| Gilbert 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 438 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | V Baseball | Derby (Scrim.) | Away - North Branford Sportsplex [Directions] | 3:45 p.m. | 2:30pm | Away Scrimmage 2:30pm Pickup bottom of the hill |
| TBA | JV Baseball | Northwestern | Away - Northwestern Varsity Field [Directions] | 12:15 p.m. | ||
| TBA | JV Baseball | Terryville | Away - Lower Fisher Elementary [Directions] | Cancelled | ||
| TBA | JV Baseball | Lewis Mills | Home - Gilbert [Directions] | Cancelled | ||
| TBA | JV Baseball | Terryville | Home - Gilbert [Directions] | Cancelled | ||
| TBA | JV Baseball | Lewis Mills | Away - Lewis Mills Baseball Field [Directions] | Cancelled | ||
| TBA | JV Baseball | Shepaug Valley | Away - Ted Alex Field [Directions] | TBA | ||
| TBA | JV Baseball | Litchfield | Away - Litchfield HS Baseball Field [Directions] | TBA | 8:00am | JV game to Litchfield 8:00am departure |
| TBA | JV Baseball | Northwestern | Home - Walker Field [Directions] | TBA | ||
| TBA | V Boys Cross Country | Nonnewaug, Terryville | Home - Gilbert [Directions] | 4:00 p.m. | ||
| TBA | JV Boys Soccer | Thomaston | Home - Rowley Field [Directions] | TBA | ||
| TBA | JV Boys Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | TBA | ||
| TBA | V Boys Swimming and Diving | Wamogo, Lewis Mills | Home [Directions] | 6:30 p.m. | ||
| TBA | V Boys Swimming and Diving | Lewis Mills | Away - Malone Aquatic Center [Directions] | 7:00 p.m. | 5:15pm bus | |
| TBA | V Boys Tennis | Northwestern | Home - Gilbert [Directions] | L 0-5 [Detailed Results] | ||
| TBA | JV Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | TBA | ||
| TBA | V Girls Cross Country | Nonnewaug, Terryville | Home - Gilbert [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Wolcott Tech | Away - Toro Field [Directions] | 3:45 p.m. | Varsity Game at Oliver Wolcott Tech HS and JV game at Toro Field | |
| TBA | JV Softball | Nonnewaug | Away - Nonnewaug HS [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Nonnewaug | Home - Rowley Field [Directions] | TBA | ||
| TBA | JV Softball | Terryville | Home - Rowley Field [Directions] | TBA | ||
| TBA | JV Softball | Litchfield | Home - Rowley Field [Directions] | TBA | ||
| TBA | JV Softball | Terryville | Away - Terryville HS [Directions] | TBA | ||
| TBA | JV Softball | Litchfield | Away - Plumb Hill Field Complex [Directions] | TBA | ||
| Wed., 8/22 | V Football | Simsbury (Scrim.) | Away [Directions] | 9:00 a.m. | 2:00pm | Legeyt bus company 7:45 am 1 bus |
| Fri., 8/31 | V Football | Torrington (Scrim.) | Away - Torrington HS [Directions] | 7:00 p.m. | Students are responsable for their own transportation to and from the game | |
| Fri., 8/31 | V Girls Soccer | Torrington (Scrim.) | Away - Torrington HS [Directions] | L 5 - 2 | 2:45pm | Legeyt bus company - 2:45pm pickup |
| Fri., 8/31 | V Girls Volleyball | Torrington Christian Academy (Scrim.) | Away | 3:30 p.m. | 2:45 pm | Van for Varsity only |
| Sat., 9/1 | V Boys Soccer | Hale-Ray Jamboree | Away | 10:00 a.m. | 8:00am | Legeyt bus company - 8:00am pickup |
| Tue., 9/4 | V Boys Cross Country | BL Scrimmage | Away - Black Rock State Park Thomaston | 4:00 p.m. | 2:45 | Legeyt bus company - 2:45 pickup |
| Tue., 9/4 | V Boys Soccer | Sacred Heart (Scrim.) | Home - Walker Field [Directions] | 6:30 p.m. | Please assign officials for the game | |
| Tue., 9/4 | V Girls Cross Country | BL Scrimmage | Away - Black Rock State Park Thomaston | 4:00 p.m. | ||
| Fri., 9/7 | V Girls Soccer | Wamogo | Home - Walker Field [Directions] | W 3 - 1 | ||
| Fri., 9/7 | V Girls Volleyball | Northwestern | Away - Northwestern Gym [Directions] | L 0-3 | 3:15pm | Legeyt bus company - Activity Bus will Drop only at Regional 7 school |
