| Gilbert 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 471 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Fri., 8/23 | V Football | Watertown (Scrim.) | Away - John J. Mills Complex @ Watertown High School [Directions] | 5:00 p.m. | ||
| Wed., 8/28 | V Football | Simsbury (Scrim.) | Away - Simsbury HS [Directions] | 4:00 p.m. | ||
| Wed., 8/28 | V Girls Volleyball | Masters School (Scrim.) | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Wed., 8/28 | V Girls Volleyball | Masters School (Scrim.) | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 8/31 | V Football | St. Paul Catholic (Scrim.) | Home - Gilbert [Directions] | 10:00 a.m. | ||
| Sat., 8/31 | V Boys Soccer | Hale Ray (Scrim.) | Away - Hale-Ray HS, Nevers Field [Directions] | 10:00 a.m. | ||
| Sat., 8/31 | JV Boys Soccer | Hale Ray (Scrim.) | Away - Hale-Ray HS, Nevers Field [Directions] | 10:00 a.m. | ||
| Tue., 9/3 | V Girls Volleyball | TCA | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/3 | V Girls Volleyball | TCA | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/5 | V Boys Cross Country | BL Scrimmage at Black Rock State Park | Away - Black Rock State Park Thomaston | 4:15 p.m. | ||
| Thu., 9/5 | V Girls Cross Country | BL Scrimmage at Black Rock State Park | Away - Black Rock State Park Thomaston | 4:15 p.m. | ||
| Thu., 9/5 | V Girls Volleyball | Torrington (Scrim.) | Away - Torrington HS [Directions] | 3:30 p.m. | ||
| Fri., 9/6 | V Boys Soccer | Wolcott Tech (Scrim.) | Home - Walker Field [Directions] | 3:30 p.m. | ||
| Fri., 9/6 | JV Boys Soccer | Wolcott Tech (Scrim.) | Home - Rowley Field [Directions] | 3:30 p.m. | ||
| Sat., 9/7 | V Football | Bullard/Kolbe (Scrim.) | Home - Gilbert [Directions] | 10:00 a.m. | ||
| Tue., 9/10 | V Boys Cross Country | Housatonic Regional, Northwestern | Away - High School CC Course [Directions] | 4:15 p.m. | ||
| Tue., 9/10 | V Boys Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | T 2-2(OT) | |
| Tue., 9/10 | JV Boys Soccer | Wamogo | Away - Wamogo JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/10 | V Girls Cross Country | Housatonic Regional, Northwestern | Away - HVRHS [Directions] | 4:15 p.m. | ||
| Tue., 9/10 | V Girls Soccer | Terryville | Home - Walker Field [Directions] | 3:45 p.m. | L 0-5 | |
| Tue., 9/10 | JV Girls Soccer | Terryville | Home - Walker Field [Directions] | 3:45 p.m. | Cancelled | |
| Tue., 9/10 | V Girls Volleyball | Canton | Home - Gilbert Gym [Directions] | 5:15 p.m. | L 3-0 | |
| Tue., 9/10 | JV Girls Volleyball | Canton | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/12 | V Football | Cromwell/Portland | Away - Pierson Park, Cromwell [Directions] | 3:30 p.m. | W 34-27 | |
| Thu., 9/12 | V Girls Volleyball | Goodwin Tech | Away - GOODWIN GYMNASIUM [Directions] | 5:15 p.m. | L 3-2 | |
| Thu., 9/12 | JV Girls Volleyball | Goodwin Tech | Away - GOODWIN GYMNASIUM [Directions] | 3:45 p.m. | ||
| Fri., 9/13 | V Boys Soccer | Terryville | Home - Walker Field [Directions] | 3:45 p.m. | T 2-2(OT) | |
| Fri., 9/13 | JV Boys Soccer | Terryville | Home - Walker Field [Directions] | 3:45 p.m. | ||
| Fri., 9/13 | V Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 5:15 p.m. | L 0-3 | |
| Fri., 9/13 | JV Girls Volleyball | Kennedy | Away - KENNEDY HIGH SCHOOL [Directions] | 4:00 p.m. | ||
| Sat., 9/14 | V Boys Cross Country | 35th Haddad Windham XC Invitational | Away - Windham HS | TBA | ||
| Sat., 9/14 | V Girls Cross Country | 35th Haddad Windham XC Invitational | Away - Windham HS | TBA | ||
| Sat., 9/14 | V Girls Soccer | Housatonic Regional | Away - High School Field [Directions] | 10:00 a.m. | L 1-7 | |
| Mon., 9/16 | JV Football | Cromwell/Portland | Home - Gilbert [Directions] | 3:45 p.m. | ||
| Mon., 9/16 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | L 1-3 | Early Dismissal 1:55 |
| Mon., 9/16 | V Girls Volleyball | Torrington | Home - Gilbert Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Mon., 9/16 | JV Girls Volleyball | Torrington | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Boys Cross Country | Shepaug Valley, Lewis Mills | Home - Gilbert [Directions] | 4:15 p.m. | ||
| Tue., 9/17 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | L 1-2 | |
| Tue., 9/17 | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | ||
| Tue., 9/17 | V Girls Cross Country | Shepaug Valley, Lewis Mills | Home - Gilbert [Directions] | 4:15 p.m. | ||
| Tue., 9/17 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Tue., 9/17 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 9/20 | V Boys Soccer | Thomaston | Home - Walker Field [Directions] | 7:15 p.m. | L 2-3 | |
| Fri., 9/20 | JV Boys Soccer | Thomaston | Home - Walker Field [Directions] | 3:45 p.m. | ||
| Fri., 9/20 | V Girls Volleyball | Housatonic Regional | Home - Gilbert Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Fri., 9/20 | JV Girls Volleyball | Housatonic Regional | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/21 | V Boys Cross Country | 33rd Stratton Brook XC Invitaitonal | Away - Simsbury | TBA | ||
| Sat., 9/21 | V Football | Granby/Canton | Home - Gilbert [Directions] | 1:00 p.m. | W 48-21 | Homecoming |
| Sat., 9/21 | V Girls Cross Country | 33rd Stratton Brook XC Invitational | Away - Simsbury | TBA | ||
| Mon., 9/23 | JV Football | Granby/Canton | Away - Ahrens Park Field [Directions] | 3:45 p.m. | ||
| Mon., 9/23 | JV Football | Canton | Home - Gilbert [Directions] | 3:45 p.m. | Cancelled | |
| Tue., 9/24 | V Boys Cross Country | Terryville, Wamogo | Home - Gilbert [Directions] | 4:15 p.m. | ||
| Tue., 9/24 | V Boys Soccer | Housatonic Regional | Home - Walker Field [Directions] | 3:45 p.m. | L 5-1 | |
| Tue., 9/24 | JV Boys Soccer | Housatonic Regional | Home - Walker Field [Directions] | 3:45 p.m. | ||
| Tue., 9/24 | V Girls Cross Country | Terryville, Wamogo | Home - Gilbert [Directions] | 4:15 p.m. | ||
| Tue., 9/24 | V Girls Soccer | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | L 1-8 | |
| Tue., 9/24 | V Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 9/24 | JV Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Football | North Branford | Away - Colafati Field - NBHS [Directions] | 6:30 p.m. | L 25-42 | |
