| Gilbert 2019-20 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 404 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/28 | V Football | Derby (Scrim.) | Home - Gilbert School-Football Field [Directions] | 4:00 p.m. | ||
| Sat., 8/31 | V Football | Northwest United | Away - Housatonic Valley Regional High-football field [Directions] | 2:00 p.m. | ||
| Tue., 9/3 | V Boys Cross Country | Thomaston, Housatonic Regional, Litchfield, Nonnewaug, Northwestern, Shepaug Valley, Terryville, Wamogo | Away - Thomaston HS-Highwoods field | 3:45 p.m. | ||
| Tue., 9/3 | V Girls Cross Country | Thomaston, Housatonic Regional, Litchfield, Nonnewaug, Northwestern, Shepaug Valley, Terryville, Wamogo | Away - Thomaston HS-Highwoods field | 3:45 p.m. | ||
| Fri., 9/6 | V Football | Torrington (Scrim.) | Away - Torrington HS [Directions] | 6:00 p.m. | ||
| Sat., 9/7 | FM Football | Torrington (Scrim.) | Away - Torrington HS [Directions] | 9:00 a.m. | ||
| Sat., 9/7 | V Boys Soccer | Hale Ray (Scrim.) | Away - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 10:30 a.m. | ||
| Tue., 9/10 | V Boys Cross Country | Nonnewaug, Terryville | Away - Nonnewaug High-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Boys Soccer | Wolcott Tech (Scrim.) | Home - Walker Field [Directions] | 3:30 p.m. | Scrimmage Vs OWTS | |
| Tue., 9/10 | V Girls Cross Country | Nonnewaug, Terryville | Away - Nonnewaug High-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Girls Soccer | Torrington (Scrim.) | Away - Torrington HS [Directions] | 4:00 p.m. | ||
| Fri., 9/13 | V Boys Soccer | Thomaston | Home - Walker Field [Directions] | 3:45 p.m. | L 3-2 | |
| Fri., 9/13 | V Girls Soccer | Thomaston | Away - Thomaston HS-Highwoods field [Directions] | 3:45 p.m. | L 0-9 | |
| Fri., 9/13 | V Girls Volleyball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Fri., 9/13 | JV Girls Volleyball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/14 | V Boys Cross Country | Stratton Brook Invitational | Away - Stratton Brook State Park | 9:00 a.m. | ||
| Sat., 9/14 | V Boys Cross Country | Stratton Brooke Invitational | Away - Not Listed-Stratton Brook Park-Simsbury | TBA | ||
| Sat., 9/14 | V Girls Cross Country | Stratton Brook Invitational | Away - Not Listed-Stratton Brook Park-Simsbury | 10:00 a.m. | ||
| Sat., 9/14 | V Girls Cross Country | Stratton Brook Invitational | Away - Stratton Brook State Park | 9:00 a.m. | ||
| Mon., 9/16 | JV Boys Soccer | Shepaug Valley (Scrim.) | Home - Winsted Rowley Field [Directions] | 3:45 p.m. | ||
| Mon., 9/16 | V Girls Soccer | Shepaug Valley | Home - Walker Field [Directions] | 3:45 p.m. | L 0-5 | |
| Tue., 9/17 | V Boys Cross Country | Wamogo, Shepaug Valley | Away - Wamogo Regional HS-White Memorial Park [Directions] | 3:45 p.m. | ||
| Tue., 9/17 | V Boys Soccer | Shepaug Valley | Home - Walker Field [Directions] | 3:45 p.m. | W 3-2 | |
| Tue., 9/17 | V Girls Volleyball | Lewis Mills | Away - Lewis Mills HS 1-Gym [Directions] | 5:00 p.m. | L 1-3 | |
| Tue., 9/17 | JV Girls Volleyball | Lewis Mills | Away - Lewis Mills HS 1-Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/18 | V Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Wed., 9/18 | JV Girls Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | V Boys Soccer | Nonnewaug | Home - Walker Field [Directions] | 3:45 p.m. | L 5-1 | |
| Fri., 9/20 | JV Boys Soccer | Nonnewaug | Home - Winsted Rowley Field [Directions] | Canceled | Cancelled | |
| Fri., 9/20 | V Girls Soccer | Nonnewaug | Away - Hollow Park-Upper Field [Directions] | 3:45 p.m. | L 0-8 | |
| Fri., 9/20 | JV Girls Soccer | Nonnewaug | Away - Hollow Park-Lower Field [Directions] | Canceled | Cancelled | |
| Sat., 9/21 | V Boys Cross Country | Winding Trails Park - Farmington Cross Country Invitational | Away - Not Listed-Winding Trails Park-Farmington | 9:00 a.m. | ||
| Sat., 9/21 | V Football | Windsor Locks/Suffield/East Granby | Away - Windsor Locks HS-Stadium [Directions] | 1:00 p.m. | L 7-21 | |
| Sat., 9/21 | V Girls Cross Country | Winding Trails Invitational | Away - Not Listed-Winding Trails Park-Farmington | 9:00 a.m. | ||
| Mon., 9/23 | JV Football | Windsor Locks/Suffield/East Granby | Home - Gilbert School-Football Field [Directions] | 3:30 p.m. | ||
| Tue., 9/24 | V Boys Cross Country | Thomaston, Litchfield | Away - Thomaston HS-Highwoods field [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | 3:45 p.m. | L 3-2 | |
| Tue., 9/24 | JV Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | Canceled | Cancelled | |
| Tue., 9/24 | V Girls Cross Country | Thomaston, Litchfield | Away - Thomaston HS-Highwoods field [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Soccer | Housatonic Regional | Home - Walker Field [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 9/24 | JV Girls Soccer | Housatonic Regional | Home - Winsted Rowley Field [Directions] | Canceled | Cancelled | |
| Tue., 9/24 | V Girls Volleyball | Terryville | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | L 2-3 | |
| Tue., 9/24 | JV Girls Volleyball | Terryville | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Boys Cross Country | Cross Country Scrimmage | Away - TBA | 3:45 p.m. | ||
| Fri., 9/27 | V Boys Cross Country | Cross Country Scrimmage | Away - Litchfield HS | 3:45 p.m. | ||
| Fri., 9/27 | V Boys Cross Country | Cross Country Scrimmage | Away - TBA | 3:45 p.m. | ||
| Fri., 9/27 | V Boys Cross Country | TBA | Away - TBA | 4:00 p.m. | ||
