| Gilbert 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 349 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/25 | V Football | East Catholic (Scrim.) | Away - Cheney Tech [Directions] | 3:00 p.m. | ||
| Sat., 8/28 | V Football | Cheney Tech (Scrim.) | Home - Gilbert School-Football Field [Directions] | 10:00 a.m. | ||
| Mon., 8/30 | V Boys Golf | Wamogo, Litchfield | Away - Wamogo HS-Stoneybrook Golf Course [Directions] | 3:00 p.m. | Wamogo- 291 (0-2) Litchfield- 182 (2-0) Gilbert- 228 (1-1) | |
| Sat., 9/4 | V Football | Torrington (Scrim.) | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 8:30 a.m. | ||
| Tue., 9/7 | V Boys Cross Country | BL Scrimmage | Away - Black Rock State Park | 4:00 p.m. | ||
| Tue., 9/7 | V Boys Golf | Housatonic Regional | Home - Green woods Country Club [Directions] | 3:00 p.m. | Housatonic- 220 (1-0) Gilbert- 247 (1-2) | |
| Tue., 9/7 | V Girls Cross Country | BL Scrimmage | Away - Black Rock State Park | 4:00 p.m. | ||
| Tue., 9/7 | V Girls Soccer | Torrington (Scrim.) | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 3:45 p.m. | ||
| Fri., 9/10 | V Girls Soccer | Canton | Home - Walker Field [Directions] | 4:00 p.m. | L 1-3 | |
| Sat., 9/11 | V Football | Stafford/East Windsor/Somers | Home - Gilbert School-Football Field [Directions] | 1:00 p.m. | L 30-35 | |
| Mon., 9/13 | JV Football | Stafford/East Windsor/Somers | Away - Stafford HS-Lighted Stadium Field (behind the school) [Directions] | 4:45 p.m. | ||
| Mon., 9/13 | V Boys Golf | Housatonic Regional, Northwestern | Away - Canaan Country Club [Directions] | 3:00 p.m. | Housatonic- 185 (4-0) Northwestern- 223 (1-2) Gilbert- 228 (1-4) | |
| Mon., 9/13 | V Boys Soccer | Litchfield | Home - Walker Field [Directions] | 3:45 p.m. | L 0-11 | |
| Mon., 9/13 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 2-6 | |
| Tue., 9/14 | V Boys Cross Country | Litchfield, Thomaston | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Boys Golf | Wamogo, Terryville | Away - Wamogo HS-Stoneybrook Golf Course [Directions] | Postponed | 269 | |
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/8, Time to 3:00 p.m. | ||||||
| Tue., 9/14 | V Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | 3:45 p.m. | L 0-8 | |
| Tue., 9/14 | JV Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | Canceled | Cancelled | |
| Tue., 9/14 | V Girls Cross Country | Litchfield, Thomaston | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Girls Soccer | Housatonic Regional | Home - Walker Field [Directions] | 3:30 p.m. | L 2-9 | |
| Tue., 9/14 | V Girls Volleyball | Wamogo | Away - Wamogo Regional HS-Large gym [Directions] | 3:45 p.m. | L 1-3 | |
| Tue., 9/14 | JV Girls Volleyball | Wamogo | Away - Wamogo Regional HS-Large Gym [Directions] | 5:00 p.m. | ||
| Thu., 9/16 | V Boys Soccer | Wamogo | Home - Walker Field [Directions] | 3:30 p.m. | L 0-8 | |
| Thu., 9/16 | V Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | W 3-1 | |
| Thu., 9/16 | V Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 9/16 | JV Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/17 | JV Football | Coventry/Windham Tech/Bolton/Lyman | Away - Coventry HS-Football Field [Directions] | 6:30 p.m. | ||
| Mon., 9/20 | V Boys Cross Country | Shepaug Valley, Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Cross Country Course [Directions] | 4:00 p.m. | ||
| Mon., 9/20 | V Boys Golf | Shepaug Valley | Home - Green woods Country Club [Directions] | 3:00 p.m. | Shepaug- 188 (3-1) Gilbert- 232 (1-5) | |
| Mon., 9/20 | V Boys Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:45 p.m. | L 0-10 | |
| Mon., 9/20 | V Girls Cross Country | Shepaug Valley, Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Cross Country Course [Directions] | 4:00 p.m. | ||
| Mon., 9/20 | V Girls Volleyball | Terryville | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Mon., 9/20 | JV Girls Volleyball | Terryville | Home - Gilbert School-Gym [Directions] | 3:45 p.m. | ||
| Tue., 9/21 | V Girls Soccer | Terryville | Home - Walker Field [Directions] | 3:30 p.m. | L 0-4 | |
| Tue., 9/21 | V Girls Volleyball | Northwestern | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 9/21 | JV Girls Volleyball | Northwestern | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/22 | V Boys Soccer | Nonnewaug | Home - Walker Field [Directions] | 3:30 p.m. | L 08 | |
| Wed., 9/22 | V Girls Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | L 1-5 | |
| Wed., 9/22 | V Girls Volleyball | Goodwin Tech | Away - Goodwin Tech-Goodwin Tech Gymnasium [Directions] | 5:15 p.m. | L 1-3 | |