| Fri., 9/27 | V Boys Soccer | Northwestern | Home - Walker Field [Directions] | 7:15 p.m. | T 2-2(OT) | |
| Fri., 9/27 | JV Boys Soccer | Northwestern | Home - Walker Field [Directions] | 3:45 p.m. | ||
| Fri., 9/27 | V Girls Soccer | Wamogo | Away - Wamogo HS [Directions] | 3:45 p.m. | L 0-2 | |
| Fri., 9/27 | JV Girls Soccer | Wamogo | Away - Wamogo [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 9/27 | V Girls Volleyball | Northwestern | Home - Gilbert Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Fri., 9/27 | JV Girls Volleyball | Northwestern | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/28 | JV Football | North Branford | Home - Gilbert [Directions] | 11:00 a.m. | ||
| Tue., 10/1 | V Boys Cross Country | Litchfield, Nonnewaug | Away - Plumb Hill Field Complex [Directions] | 4:15 p.m. | ||
| Tue., 10/1 | V Boys Soccer | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | L 0-5 | |
| Tue., 10/1 | JV Boys Soccer | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | Cancelled | |
| Tue., 10/1 | V Girls Cross Country | Litchfield, Nonnewaug | Away - Plumb Hill Field Complex [Directions] | 4:15 p.m. | ||
| Tue., 10/1 | V Girls Soccer | Northwestern | Home - Walker Field [Directions] | 7:15 p.m. | L 0-2 | |
| Tue., 10/1 | V Girls Volleyball | Terryville | Home - gilbert school [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 10/1 | JV Girls Volleyball | Terryville | Away - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/2 | V Girls Volleyball | Kennedy | Home - Gilbert Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Wed., 10/2 | JV Girls Volleyball | Kennedy | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | V Girls Soccer | Nonnewaug | Away - Nonnewaug High School [Directions] | 3:45 p.m. | L 0-5 | Early Dismissal |
| Thu., 10/3 | JV Girls Soccer | Nonnewaug | Away - Nonnewaug HS JV Field [Directions] | 3:45 p.m. | Cancelled | |
| Thu., 10/3 | V Girls Volleyball | Wolcott Tech | Home - Gilbert Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 10/3 | JV Girls Volleyball | Wolcott Tech | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/4 | V Boys Cross Country | 55th Nonnewaug XC Invitational | Away - Nonnewaug HS | TBA | ||
| Fri., 10/4 | V Boys Soccer | Nonnewaug | Home - Walker Field [Directions] | 3:45 p.m. | L 4-1 | |
| Fri., 10/4 | JV Boys Soccer | Nonnewaug | Home - Rowley Field [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 10/4 | V Girls Cross Country | 55th Nonnewaug XC Invitatonal | Away - Nonnewaug HS | TBA | ||
| Sat., 10/5 | V Football | Lewis Mills | Home - Gilbert [Directions] | 2:30 p.m. | W 44-12 | |
| Mon., 10/7 | JV Girls Soccer | Housatonic Regional | Home - High School Field [Directions] | 3:45 p.m. | Cancelled | |
| Tue., 10/8 | V Boys Cross Country | Terryville, Thomaston, Lewis Mills | Away - New Terryville High School [Directions] | 4:15 p.m. | ||
| Tue., 10/8 | JV Football | Lewis Mills | Home - Gilbert [Directions] | 3:45 p.m. | ||
| Tue., 10/8 | V Boys Soccer | Shepaug Valley | Home - Walker Field [Directions] | 3:45 p.m. | L 2-1 | |
| Tue., 10/8 | JV Boys Soccer | Shepaug Valley | Home - Walker Field [Directions] | 3:45 p.m. | ||
| Tue., 10/8 | V Girls Cross Country | Terryville, Thomaston, Lewis Mills | Away [Directions] | 4:15 p.m. | ||
| Thu., 10/10 | V Boys Soccer | Wamogo | Home - Walker Field [Directions] | 3:45 p.m. | L 5-0 | |
| Thu., 10/10 | JV Boys Soccer | Wamogo | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Thu., 10/10 | V Girls Soccer | Terryville | Away - New Terryville High School [Directions] | 3:45 p.m. | L 1-2 | |
| Thu., 10/10 | V Girls Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Thu., 10/10 | JV Girls Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/12 | V Boys Cross Country | Wickham Park Invitational | Away - Wickham Park East Hartford | TBA | ||
| Sat., 10/12 | V Football | Ellington | Away - Ellington High School [Directions] | 1:30 p.m. | W 20-14 (OT) | |
| Sat., 10/12 | V Girls Cross Country | Wickham Park Invitational | Away - Wickham Park East Hartford | TBA | ||
| Sat., 10/12 | JV Girls Soccer | Terryville | Away - New Terryville High School [Directions] | 3:45 p.m. | Cancelled | |
| Mon., 10/14 | JV Football | Ellington | Home - Gilbert [Directions] | 11:00 a.m. | ||
| Tue., 10/15 | V Boys Soccer | Terryville | Away - Muzzy Field Bristol [Directions] | 7:00 p.m. | W 6-3 | Muzzy Field |
| Tue., 10/15 | JV Boys Soccer | Terryville | Away - New Terryville High School [Directions] | 3:45 p.m. | Cancelled | |
| Tue., 10/15 | V Girls Soccer | Shepaug Valley | Home - Walker Field [Directions] | 3:45 p.m. | L 1-2 | |
| Tue., 10/15 | V Girls Volleyball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 10/15 | JV Girls Volleyball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | V Girls Soccer | Litchfield | Home - Walker Field [Directions] | 7:15 p.m. | L 1-4 | |
| Thu., 10/17 | V Girls Volleyball | O'Brien Tech | Away - O'Brien Tech Gymnasium [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 10/17 | JV Girls Volleyball | O'Brien Tech | Away - O'Brien Tech Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | V Boys Cross Country | BL Championships | Away - Black Rock State Park Thomaston | 2:45 p.m. | JV 2:45; Girls 3:30; Boys 4:15 | |
| Fri., 10/18 | V Boys Soccer | Litchfield | Home - Walker Field [Directions] | 7:15 p.m. | L 1-2 | |
| Fri., 10/18 | JV Boys Soccer | Litchfield | Home - Walker Field [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 10/18 | V Girls Cross Country | BL Championships | Away | 2:45 p.m. | 2:45 JV; 3:30 Girls; 4:15 Boys | |
| Fri., 10/18 | V Girls Volleyball | Lewis Mills | Home - Gilbert Gym [Directions] | 5:15 p.m. | L 2-3 | |
| Fri., 10/18 | JV Girls Volleyball | Lewis Mills | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/19 | V Boys Cross Country | BL Championships Rain Date | Away - Black Rock State Park Thomaston | 10:30 a.m. | JV 10:30; Varsity 12:00 | |
| Sat., 10/19 | V Girls Cross Country | BL Championships Rain Date | Away - Black Rock State Park | 10:30 p.m. | 10:30 JV; 12 Varsity | |