| Fri., 9/27 | V Boys Cross Country | Litchfield, Lewis Mills (Scrim.) | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Boys Soccer | Wamogo | Home - Walker Field [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 9/27 | V Girls Cross Country | Litchfield, Lewis Mills (Scrim.) | Away - Plumb Hill Field Complex-Plumb Hill Track [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Girls Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 0-4 | |
| Fri., 9/27 | V Girls Volleyball | Goodwin Tech | Away - Goodwin Tech-Goodwin Tech Gymnasium [Directions] | 5:15 p.m. | L 0-3 | |
| Fri., 9/27 | JV Girls Volleyball | Goodwin Tech | Away - Goodwin Tech-Goodwin Tech Gymnasium [Directions] | 3:45 p.m. | ||
| Sat., 9/28 | V Football | Ellington | Away - Ellington HS-Football Field [Directions] | 1:00 p.m. | L 10-14 | |
| Mon., 9/30 | JV Football | Ellington | Home - Gilbert School-Football Field [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Boys Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:45 p.m. | W 2-0 | |
| Tue., 10/1 | JV Boys Soccer | Terryville | Away - Upper Fisher Field [Directions] | 3:45 p.m. | ||
| Tue., 10/1 | V Girls Soccer | Terryville | Home - Walker Field [Directions] | 3:45 p.m. | L 0-6 | |
| Tue., 10/1 | V Girls Volleyball | Northwestern | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 10/1 | JV Girls Volleyball | Northwestern | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | V Girls Volleyball | Cromwell | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Thu., 10/3 | JV Girls Volleyball | Cromwell | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/4 | V Boys Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 7:30 p.m. | T 1-1 | |
| Fri., 10/4 | V Girls Soccer | Northwestern | Away - Northwestern Regional H.S.-Varsity Soccer Field [Directions] | 6:00 p.m. | L 0-6 | |
| Sat., 10/5 | V Football | Haddam-Killingworth | Home - Gilbert School-Football Field [Directions] | 3:00 p.m. | W 20-0 | |
| Mon., 10/7 | JV Football | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | 3:45 p.m. | ||
| Tue., 10/8 | V Boys Cross Country | Housatonic Regional, Northwestern | Home - Gilbert School-Football Field [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:45 p.m. | L 2-1 | |
| Tue., 10/8 | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | Canceled | Cancelled | |
| Tue., 10/8 | V Girls Cross Country | Northwestern | Home - Gilbert School-Football Field [Directions] | 3:30 p.m. | ||
| Tue., 10/8 | V Girls Cross Country | St. Bernard MS | Home - Gilbert School [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Girls Soccer | Litchfield | Home - Walker Field [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 10/8 | JV Girls Soccer | Litchfield | Home - Winsted Rowley Field [Directions] | Canceled | Cancelled | |
| Wed., 10/9 | V Girls Volleyball | Lewis Mills | Home - Gilbert School-Gym [Directions] | 5:00 p.m. | L 2-3 | |
| Wed., 10/9 | JV Girls Volleyball | Lewis Mills | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/10 | JV Boys Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | 3:45 p.m. | ||
| Sat., 10/12 | V Boys Cross Country | Wickham Park Invitational | Away - Not Listed-Wickham Park | 10:00 a.m. | ||
| Sat., 10/12 | V Football | Old Saybrook | Home - Gilbert School-Football Field [Directions] | 1:00 p.m. | W 22-21 | |
| Sat., 10/12 | V Girls Cross Country | Wickham Park Invitational | Away - Not Listed-Wickham Park | 10:00 a.m. | ||
| Mon., 10/14 | JV Football | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Back Field [Directions] | 11:00 a.m. | ||
| Mon., 10/14 | V Girls Volleyball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 10/14 | JV Girls Volleyball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 10/15 | V Boys Soccer | Thomaston | Away - Nystrom Park-Nystrom Park Field [Directions] | 3:45 p.m. | L 3-1 | |
| Tue., 10/15 | V Girls Soccer | Thomaston | Home - Walker Field [Directions] | 3:45 p.m. | L 0-1 | |
| Tue., 10/15 | V Girls Volleyball | Nonnewaug | Away - Woodbury MS-gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/15 | JV Girls Volleyball | Nonnewaug | Away - Woodbury MS-gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 10/18 | V Boys Cross Country | Berkshire League Championships | Away - Thomaston HS-Highwoods field | 4:15 p.m. | ||
| Fri., 10/18 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 7:15 p.m. | L 2-1 | |
| Fri., 10/18 | JV Boys Soccer | Shepaug Valley | Away - Washington Primary School-Washington Primary School Soccer Field [Directions] | Canceled | Cancelled | |
| Fri., 10/18 | V Girls Cross Country | Berkshire League Championships | Away - Thomaston HS-Highwoods field | 3:30 p.m. | ||
| Fri., 10/18 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 5:15 p.m. | L 0-5 | |
| Fri., 10/18 | V Girls Volleyball | Canton | Away - Canton HS-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Fri., 10/18 | JV Girls Volleyball | Canton | Away - Canton HS-Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug HS-JV Field [Directions] | Canceled | Cancelled | |
| Mon., 10/21 | V Girls Soccer | Nonnewaug | Home - Walker Field [Directions] | 3:45 p.m. | L 0-7 | |
| Mon., 10/21 | JV Girls Soccer | Nonnewaug | Home - Winsted Rowley Field [Directions] | Canceled | Cancelled | |
| Wed., 10/23 | V Boys Soccer | Housatonic Regional | Home - Walker Field [Directions] | 3:45 p.m. | L 4-0 | |
| Wed., 10/23 | JV Boys Soccer | Housatonic Regional | Home - Winsted Rowley Field [Directions] | Canceled | Cancelled | |
| Wed., 10/23 | V Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Girls Varsity/JV Boys Soccer [Directions] | 3:45 p.m. | L 1-8 | |
| Wed., 10/23 | JV Girls Soccer | Housatonic Regional | Away - Housatonic Valley Regional High-Boys Varsity/JV Girls Soccer Field [Directions] | Canceled | Cancelled | |