| Wed., 9/22 | JV Girls Volleyball | Goodwin Tech | Away - Goodwin Tech-Goodwin Tech Gymnasium [Directions] | 4:15 p.m. | ||
| Thu., 9/23 | V Boys Golf | Nonnewaug | Away - Western Hills Golf Course (Wtby) [Directions] | 3:00 p.m. | Nonnewaug- 182 (4-3) Gilbert- 227 (1-6) | |
| Fri., 9/24 | V Football | Rockville | Away - Rockville HS-Stadium Field [Directions] | 7:00 p.m. | L 12-42 | |
| Mon., 9/27 | JV Football | East Catholic | Home - Gilbert School-Football Field [Directions] | 4:00 p.m. | ||
| Mon., 9/27 | JV Girls Soccer | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 3:45 p.m. | ||
| Tue., 9/28 | V Girls Volleyball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 9/28 | JV Girls Volleyball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | V Boys Golf | Litchfield, Shepaug Valley | Away - Litchfield Country Club [Directions] | 3:00 p.m. | Litchfield- 187* 10-0 Shepaug- 187 5-4 Gilbert- 245 1-8 | |
| Wed., 9/29 | V Boys Soccer | Shepaug Valley | Home - Walker Field [Directions] | 3:30 p.m. | L 011 | |
| Wed., 9/29 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-5 | |
| Thu., 9/30 | V Girls Cross Country | Housatonic Regional, Northwestern | Away - Housatonic Valley Regional High-Cross Country Course [Directions] | 4:00 p.m. | ||
| Fri., 10/1 | V Football | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 6:30 p.m. | W 29-18 | |
| Fri., 10/1 | V Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 7:30 p.m. | L 0-9 | |
| Fri., 10/1 | V Girls Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 5:45 p.m. | L 1-5 | |
| Sat., 10/2 | JV Football | Granby/Canton | Away - Granby Memorial HS-Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 10/2 | JV Football | Rockville | Home - Gilbert School-Football Field [Directions] | 11:00 a.m. | ||
| Mon., 10/4 | V Boys Golf | Nonnewaug, Terryville | Home - Green woods Country Club [Directions] | 3:00 p.m. | ||
| Tue., 10/5 | V Boys Golf | Northwestern, Wamogo | Home - Green woods Country Club [Directions] | 3:00 p.m. | 224 | |
| Tue., 10/5 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-8 | |
| Tue., 10/5 | V Girls Soccer | Litchfield | Home - Walker Field [Directions] | 3:30 p.m. | L 1-8 | |
| Tue., 10/5 | V Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 10/5 | JV Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 5:15 p.m. | ||
| Wed., 10/6 | V Boys Golf | Nonnewaug, Shepaug Valley, Wamogo | Away - Western Hills Golf Course (Wtby) [Directions] | 3:00 p.m. | 227 | |
| Wed., 10/6 | V Boys Soccer | Thomaston | Away - Thomaston HS-Nystrom Park [Directions] | 3:45 p.m. | L 2-8 | |
| Wed., 10/6 | V Girls Soccer | Thomaston | Home - Walker Field [Directions] | 3:45 p.m. | L 1-9 | |
| Thu., 10/7 | V Boys Golf | Shepaug Valley, Litchfield, Terryville | Away - Lake Waramaug Country Club [Directions] | 3:00 p.m. | 226 | |
| Thu., 10/7 | V Girls Volleyball | Wolcott Tech | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 10/7 | JV Girls Volleyball | Wolcott Tech | Home - Gilbert School-Gym [Directions] | 3:45 p.m. | ||
| Fri., 10/8 | V Boys Soccer | Housatonic Regional | Home - Walker Field [Directions] | 3:30 p.m. | L 0-10 | |
| Fri., 10/8 | V Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | 3:45 p.m. | L 3-8 | |
| Sat., 10/9 | V Football | Windsor Locks/Suffield/East Granby | Home - Gilbert School-Football Field [Directions] | 1:00 p.m. | W 39-12 | |
| Tue., 10/12 | V Boys Cross Country | Nonnewaug, Terryville | Home - Gilbert School-Cross Country [Directions] | 3:30 p.m. | ||
| Tue., 10/12 | JV Football | Windsor Locks/Suffield/East Granby | Away - Windsor Locks HS-Patrick Scelza Field [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Boys Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-8 | |
| Tue., 10/12 | V Girls Cross Country | Nonnewaug, Terryville | Home - Gilbert School-Cross Country [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | V Boys Soccer | Terryville | Home - Walker Field [Directions] | 3:30 p.m. | L 0-10 | |
| Thu., 10/14 | V Girls Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:45 p.m. | L 2-3 | |
| Thu., 10/14 | V Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Thu., 10/14 | JV Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/15 | JV Girls Soccer | Wamogo | Away - Wamogo Regional HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/15 | V Girls Volleyball | Goodwin Tech | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Fri., 10/15 | JV Girls Volleyball | Goodwin Tech | Home - Gilbert School-Gym [Directions] | 3:45 p.m. | ||