| Mon., 10/21 | V Girls Soccer | Housatonic Regional | Home - Walker Field [Directions] | 3:45 p.m. | L 0-3 | |
| Mon., 10/21 | V Girls Volleyball | Nonnewaug | Home - Gilbert Gym [Directions] | 5:15 p.m. | L 2-3 | |
| Mon., 10/21 | JV Girls Volleyball | Nonnewaug | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Boys Soccer | Thomaston | Away - Thomaston [Directions] | 3:45 p.m. | T 1-1 | |
| Tue., 10/22 | JV Boys Soccer | Thomaston | Away - Thomaston [Directions] | 3:45 p.m. | Cancelled | |
| Tue., 10/22 | V Girls Soccer | Lewis Mills | Home - Walker Field [Directions] | 3:45 p.m. | L 0-8 | |
| Tue., 10/22 | V Girls Volleyball | Northwestern | Away - Northwestern Gym [Directions] | 5:15 p.m. | L 1-3 | |
| Tue., 10/22 | JV Girls Volleyball | Northwestern | Away - Northwestern Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | V Girls Soccer | Wamogo | Home - Walker Field [Directions] | 7:15 p.m. | T 1-1 | |
| Thu., 10/24 | JV Girls Soccer | Wamogo | Home - Walker Field [Directions] | 3:45 p.m. | Cancelled | |
| Thu., 10/24 | V Girls Volleyball | O'Brien Tech | Home - Gilbert Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Thu., 10/24 | JV Girls Volleyball | O'Brien Tech | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | V Boys Soccer | Housatonic Regional | Away - High School Field [Directions] | 3:45 p.m. | W 3-1 | |
| Fri., 10/25 | JV Boys Soccer | Housatonic Regional | Away - High School Field [Directions] | 3:45 p.m. | ||
| Fri., 10/25 | V Girls Volleyball | Terryville | Away - New Terryville High School [Directions] | 4:00 p.m. | L 1-3 | |
| Fri., 10/25 | JV Girls Volleyball | Terryville | Away - New Terryville High School [Directions] | 5:15 p.m. | ||
| Sat., 10/26 | V Boys Cross Country | CIAC State Class Championships | Away - Wickham Park East Hartford | TBA | ||
| Sat., 10/26 | V Football | Canton | Away - Canton H.S. [Directions] | 1:00 p.m. | W 28-15 | |
| Sat., 10/26 | V Girls Cross Country | CIAC State Class Championships | Away - Wickham Park East Hartford | TBA | ||
| Mon., 10/28 | JV Football | Taft | Away - Taft School - Watertown | 3:45 p.m. | Cancelled | |
| Mon., 10/28 | V Boys Soccer | Nonnewaug | Away - Nonnewaug High School Field [Directions] | 3:45 p.m. | L 0-7 | Early Dismissal - 1:55 |
| Mon., 10/28 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug High School Field [Directions] | 3:45 p.m. | ||
| Mon., 10/28 | V Girls Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | 3:45 p.m. | L 0-1 | Drop off only |
| Wed., 10/30 | V Boys Soccer | Northwestern | Away - Northwestern Field [Directions] | 3:45 p.m. | L 0-1 | Early Dismissal - No bus |
| Wed., 10/30 | JV Boys Soccer | Northwestern | Away - Northwestern Field [Directions] | 3:45 p.m. | Early dismissal - no bus | |
| Wed., 10/30 | V Girls Soccer | Nonnewaug | Home - Walker Field [Directions] | 3:45 p.m. | L 0-3 | |
| Wed., 10/30 | JV Girls Soccer | Nonnewaug | Home - Walker Field [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 11/1 | V Boys Cross Country | CIAC State Open Championships | Away | TBA | ||
| Fri., 11/1 | V Girls Cross Country | CIAC State Open Championships | Away - TBA | TBA | ||
| Sat., 11/2 | V Football | Avon | Home - Gilbert [Directions] | 2:30 p.m. | W 34-33 | |
| Mon., 11/4 | JV Football | Avon | Away - Avon High School [Directions] | 3:45 p.m. | ||
| Sat., 11/9 | V Boys Cross Country | New England Championships | Away | TBA | ||
| Sat., 11/9 | V Football | Enfield | Home - Gilbert [Directions] | 1:00 p.m. | W 34-13 | |
| Sat., 11/9 | V Girls Cross Country | New England Championships | Away - TBA | TBA | ||
| Mon., 11/11 | JV Football | Enfield | Away - Enfield High Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 11/16 | V Football | Nonnewaug | Away - Nonnewaug High School Football Field [Directions] | 1:00 p.m. | W 27-7 | |
| Mon., 11/18 | JV Football | Nonnewaug | Home - Gilbert [Directions] | 3:00 p.m. | ||
| Fri., 11/22 | V Football | Valley Regional/Old Lyme | Away - Valley Regional High School [Directions] | 6:30 p.m. | L 0-35 | |
| Sat., 11/23 | JV Football | Valley Regional/Old Lyme | Home - Gilbert [Directions] | 10:30 a.m. | Cancelled | |
| Thu., 11/28 | V Football | Housatonic Regional | Home - Gilbert [Directions] | 10:00 a.m. | W 27-22 | |
| Tue., 12/3 | V Girls Basketball | Kaynor Tech (Scrim.) | Away - Kaynor Tech Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 12/4 | V Girls Basketball | Wolcott Tech (Scrim.) | Home - Gilbert Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/7 | V Boys Basketball | Windsor Hoops for Food Jamboree | Away - Windsor HS | 1:30 p.m. | Games at 1:30/2:00/2:30 | |
| Sat., 12/7 | V Girls Basketball | Enfield (Scrim.) | Home - Gilbert Gym [Directions] | 8:30 a.m. | ||
| Wed., 12/11 | V Girls Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 67-24 | |
| Wed., 12/11 | JV Girls Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/12 | V Boys Basketball | East Granby (Scrim.) | Home - Gilbert Gym [Directions] | 6:00 p.m. | ||
| Thu., 12/12 | V Boys Basketball | East Granby (Scrim.) | Home - Gilbert Gym [Directions] | 6:00 p.m. | ||
| Thu., 12/12 | V Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 7:30 p.m. | L 61-13 | |
| Thu., 12/12 | JV Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 6:00 p.m. | Cancelled | |
| Fri., 12/13 | V Boys Basketball | Monument Mountain (MA) (Scrim.) | Home - Gilbert Gym [Directions] | 4:30 p.m. | Var only | |
| Fri., 12/13 | V Boys Swimming and Diving | Berkshire League Relays | Away - Shepaug HS | 4:00 p.m. | ||
| Sat., 12/14 | V Boys Basketball | Sydney Grammar School - Australia | Home - Gilbert Gym [Directions] | 1:00 p.m. | ||
| Sat., 12/14 | V Boys Basketball | Sydney Grammar School - Australia | Home - Gilbert Gym [Directions] | 1:00 p.m. | ||
| Wed., 12/18 | V Boys Basketball | Wamogo | Home - Gilbert Gym [Directions] | 7:00 p.m. | W 40-39 | |
| Wed., 12/18 | JV Boys Basketball | Wamogo | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/18 | FR Boys Basketball | Wamogo | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Wed., 12/18 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss Pool [Directions] | 4:00 p.m. | Early Dismissal | |