| Wed., 10/23 | V Girls Volleyball | Jonathan Law | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 10/23 | JV Girls Volleyball | Jonathan Law | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | ||
| Fri., 10/25 | V Boys Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-3 | |
| Fri., 10/25 | JV Boys Soccer | Wamogo | Away - Wamogo Regional HS-Wamogo JV Soccer Field [Directions] | Canceled | Cancelled | |
| Fri., 10/25 | V Girls Soccer | Wamogo | Home - Walker Field [Directions] | 6:30 p.m. | L 1-2 | |
| Sat., 10/26 | V Boys Cross Country | CIAC Boys Class S Divisional Championship | Away - Wickham Park | 9:50 a.m. | ||
| Sat., 10/26 | V Football | Rockville | Home - Gilbert School-Football Field [Directions] | 1:00 p.m. | L 3-31 | |
| Sat., 10/26 | V Girls Cross Country | CIAC Girls Class S Divisional Championship | Away - Wickham Park | 9:15 a.m. | ||
| Mon., 10/28 | JV Football | Rockville | Away - Rockville HS (Varsity Field right side of school)-Football Field [Directions] | 5:00 p.m. | ||
| Mon., 10/28 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | L 3-1 | |
| Mon., 10/28 | V Girls Volleyball | O'Brien Tech | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | W 3-2 | |
| Mon., 10/28 | JV Girls Volleyball | O'Brien Tech | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/29 | V Boys Soccer | Terryville | Home - Walker Field [Directions] | 3:45 p.m. | W 4-1 | |
| Tue., 10/29 | JV Boys Soccer | Terryville | Home - Walker Field-Rowley Field [Directions] | Canceled | Cancelled | |
| Tue., 10/29 | V Girls Soccer | Terryville | Away - Terryville HS-Soccer Field [Directions] | 3:45 p.m. | L 0-8 | |
| Tue., 10/29 | V Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 5:15 p.m. | L 2-3 | |
| Tue., 10/29 | JV Girls Volleyball | Terryville | Away - Terryville HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 11/1 | V Boys Cross Country | CIAC Boys State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/1 | V Boys Soccer | Northwestern | Home - Walker Field [Directions] | 7:00 p.m. | T 0-0 | |
| Fri., 11/1 | JV Boys Soccer | Northwestern | Home - Walker Field [Directions] | Canceled | Cancelled | |
| Fri., 11/1 | V Girls Cross Country | CIAC Girls State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/1 | V Girls Soccer | Northwestern | Home - Walker Field [Directions] | 5:30 p.m. | L 0-6 | |
| Fri., 11/1 | JV Girls Soccer | Northwestern | Home - Winsted Rowley Field [Directions] | Canceled | Cancelled | |
| Fri., 11/1 | V Girls Volleyball | Northwestern | Home - Gilbert School-Gym [Directions] | 5:00 p.m. | L 0-3 | |
| Fri., 11/1 | JV Girls Volleyball | Northwestern | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | ||
| Sat., 11/2 | V Football | Coventry/Windham Tech/Bolton/Lyman | Home - Gilbert School-Football Field [Directions] | 1:00 p.m. | W 35-14 | |
| Mon., 11/4 | JV Football | Coventry/Windham Tech/Bolton/Lyman | Away - Coventry HS-Football Field [Directions] | 3:45 p.m. | ||
| Mon., 11/4 | V Boys Soccer | Litchfield | Home - Walker Field [Directions] | 3:30 p.m. | T 1-1 | |
| Mon., 11/4 | JV Boys Soccer | Litchfield | Home - Winsted Rowley Field [Directions] | Canceled | Cancelled | |
| Mon., 11/4 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 3:30 p.m. | L 0-3 | |
| Mon., 11/4 | JV Girls Soccer | Litchfield | Away - Plumb Hill Field Complex-Field JV Soccer Field [Directions] | Canceled | Cancelled | |
| Wed., 11/6 | V Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Wed., 11/6 | JV Girls Volleyball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 4:00 p.m. | ||
| Thu., 11/7 | V Girls Volleyball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 11/7 | JV Girls Volleyball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 5:15 p.m. | ||
| Fri., 11/8 | V Football | Stafford/East Windsor/Somers | Away - Stafford HS-Lighted Field behind the High School [Directions] | 6:30 p.m. | L 14-24 | |
| Sat., 11/9 | JV Football | Stafford/East Windsor/Somers | Home - Gilbert School-Football Field [Directions] | 10:00 a.m. | ||
| Fri., 11/15 | V Football | Granby/Canton | Away - Granby Memorial HS-Stadium Field [Directions] | 6:30 p.m. | L 14-54 | |
| Sat., 11/16 | JV Football | Granby/Canton | Home - Gilbert School-Football Field [Directions] | 10:00 a.m. | ||
| Thu., 11/21 | V Football | Valley Regional/Old Lyme | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 6:30 p.m. | L 14-49 | |
| Tue., 11/26 | V Football | WCA | Away - Municipal Stadium-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | L 14-38 | |
| Mon., 12/9 | V Boys Basketball | Oxford (Scrim.) | Away - Oxford HS-Main Gym [Directions] | 6:00 p.m. | ||
| Mon., 12/9 | V Girls Basketball | Wolcott Tech (Scrim.) | Home - Gilbert School-Gym [Directions] | 3:00 p.m. | ||
| Thu., 12/12 | V Girls Basketball | Scrimmage at Windsor Locks 6:00pm bus leaves at 4:30pm | Away - Not Listed | 6:00 p.m. | ||
| Sat., 12/14 | V Girls Basketball | Avon (Scrim.) | Away - Avon HS-Large Gym [Directions] | 10:00 a.m. | ||
| Mon., 12/16 | V Boys Basketball | TBA | Home - Gilbert School-Gym [Directions] | 3:45 p.m. | ||
| Mon., 12/16 | V Boys Basketball | O'Brien Tech (Scrim.) | Home - Gilbert School-Gym [Directions] | 3:45 p.m. | ||
| Mon., 12/16 | V Girls Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 6:00 p.m. | L 38-34 | |
| Wed., 12/18 | V Wrestling | Thomaston | Away - Thomaston HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 12/19 | V Boys Basketball | Thomaston | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | W 66-61 | |