| Sat., 10/16 | V Football | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | W 42-0 | |
| Mon., 10/18 | JV Football | Old Saybrook | Home - Gilbert School-Football Field [Directions] | 4:00 p.m. | ||
| Mon., 10/18 | V Boys Golf | CIAC Fall Division II Boys Golf Championship | Away - Silo Point GC | 8:30 a.m. | ||
| Tue., 10/19 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | L 0-11 | |
| Tue., 10/19 | V Girls Soccer | Nonnewaug | Home - Walker Field [Directions] | 3:30 p.m. | L 1-10 | |
| Tue., 10/19 | V Girls Volleyball | Wamogo | Away - Wamogo Regional HS-Large gym [Directions] | 5:15 p.m. | W 3-2 | |
| Tue., 10/19 | JV Girls Volleyball | Wamogo | Away - Wamogo Regional HS-Large Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/21 | V Boys Cross Country | Berkshire League Championship | Home - Black Rock State Park [Directions] | 4:15 p.m. | ||
| Thu., 10/21 | V Girls Cross Country | Berkshire League Championship | Home - Black Rock State Park [Directions] | 3:30 p.m. | ||
| Thu., 10/21 | V Girls Volleyball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 10/21 | JV Girls Volleyball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/22 | V Football | Amistad | Home - Gilbert School-Football Field [Directions] | 3:30 p.m. | W 56-14 | |
| Fri., 10/22 | V Boys Soccer | Northwestern | Home - Walker Field [Directions] | 3:30 p.m. | L 0-5 | |
| Fri., 10/22 | V Girls Soccer | Northwestern | Home - Walker Field [Directions] | 5:30 p.m. | L 0-4 | |
| Mon., 10/25 | JV Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/26 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 10/26 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/28 | V Girls Volleyball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 10/28 | JV Girls Volleyball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 3:45 p.m. | ||
| Fri., 10/29 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-9 | |
| Fri., 10/29 | V Girls Soccer | Shepaug Valley | Home - Walker Field [Directions] | 6:00 p.m. | L 2-6 | |
| Sat., 10/30 | V Football | Ellington | Home - Gilbert School-Football Field [Directions] | 10:30 a.m. | W 14-0 | |
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class S Championship | Away - Wickham Park | 2:05 p.m. | ||
| Mon., 11/1 | JV Football | Ellington | Away - Ellington HS-Main Field [Directions] | 4:00 p.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class S Championship | Away - Wickham Park | 2:35 p.m. | ||
| Tue., 11/2 | V Boys Soccer | Thomaston | Home - Walker Field [Directions] | 3:30 p.m. | L 1-9 | |
| Tue., 11/2 | V Girls Soccer | Thomaston | Away - Thomaston HS-Nystrom Park [Directions] | 3:45 p.m. | L 0-6 | |
| Wed., 11/3 | V Girls Soccer | Wamogo | Home - Walker Field [Directions] | 3:30 p.m. | W 6-0 | |
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | FM Football | Torrington | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 10:00 a.m. | ||
| Mon., 11/8 | JV Football | SMSA Coop | Home - Gilbert School-Football Field [Directions] | Canceled | Cancelled | |
| Wed., 11/17 | JV Football | Capital/Achievement | Home - Gilbert School-Torrington HS [Directions] | 4:00 p.m. | This game will be held at the Torrington HS Football field. | |
| Thu., 11/18 | V Football | Derby | Away - Leo F. Ryan Athletic Complex-DeFilippo Field [Directions] | 7:00 p.m. | W Forfeit | |
| Thu., 11/25 | V Football | Granby/Canton | Home - Gilbert School-Football Field [Directions] | 10:30 a.m. | W 21-0 | |
| Tue., 11/30 | V Football | Killingly | Away - Killingly HS-Morgan Field [Directions] | 6:30 p.m. | ||
| Sun., 12/5 | V Boys Basketball | Monument Mountain (MA) (Scrim.) | Home - Gilbert School-Gym [Directions] | 1:00 p.m. | ||
| Mon., 12/6 | V Girls Basketball | Wolcott Tech (Scrim.) | Home - Gilbert School-Gym [Directions] | 3:00 p.m. | ||
| Tue., 12/7 | V Girls Basketball | Lewis Mills (Scrim.) | Away - Lewis Mills HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:30 p.m. | ||||||
| Thu., 12/9 | V Girls Basketball | Torrington (Scrim.) | Home - Gilbert School-Gym [Directions] | 3:00 p.m. | ||
| Mon., 12/13 | V Girls Basketball | East Granby | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | W 53-29 | |
| Mon., 12/13 | JV Girls Basketball | East Granby | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/16 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | L 48-54 | |
| Thu., 12/16 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:30 p.m. | ||