| Wed., 12/18 | V Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 7:00 p.m. | L 47-39 | |
| Wed., 12/18 | JV Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | ||
| Thu., 12/19 | V Wrestling | Wolcott Tech | Home - Gilbert Gym [Directions] | 6:30 p.m. | 5:30 weigh in | |
| Fri., 12/20 | V Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 7:00 p.m. | W 73-44 | |
| Fri., 12/20 | JV Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/20 | FR Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 12/20 | V Boys Swimming and Diving | Bulkeley Diving | Away - Bulkeley HS | 3:30 p.m. | ||
| Fri., 12/20 | V Boys Swimming and Diving | Bulkeley Relays | Away - Bulkeley HS - Hartford | 5:45 p.m. | ||
| Fri., 12/20 | V Girls Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 24-22 | |
| Fri., 12/20 | JV Girls Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Sat., 12/21 | V Boys Swimming and Diving | Northwestern | Away - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 12/21 | V Boys Swimming and Diving | Gilbert | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 12/21 | V Wrestling | Derby Invitational | Away - Derby HS | 10:00 a.m. | 8:00 weigh in | |
| Mon., 12/23 | V Girls Basketball | Canton | Away - Canton H.S. [Directions] | 3:00 p.m. | L 55-17 | |
| Mon., 12/23 | JV Girls Basketball | Canton | Away - Canton H.S. [Directions] | 1:30 p.m. | ||
| Thu., 12/26 | V Wrestling | Terryville-Thomaston | Away - New Terryville High School [Directions] | 6:30 p.m. | 5:30 weigh in | |
| Sat., 12/28 | V Wrestling | J Law Duals | Away - Jonathan Law HS | 9:00 a.m. | 8:00 a.m. weigh in | |
| Mon., 12/30 | V Boys Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 7:00 p.m. | W 57-52 | |
| Mon., 12/30 | JV Boys Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Mon., 12/30 | FR Boys Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Mon., 12/30 | V Boys Swimming and Diving | Simsbury | Away - Westminster School [Directions] | 8:00 p.m. | 7:30 warm up | |
| Mon., 12/30 | V Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 7:00 p.m. | L 53-12 | |
| Mon., 12/30 | JV Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/4 | V Boys Swimming and Diving | Holy Cross | Home - Winsted YMCA [Directions] | 4:30 p.m. | 4:00 Warmup | |
| Sat., 1/4 | V Wrestling | Granby Memorial | Home - Gilbert Gym [Directions] | 10:00 a.m. | 9:00 weigh in | |
| Sat., 1/4 | V Girls Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 5:00 p.m. | L 68-28 | |
| Sat., 1/4 | JV Girls Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 3:00 p.m. | ||
| Tue., 1/7 | V Boys Basketball | Litchfield | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 41-42 | |
| Tue., 1/7 | JV Boys Basketball | Litchfield | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/7 | FR Boys Basketball | Litchfield | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/7 | V Boys Swimming and Diving | Litchfield | Home - Winsted YMCA [Directions] | 8:15 p.m. | 7:45 Warmup | |
| Tue., 1/7 | V Girls Basketball | Litchfield | Away - Litchfield High School [Directions] | 7:00 p.m. | L 40-27 | |
| Tue., 1/7 | JV Girls Basketball | Litchfield | Away - Litchfield High School [Directions] | 5:30 p.m. | ||
| Wed., 1/8 | V Wrestling | Westbrook | Home - Gilbert Gym [Directions] | 6:30 p.m. | 5:30 p.m. weigh in | |
| Thu., 1/9 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Pool [Directions] | 7:30 p.m. | ||
| Thu., 1/9 | V Wrestling | Nonnewaug | Home - Gilbert Gym [Directions] | 6:30 p.m. | 5:30 weigh in | |
| Fri., 1/10 | V Boys Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | 7:00 p.m. | W 63-50 | |
| Fri., 1/10 | JV Boys Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/10 | V Boys Swimming and Diving | Housatonic Regional | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Fri., 1/10 | V Girls Basketball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | 7:00 p.m. | L 44-15 | |
| Fri., 1/10 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/11 | FR Boys Basketball | O'Brien Tech | Home - Gilbert Gym [Directions] | 9:30 a.m. | ||
| Sat., 1/11 | V Boys Swimming and Diving | Shepaug Valley | Home - Winsted YMCA [Directions] | 4:30 p.m. | 4:00 Warmup | |
| Sat., 1/11 | V Wrestling | Canton Quad | Away - Canton HS | 10:00 a.m. | 9:00 weigh in | |
| Tue., 1/14 | V Boys Basketball | Terryville | Away - New Terryville High School [Directions] | 7:00 p.m. | L 69-45 | |
| Tue., 1/14 | JV Boys Basketball | Terryville | Away - New Terryville High School [Directions] | 5:30 p.m. | ||
| Tue., 1/14 | V Girls Basketball | Terryville | Home - Gilbert Gym [Directions] | 5:30 p.m. | L 49-32 | |
| Tue., 1/14 | JV Girls Basketball | Terryville | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/16 | V Girls Basketball | Northwestern | Home - Gilbert Gym [Directions] | 5:30 p.m. | L 11-39 | |
| Thu., 1/16 | JV Girls Basketball | Northwestern | Home - Gilbert Gym [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 1/17 | V Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 46-53 | |
| Fri., 1/17 | JV Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/17 | FR Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/17 | V Boys Swimming and Diving | Litchfield | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Sat., 1/18 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 12:30 p.m. | ||
| Sat., 1/18 | V Wrestling | Derby/Oxford/Holy Cross, Canton, Seymour, Weston | Home - Gilbert Gym [Directions] | 10:00 a.m. | 9:00 weigh in | |
| Thu., 1/23 | V Boys Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 7:00 p.m. | W 63-43 | |
| Thu., 1/23 | JV Boys Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/23 | FR Boys Basketball | Housatonic Regional | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/23 | V Wrestling | Housatonic Regional | Away - Housatonic [Directions] | 6:30 p.m. | 5:30 weigh in | |
| Fri., 1/24 | V Boys Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 7:00 p.m. | W 73-32 | |
| Fri., 1/24 | JV Boys Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/24 | FR Boys Basketball | Shepaug Valley | Home - Gilbert Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/24 | V Boys Swimming and Diving | Housatonic Regional | Home - Winsted YMCA [Directions] | 7:30 p.m. | 7:00 Warmup | |