| Fri., 9/7 | JV Girls Volleyball | Northwestern | Away - Northwestern Gym [Directions] | 4:00 p.m. | 3:15 pm | Legeyt bus company - Activity Bus will Drop only at Regional 7 school gym. Parent Pickup |
| Sat., 9/8 | V Boys Cross Country | Windham Invitational | Away - Windham HS | TBA | 7:30am | Legeyt bus company - 7:30 am pickup |
| Sat., 9/8 | V Football | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | W 20-7 | 10:30am | Legeyt Bus Compan 10:30am pickup Two busses |
| Sat., 9/8 | V Girls Cross Country | Windham Invitational | Away - Windham HS | TBA | ||
| Mon., 9/10 | JV Football | Old Saybrook | Home - Gilbert [Directions] | Cancelled | ||
| Mon., 9/10 | V Girls Volleyball | Terryville | Home - Gilbert HS [Directions] | L 0-3 | ||
| Mon., 9/10 | JV Girls Volleyball | Terryville | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Boys Cross Country | Northwestern, Litchfield | Away - Northwestern [Directions] | 4:00 p.m. | 3:00pm | Legeyt activity bus drop off only - Parent pickup |
| Tue., 9/11 | V Boys Soccer | Thomaston | Away - Highwood Farm [Directions] | L 2-4 | 2:45pm | Legeyt bus company - 2:45pm pickup - Varsity at Highwood Farm and JV at Nystroms Park |
| Tue., 9/11 | V Girls Cross Country | Northwestern, Litchfield | Away - Northwestern HS [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Girls Soccer | Thomaston | Home - Walker Field [Directions] | W 1-0 | ||
| Fri., 9/14 | V Football | Rockville | Away - RHS football field [Directions] | L 7-48 | 3:15pm | Legeyt bus company pickup at 3:15pm - Two busses |
| Fri., 9/14 | V Boys Soccer | Litchfield | Home - Walker Field [Directions] | L 0-5 | ||
| Fri., 9/14 | JV Boys Soccer | Litchfield | Home - Rowley Field [Directions] | Cancelled | ||
| Fri., 9/14 | V Girls Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | L 3-7 | 2:45pm | Legeyt bus company - 2:45pm pickup JV/Varsity |
| Fri., 9/14 | V Girls Volleyball | Wolcott Tech | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Fri., 9/14 | JV Girls Volleyball | Wolcott Tech | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/15 | V Boys Cross Country | Stratton Brook Invitational | Away - Stratton Brook Park Simsbury | TBA | 9:00am | Legeyt bus company - 9:00am pickup |
| Sat., 9/15 | JV Football | Rockville | Home - Gilbert [Directions] | 10:00 a.m. | ||
| Sat., 9/15 | V Girls Cross Country | Stratton Brook Invitational | Away - Stratton Brook Park Simsbury | TBA | ||
| Mon., 9/17 | V Boys Soccer | Nonnewaug | Away - Nonnewaug HS Varsity Field [Directions] | L 1-5 | 2:15pm | Legeyt Bus company - 2:15pm pickup at tennis courts - Varsity and JV go to same field |
| Tue., 9/18 | JV Boys Soccer | Nonnewaug | Away - Nonnewaug HS JV Field [Directions] | Cancelled | ||
| Tue., 9/18 | V Girls Volleyball | Jonathan Law | Away - Jonathan Law HS-Richetelli Gymnasium [Directions] | L 0-3 | 2:45pm | All-star bus company - Varsity only |
| Wed., 9/19 | V Girls Soccer | Nonnewaug | Home - Walker Field [Directions] | L 2-6 | ||
| Wed., 9/19 | V Girls Volleyball | Canton | Away - Canton H.S. [Directions] | L 2-3 | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Wed., 9/19 | JV Girls Volleyball | Canton | Away - Canton H.S. [Directions] | 4:00 p.m. | 2:45pm | |
| Fri., 9/21 | V Football | Stafford/East Windsor/Somers | Away - Stafford High, Lighted field behind school [Directions] | L 12-35 | 3:15pm | Legeyt Bus Company - Pickup at 3:15pm - Two busses |
| Fri., 9/21 | V Boys Soccer | Lewis Mills | Home - Walker Field [Directions] | L 0-7 | ||
| Fri., 9/21 | JV Boys Soccer | Lewis Mills | Home - Walker Field [Directions] | 4:00 p.m. | ||