| Thu., 12/16 | V Girls Basketball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | W 49-42 | |
| Thu., 12/16 | JV Girls Basketball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 4:30 p.m. | ||
| Tue., 12/21 | V Boys Basketball | Litchfield | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 37-48 | |
| Tue., 12/21 | JV Boys Basketball | Litchfield | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/21 | V Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 7:00 p.m. | W 48-34 | |
| Tue., 12/21 | JV Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/22 | FR Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | Canceled | Cancelled | |
| Wed., 12/22 | V Wrestling | Northwestern | Away - Northwestern Regional H.S.-Small Gym [Directions] | 6:00 p.m. | ||
| Thu., 12/23 | V Girls Basketball | Shepaug Valley | Home - Gilbert School-Gym [Directions] | 5:00 p.m. | W 25-15 | |
| Thu., 12/23 | JV Girls Basketball | Shepaug Valley | Home - Gilbert School-Gym [Directions] | 3:30 p.m. | ||
| Tue., 12/28 | V Boys Basketball | Housatonic Regional | Home - Emmett O' Brien Reg Voc Tech School-Emmett O'Brien Gymnasium [Directions] | 5:00 p.m. | W 58-30 | |
| Tue., 12/28 | V Girls Basketball | Wolcott Tech | Away - Bristol Central Holiday Classic [Directions] | 3:00 p.m. | W 47-38 | |
| Wed., 12/29 | V Boys Basketball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Gym [Directions] | 6:00 p.m. | W 58-57 | |
| Thu., 12/30 | V Girls Basketball | Bristol Central | Away - Bristol Central HS-Charles C. Marsh Gymnasium [Directions] | 4:30 p.m. | W 62-56 | |
| Tue., 1/4 | V Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 44-74 | |
| Tue., 1/4 | JV Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/5 | V Wrestling | Derby/Oxford/Holy Cross | Away - Derby HS-DHS Vitello Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/6 | V Girls Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | L 44-33 | |
| Thu., 1/6 | JV Girls Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | Canceled | Cancelled | |
| Fri., 1/7 | V Boys Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 47-70 | |
| Fri., 1/7 | JV Boys Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | Postponed | ||
| Fri., 1/7 | V Boys Swimming and Diving | Housatonic Regional | Home - Winsted YMCA-Pool [Directions] | 7:00 p.m. | ||
| Sat., 1/8 | FR Boys Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | Canceled | Cancelled | |
| Tue., 1/11 | V Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 6:00 p.m. | L 44-55 | |
| Tue., 1/11 | JV Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | Postponed | ||
| Tue., 1/11 | V Girls Basketball | Thomaston | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | L 49-34 | |
| Tue., 1/11 | JV Girls Basketball | Thomaston | Home - Gilbert School-Gym [Directions] | Postponed | ||
| Wed., 1/12 | V Boys Swimming and Diving | Wamogo | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 7:00 p.m. | ||
| Thu., 1/13 | V Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | 6:00 p.m. | L 51-87 | |
| Thu., 1/13 | JV Boys Basketball | Ansonia | Away - Ansonia HS-Gym [Directions] | Postponed | ||
| Thu., 1/13 | JV Girls Basketball | East Granby | Away - East Granby HS-Gym [Directions] | Postponed | ||
| Fri., 1/14 | V Boys Basketball | Terryville | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | L 47-70 | |
| Fri., 1/14 | JV Boys Basketball | Terryville | Home - Gilbert School-Gym [Directions] | Postponed | ||
| Fri., 1/14 | V Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 6:00 p.m. | W 51-40 | |
| Tue., 1/18 | V Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 6:00 p.m. | L 45-61 | |
| Tue., 1/18 | JV Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | Postponed | ||
| Tue., 1/18 | V Girls Basketball | Wamogo | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | W 49-34 | |
| Tue., 1/18 | JV Girls Basketball | Wamogo | Home - Gilbert School-Gym [Directions] | Postponed | ||
| Wed., 1/19 | V Boys Swimming and Diving | Torrington | Away - Torrington YMCA-pool [Directions] | 7:30 p.m. | ||
| Thu., 1/20 | JV Girls Basketball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | Postponed | ||
| Fri., 1/21 | V Boys Basketball | University | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | L 42-51 | |
| Fri., 1/21 | JV Boys Basketball | University | Home - Gilbert School-Gym [Directions] | Postponed | ||
| Fri., 1/21 | V Wrestling | Avon, East Lyme/Norwich Tech, Farmington | Away - Avon HS-Small gym [Directions] | 4:00 p.m. | ||