| Fri., 1/24 | V Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 7:00 p.m. | L 34-23 | |
| Fri., 1/24 | JV Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 1/25 | V Boys Swimming and Diving | Shepaug Valley | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 1/25 | V Wrestling | Portland Duals | Away - Portland HS | 10:00 a.m. | 9:00 weigh in | |
| Mon., 1/27 | V Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 7:00 p.m. | W 68-35 | |
| Mon., 1/27 | JV Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 1/27 | FR Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 3:45 p.m. | ||
| Mon., 1/27 | V Girls Basketball | Thomaston | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 59-21 | |
| Mon., 1/27 | JV Girls Basketball | Thomaston | Home - Gilbert Gym [Directions] | 5:30 p.m. | Cancelled | |
| Tue., 1/28 | V Boys Basketball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | 7:00 p.m. | W 63-59 | |
| Tue., 1/28 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/28 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Pool [Directions] | 7:00 p.m. | ||
| Tue., 1/28 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 8:15 p.m. | 7:45 Warmup | |
| Tue., 1/28 | V Girls Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | 4:30 p.m. | L 51-14 | |
| Tue., 1/28 | JV Girls Basketball | Nonnewaug | Home - Gilbert Gym [Directions] | 4:30 p.m. | Cancelled | |
| Thu., 1/30 | V Boys Basketball | Granby Memorial | Away - Granby Memorial High School [Directions] | 7:00 p.m. | L 36-62 | |
| Thu., 1/30 | JV Boys Basketball | Granby Memorial | Away - Granby Memorial High School [Directions] | 5:30 p.m. | ||
| Thu., 1/30 | FR Boys Basketball | Granby Memorial | Away - Granby Memorial High School [Directions] | 3:45 p.m. | ||
| Fri., 1/31 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Sat., 2/1 | V Boys Basketball | Torrington | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 53-39 | |
| Sat., 2/1 | JV Boys Basketball | Torrington | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Sat., 2/1 | FR Boys Basketball | Torrington | Home - Gilbert Gym [Directions] | 3:45 p.m. | Cancelled | |
| Sat., 2/1 | V Boys Swimming and Diving | Wamogo | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 2/1 | V Wrestling | Pomperaug Quad | Away - Pomperaug HS | 10:00 a.m. | 8:00 weigh in | |
| Tue., 2/4 | V Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 7:00 p.m. | L 63-34 | |
| Tue., 2/4 | JV Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/4 | FR Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 3:45 p.m. | Cancelled | |
| Tue., 2/4 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Pool [Directions] | 7:30 p.m. | ||
| Tue., 2/4 | V Girls Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 4:30 p.m.p.m. | L 53-18 | |
| Tue., 2/4 | JV Girls Basketball | Lewis Mills | Home - Gilbert Gym [Directions] | 5:30 p.m. | Cancelled | |
| Thu., 2/6 | V Boys Swimming and Diving | Woodland | Away - Woodland High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/7 | V Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 7:00 p.m. | W 48-21 | |
| Fri., 2/7 | JV Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | ||
| Fri., 2/7 | FR Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 2/7 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley High School Pool [Directions] | 4:30 p.m. | ||
| Fri., 2/7 | V Girls Basketball | Wamogo | Home - Gilbert Gym [Directions] | 5:30 p.m. | W 64-55 | |
| Fri., 2/7 | JV Girls Basketball | Wamogo | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Sat., 2/8 | V Boys Swimming and Diving | Girls Sprint | Away - Shepaug HS | 11:00 a.m. | ||
| Sat., 2/8 | V Boys Swimming and Diving | Girls Sprints | Away - Shepaug HS | 11:00 a.m. | ||
| Sat., 2/8 | V Wrestling | Woodstock Tournament | Away - Woodstock Academy | 10:00 a.m. | 8:00 weigh in | |
| Mon., 2/10 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss Pool [Directions] | 6:30 p.m. | ||
| Mon., 2/10 | V Wrestling | Northwestern | Away - Northwestern Gym [Directions] | 5:00 p.m. | 5:30 weigh in | |
| Tue., 2/11 | V Boys Basketball | Terryville | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 42-77 | |
| Tue., 2/11 | JV Boys Basketball | Terryville | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/11 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Pool [Directions] | 7:30 p.m. | ||
| Tue., 2/11 | V Girls Basketball | Terryville | Away - New Terryville High School [Directions] | 5:00 p.m. | L 57-15 | |
| Tue., 2/11 | JV Girls Basketball | Terryville | Away - New Terryville High School [Directions] | 5:30 p.m. | Cancelled | |
| Wed., 2/12 | JV Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/12 | V Wrestling | Holy Cross | Home - Gilbert Gym [Directions] | 6:30 p.m. | Cancelled | 5:30 weigh in |
| Wed., 2/12 | JV Girls Basketball | Northwestern | Away - NWR7 [Directions] | 5:30 p.m. | ||
| Sat., 2/15 | FR Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 10:00 a.m. | Cancelled | |
| Sat., 2/15 | V Wrestling | BL Championships | Away - Nonnewaug HS | 10:00 a.m. | 8:00 weigh in | |
| Mon., 2/17 | V Boys Basketball | Northwestern | Away - Northwestern Gym [Directions] | 7:30 p.m. | L 59-65 | |
| Mon., 2/17 | V Girls Basketball | Northwestern | Away - Northwestern Gym [Directions] | 5:30 p.m. | L 26-43 | |
| Wed., 2/19 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley High School Pool [Directions] | 5:00 p.m. | ||
| Wed., 2/19 | V Girls Basketball | Litchfield | Home - Gilbert Gym [Directions] | 7:00 p.m. | L 30-63 | |
| Wed., 2/19 | JV Girls Basketball | Litchfield | Home - Gilbert Gym [Directions] | 5:30 p.m. | Cancelled | |
| Thu., 2/20 | V Boys Swimming and Diving | Wamogo | Home - Winsted YMCA [Directions] | 8:00 p.m. | 4:00 Warmup | |
| Thu., 2/20 | V Boys Swimming and Diving | Wamogo | Home - Winsted YMCA [Directions] | 8:15 p.m. | Make from 1.18 | |
| Thu., 2/20 | V Girls Basketball | Oxford | Home - Gilbert Gym [Directions] | 5:30 p.m. | L 65-24 | |
| Thu., 2/20 | JV Girls Basketball | Oxford | Home - Gilbert Gym [Directions] | 5:30 p.m. | Cancelled | |