| Fri., 9/21 | V Girls Soccer | Lewis Mills | Away - Lewis Mills Varsity Soccer Field [Directions] | L 0-8 | 2:45pm | Legeyt bus company - 2:45pm pickup - Varsity/JV |
| Fri., 9/21 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | L 0-3 | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Fri., 9/21 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 4:00 p.m. | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Sat., 9/22 | V Boys Cross Country | Winding Trails Invitational | Away | TBA | 7:30am | Legeyt -7:30am pickup |
| Sat., 9/22 | JV Football | Stafford/East Windsor/Somers | Home - Gilbert [Directions] | 10:30 a.m. | ||
| Sat., 9/22 | V Girls Cross Country | Winding Trails Invitational | Away | TBA | ||
| Mon., 9/24 | V Boys Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | W 4-0 | 2:45pm | Legeyt bus company - Pickup 2:45pm - Varsity and JV |
| Mon., 9/24 | JV Boys Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/25 | V Girls Volleyball | Housatonic Regional | Away - Housatonic [Directions] | L 2-3 | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Tue., 9/25 | JV Girls Volleyball | Housatonic Regional | Away - Housatonic [Directions] | 4:00 p.m. | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Wed., 9/26 | V Boys Cross Country | Lewis Mills, Wamogo | Away - Lewis Mills H.S. [Directions] | 4:00 p.m. | 2:45pm | Legeyt bus company - 2:45pm pickup |
| Wed., 9/26 | V Girls Cross Country | Lewis Mills, Wamogo | Away - Lewis Mills H.S. [Directions] | 4:00 p.m. | ||
| Wed., 9/26 | V Girls Volleyball | Aerospace | Away - Academy of Aerospace and Engineering [Directions] | W 3-2 | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Wed., 9/26 | JV Girls Volleyball | Aerospace | Away - Academy of Aerospace and Engineering [Directions] | 4:00 p.m. | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Fri., 9/28 | JV Girls Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | Cancelled | ||
| Fri., 9/28 | V Girls Volleyball | Lewis Mills | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Fri., 9/28 | JV Girls Volleyball | Lewis Mills | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/29 | V Football | Canton | Home - Gilbert [Directions] | W 45-14 | ||
| Mon., 10/1 | JV Football | Canton | Away - Canton H.S. Grass [Directions] | 3:45 p.m. | 2:45pm | Legeyt bus company - 1 bus for JV game |
| Mon., 10/1 | V Boys Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | L 1-4 | 3:15pm | No bus provided - Student find transportation to the game |
| Mon., 10/1 | JV Boys Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | 4:30 p.m. | 3:15 | Legeyt activity bus - second loop pickup after dropping student off at walker/rawly |
| Tue., 10/2 | V Boys Soccer | Shepaug Valley | Away - Shepaug Valley Varsity Soccer Field [Directions] | L 0-1 | 2:15pm | Legeyt bus company - 2:15pm pickup at tennis courts. |
| Tue., 10/2 | JV Boys Soccer | Shepaug Valley | Away - Shepaug Valley HS JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/2 | V Girls Volleyball | Northwestern | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Tue., 10/2 | JV Girls Volleyball | Northwestern | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/4 | V Boys Soccer | Terryville | Home - Walker Field [Directions] | L 2-3 | ||
| Thu., 10/4 | JV Boys Soccer | Terryville | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Thu., 10/4 | V Girls Soccer | Terryville | Away - Terryville HS [Directions] | W 4-3 | 2:45pm | legeyt bus company - 2:45pm pickup JV/Varsity |
| Sat., 10/6 | V Boys Cross Country | Wickham Invitational | Away - Wickham Park East Hartford | TBA | TBD | Legeyt bus company - waiting on a time for the event |
| Sat., 10/6 | V Football | Windsor Locks/Suffield/East Granby | Home - Gilbert [Directions] | L 14-27 | ||