| Thu., 12/19 | JV Boys Basketball | Thomaston | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/19 | FR Boys Basketball | Thomaston | Home - Gilbert School-Gym [Directions] | 3:45 p.m. | ||
| Thu., 12/19 | V Boys Swimming and Diving | Woodland | Away - Woodland HS-pool [Directions] | 4:30 p.m. | ||
| Thu., 12/19 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 7:00 p.m. | L 42-23 | |
| Thu., 12/19 | JV Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/20 | V Boys Indoor Track | Hillhouse Invite - Hillhouse High School | Away - Not Listed | 4:00 p.m. | ||
| Fri., 12/20 | V Girls Indoor Track | Hillhouse Invite - Hillhouse High School | Away - Not Listed | 4:00 p.m. | ||
| Sat., 12/21 | V Boys Indoor Track | Hillhouse Invite - Hillhouse High School | Away - Not Listed | 9:30 a.m. | ||
| Sat., 12/21 | V Wrestling | Pawling NY - Pawling Invitation | Away - Not Listed | 8:00 a.m. | ||
| Sat., 12/21 | V Girls Basketball | Torrington | Away - Torrington HS-High School Gym [Directions] | 7:00 p.m. | L 40-32 | |
| Sat., 12/21 | JV Girls Basketball | Torrington | Away - Torrington HS-High School Gym [Directions] | 5:15 p.m. | ||
| Sat., 12/21 | V Girls Indoor Track | Hillhouse Invite - Hillhouse High School | Home - Gilbert School-Gym [Directions] | 9:30 a.m. | ||
| Mon., 12/23 | V Girls Basketball | Terryville | Home - Gilbert School-Gym [Directions] | 3:30 p.m. | W 26-24 | |
| Thu., 12/26 | V Wrestling | Terryville-Thomaston | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | ||
| Fri., 12/27 | V Girls Basketball | Lewis Mills | Home - Gilbert School-Gym [Directions] | 1:00 p.m. | L 40-22 | |
| Fri., 12/27 | JV Girls Basketball | Lewis Mills | Home - Gilbert School-Gym [Directions] | 11:30 a.m. | ||
| Sat., 12/28 | V Wrestling | RHAM Duals - RHAM High School | Away - Not Listed | 8:00 a.m. | ||
| Sat., 12/28 | V Wrestling | RHAM, E.O. Smith, East Hartford, Montville, Morgan, Windham | Away - RHAM HS-Gym | 9:30 a.m. | ||
| Sat., 12/28 | V Girls Basketball | Innovation | Away - Bristol Central Holiday Classic [Directions] | 1:30 p.m. | W 54-27 | |
| Tue., 12/31 | V Girls Basketball | Bristol Central | Away - Bristol Central HS-Charles C. Marsh Gymnasium [Directions] | 12:30 p.m. | L 32-24 | |
| Thu., 1/2 | V Wrestling | Northwestern | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | ||
| Fri., 1/3 | V Boys Basketball | Litchfield | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | W 77-54 | |
| Fri., 1/3 | JV Boys Basketball | Litchfield | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/3 | V Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:30 p.m. | W 40-23 | |
| Fri., 1/3 | JV Girls Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 7:00 p.m. | ||
| Sat., 1/4 | V Boys Indoor Track | Elm City Coaches Invite - Hillhouse High School | Away - Not Listed | 9:30 a.m. | ||
| Sat., 1/4 | V Boys Swimming and Diving | Nonnewaug | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 4:30 p.m. | ||
| Sat., 1/4 | V Wrestling | Chris Hernandez Memorial Wrestling Tournament - Yonkers High School | Away - Not Listed | 8:00 a.m. | ||
| Sat., 1/4 | V Girls Indoor Track | Elm City coaches invite - 8:00am bus to Hillhouse High School | Away - Not Listed | 9:00 a.m. | ||
| Tue., 1/7 | V Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 76-83 | |
| Tue., 1/7 | JV Boys Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/7 | V Boys Indoor Track | James Barber Invite- Southern Connecticut State University | Away - Not Listed | 4:30 p.m. | ||
| Tue., 1/7 | V Girls Basketball | Shepaug Valley | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 56-33 | |
| Tue., 1/7 | JV Girls Basketball | Shepaug Valley | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/7 | V Girls Indoor Track | James Barber Invite- Southern Connecticut State University | Away - Not Listed | 4:30 p.m. | ||
| Thu., 1/9 | V Girls Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 27-53 | |
| Thu., 1/9 | JV Girls Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/10 | V Boys Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | W 63-60 | |
| Fri., 1/10 | JV Boys Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/10 | V Boys Swimming and Diving | Housatonic Regional | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 7:00 p.m. | ||
| Sat., 1/11 | FR Boys Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | 10:30 a.m. | ||
| Sat., 1/11 | V Boys Indoor Track | Yale-Qualifiers Only | Away - Not Listed | 8:00 a.m. | ||
| Sat., 1/11 | V Boys Swimming and Diving | Shepaug Valley | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 4:30 p.m. | ||
| Sat., 1/11 | V Wrestling | Mt Anthony VT Tournament | Away - Not Listed | 8:00 a.m. | ||
| Sat., 1/11 | V Girls Indoor Track | Yale-Qualifiers Only | Away - Not Listed | 8:00 a.m. | ||
| Tue., 1/14 | V Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 7:00 p.m. | W 99-65 | |
| Tue., 1/14 | JV Boys Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/14 | V Girls Basketball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 42-26 | |
| Tue., 1/14 | JV Girls Basketball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/15 | V Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 7:00 p.m. | L 57-74 | |
| Wed., 1/15 | JV Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/15 | V Boys Indoor Track | Northwestern | Away - Northwestern Regional H.S.-Track [Directions] | 3:00 p.m. | ||
| Wed., 1/15 | V Wrestling | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/15 | V Girls Indoor Track | Northwestern | Away - Northwestern Regional H.S.-Track [Directions] | 3:00 p.m. | ||
| Thu., 1/16 | V Boys Indoor Track | Wesleyan Developmental Meet | Away - Not Listed | Canceled | Cancelled | |
