 6:00 p.m. | L 38-68 | Senior Night |
| Mon., 2/20 | JV Boys Basketball | Wolcott Tech | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 3:00 p.m. | ||
| Mon., 2/20 | V Girls Basketball | Wolcott Tech | Home - Housatonic Valley Regional High-Edward S. Tyburski Gym [Directions] | 4:30 p.m. | W 73-11 | |
| Fri., 2/24 | V Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 43-84 | |
| Fri., 2/24 | JV Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/24 | FR Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | Postponed | ||
| Fri., 2/24 | V Boys Ice Hockey | Simsbury | Away - Simsbury - ISCC-Olympic [Directions] | 7:10 p.m. | Cancelled | |
| 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 | Wamogo | Away - 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 | |
| Mon., 4/3 | V Boys Tennis | Gilbert | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Mon., 4/3 | V Girls Lacrosse | Granby Memorial | Away - Granby Memorial HS-Granby [Directions] | 4:00 p.m. | L 5-14 | |
| Mon., 4/3 | V Girls Tennis | Gilbert | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | W 6-0 | |
| Tue., 4/4 | V Baseball | Nonnewaug | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | L 9-2 | |
| 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 | Nonnewaug | Home - Housatonic Valley Regional High-softball field [Directions] | 4:00 p.m. | L 7-2 | |
| Wed., 4/5 | V Boys Tennis | Northwestern | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | W 4-1 [Detailed Results] | |
| Wed., 4/5 | V Girls Lacrosse | St. Paul Catholic | Away - St. Paul Catholic HS -McPhee Field [Directions] | 6:00 p.m. | W 14-11 | |
| Wed., 4/5 | JV Softball | Shepaug Valley | Home - Housatonic Valley Regional High-Softball Diamond [Directions] | 4:15 p.m. | ||
| Wed., 4/5 | V Girls Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 [Detailed Results] | |
| Thu., 4/6 | V Baseball | Gilbert | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | W 7-2 | |
| Thu., 4/6 | V Softball | Gilbert | Home - Housatonic Valley Regional High-softball field [Directions] | 4:15 p.m. | W 17-2 | |
| Thu., 4/6 | V Girls Tennis | Lewis Mills | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | W 4-2 [Detailed Results] | |
| Wed., 4/12 | JV Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | Canceled | Cancelled | |
| Mon., 4/17 | V Baseball | Shepaug Valley | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | L 15-3 | |
| Mon., 4/17 | V Softball | Shepaug Valley | Away - Washington Primary School-Dick Ayer Field [Directions] | 4:15 p.m. | L 11-0 | |
| Tue., 4/18 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | L 4-1 [Detailed Results] | |
| Tue., 4/18 | V Girls Lacrosse | Wolcott | Home - Housatonic Valley Regional High-football field [Directions] | 3:45 p.m. | L 11-13 | |
| Tue., 4/18 | V Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 4:15 p.m. | L 6-3 | |
| Tue., 4/18 | V Girls Tennis | Shepaug Valley | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 [Detailed Results] | |
| Wed., 4/19 | V Baseball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | L 10-0 | |
| Wed., 4/19 | V Softball | Thomaston | Home - Housatonic Valley Regional High-softball field [Directions] | 4:15 p.m. | L 10-2 | |
| Wed., 4/19 | V Girls Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Thu., 4/20 | V Boys Tennis | Wamogo | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | L 4-1 [Detailed Results] | |
| Fri., 4/21 | V Baseball | Mt. Everett (MA) | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | L 9-8 | |
| Fri., 4/21 | V Boys Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | L 4-1 [Detailed Results] | |
| Fri., 4/21 | V Girls Lacrosse | Litchfield Coop | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 6-9 | |
| Fri., 4/21 | JV Girls Lacrosse | Litchfield Coop | Away - Plumb Hill Field Complex-Softball Field [Directions] | Postponed | ||
| Fri., 4/21 | V Softball | Dover (NY) | Home - Housatonic Valley Regional High-softball field [Directions] | 4:15 p.m. | W 12-8 | |
| Fri., 4/21 | V Girls Tennis | Nonnewaug | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Sat., 4/22 | V Baseball | Northwestern | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 11:00 a.m. | L 15-3 | |