| Sat., 10/6 | V Girls Cross Country | Wickham Invitational | Away - Wickham Park East Hartford | TBA | ||
| Mon., 10/8 | JV Football | Windsor Locks/Suffield/East Granby | Away - Windsor Locks HS [Directions] | 11:00 a.m. | 9:00am | Legeyt bus company - 9:00am pickup - 1 bus |
| Tue., 10/9 | V Boys Cross Country | Shepaug Valley, Thomaston | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Boys Soccer | Wamogo | Home - Walker Field [Directions] | T 1-1 | ||
| Tue., 10/9 | JV Boys Soccer | Wamogo | Home - Walker Field [Directions] | 5:00 p.m. | ||
| Tue., 10/9 | V Girls Cross Country | Shepaug Valley, Thomaston | Home - Gilbert [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Girls Soccer | Wamogo | Away - Wamogo Varsity Soccer Field [Directions] | W 4-3 | 2:45pm | legeyt bus company - 2:45pm pickup |
| Tue., 10/9 | V Girls Volleyball | Terryville | Away - Terryville HS [Directions] | L 0-3 | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Tue., 10/9 | JV Girls Volleyball | Terryville | Away - Terryville HS [Directions] | 4:00 p.m. | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Thu., 10/11 | JV Girls Soccer | Thomaston | Away - Nystroms Park [Directions] | Cancelled | ||
| Thu., 10/11 | V Girls Volleyball | International | Away - MLC [Directions] | W 3-0 | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Thu., 10/11 | JV Girls Volleyball | International | Away - MLC [Directions] | 4:00 p.m. | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Mon., 10/15 | V Boys Cross Country | Housatonic Regional | Away - Housatonic [Directions] | 4:00 p.m. | 2:45pm | legeyt bus company - 2:45pm pickup |
| Mon., 10/15 | V Girls Cross Country | Housatonic Regional | Away - Housatonic [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | V Boys Soccer | Litchfield | Away - Plumb Hill Field Complex [Directions] | L 0-7 | 2:45pm | legeyt bus company - 2:45pm pickup |
| Tue., 10/16 | V Girls Soccer | Litchfield | Home - Walker Field [Directions] | L 0-4 | ||
| Tue., 10/16 | V Girls Volleyball | O'Brien Tech | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Tue., 10/16 | JV Girls Volleyball | O'Brien Tech | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/17 | V Girls Soccer | Shepaug Valley | Home - Walker Field [Directions] | T 2-2 | ||
| Wed., 10/17 | V Girls Volleyball | Jonathan Law | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Wed., 10/17 | JV Girls Volleyball | Jonathan Law | Home - Gilbert Gym [Directions] | 5:00 p.m. | ||
| Thu., 10/18 | V Girls Soccer | Northwestern | Away - Northwestern Varsity Field [Directions] | L 0-1 | 2:45pm | Legeyt bus company - Activity bus double loop - 3:00pm activity bus will bring JV players to Regional - Varsity can take bus or have own transportation to the game. |
| Fri., 10/19 | V Boys Cross Country | BL Championships | Away - Black Rock State Park Thomaston | 3:30 p.m. | 2:30 pm | legeyt bus company - 2:30pm pickup at bottom of the hill near tennis courts |
| Fri., 10/19 | V Boys Cross Country | BL Championships Rain Date | Away - Black Rock State Park Thomaston | 3:30 p.m. | ||
| Fri., 10/19 | V Football | Coventry/Windham Tech/Bolton/Lyman | Away - Coventry HS [Directions] | W 42-24 | 3:45pm | Legeyt bus company - 3:45pm pickup - 2 busses |
| Fri., 10/19 | V Boys Soccer | Housatonic Regional | Away - Housatonic [Directions] | L 0-8 | 2:45pm | Legeyt bus company - 2:45pm pickup |
| Fri., 10/19 | JV Boys Soccer | Housatonic Regional | Away - Housatonic [Directions] | Cancelled | ||
| Fri., 10/19 | V Girls Cross Country | BL Championships | Away - Black Rock State Park Thomaston | 3:30 p.m. | ||