| Fri., 2/21 | V Boys Basketball | Litchfield | Away - Litchfield High School [Directions] | 7:00 p.m. | W 66-56 | |
| Fri., 2/21 | JV Boys Basketball | Litchfield | Away - Litchfield High School [Directions] | 5:30 p.m. | ||
| Fri., 2/21 | FR Boys Basketball | Litchfield | Away - Litchfield High School [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 2/21 | V Boys Swimming and Diving | Torrington | Away - Torrington Y [Directions] | 7:30 p.m. | 7:00 warm-up | |
| Fri., 2/21 | V Wrestling | CIAC Class S State Tournament | Away - Windham HS | TBA | ||
| Sat., 2/22 | V Boys Swimming and Diving | Splash | Away - Plainville HS | 2:00 p.m. | 12:30 Warm up | |
| Sat., 2/22 | V Wrestling | CIAC Class S Tournament | Away - Windham HS | TBA | ||
| Sat., 2/22 | V Girls Basketball | BL Tournament Quarterfinals | Away - Wamogo HS | TBA | ||
| Mon., 2/24 | V Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 7:00 p.m. | W 65-50 | |
| Mon., 2/24 | JV Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/24 | FR Boys Basketball | Housatonic Regional | Away - HVRHS. Gymnasium [Directions] | 3:45 p.m. | Cancelled | |
| Mon., 2/24 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 8:15 p.m. | warm-ups 7:45 | |
| Tue., 2/25 | V Boys Swimming and Diving | Granby Memorial | Home - Winsted YMCA [Directions] | 8:15 p.m. | 7:45 Warm up | |
| Tue., 2/25 | V Girls Basketball | BL Tournament Semifinals | Away - Wamogo HS | TBA | ||
| Wed., 2/26 | V Boys Basketball | Thomaston | Home - Gilbert Gym [Directions] | 7:00 p.m. | W 64-45 | |
| Wed., 2/26 | JV Boys Basketball | Thomaston | Home - Gilbert Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/26 | FR Boys Basketball | Thomaston | Home - Gilbert Gym [Directions] | 3:45 p.m. | Cancelled | |
| Thu., 2/27 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 8:15 p.m. | 7:45 Warmup | |
| Fri., 2/28 | V Wrestling | CIAC State Opens | Away - New Have Athletic Center Hillhouse | TBA | ||
| Fri., 2/28 | V Girls Basketball | BL Tournament Championship | Away - Wamogo HS | TBA | ||
| Sat., 3/1 | V Boys Basketball | BL Tournament Quarterfinals | Away - Thomaston HS | TBA | ||
| Sat., 3/1 | V Boys Swimming and Diving | Gilbert | Away - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 3/1 | V Boys Swimming and Diving | Northwestern | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 3/1 | V Wrestling | CIAC State Opens | Away - Hillhouse | TBA | ||
| Tue., 3/4 | V Boys Basketball | BL Tournament Semifinals | Away - Thomaston HS | TBA | ||
| Wed., 3/5 | V Boys Swimming and Diving | Granby Memorial | Away - FVYMCA [Directions] | 7:45 p.m. | 7:15 Warm up | |
| Fri., 3/7 | V Boys Basketball | BL Tournament Championship | Away - Thomaston HS | TBA | ||
| Fri., 3/7 | V Boys Swimming and Diving | BL Diving Championships | Away - Shepaug HS | 6:00 p.m. | 4:00 p.m. Warmups | |
| Fri., 3/7 | V Boys Swimming and Diving | BL Diving Championships | Away - Shepaug HS | TBA | ||
| Fri., 3/7 | V Wrestling | New England Tournament | Away - Providence Athletic Center | TBA | ||
| Sat., 3/8 | V Boys Swimming and Diving | BL Championships | Away - Hotchkiss | 1:00 p.m. | 12 noon warm ups | |
| Sat., 3/8 | V Boys Swimming and Diving | BL Swimming Championships | Away | TBA | ||
| Mon., 3/10 | V Boys Basketball | Creed | Home - Gilbert Gym [Directions] | 7:00 p.m. | ||
| Wed., 3/12 | V Boys Swimming and Diving | State Diving Championships | Away - TBA | TBA | ||
| Sat., 3/15 | V Boys Swimming and Diving | States | Away | TBA | ||
| Sat., 3/15 | V Boys Swimming and Diving | State Qualifying | Away - Plainville HS | TBA | ||
| Tue., 3/18 | V Boys Swimming and Diving | State Class Meet | Away - Wesleyan | 7:15 p.m. | ||
| Tue., 4/1 | V Baseball | Naugatuck (Scrim.) | Away - Rotary Field [Directions] | 3:30 p.m. | ||
| Thu., 4/3 | V Baseball | Watertown (Scrim.) | Away - Deland Field [Directions] | 3:30 p.m. | ||
| Fri., 4/4 | V Softball | Wolcott Tech (Scrim.) | Away - OWTS School Field [Directions] | 4:30 p.m. | ||
| Mon., 4/7 | V Softball | Canton (Scrim.) | Away - Canton H.S. [Directions] | 3:45 p.m. | ||
| Wed., 4/9 | V Baseball | Thomaston | Home - Walker Field [Directions] | 3:45 p.m. | L 16-0 | |
| Wed., 4/9 | V Boys Outdoor Track | Litchfield, Terryville, Thomaston | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | ||
| Wed., 4/9 | V Boys Tennis | Lewis Mills | Home - Gilbert HS [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 4/9 | V Girls Outdoor Track | Litchfield, Terryville, Thomaston | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | ||
| Wed., 4/9 | V Softball | Thomaston | Away - Bev Lowden Softball Field (T.H.S.) [Directions] | 3:45 p.m. | L 15-0 | |
| Wed., 4/9 | V Girls Tennis | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | L 0-7 | |
| Mon., 4/14 | V Boys Tennis | Thomaston | Away - Thomaston Center School [Directions] | 3:45 p.m. | L 1-4 | |
| Mon., 4/14 | V Softball | Windsor Locks | Away - Windsor Locks High School [Directions] | 4:00 p.m. | L 6-7 | |
| Mon., 4/14 | V Girls Tennis | Thomaston | Home - Gilbert [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/15 | V Boys Outdoor Track | Litchfield, Lewis Mills | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | ||
| Tue., 4/15 | V Girls Outdoor Track | Litchfield, Lewis Mills | Away - Plumb Hill Field Complex, Litchfield [Directions] | 3:45 p.m. | ||
| Thu., 4/17 | V Baseball | Nonnewaug | Home - Walker Field [Directions] | 3:45 p.m. | W 5-3 | |
| Thu., 4/17 | V Boys Outdoor Track | Shepaug Valley, Housatonic Regional | Away - Shepaug Valley High School Track [Directions] | 12:00 p.m. | Cancelled | |
| Thu., 4/17 | V Boys Tennis | Shepaug Valley | Home - Gilbert [Directions] | 3:45 p.m. | L 1-4 | |
| Thu., 4/17 | V Girls Outdoor Track | Shepaug Valley, Housatonic Regional | Away - Shepaug Valley High School Track [Directions] | 12:00 p.m. | Cancelled | |
| Thu., 4/17 | V Softball | Nonnewaug | Away - Nonnewaug High School [Directions] | 3:45 p.m. | L 7-17 | |
| Sat., 4/19 | V Baseball | Wamogo (Scrim.) | Away - Doubleday Field - Cooperstown [Directions] | 10:00 a.m. | ||
| Sat., 4/19 | V Baseball | Wamogo (Scrim.) | Away - Doubleday Field - Cooperstown [Directions] | 10:00 a.m. | ||