| Sat., 1/22 | V Boys Swimming and Diving | Shepaug Valley | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 3:30 p.m. | ||
| Sat., 1/22 | V Wrestling | Mt. Everett (MA), Gateway (MA), Mohawk Trail (MA), Monument Mountain (MA), Mt. Greylock (MA), Smith Vocational (MA), Southwick-Tolland Regional (MA), St. Paul Catholic, Taconic (MA) | Away - Mount Everett Regional-Gym | 10:00 a.m. | ||
| Tue., 1/25 | V Boys Basketball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | L 58-67 | |
| Tue., 1/25 | JV Boys Basketball | Nonnewaug | Home - Gilbert School-Gym [Directions] | Postponed | ||
| Tue., 1/25 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 5:00 p.m. | W 48-27 | |
| Tue., 1/25 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | Postponed | ||
| Wed., 1/26 | V Wrestling | Nonnewaug, St. Paul Catholic | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/27 | V Girls Basketball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | L 39-33 | |
| Fri., 1/28 | V Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:15 p.m. | L 36-67 | |
| Fri., 1/28 | JV Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | Postponed | ||
| Fri., 1/28 | V Girls Basketball | Litchfield | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | W 47-38 | |
| Fri., 1/28 | JV Girls Basketball | Litchfield | Home - Gilbert School-Gym [Directions] | Canceled | Cancelled | |
| Sat., 1/29 | V Wrestling | Portland, Avon, Cheshire, Coventry, Daniel Hand, East Haven, Glastonbury, Griswold/Wheeler, Morgan, TBA, TBA, New Britain, Nonnewaug, Plainville, Somers, St. Paul Catholic, Terryville/Thomaston, Thomaston, New Haven Wrestling | Away - Portland HS-Portland HS | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Tue., 2/1 | V Boys Basketball | Shepaug Valley | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | L 44-86 | |
| Tue., 2/1 | JV Boys Basketball | Shepaug Valley | Home - Gilbert School-Gym [Directions] | Postponed | ||
| Tue., 2/1 | V Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 42-45 | |
| Tue., 2/1 | JV Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/2 | V Wrestling | Terryville-Thomaston | Away - Terryville HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 2/3 | V Girls Basketball | East Granby | Away - East Granby HS-Gym [Directions] | 6:00 p.m. | W 51-38 | |
| Sat., 2/5 | V Boys Swimming and Diving | Nonnewaug | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 3:30 p.m. | ||
| Mon., 2/7 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | Canceled | Cancelled | |
| Tue., 2/8 | V Boys Basketball | Thomaston | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 44-51 | |
| Tue., 2/8 | JV Boys Basketball | Thomaston | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/8 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 7:00 p.m. | L 60-37 | |
| Tue., 2/8 | JV Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/9 | V Boys Swimming and Diving | Housatonic Regional | Away - Winsted YMCA-Pool [Directions] | 7:30 p.m. | ||
| Thu., 2/10 | JV Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | ||
| Thu., 2/10 | JV Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/11 | V Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | L 39-70 | |
| Fri., 2/11 | V Boys Swimming and Diving | Nonnewaug | Away - John F. Kennedy HS-JFK Pool [Directions] | 7:00 p.m. | ||
| Fri., 2/11 | V Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 4:30 p.m. | L 51-41 | |
| Sat., 2/12 | V Boys Swimming and Diving | Wamogo | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 3:30 p.m. | ||
| Sat., 2/12 | V Boys Swimming and Diving | Litchfield | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 3:30 p.m. | ||
| Sat., 2/12 | V Wrestling | Derby, Holy Cross, Berkshire League Tournament, Nonnewaug, Northwestern, Seymour, St. Paul Catholic, Terryville/Thomaston, Thomaston | Home - Gilbert School-Gym [Directions] | 9:00 a.m. | Weigh in is at 9:00 AM Matches start at 10:00 AM | |
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Mon., 2/14 | V Boys Basketball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 57-62(OT) | |
| Mon., 2/14 | JV Boys Basketball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/14 | V Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 7:00 p.m. | L 45-36 | |
| Mon., 2/14 | JV Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/15 | V Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 7:00 p.m. | L 32-90 | |
| Tue., 2/15 | JV Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/15 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/15 | V Girls Basketball | Terryville | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | W 47-26 | |