| Mon., 4/24 | V Baseball | Litchfield | Away - Litchfield HS-Litchfield High School Baseball Field [Directions] | 3:45 p.m. | L 12-2 | |
| Mon., 4/24 | V Boys Tennis | Thomaston | Away - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 3:45 p.m. | W 4-1 [Detailed Results] | |
| Mon., 4/24 | V Girls Lacrosse | Watertown | Home - Housatonic Valley Regional High-football field [Directions] | 3:45 p.m. | L 9-18 | |
| Tue., 4/25 | V Boys Outdoor Track | Thomaston, Wamogo | Away - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Girls Outdoor Track | Thomaston | Away - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | JV Softball | Shepaug Valley | Away - Washington Primary School-Washington Primary School Softball Field [Directions] | 4:15 p.m. | W 19-6 | |
| Tue., 4/25 | V Girls Tennis | Thomaston | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Wed., 4/26 | V Baseball | Wamogo | Away - Wamogo Regional HS-Varsity Baseball Field [Directions] | 3:45 p.m. | L 10-5 | |
| Wed., 4/26 | V Boys Tennis | Litchfield | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | L 4-1 [Detailed Results] | |
| Wed., 4/26 | V Softball | Wamogo/Litchfield | Home - Housatonic Valley Regional High-softball field [Directions] | 4:15 p.m. | W 9-4 | |
| Wed., 4/26 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Thu., 4/27 | V Boys Tennis | Gilbert | Away - Gilbert School-PineWoods Racquet Club [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Thu., 4/27 | V Girls Tennis | Gilbert | Away - Gilbert School-PineWoods Racquet Club [Directions] | 3:45 p.m. | W 4-0 | |
| Sat., 4/29 | JV Girls Lacrosse | Berkshire (MA) | Away - Berkshire School-Lacrosse | 2:00 p.m. | ||
| Mon., 5/1 | V Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 3:45 p.m. | L Forfeit | |
| Mon., 5/1 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 4:15 p.m. | L 6-3 | |
| Tue., 5/2 | V Boys Outdoor Track | Litchfield, Terryville | Home - Housatonic Valley Regional High-Track [Directions] | 3:45 p.m. | Litchfield 87-Housatonic 50 Housatonic 76-Terryville 52 Litchfield 96-Terryville 34 | Senior Day |
| Tue., 5/2 | V Girls Outdoor Track | Litchfield, Terryville | Home - Housatonic Valley Regional High-Track [Directions] | 3:45 p.m. | Housatonic 63- Litchfield 50 Housatonic 75- Terryville 51 Litchfield 78- Terryville 45 | Senior Day |
| Wed., 5/3 | V Baseball | Gilbert | Away - Walker Field [Directions] | 4:15 p.m. | L 11-8 | |
| Wed., 5/3 | V Boys Tennis | Shepaug Valley | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | L 5-0 [Detailed Results] | |
| Wed., 5/3 | V Softball | Gilbert | Away - Winsted Rowley Field [Directions] | 4:15 p.m. | W 23-1 | |
| Wed., 5/3 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | L 0-7 [Detailed Results] | |
| Thu., 5/4 | V Softball | Terryville | Away - Terryville HS-Softball Field [Directions] | 4:15 p.m. | W 24-9 | |
| Thu., 5/4 | V Girls Tennis | Wamogo | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Mon., 5/8 | V Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | L 16-1 | |
| Mon., 5/8 | V Boys Tennis | Nonnewaug | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | L 5-0 [Detailed Results] | |
| Mon., 5/8 | V Softball | Northwestern | Home - Housatonic Valley Regional High-softball field [Directions] | 4:15 p.m. | L 17-8 | |
| Mon., 5/8 | V Girls Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Tue., 5/9 | V Boys Outdoor Track | Gilbert, Northwestern | Away - Northwestern Regional H.S.-Track [Directions] | 3:45 p.m. | ||
| Tue., 5/9 | V Boys Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | L 3-2 [Detailed Results] | |
| Tue., 5/9 | V Girls Lacrosse | Litchfield Coop | Home - Housatonic Valley Regional High-football field [Directions] | 6:15 p.m. | L 6-9 | |
| Tue., 5/9 | V Girls Outdoor Track | Gilbert, Northwestern | Away - Northwestern Regional H.S.-Track [Directions] | 3:45 p.m. | ||
| Tue., 5/9 | V Girls Tennis | Northwestern | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Wed., 5/10 | V Baseball | Dover (NY) | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 5/10 | V Boys Tennis | Thomaston | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | W 4-1 [Detailed Results] | |