| Thu., 1/16 | V Girls Indoor Track | Wesleyan Developmental Meet | Away - Not Listed | Canceled | Cancelled | |
| Fri., 1/17 | V Boys Basketball | Capital Prep | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 54-95 | |
| Fri., 1/17 | JV Boys Basketball | Capital Prep | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/18 | V Boys Indoor Track | SCC Coaches Invite - Qualifiers only and VAN | Away - Not Listed | Canceled | Cancelled | |
| Sat., 1/18 | V Wrestling | Mt Everett Duals | Away - Not Listed | 8:00 a.m. | ||
| Sat., 1/18 | V Girls Indoor Track | SCC Coaches Invite - Qualifiers only and VAN | Away - Not Listed | Canceled | Cancelled | |
| Tue., 1/21 | V Boys Basketball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 73-85 | |
| Tue., 1/21 | JV Boys Basketball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/21 | V Wrestling | Derby/Oxford/Holy Cross | Away - Derby HS-Gym [Directions] | 6:00 p.m. | ||
| Tue., 1/21 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Nonnewaug's Gym [Directions] | 6:00 p.m. | L 59-24 | |
| Tue., 1/21 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS-Nonnewaug's Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/22 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss School-Pool [Directions] | 5:30 p.m. | ||
| Fri., 1/24 | V Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 7:00 p.m. | L 59-77 | |
| Fri., 1/24 | JV Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/24 | FR Boys Basketball | Wamogo | Away - Wamogo HS-Wamogo Large Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/24 | V Boys Indoor Track | HK Invite - Hillhouse High School | Away - Not Listed | 4:00 p.m. | ||
| Fri., 1/24 | V Boys Swimming and Diving | Litchfield | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 7:30 p.m. | ||
| Fri., 1/24 | V Wrestling | Avon, Farmington, Terryville-Thomaston | Away - Avon HS-Large Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/24 | V Girls Basketball | Wamogo | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | W 53-37 | |
| Fri., 1/24 | V Girls Indoor Track | HK Invite - Hillhouse High School | Away - Not Listed | 4:00 p.m. | ||
| Sat., 1/25 | V Boys Swimming and Diving | Wamogo | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 4:30 p.m. | ||
| Tue., 1/28 | V Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 7:00 p.m. | L 72-76 | |
| Tue., 1/28 | JV Boys Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/28 | V Boys Swimming and Diving | Sacred Heart | Away - John F. Kennedy HS-John Reardon Pool | 7:00 p.m. | ||
| Tue., 1/28 | V Girls Basketball | Thomaston | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 40-39 | |
| Tue., 1/28 | JV Girls Basketball | Thomaston | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/29 | V Wrestling | St. Paul Catholic | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/30 | V Boys Swimming and Diving | Nonnewaug | Away - Woodland HS-pool [Directions] | 6:00 p.m. | ||
| Fri., 1/31 | V Boys Basketball | Terryville | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | W 57-56 | |
| Fri., 1/31 | JV Boys Basketball | Terryville | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Sat., 2/1 | V Wrestling | Portland Wrestling Tournament - Portland HS | Away - Not Listed | 8:30 a.m. | ||
| Mon., 2/3 | FR Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 2/4 | V Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 7:00 p.m. | L 64-76 | |
| Tue., 2/4 | JV Boys Basketball | Litchfield | Away - Litchfield HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/4 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 7:30 p.m. | ||
| Tue., 2/4 | V Girls Basketball | Litchfield | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | W 48-34 | |
| Tue., 2/4 | JV Girls Basketball | Litchfield | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/5 | V Wrestling | Oxford | Away - Oxford HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/5 | V Girls Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 6:00 p.m. | W 40-35 | |
| Fri., 2/7 | V Boys Basketball | Shepaug Valley | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 77-56 | |
| Fri., 2/7 | JV Boys Basketball | Shepaug Valley | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/7 | FR Boys Basketball | Shepaug Valley | Home - Gilbert School-Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/7 | V Boys Swimming and Diving | Wamogo | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 7:00 p.m. | ||
| Fri., 2/7 | V Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 50-16 | |
| Fri., 2/7 | JV Girls Basketball | Shepaug Valley | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 2/8 | V Wrestling | Southwick MASS - Tournament | Away - Not Listed | 8:00 a.m. | ||
| Mon., 2/10 | V Boys Indoor Track | Capital Prep Last Chance - Hillhouse High School | Away - Not Listed | 4:00 p.m. | ||
| Mon., 2/10 | V Girls Indoor Track | Capital Prep Last Chance - Hillhouse High School | Away - Not Listed | 4:00 p.m. | ||
| Tue., 2/11 | V Boys Basketball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | W 78-58 | |
| Tue., 2/11 | JV Boys Basketball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/11 | FR Boys Basketball | Housatonic Regional | Home - Gilbert School-Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/11 | V Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 7:00 p.m. | L 39-24 | |
| Tue., 2/11 | JV Girls Basketball | Housatonic Regional | Away - Housatonic Valley Regional High-Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/12 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool [Directions] | 4:30 p.m. | ||