| Tue., 2/15 | JV Girls Basketball | Terryville | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/17 | V Boys Basketball | Wamogo | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 44-68 | |
| Thu., 2/17 | JV Boys Basketball | Wamogo | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/17 | V Girls Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | W 50-30 | |
| Thu., 2/17 | JV Girls Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | Postponed | ||
| Fri., 2/18 | V Wrestling | Class S Championship - Day 1 | Away - Killingly | 3:00 p.m. | ||
| Sat., 2/19 | FR Boys Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/19 | V Boys Swimming and Diving | Lewis Mills | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 4:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class S Championship - Day 2 | Away - Killingly | 9:00 a.m. | ||
| Sat., 2/19 | V Girls Basketball | Northwestern | Away - Thomaston HS-Gym [Directions] | 4:45 p.m. | ||
| Tue., 2/22 | V Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 7:00 p.m. | ||
| Tue., 2/22 | JV Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | Canceled | Cancelled | |
| Tue., 2/22 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/23 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:00 p.m. | ||
| Thu., 2/24 | V Girls Basketball | Nonnewaug | Away - Thomaston HS-Gym [Directions] | 7:00 p.m. | ||
| Sat., 2/26 | V Boys Basketball | Terryville | Away - Nonnewaug HS-Gym [Directions] | 1:15 p.m. | ||
| Sat., 2/26 | V Boys Swimming and Diving | TBA, Housatonic Regional, Litchfield, TBA, Nonnewaug, Shepaug Valley, Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool | 11:00 a.m. | ||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Tue., 3/1 | V Girls Basketball | Wheeler | Home - Gilbert School-Gym [Directions] | 6:30 p.m. | W 46-38 | |
| Fri., 3/4 | V Boys Swimming and Diving | Berkshire League Dive Championship | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool | 5:30 p.m. | ||
| Fri., 3/4 | V Girls Basketball | Shepaug Valley | Home - Gilbert School-Gym [Directions] | 6:30 p.m. | W 43-34 | |
| Sat., 3/5 | V Boys Swimming and Diving | Litchfield, Housatonic Regional, Nonnewaug, Shepaug Valley, Wamogo | Away - John F. Kennedy HS-JFK Pool | 4:30 p.m. | ||
| Tue., 3/8 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 7:00 p.m. | ||
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 4:00 p.m. | ||
| Fri., 3/11 | V Boys Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cornerstone Pool | 1:00 p.m. | ||
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class S Swimming Championships | Away - Cornerstone Pool | 6:30 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Sat., 3/26 | V Baseball | Woodland (Scrim.) | Away - Woodland HS-Baseball Diamond [Directions] | 12:00 p.m. | ||
| Tue., 3/29 | V Baseball | Granby Memorial (Scrim.) | Away - Granby Memorial HS-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Baseball | East Granby (Scrim.) | Home - Gilbert School-Riverton Baseball Field [Directions] | 3:45 p.m. | Cancelled | |
| Wed., 3/30 | V Baseball | East Granby (Scrim.) | Away - East Granby HS-Baseball Diamond [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 3/30 | JV Softball | Wolcott Tech (Scrim.) | Home - Winsted Rowley Field [Directions] | 3:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 3/31 | ||||||
| Thu., 3/31 | V Softball | Wolcott Tech (Scrim.) | Home - Winsted Rowley Field [Directions] | 3:00 p.m. | ||
| Fri., 4/1 | V Baseball | Wolcott Tech (Scrim.) | Home - Gilbert School-Riverton Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 4/4 | V Baseball | Canton | Away - Bowdoin Field-Baseball Diamond [Directions] | 3:45 p.m. | L 1-19 (5) | |
| Tue., 4/5 | V Softball | East Granby | Away - East Granby HS-Softball Diamond [Directions] | 4:00 p.m. | W 11-7 | |
| Fri., 4/8 | V Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | L 14-1 (5) | |
| Fri., 4/8 | V Boys Outdoor Track | Lewis Mills | Away - Lewis Mills HS-Lewis Mills Track [Directions] | 3:45 p.m. | ||
| Fri., 4/8 | V Girls Outdoor Track | Lewis Mills | Away - Lewis Mills HS-Lewis Mills Track [Directions] | 3:45 p.m. | ||
| Fri., 4/8 | V Softball | Shepaug Valley | Home - Winsted Rowley Field [Directions] | 3:45 p.m. | L 0-15 | |
| Mon., 4/11 | V Boys Outdoor Track | Terryville Invitational | Away - Terryville HS-Default Facility | 4:00 p.m. | ||
| Mon., 4/11 | V Girls Outdoor Track | Terryville Invitational | Away - Terryville HS-Track | 4:00 p.m. | ||