| Sat., 4/19 | V Boys Outdoor Track | Panther Invite | Away - Plainfield HS | 9:30 a.m. | ||
| Sat., 4/19 | V Boys Outdoor Track | Panther Invite | Away - Plainfield HS | TBA | ||
| Sat., 4/19 | V Girls Outdoor Track | Panther Invite | Away - Plainfield HS | 9:30 a.m. | ||
| Sat., 4/19 | V Softball | New Fairfield | Home - Walker Field [Directions] | 10:30 a.m. | W 16-15 | |
| Mon., 4/21 | V Baseball | Lewis Mills | Home - Walker Field [Directions] | 3:45 p.m. | L 12-8 | |
| Mon., 4/21 | JV Baseball | Lewis Mills | Home - Gilbert [Directions] | 3:45 p.m. | Cancelled | |
| Mon., 4/21 | V Boys Tennis | Litchfield | Away - Litchfield High School [Directions] | 3:45 p.m. | W 4-1 | |
| Mon., 4/21 | V Softball | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | L 0-10 | School Break |
| Mon., 4/21 | V Girls Tennis | Litchfield | Home - Gilbert [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/22 | V Baseball | Housatonic Regional | Away - High School Field [Directions] | 4:00 p.m. | L 10-1 | |
| Tue., 4/22 | V Boys Outdoor Track | Nonnewaug, Shepaug Valley | Away - Nonnewaug High School [Directions] | 3:45 p.m. | ||
| Tue., 4/22 | V Girls Outdoor Track | Nonnewaug, Shepaug Valley | Away - Paul Burns Memorial Track [Directions] | 3:45 p.m. | ||
| Wed., 4/23 | V Baseball | Northwestern | Away - NWR Varsity Field [Directions] | 3:45 p.m. | L 1-4 | No bus |
| Wed., 4/23 | V Boys Golf | Thomaston | Away - Stonybrook Golf Course [Directions] | 3:00 p.m. | Thomaston 187 Gilbert 265 | |
| Wed., 4/23 | V Boys Tennis | Nonnewaug | Away - Edgewood Bath and Tennis [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 4/23 | V Softball | Northwestern | Home - Walker Field [Directions] | 3:45 p.m. | L 3-20 | |
| Wed., 4/23 | V Girls Tennis | Nonnewaug | Home - Gilbert [Directions] | 3:45 p.m. | L 2-4 | |
| Fri., 4/25 | V Baseball | Litchfield | Home - Walker Field [Directions] | 3:45 p.m. | L 2-8 | |
| Fri., 4/25 | V Boys Tennis | Wamogo | Home - Gilbert [Directions] | 3:45 p.m. | L 2-3 | |
| Fri., 4/25 | V Softball | Litchfield | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | W 10-3 | School break |
| Fri., 4/25 | V Girls Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 4/26 | V Boys Outdoor Track | Fermi HS Co-ed Invitational | Away - Fermi HS | 10:00 a.m. | ||
| Sat., 4/26 | V Girls Outdoor Track | Fermi HS Co-ed Invitational | Away | 10:00 a.m. | ||
| Mon., 4/28 | V Baseball | Shepaug Valley | Away - Ted Alex Field [Directions] | 4:00 p.m. | L 2-6 | |
| Mon., 4/28 | V Boys Tennis | Northwestern | Away - Northwestern [Directions] | 3:45 p.m. | L 0-5 | Drop only |
| Mon., 4/28 | V Softball | Shepaug Valley | Home - Walker Field [Directions] | 3:45 p.m. | L 6-17 | |
| Mon., 4/28 | V Girls Tennis | Northwestern | Home - Gilbert [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/29 | V Boys Outdoor Track | Wamogo | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | ||
| Tue., 4/29 | V Girls Outdoor Track | Wamogo | Away - Plumb Hill Field Complex [Directions] | 3:45 p.m. | ||
| Tue., 4/29 | V Softball | Wamogo/Litchfield | Away - Wamogo Varsity Softball Field [Directions] | 3:45 p.m. | L 3-14 | |
| Tue., 4/29 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley High School Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 4/30 | JV Baseball | Wamogo | Away - Wamogo Baseball Field [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 5/2 | V Baseball | Terryville | Away - New Terryville High School [Directions] | 4:00 p.m. | L 1-6 | |
| Fri., 5/2 | JV Baseball | Terryville | Away - Lower Fisher Elementary [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 5/2 | V Boys Outdoor Track | Lewis Mills | Away - Lewis Mills Track [Directions] | 3:45 p.m. | ||
| Fri., 5/2 | V Boys Tennis | Lewis Mills | Away - Lewis Mills H.S. [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 5/2 | V Girls Outdoor Track | Lewis Mills | Away - Lewis Mills High School [Directions] | 3:45 p.m. | ||
| Fri., 5/2 | V Softball | Terryville | Home - Walker Field [Directions] | 3:45 p.m. | W 4-2 | |
| Fri., 5/2 | V Girls Tennis | Lewis Mills | Home - Gilbert HS [Directions] | 3:45 p.m. | L 0-7 | |
| Mon., 5/5 | V Baseball | Thomaston | Away - Thomaston HS Field [Directions] | 4:00 p.m. | L 13-9 | |
| Mon., 5/5 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley High School Courts [Directions] | 3:45 p.m. | L 2-3 | |
| Mon., 5/5 | V Softball | Thomaston | Home - Walker Field [Directions] | 3:45 p.m. | L 0-15 | |
| Mon., 5/5 | V Girls Tennis | Shepaug Valley | Home - Gilbert [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 5/6 | V Boys Golf | Thomaston, Litchfield | Home - Greenwood Country Club [Directions] | 3:00 p.m. | Litchfield 179 Thomaston 182 Gilbert 257 | |
| Tue., 5/6 | V Boys Outdoor Track | Northwestern, Shepaug Valley, Terryville | Away - Northwestern [Directions] | 3:45 p.m. | Drop off only | |
| Tue., 5/6 | V Boys Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | 3:45 p.m. | L 2-3 | |
| Tue., 5/6 | V Girls Outdoor Track | Northwestern, Shepaug Valley, Terryville | Away - Northwestern [Directions] | 3:45 p.m. | Drop off only | |
| Tue., 5/6 | V Girls Tennis | Wamogo | Home - Gilbert [Directions] | 3:45 p.m. | L 1-6 | |
| Wed., 5/7 | V Boys Golf | Lewis Mills, Housatonic Regional | Home - Fairview Farm GC [Directions] | 3:00 p.m. | Lewis Mills 186 Housatonic Regional 227 Gilbert 246 | |
| Wed., 5/7 | V Boys Tennis | Thomaston | Home - Gilbert [Directions] | 3:45 p.m. | L 1-4 | |
| Wed., 5/7 | V Girls Tennis | Thomaston | Away - Thomaston Center School [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 5/8 | V Baseball | Bethel | Away - Hunt Field at Bethel High School [Directions] | 4:15 p.m. | L 18-2 | |
| Thu., 5/8 | V Boys Golf | Terryville, Nonnewaug | Away - Pequabuck Golf Course, Bristol [Directions] | 3:15 p.m. | Cancelled | |
| Fri., 5/9 | V Baseball | Wamogo | Home - Walker Field [Directions] | 4:00 p.m. | L 3-20 | |
| Fri., 5/9 | V Boys Tennis | Housatonic Regional | Home - Housatonic [Directions] | 3:45 p.m. | L 1-4 | |