| Fri., 10/19 | V Girls Cross Country | BL Championships Rain Date | Away - Black Rock State Park Thomaston | 3:30 p.m. | ||
| Fri., 10/19 | V Girls Soccer | Housatonic Regional | Home - Walker Field [Directions] | L 0-7 | ||
| Fri., 10/19 | V Girls Volleyball | Goodwin Tech | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Fri., 10/19 | JV Girls Volleyball | Goodwin Tech | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/20 | JV Football | Coventry/Windham Tech/Bolton/Lyman | Home - Gilbert [Directions] | 10:00 a.m. | ||
| Tue., 10/23 | V Boys Soccer | Shepaug Valley | Home - Walker Field [Directions] | T 1-1 | ||
| Tue., 10/23 | JV Boys Soccer | Shepaug Valley | Home - Rowley Field [Directions] | Cancelled | ||
| Tue., 10/23 | V Girls Soccer | Shepaug Valley | Away - Shepaug Valley Varsity Soccer Field [Directions] | L 2-3 | 2:15pm | legeyt bus company - 2:15pm pickup next to tennis courts |
| Tue., 10/23 | V Girls Volleyball | Nonnewaug | Home - Gilbert Gym [Directions] | L 0-3 | ||
| Tue., 10/23 | JV Girls Volleyball | Nonnewaug | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/24 | V Boys Soccer | Housatonic Regional | Home - Walker Field [Directions] | L 1-0 | 2:40pm | Legeyt - Pickup 2:40pm |
| Wed., 10/24 | JV Boys Soccer | Housatonic Regional | Home - Rowley Field [Directions] | Cancelled | ||
| Wed., 10/24 | V Girls Soccer | Housatonic Regional | Away - Housatonic [Directions] | L 0-7 | 2:45pm | legeyt bus company - 2:45pm - JV/Varsity |
| Wed., 10/24 | V Girls Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | L 2-3 | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Wed., 10/24 | JV Girls Volleyball | Wolcott Tech | Away - Wolcott Tech Gym [Directions] | 4:00 p.m. | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Thu., 10/25 | V Boys Soccer | Thomaston | Home - Walker Field [Directions] | L 3-1 | ||
| Thu., 10/25 | V Girls Soccer | Thomaston | Away - Nystroms Park [Directions] | L 0-2 | 2:45pm | Legeyt bus company - 2:45pm pickup - Varsity at Highwood Farm JV at Nystroms Park |
| Fri., 10/26 | V Football | Ellington | Home - Torrington HS Turf Football Field [Directions] | W 23-0 | Homecoming | |
| Fri., 10/26 | V Boys Soccer | Terryville | Away - Terryville HS [Directions] | L 0-2 | 2:45pm | Legeyt bus company - 2:45pm pickup - Varsity at New terryville HS JV at Upper fisher field |
| Fri., 10/26 | JV Boys Soccer | Terryville | Away - Upper Fisher Field [Directions] | Cancelled | ||
| Fri., 10/26 | V Girls Soccer | Terryville | Home - Walker Field [Directions] | T 2-2 | ||
| Fri., 10/26 | V Girls Volleyball | Housatonic Regional | Home - Gilbert Gym [Directions] | W 3-1 | ||
| Fri., 10/26 | JV Girls Volleyball | Housatonic Regional | Home - Gilbert Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/27 | V Boys Cross Country | CIAC Class S Championships | Away - Wickham Park East Hartford | TBA | tbd | Legeyt bus company - pickup TBD |
| Sat., 10/27 | V Girls Cross Country | CIAC Class S Championships | Away - Wickham Park East Hartford | TBA | ||
| Mon., 10/29 | JV Football | Ellington | Away - Ellington HS [Directions] | 3:45 p.m. | 2:15pm | Legeyt - Pickup at Regional for 2:15pm and then go to Gilbert to pick up players and coaches. |
| Mon., 10/29 | V Girls Soccer | Northwestern | Home - Walker Field [Directions] | L 0-6 | ||
| Mon., 10/29 | JV Girls Soccer | Northwestern | Home - Walker Field [Directions] | Cancelled | ||
| Tue., 10/30 | V Boys Soccer | Northwestern | Home - Walker Field [Directions] | L 1-3 | ||
| Tue., 10/30 | JV Boys Soccer | Northwestern | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Tue., 10/30 | V Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | L 0-3 | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Tue., 10/30 | JV Girls Volleyball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 4:00 p.m. | 2:45pm | All-Star Bus Pickup 2:45pm Varsity and JV |