| Mon., 4/11 | V Girls Tennis | Housatonic Regional | Away - Housatonic Valley Regional High-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/12 | V Softball | Kaynor Tech | Home - Winsted Rowley Field [Directions] | 3:45 p.m. | W 22-9 | |
| Tue., 4/12 | V Girls Tennis | Litchfield | Home - Walker Field-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 4/13 | V Baseball | Terryville | Away - Terryville HS-Baseball Field [Directions] | 3:45 p.m. | W 14-3 (6) | |
| Wed., 4/13 | V Girls Tennis | Wamogo | Home - Gilbert School-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 4/14 | V Girls Tennis | Thomaston | Home - Walker Field-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 4/15 | V Baseball | Wolcott Tech | Home - Walker Field [Directions] | 11:00 a.m. | L 18-4 | |
| Fri., 4/15 | JV Baseball | Wolcott Tech | Home - Walker Field [Directions] | Postponed | ||
| Mon., 4/18 | JV Baseball | Northwestern | Home - Walker Field [Directions] | 1:00 p.m. | ||
| Mon., 4/18 | V Softball | Canton | Away - Canton HS-Softball Diamond [Directions] | 4:00 p.m. | L 3-18 | |
| Wed., 4/20 | V Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | 3:45 p.m. | L 13-0 (5) | |
| Wed., 4/20 | V Softball | Northwestern | Home - Winsted Rowley Field [Directions] | 3:45 p.m. | L 2-18 | |
| Thu., 4/21 | JV Softball | Northwestern | Home - Gilbert (RowleySt) Field #1-Gilbert (Rowley Street) Field #2 [Directions] | 3:45 p.m. | ||
| Fri., 4/22 | V Baseball | Wamogo | Away - Fuessenich Park-Baseball Diamond [Directions] | 3:45 p.m. | L 21-11 (5) | |
| Mon., 4/25 | V Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 4:00 p.m. | L 19-0 (5) | |
| Mon., 4/25 | JV Baseball | Nonnewaug | Away - Woodbury MS [Directions] | Postponed | ||
| Mon., 4/25 | V Softball | Nonnewaug | Home - Winsted Rowley Field [Directions] | 3:45 p.m. | L 0-16 | |
| Mon., 4/25 | V Girls Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/26 | V Boys Outdoor Track | Thomaston, Litchfield | Away - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Girls Outdoor Track | Thomaston, Litchfield | Away - Thomaston Nystrom Park-Nystroms Park Track [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Baseball | Litchfield | Home - Walker Field [Directions] | 3:45 p.m. | L 15-0(5) | |
| Wed., 4/27 | V Girls Tennis | Shepaug Valley | Home - Walker Field-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 4/29 | V Baseball | Housatonic Regional | Home - Walker Field [Directions] | 3:45 p.m. | L 20-7 (6) | |
| Fri., 4/29 | V Softball | Housatonic Regional | Away - Housatonic Valley Regional High-softball field [Directions] | 3:45 p.m. | L 7-15 | |
| Fri., 4/29 | JV Softball | Housatonic Regional | Away - Housatonic Valley Regional High-Softball Diamond [Directions] | 3:45 p.m. | ||
| Fri., 4/29 | V Girls Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Sat., 4/30 | JV Softball | Nonnewaug | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 9:30 a.m. | ||
| Mon., 5/2 | V Baseball | Derby | Away - Derby HS-Payden Park [Directions] | 5:30 p.m. | L 6-0 | |
| Mon., 5/2 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Tue., 5/3 | V Boys Outdoor Track | Shepaug Valley, Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Track [Directions] | 3:45 p.m. | ||
| Tue., 5/3 | V Girls Outdoor Track | Shepaug Valley, Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Track [Directions] | 3:45 p.m. | ||
| Fri., 5/6 | V Baseball | Shepaug Valley | Home - Walker Field [Directions] | 3:45 p.m. | L 6-2 | |
| Fri., 5/6 | V Softball | Shepaug Valley | Away - Washington Primary School-Dick Ayer Field [Directions] | 4:00 p.m. | L 0-17 | |
| Fri., 5/6 | V Girls Tennis | Housatonic Regional | Home - Walker Field-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Mon., 5/9 | V Girls Tennis | Nonnewaug | Home - Walker Field-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Mon., 5/9 | V Girls Tennis | Nonnewaug | Home - Walker Field-Tennis Courts [Directions] | 5:00 p.m. | L 1-6 | |
| Tue., 5/10 | V Baseball | Thomaston | Away - Thomaston HS-Baseball/Softball Field [Directions] | 3:45 p.m. | W 13-12 | |
| Tue., 5/10 | V Boys Outdoor Track | Nonnewaug, Terryville | Away - Nonnewaug HS-Paul Burns Memorial Track [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Girls Outdoor Track | Nonnewaug, Terryville | Away - Nonnewaug HS-Paul Burns Memorial Track [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Softball | Thomaston | Home - Winsted Rowley Field [Directions] | 3:45 p.m. | L 2-9 | |