| Wed., 2/12 | V Wrestling | Portland/Cromwell | Away - Portland HS-Portland HS [Directions] | 6:30 p.m. | ||
| Thu., 2/13 | JV Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | ||
| Thu., 2/13 | JV Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/14 | V Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 7:00 p.m. | L 52-75 | |
| Fri., 2/14 | V Girls Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 5:30 p.m. | L 65-36 | |
| Sat., 2/15 | FR Boys Basketball | Northwestern | Home - Gilbert School-Gym [Directions] | 10:30 a.m. | ||
| Sat., 2/15 | V Boys Swimming and Diving | Lewis Mills | Home - Northwestern Regional H.S.-YMCA Swim [Directions] | 4:30 p.m. | ||
| Sat., 2/15 | V Wrestling | Thomaston/Holy Cross, Derby, Nonnewaug, Northwestern, Oxford, St. Paul Catholic, Terryville | Away - Thomaston HS-Gym | 10:00 a.m. | ||
| Mon., 2/17 | V Boys Basketball | Dracut (MA) | Away - Monument Mtn. Regional HS-Gym | 5:30 p.m. | L 77-109 | |
| Tue., 2/18 | V Boys Basketball | Granby (MA) | Away - Monument Mtn. Regional HS | 5:30 p.m. | W 74-63 | |
| Wed., 2/19 | V Boys Swimming and Diving | Torrington | Away - Torrington YMCA-pool [Directions] | 7:30 p.m. | ||
| Thu., 2/20 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 7:00 p.m. | L 53-86 | |
| Thu., 2/20 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/20 | V Girls Basketball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 6:00 p.m. | L 64-32 | |
| Thu., 2/20 | JV Girls Basketball | Nonnewaug | Home - Gilbert School-Gym [Directions] | 4:30 p.m. | ||
| Fri., 2/21 | V Wrestling | CIAC Class S Divisional Championship | Away - Killingly HS-Gym | 3:00 p.m. | ||
| Sat., 2/22 | V Wrestling | CIAC Class S Divisional Championship | Away - Killingly HS-Gym | 9:00 a.m. | ||
| Sat., 2/22 | V Girls Basketball | Northwestern | Home - Northwestern Regional H.S.-Main Gym [Directions] | 1:00 p.m. | ||
| Mon., 2/24 | V Boys Basketball | Wamogo | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 49-58 | |
| Mon., 2/24 | JV Boys Basketball | Wamogo | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/24 | FR Boys Basketball | Wamogo | Home - Gilbert School-Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/27 | V Boys Basketball | Ansonia | Home - Gilbert School-Gym [Directions] | 7:00 p.m. | L 61-70 | |
| Thu., 2/27 | JV Boys Basketball | Ansonia | Home - Gilbert School-Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/28 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-Field House | 3:00 p.m. | ||
| Fri., 2/28 | V Girls Basketball | Lewis Mills (Scrim.) | Home - Gilbert School-Gym [Directions] | 3:00 p.m. | ||
| Sat., 2/29 | V Boys Basketball | Nonnewaug | Away - Shepaug Valley HS-Ted Alex Gymnasium [Directions] | 12:30 p.m. | ||
| Sat., 2/29 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-Field House | 9:00 a.m. | ||
| Tue., 3/3 | V Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:00 p.m. | ||
| Thu., 3/5 | JV Girls Basketball | Litchfield (Scrim.) | Away - Litchfield HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 3/6 | V Boys Swimming and Diving | Shepaug Valley, Housatonic Regional, Litchfield, TBA, Nonnewaug, Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Pool | 5:30 p.m. | ||
| Sat., 3/7 | V Boys Swimming and Diving | Berkshire League Swim Championships | Away - Kennedy HS (Waterbury) | 2:00 p.m. | ||
| Wed., 3/11 | V Boys Swimming and Diving | CIAC Boys Class S Diving Championship | Away - Plainville HS-Pool | Canceled | Cancelled | |
| Wed., 3/11 | V Boys Swimming and Diving | CIAC Boys Class S Diving Championship | Away - Plainville HS-Pool | Canceled | Cancelled | |
| Sat., 3/14 | V Boys Swimming and Diving | CIAC Boys Class S Trials | Away - Cheshire Community Pool | Canceled | Cancelled | |
| Sat., 3/14 | V Boys Swimming and Diving | CIAC Boys Class S Trials | Away - Cheshire Community Pool | Canceled | Cancelled | |
| Wed., 3/18 | V Boys Swimming and Diving | CIAC Boys Class S Finals | Away - Wesleyan University-Pool | Canceled | Cancelled | |
| Wed., 3/18 | V Boys Swimming and Diving | CIAC Boys Class S Finals | Away - Wesleyan University-Pool | Canceled | Cancelled | |
| Thu., 3/19 | V Boys Swimming and Diving | CIAC Boys State Open Diving | Away - Bulkeley HS-Pool | Canceled | Cancelled | |
| Thu., 3/19 | V Boys Swimming and Diving | CIAC Boys State Open Diving | Away - Bulkeley HS-Pool | Canceled | Cancelled | |
| Sat., 3/21 | V Boys Swimming and Diving | CIAC Boys State Open Swimming | Away - Yale | Canceled | Cancelled | |
| Sat., 3/21 | V Boys Swimming and Diving | CIAC Boys State Open Swimming | Away - Yale | Canceled | Cancelled | |
| Wed., 3/25 | V Baseball | Derby (Scrim.) | Away - Payden Park-Payden Field [Directions] | Cancelled | ||
| Thu., 3/26 | V Baseball | Avon (Scrim.) | Away - Buckingham Fields-90 ft. Baseball Diamond [Directions] | Cancelled | Cancelled | |
| Mon., 3/30 | V Softball | East Granby (Scrim.) | Away - East Granby HS -Softball Diamond [Directions] | Cancelled | ||
| Tue., 3/31 | V Baseball | Naugatuck (Scrim.) | Home - Walker Field [Directions] | Cancelled | Cancelled | |
| Sat., 4/4 | V Baseball | Litchfield | Away - Litchfield HS-Litchfield High School Baseball Field [Directions] | Cancelled | ||
| Sat., 4/4 | JV Baseball | Litchfield | Away - Litchfield HS-Litchfield High School Baseball Field [Directions] | Cancelled | ||
| Sat., 4/4 | V Softball | Litchfield | Home - Walker Field-Rowley Field [Directions] | Cancelled | ||
| Sat., 4/4 | JV Softball | Litchfield | Home - Winsted Rowley Field [Directions] | Cancelled | ||
| Mon., 4/6 | V Baseball | Nonnewaug | Home - Walker Field [Directions] | Cancelled | Cancelled | |