| Fri., 5/9 | V Boys Tennis | Housatonic Regional | Away - High School Courts [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 5/9 | V Softball | Housatonic Regional | Home - Walker Field [Directions] | 3:45 p.m. | W 18-17 | |
| Sat., 5/10 | V Boys Outdoor Track | 5th Annual Spartan Invitational | Away - Shepaug HS | 10:00 a.m. | ||
| Sat., 5/10 | V Boys Outdoor Track | 5th Annual Spartan Invitational | Away - Shepaug HS | 10:00 a.m. | ||
| Sat., 5/10 | V Girls Outdoor Track | 5th Annual Spartan Invitational | Away - Shepaug HS | 10:00 a.m. | ||
| Mon., 5/12 | V Baseball | Housatonic Regional | Home - Walker Field [Directions] | 3:45 p.m. | L 5-3 | |
| Mon., 5/12 | V Boys Golf | Shepaug Valley, Terryville | Home - Greenwood Country Club [Directions] | 3:00 p.m. | Shepaug Valley 186 Terryville 215 Gilbert 257 | |
| Mon., 5/12 | V Boys Outdoor Track | Housatonic Regional, Terryville, Wolcott Tech | Away - Housatonic Track [Directions] | 3:45 p.m. | ||
| Mon., 5/12 | V Boys Tennis | Litchfield | Home - Gilbert [Directions] | 3:45 p.m. | W 3-2 | |
| Mon., 5/12 | V Girls Outdoor Track | Housatonic Regional, Terryville | Away [Directions] | 3:45 p.m. | ||
| Mon., 5/12 | V Softball | Housatonic Regional | Away - High School Field [Directions] | 3:45 p.m. | L 5-1 | |
| Mon., 5/12 | V Girls Tennis | Litchfield | Away - Litchfield High School [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 5/13 | V Baseball | Nonnewaug | Away - Nonnewaug High School Field [Directions] | 4:00 p.m. | L 4-3 | |
| Tue., 5/13 | V Boys Golf | Housatonic Regional, Northwestern | Away - Hotchkiss Golf Course [Directions] | 3:00 p.m. | Northwestern 199 Housatonic 201 Gilbert 238 | |
| Tue., 5/13 | V Boys Tennis | Northwestern | Home - Gilbert [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 5/14 | V Boys Golf | Litchfield, Shepaug Valley | Away - Litchfield CC [Directions] | 3:45 p.m. | Litchfield 162 Shepaug Valley 167 Gilbert 249 | |
| Wed., 5/14 | V Boys Tennis | Nonnewaug | Home - Gilbert [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 5/14 | V Softball | Nonnewaug | Home - Walker Field [Directions] | 3:45 p.m. | L 16-3 | |
| Wed., 5/14 | V Girls Tennis | Nonnewaug | Away - Edgewood Bath and Tennis [Directions] | 3:45 p.m. | L 3-4 | |
| Thu., 5/15 | V Girls Tennis | Housatonic Regional | Away - Gilbert [Directions] | 3:45 p.m. | L 1-6 | |
| Fri., 5/16 | JV Baseball | Lewis Mills | Away - Lewis Mills JV Baseball Field [Directions] | 3:45 p.m. | Cancelled | |
| Sat., 5/17 | V Boys Outdoor Track | Berkshire League Championships | Away - Plumb Hill Field Complex, Litchfield | 9:00 a.m. | ||
| Sat., 5/17 | V Boys Tennis | Berkshire League Singles Championships | Away - Litchfield HS | 12:00 p.m. | ||
| Sat., 5/17 | V Girls Outdoor Track | Berkshire League Championships | Away - Plumb Hill Field Complex, Litchfield | 9:00 a.m. | ||
| Sat., 5/17 | V Girls Tennis | Berkshire League Singles Championships | Away - Wamogo HS | 12:00 p.m. | ||
| Sun., 5/18 | V Boys Outdoor Track | BL Championships - Rain Date | Away - Plumb Hill Field Complex - Litchfield | 9:00 a.m. | ||
| Sun., 5/18 | V Girls Outdoor Track | BL Championships - Rain Date | Away - Plumb Hill Field Complex, Litchfield | 9:00 a.m. | ||
| Mon., 5/19 | V Baseball | Northwestern | Home - Walker Field [Directions] | 3:45 p.m. | L 10-1 | |
| Mon., 5/19 | V Boys Golf | Northwestern | Home - Greenwood Country Club [Directions] | 3:00 p.m. | Northwestern 188 Gilbert 248 | |
| Mon., 5/19 | V Softball | Northwestern | Away - Northwestern Field [Directions] | 3:45 p.m. | L 2-21 | Drop off only |
| Mon., 5/19 | V Girls Tennis | Northwestern | Away - Northwestern [Directions] | 3:45 p.m. | L 0-7 | Drop only |
| Tue., 5/20 | V Baseball | Lewis Mills | Away - Lewis Mills Baseball Field [Directions] | 4:15 p.m. | L 5-3 | |
| Tue., 5/20 | V Boys Tennis | BL Doubles Championships | Away - Litchfield HS | 11:00 a.m. | ||
| Tue., 5/20 | V Softball | Lewis Mills | Home - Walker Field [Directions] | 3:45 p.m. | L 0-11 | |
| Tue., 5/20 | V Girls Tennis | BL Doubles Championships | Away - Wamogo HS | 11:00 a.m. | ||
| Wed., 5/21 | V Baseball | Litchfield | Away - Community Field [Directions] | 4:00 p.m. | L 5-0 | |
| Wed., 5/21 | V Boys Golf | Lewis Mills, Nonnewaug | Away - Fairview Farms Golf Course - Harwinton [Directions] | 3:15 p.m. | Nonnewaug 173 Lewis Mills 186 Gilbert 242 | |
| Wed., 5/21 | V Softball | Litchfield | Home - Walker Field [Directions] | 3:45 p.m. | W 25-9 | |
| Fri., 5/23 | V Softball | Shepaug Valley | Away - Dick Ayer Field [Directions] | 3:45 p.m. | L 5-7 | |
| Mon., 5/26 | V Baseball | Shepaug Valley | Home - Walker Field [Directions] | 3:00 p.m. | W 7-6 | |
| Tue., 5/27 | V Baseball | Wamogo | Away - Wamogo Baseball Field [Directions] | 4:00 p.m. | W 4-3 | |
| Tue., 5/27 | JV Baseball | Wamogo | Home - Walker Field [Directions] | 3:45 p.m. | Cancelled | |
| Tue., 5/27 | V Boys Outdoor Track | BL Festival | Away - HRVHS | TBA | ||
| Tue., 5/27 | V Girls Outdoor Track | BL Festival | Away - HVRHS | TBA | ||
| Tue., 5/27 | V Softball | Wamogo/Litchfield | Home - Walker Field [Directions] | 3:45 p.m. | L 6-8 | |
| Wed., 5/28 | V Baseball | Terryville | Home - Walker Field [Directions] | 3:45 p.m. | W 9-3 | |
| Wed., 5/28 | JV Baseball | Terryville | Home - Gilbert [Directions] | 3:45 p.m. | Cancelled | |
| Wed., 5/28 | V Boys Outdoor Track | BL Festival | Away - HVRHS | TBA | ||
| Wed., 5/28 | V Girls Outdoor Track | BL Festival | Away - HVRHS | TBA | ||
| Wed., 5/28 | V Softball | Terryville | Away - New Terryville High School [Directions] | 4:45 p.m. | W 23-8 | |
| Wed., 5/28 | V Girls Tennis | Housatonic Regional | Home - Gilbert [Directions] | 3:45 p.m. | L 4-3 | |
| Thu., 5/29 | V Baseball | Wolcott Tech | Home - Walker Field [Directions] | 3:45 p.m. | W 21-2 | |
| Wed., 6/4 | V Boys Outdoor Track | CIAC Class S Championships | Away - Danbury HS | 2:30 p.m. | Noon Dismissal | |
| Wed., 6/4 | V Girls Outdoor Track | CIAC Class S Championships | Away - Danbury HS | 2:30 p.m. | ||
| Mon., 6/9 | V Boys Outdoor Track | CIAC Open Championships | Away - Middletown HS | 1:30 p.m. | 11:00 Dismissal | |
| Mon., 6/9 | V Girls Outdoor Track | CIAC Open Championships | Away | 1:30 p.m. | ||