| Tue., 5/10 | V Softball | Thomaston | Home - Winsted Rowley Field [Directions] | 5:30 p.m. | L 4-5 | |
| Tue., 5/10 | V Girls Tennis | Thomaston | Away - Thomaston Nystrom Park-Nystroms Park courts [Directions] | 4:30 p.m. | L 2-5 | |
| Wed., 5/11 | V Baseball | Terryville | Home - Walker Field [Directions] | 3:45 p.m. | L 19-13 | |
| Wed., 5/11 | V Girls Tennis | Northwestern | Home - Walker Field [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 5/12 | V Baseball | Nonnewaug | Home - Walker Field [Directions] | 3:45 p.m. | L 22-3 (5) | |
| Sat., 5/14 | JV Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 9:30 a.m. | ||
| Mon., 5/16 | V Baseball | Northwestern | Home - Walker Field [Directions] | 2:45 p.m. | L 22-1 (5) | |
| Mon., 5/16 | V Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | 2:45 p.m. | L 4-20 | |
| Mon., 5/16 | JV Softball | Northwestern | Away - Northwestern Regional H.S.-JV Softball Field [Directions] | Canceled | Cancelled | |
| Tue., 5/17 | V Baseball | Wolcott Tech | Away - Dunkin' Donuts Park (Hartford, CT)-Yard Goats [Directions] | 3:30 p.m. | L 12-2 (5) | |
| Tue., 5/17 | V Boys Outdoor Track | Housatonic Regional, Northwestern | Home - Northwestern Regional H.S.-Track [Directions] | 3:45 p.m. | ||
| Tue., 5/17 | V Girls Outdoor Track | Housatonic Regional, Northwestern | Home - Northwestern Regional H.S.-Track [Directions] | 3:45 p.m. | ||
| Tue., 5/17 | V Softball | Wamogo/Litchfield | Home - Winsted Rowley Field [Directions] | 4:00 p.m. | W 14-12 | |
| Tue., 5/17 | V Softball | Wamogo/Litchfield | Home - Winsted Rowley Field [Directions] | 5:30 p.m. | L 0-13 | |
| Wed., 5/18 | V Softball | Terryville | Home - Winsted Rowley Field [Directions] | 3:45 p.m. | W 16-1 | |
| Wed., 5/18 | V Girls Tennis | Berkshire League Girls Tennis Tournament | Away - Nonnewaug HS-Nonnewaug | 8:00 a.m. | ||
| Sat., 5/21 | V Boys Outdoor Track | Berkshire League Track Championships | Away - Plumb Hill Field Complex-Plumb Hill Track | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Sat., 5/21 | V Girls Outdoor Track | Berkshire League Track Championships | Away - Plumb Hill Field Complex-Plumb Hill Track | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Mon., 5/23 | V Softball | Housatonic Regional | Home - Winsted Rowley Field [Directions] | 3:45 p.m. | L 4-6 | |
| Mon., 5/23 | V Girls Tennis | Berkshire League Girls Tennis Tournament Semi & Finals | Away - Nonnewaug HS-Nonnewaug | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:00 p.m. | ||||||
| Tue., 5/24 | V Baseball | Wamogo | Home - Walker Field [Directions] | 5:00 p.m. | L 12-0 (6) | |
| Tue., 5/24 | V Boys Outdoor Track | Berkshire League Festival Hammer Throw Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Away - Housatonic Valley Regional High-Track | 3:30 p.m. | ||
| Tue., 5/24 | V Girls Outdoor Track | Berkshire League Festival Hammer Throw Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Away - Housatonic Valley Regional High-Track | 3:30 p.m. | ||
| Tue., 5/24 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 4:00 p.m. | L 0-13 | |
| Tue., 5/24 | JV Softball | Housatonic Regional | Home - Winsted Rowley Field [Directions] | 4:15 p.m. | ||
| Tue., 5/24 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 5/25 | V Baseball | Housatonic Regional | Away - Housatonic Valley Regional High-Varsity Baseball Diamond [Directions] | 3:45 p.m. | L 3-7 | |
| Wed., 5/25 | JV Baseball | Housatonic Regional | Away - Housatonic Valley Regional High-JV Baseball Diamond [Directions] | Postponed | ||
| Wed., 5/25 | V Boys Outdoor Track | Berkshire League Festival Hammer Throw Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Away - Thomaston Nystrom Park-Nystroms Park Track | 3:30 p.m. | ||
| Wed., 5/25 | V Girls Outdoor Track | Berkshire League Festival Hammer Throw Decathlon: 100 Meter Dash, Long Jump, Shot Put, High Jump, 400 Meter Run - Heptathlon: 100 Meter Hurdles, Javelin, Long Jump, 200 Meter Sprint) | Away - Thomaston Nystrom Park-Nystroms Park Track | 3:30 p.m. | ||
| Wed., 5/25 | V Softball | Terryville | Away - Terryville HS-Softball Field [Directions] | 3:45 p.m. | W Forfeit | |
| Wed., 5/25 | JV Softball | Housatonic Regional | Home - Winsted Rowley Field [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Thu., 5/26 | V Baseball | Litchfield | Away - Litchfield HS-Litchfield High School Baseball Field [Directions] | 4:00 p.m. | L 10-0 (5) | |
| Tue., 5/31 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/31 | V Girls Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||