| Mon., 4/6 | V Boys Tennis | Housatonic Regional | Away - Housatonic Valley Regional High-Tennis Courts [Directions] | Cancelled | ||
| Mon., 4/6 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Softball [Directions] | Cancelled | Cancelled | |
| Mon., 4/6 | V Girls Tennis | Housatonic Regional | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | ||
| Wed., 4/8 | V Baseball | Housatonic Regional | Away - Housatonic Valley Regional High-Varsity Baseball Diamond [Directions] | Cancelled | ||
| Wed., 4/8 | V Boys Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | Cancelled | ||
| Wed., 4/8 | V Softball | Housatonic Regional | Home - Winsted Rowley Field [Directions] | Cancelled | ||
| Wed., 4/8 | V Girls Tennis | Wamogo | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | ||
| Thu., 4/9 | V Softball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Athletic Complex [Directions] | Cancelled | ||
| Mon., 4/13 | V Baseball | Terryville | Home - Walker Field [Directions] | Cancelled | ||
| Mon., 4/13 | V Boys Tennis | Shepaug Valley | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | Cancelled | |
| Mon., 4/13 | V Softball | Terryville | Away - Terryville HS-Softball Field [Directions] | Cancelled | ||
| Mon., 4/13 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | Cancelled | Cancelled | |
| Wed., 4/15 | V Baseball | Wolcott Tech | Home - Walker Field [Directions] | Cancelled | ||
| Fri., 4/17 | V Baseball | Thomaston | Away - Thomaston HS-Baseball Field [Directions] | Cancelled | ||
| Fri., 4/17 | V Softball | Thomaston | Home - Walker Field-Rowley Field [Directions] | Cancelled | ||
| Mon., 4/20 | V Boys Golf | Terryville | Home - Green woods Country Club [Directions] | Cancelled | ||
| Mon., 4/20 | V Boys Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | Cancelled | ||
| Mon., 4/20 | V Girls Tennis | Northwestern | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | ||
| Tue., 4/21 | V Boys Outdoor Track | Nonnewaug, Terryville | Away - Nonnewaug HS-Paul Burns Memorial Track [Directions] | Cancelled | ||
| Tue., 4/21 | V Girls Outdoor Track | Nonnewaug, Terryville | Away - Nonnewaug HS-Paul Burns Memorial Track [Directions] | Cancelled | ||
| Wed., 4/22 | V Baseball | Shepaug Valley | Home - Walker Field [Directions] | Cancelled | Cancelled | |
| Wed., 4/22 | V Boys Golf | Litchfield | Away - Litchfield Country Club [Directions] | Cancelled | ||
| Wed., 4/22 | V Boys Tennis | Nonnewaug | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | ||
| Wed., 4/22 | V Girls Tennis | Nonnewaug | Away - Edgewood Bath and Tennis Club [Directions] | Cancelled | ||
| Thu., 4/23 | V Softball | Shepaug Valley | Away - Washington Primary School-Dick Ayer Field [Directions] | Cancelled | Cancelled | |
| Fri., 4/24 | V Boys Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | Cancelled | ||
| Fri., 4/24 | V Softball | Cheney Tech | Away - Cheney Tech.-Softball Diamond [Directions] | Cancelled | ||
| Fri., 4/24 | V Girls Tennis | Litchfield | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | ||
| Mon., 4/27 | V Baseball | Wamogo | Away - Wamogo Regional HS-Varsity Baseball Field [Directions] | Cancelled | ||
| Mon., 4/27 | V Boys Golf | Housatonic Regional, Wamogo | Away - Sharon Country Club [Directions] | Cancelled | ||
| Mon., 4/27 | V Boys Tennis | Thomaston | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | ||
| Mon., 4/27 | V Softball | Wamogo/Litchfield | Home - Winsted Rowley Field [Directions] | Cancelled | ||
| Mon., 4/27 | V Girls Tennis | Thomaston | Away - Nystrom Park-Nystroms Park courts [Directions] | Cancelled | ||
| Tue., 4/28 | V Baseball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Athletic Complex [Directions] | Cancelled | ||
| Tue., 4/28 | V Boys Outdoor Track | Shepaug Valley, Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Track [Directions] | Cancelled | Cancelled | |
| Tue., 4/28 | V Girls Outdoor Track | Shepaug Valley, Wamogo | Away - Shepaug Valley HS-Shepaug Valley Middle & High School Track [Directions] | Cancelled | Cancelled | |
| Wed., 4/29 | V Boys Tennis | Housatonic Regional | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | ||
| Wed., 4/29 | V Girls Tennis | Housatonic Regional | Away - Housatonic Valley Regional High-Tennis Courts [Directions] | Cancelled | ||
| Thu., 4/30 | V Boys Golf | Housatonic Regional, Shepaug Valley | Home - Green woods Country Club [Directions] | Cancelled | Cancelled | |
| Thu., 4/30 | V Softball | Wolcott Tech | Home - Winsted Rowley Field [Directions] | Cancelled | ||
| Fri., 5/1 | V Baseball | Northwestern | Home - Walker Field [Directions] | Cancelled | Cancelled | |
| Fri., 5/1 | V Boys Tennis | Wamogo | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | ||
| Fri., 5/1 | V Softball | Northwestern | Away - Northwestern Regional H.S.-Varsity Softball Field [Directions] | Cancelled | Cancelled | |
| Fri., 5/1 | JV Softball | Northwestern | Away - Northwestern Regional H.S.-JV Softball Field [Directions] | Cancelled | Cancelled | |
| Fri., 5/1 | V Girls Tennis | Wamogo | Away - Wamogo Regional HS-Tennis Courts [Directions] | Cancelled | ||
| Mon., 5/4 | V Baseball | Litchfield | Home - Walker Field [Directions] | Cancelled | ||
| Mon., 5/4 | V Boys Golf | Northwestern, Wamogo | Away - Northwestern Regional H.S.-Norfolk CC [Directions] | Cancelled | Cancelled | |
| Mon., 5/4 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS-Shepaug Valley Tennis Courts [Directions] | Cancelled | Cancelled | |
| Mon., 5/4 | V Softball | Litchfield | Away - Plumb Hill Field Complex-Softball Field [Directions] | Cancelled | ||