| Wed., 5/10 | V Girls Lacrosse | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 5:00 p.m. | L 11-16 | |
| Wed., 5/10 | JV Girls Lacrosse | Berkshire (MA) | Home - Housatonic Valley Regional High-football field [Directions] | Postponed | ||
| Wed., 5/10 | V Softball | Shepaug Valley | Home - Housatonic Valley Regional High-softball field [Directions] | 4:15 p.m. | L 10-20 | |
| Wed., 5/10 | V Girls Tennis | Thomaston | Away - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 4:30 p.m. | W 4-3 [Detailed Results] | |
| Thu., 5/11 | V Girls Lacrosse | St. Paul Catholic | Home - Housatonic Valley Regional High-football field [Directions] | 5:00 p.m. | L 13-14 | Stick it to Cancer Game |
| Thu., 5/11 | V Softball | Windsor Locks | Away - Windsor Locks HS-Softball Diamond [Directions] | 4:00 p.m. | W 23-8 | |
| Fri., 5/12 | V Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | L 10-0 | |
| Fri., 5/12 | V Boys Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | L 5-0 [Detailed Results] | |
| Fri., 5/12 | V Softball | Dover (NY) | Away - Dover HS | 4:30 p.m. | Cancelled | |
| Fri., 5/12 | V Girls Tennis | Litchfield | Home - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 [Detailed Results] | Senior Day |
| Mon., 5/15 | V Baseball | Thomaston | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | L 6-3 | |
| Mon., 5/15 | V Boys Outdoor Track | Shepaug Valley, Nonnewaug | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Track [Directions] | 3:45 p.m. | ||
| Mon., 5/15 | V Girls Outdoor Track | Shepaug Valley, Nonnewaug | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Track [Directions] | 3:45 p.m. | ||
| Mon., 5/15 | V Softball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 4:15 p.m. | L 8-0 | |
| Tue., 5/16 | V Baseball | Terryville | Away - Terryville HS-Baseball Field [Directions] | 3:45 p.m. | W 20-5 | This will be a double header (5 innings each game) |
| Tue., 5/16 | V Boys Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | 3:15 p.m. | W 4-1 [Detailed Results] | |
| Tue., 5/16 | V Girls Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | L 15-16 | |
| Tue., 5/16 | V Softball | Terryville | Home - Housatonic Valley Regional High-softball field [Directions] | 4:15 p.m. | W 9-4 | Strike Out Cancer Game |
| Wed., 5/17 | V Girls Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | Cancelled | |
| Thu., 5/18 | V Baseball | Terryville | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | L 4-6 | |
| Thu., 5/18 | V Baseball | Dover (NY) | Away - Dover HS | 4:30 p.m. | Cancelled | |
| Thu., 5/18 | V Girls Lacrosse | Somers | Home - Housatonic Valley Regional High-football field [Directions] | 5:15 p.m. | L 2-21 | |
| Thu., 5/18 | V Softball | Granby Memorial | Home - Housatonic Valley Regional High-softball field [Directions] | 4:00 p.m. | L 13-3 | Senior Day |
| Fri., 5/19 | V Baseball | Litchfield | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | L 4-15 | |
| Fri., 5/19 | V Girls Lacrosse | Lewis Mills | Away - Lewis Mills HS-Lewis Mills Track [Directions] | 5:00 p.m. | L 9-19 | |
| Fri., 5/19 | JV Softball | Northwestern | Away - Northwestern Regional H.S.-JV Softball Field [Directions] | 3:45 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 | Wamogo | Home - Housatonic Valley Regional High-Ed Kirby Field [Directions] | 3:45 p.m. | L 5-10 | Senior Day |
| Mon., 5/22 | V Girls Lacrosse | Northwest Catholic | Away - Northwest Catholic HS (Primary)-NWC Lacrosse Field [Directions] | 3:45 p.m. | L 11-23 | |
| Mon., 5/22 | V Softball | Wamogo/Litchfield | Away - Wamogo Regional HS-Wamogo Regional High School Varsity Ladies Softbal [Directions] | 5:15 p.m. | W 12-2 | |
| 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. | ||
| 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) | Home - Housatonic Valley Regional High-Track [Directions] | 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) | Home - Housatonic Valley Regional High-Track [Directions] | 3:30 p.m. | ||
| Wed., 5/24 | V Softball | East Granby | Away - East Granby HS-Softball Diamond [Directions] | 4:00 p.m. | W 12-2 | |