| Mon., 5/4 | V Girls Tennis | Shepaug Valley | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | Cancelled | |
| Tue., 5/5 | V Boys Golf | Shepaug Valley, Terryville | Away - Lake Waramaug Country Club [Directions] | Cancelled | Cancelled | |
| Wed., 5/6 | V Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 5/6 | V Boys Golf | Forman School (Scrim.) | Away - Forman School | Cancelled | ||
| Wed., 5/6 | V Boys Tennis | Northwestern | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | Cancelled | |
| Wed., 5/6 | V Softball | Nonnewaug | Home - Walker Field-Rowley Field [Directions] | Cancelled | ||
| Wed., 5/6 | V Girls Tennis | Northwestern | Away - Northwestern Regional H.S.-Tennis Courts [Directions] | Cancelled | Cancelled | |
| Fri., 5/8 | V Baseball | Housatonic Regional | Home - Walker Field [Directions] | Cancelled | ||
| Fri., 5/8 | V Boys Tennis | Nonnewaug | Away - Edgewood Bath and Tennis Club [Directions] | Cancelled | ||
| Fri., 5/8 | V Softball | Housatonic Regional | Away - Housatonic Valley Regional High-softball field [Directions] | Cancelled | ||
| Fri., 5/8 | V Girls Tennis | Nonnewaug | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | ||
| Mon., 5/11 | V Baseball | Terryville | Away - Terryville HS-Baseball Field [Directions] | Cancelled | ||
| Mon., 5/11 | V Boys Golf | Litchfield | Home - Green woods Country Club [Directions] | Cancelled | ||
| Mon., 5/11 | V Boys Outdoor Track | Northwestern, Housatonic Regional | Away - Northwestern Regional H.S.-Track [Directions] | Cancelled | Cancelled | |
| Mon., 5/11 | V Boys Tennis | Litchfield | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | ||
| Mon., 5/11 | V Girls Outdoor Track | Northwestern, Housatonic Regional | Away - Northwestern Regional H.S.-Track [Directions] | Cancelled | Cancelled | |
| Mon., 5/11 | V Softball | Terryville | Home - Walker Field-Rowley Field [Directions] | Cancelled | ||
| Mon., 5/11 | V Girls Tennis | Litchfield | Away - Litchfield HS-LHS Tennis Courts [Directions] | Cancelled | ||
| Tue., 5/12 | V Boys Golf | Nonnewaug, Northwestern | Home - Green woods Country Club [Directions] | Cancelled | Cancelled | |
| Wed., 5/13 | V Baseball | Thomaston | Home - Walker Field [Directions] | Cancelled | ||
| Wed., 5/13 | V Boys Tennis | Thomaston | Away - Nystrom Park-Nystroms Park courts [Directions] | Cancelled | ||
| Wed., 5/13 | V Softball | Thomaston | Away - Thomaston HS-Black Rock Field [Directions] | Cancelled | ||
| Wed., 5/13 | V Girls Tennis | Thomaston | Home - Gilbert School-Tennis Courts [Directions] | Cancelled | ||
| Fri., 5/15 | V Baseball | Canton | Home - Walker Field [Directions] | Cancelled | ||
| Sat., 5/16 | V Boys Outdoor Track | Berkshire League Outdoor Track Championships | Away - Plumb Hill Field Complex-Plumb Hill Track | Cancelled | Cancelled | |
| Sat., 5/16 | V Girls Outdoor Track | Berkshire League Outdoor Track Championships | Away - Plumb Hill Field Complex-Plumb Hill Track | Cancelled | Cancelled | |
| Tue., 5/19 | V Baseball | Shepaug Valley | Away - Washington Primary School-Ted Alex Field [Directions] | Cancelled | Cancelled | |
| Tue., 5/19 | V Boys Outdoor Track | Thomaston, Housatonic Regional, Litchfield, Nonnewaug, Northwestern, Shepaug Valley, Terryville, Wamogo | Away - Nystrom Park-Nystroms Park Track | Cancelled | Cancelled | |
| Tue., 5/19 | V Boys Outdoor Track | Berkshire League Track Festival | Away - TBA | Cancelled | ||
| Tue., 5/19 | V Girls Outdoor Track | Thomaston, Housatonic Regional, Litchfield, Nonnewaug, Northwestern, Shepaug Valley, Terryville, Wamogo | Away - Nystrom Park-Nystroms Park Track | Cancelled | Cancelled | |
| Tue., 5/19 | V Girls Outdoor Track | Berkshire League Track Festival | Away - TBA | Cancelled | ||
| Tue., 5/19 | V Softball | Shepaug Valley | Home - Walker Field-Rowley Field [Directions] | Cancelled | Cancelled | |
| Wed., 5/20 | V Baseball | Wamogo | Home - Walker Field [Directions] | Cancelled | ||
| Wed., 5/20 | V Boys Golf | Nonnewaug, Northwestern | Away - Heritage Village Country Club [Directions] | Cancelled | Cancelled | |
| Wed., 5/20 | V Boys Outdoor Track | Berkshire League Track Festival | Away - TBA | Cancelled | ||
| Wed., 5/20 | V Boys Outdoor Track | Berkshire League Track Festival | Away - Housatonic Valley Regional High-Track | Cancelled | Cancelled | |
| Wed., 5/20 | V Girls Outdoor Track | Berkshire League Track Festival | Away - TBA | Cancelled | ||
| Wed., 5/20 | V Girls Outdoor Track | Berkshire League Track Festival | Away - Housatonic Valley Regional High-Track | Cancelled | Cancelled | |
| Wed., 5/20 | V Softball | Wamogo/Litchfield | Away - Wamogo Regional HS-Varsity Softball Field [Directions] | Cancelled | ||
| Wed., 5/20 | V Girls Tennis | Berkshire League Girls Tennis Tournament | Away - Hotchkiss School-Tennis Courts | Cancelled | Cancelled | |
| Thu., 5/21 | V Boys Tennis | Berkshire League Boys Tennis Tournament | Away - Hotchkiss School-Tennis Courts | Cancelled | Cancelled | |
| Thu., 5/21 | V Softball | Canton | Away - Canton HS-Softball Diamond [Directions] | Cancelled | ||
| Tue., 5/26 | V Baseball | Northwestern | Away - Northwestern Regional H.S.-Varsity Baseball Field [Directions] | Cancelled | Cancelled | |
| Tue., 5/26 | V Boys Golf | Berkshire League Golf All-Star Tournament | Away - Fairfiew Farm Golf Course | Cancelled | Cancelled | |
| Tue., 5/26 | V Softball | Northwestern | Home - Walker Field-Rowley Field [Directions] | Cancelled | Cancelled | |
| Wed., 5/27 | V Baseball | Northwest Catholic | Away - Northwest Catholic HS (Primary)-Neil J. Brewer Field [Directions] | Cancelled | ||