| Fri., 11/2 | V Boys Cross Country | CIAC State Open Championships | Away | TBA | TBD | Legeyt bus company - TBD |
| Fri., 11/2 | V Football | Granby/Canton | Away - Granby Memorial HS [Directions] | L 0-39 | 4:30pm | Legeyt bus company - 4:30pm pickup - 2 busses |
| Fri., 11/2 | V Girls Cross Country | CIAC State Open Championships | Away | TBA | ||
| Sat., 11/3 | JV Football | Granby/Canton | Away - Granby Memorial HS [Directions] | 10:00 a.m. | ||
| Sat., 11/10 | V Boys Cross Country | New England Championships | Away | TBA | TBD | Legeyt bus company - TBD |
| Sat., 11/10 | V Football | SMSA Coop | Home - Gilbert [Directions] | L 0-20 | ||
| Sat., 11/10 | V Girls Cross Country | New England Championships | Away | TBA | ||
| Mon., 11/12 | JV Football | SMSA Coop | Home - Gilbert [Directions] | 3:00 p.m. | ||
| Fri., 11/23 | V Football | WCA | Home - Gilbert [Directions] | L 21-62 | ||
| Mon., 12/3 | V Boys Basketball | Ansonia (Scrim.) | Home - Gilbert [Directions] | 6:00 p.m. | ||
| Tue., 12/4 | V Girls Basketball | Avon (Scrim.) | Home - Gilbert [Directions] | 3:45 p.m. | ||
| Wed., 12/5 | V Boys Basketball | Monument Mountain (MA) (Scrim.) | Home - Gilbert [Directions] | 6:00 p.m. | ||
| Thu., 12/6 | V Girls Basketball | Torrington (Scrim.) | Home - Gilbert [Directions] | 3:00 p.m. | ||
| Fri., 12/7 | V Boys Basketball | Oxford (Scrim.) | Away - OHS-Main Gym [Directions] | 6:00 p.m. | 4:40pm | |
| Mon., 12/10 | V Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | W 48-33 | 4:15pm | |
| Mon., 12/10 | JV Girls Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 12/12 | V Wrestling | Thomaston | Home - Gilbert [Directions] | 5:00 p.m. | 4:30pm Weigh in | |
| Wed., 12/12 | V Girls Basketball | Achievement First | Away - Achievement First HS [Directions] | W 51-3 | 5:15pm | |
| Fri., 12/14 | V Boys Basketball | Nonnewaug | Home - Gilbert [Directions] | L 50-63 | ||
| Fri., 12/14 | JV Boys Basketball | Nonnewaug | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Fri., 12/14 | V Boys Swimming and Diving | Berkshire League Relays | Away - Shepaug HS | 3:30 p.m. | 2:15pm bus | 2:00 pm Dismal 2:15pm bus |
| Fri., 12/14 | V Girls Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | W 39-33 | 3:00pm | |
| Fri., 12/14 | JV Girls Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/15 | V Wrestling | Pawling (NY) Tournament | Away | 9:00 a.m. | 6:30am | 7:30am to 8:30am weigh in (6:30am bus) |
| Tue., 12/18 | V Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | L 53-72 | 4:15pm | |
| Tue., 12/18 | JV Boys Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | 5:30 p.m. | ||
| Tue., 12/18 | V Girls Basketball | Wamogo | Home - Gilbert [Directions] | W 50-32 | ||
| Tue., 12/18 | JV Girls Basketball | Wamogo | Home - Gilbert [Directions] | Cancelled | ||
| Wed., 12/19 | V Wrestling | Terryville-Thomaston | Away - Terryville HS [Directions] | 6:30 p.m. | 5:00pm | 5:30pm weigh in (5:00pm bus departure) |
| Thu., 12/20 | V Boys Swimming and Diving | Woodland | Away - Woodland HS Pool [Directions] | 4:30 p.m. | ||
| Fri., 12/21 | V Boys Basketball | Lewis Mills | Home - Gilbert [Directions] | W 57-55 | ||
| Fri., 12/21 | JV Boys Basketball | Lewis Mills | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Fri., 12/21 | V Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | L 50-42 | 4:15pm | |
| Fri., 12/21 | JV Girls Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | ||
| Sat., 12/22 | V Boys Indoor Track | Hillhouse | Away - Hillhouse | TBA | 8:00am | 8:00am bus pickup - Legeyt |
| Sat., 12/22 | V Wrestling | SACHEM Duals | Away | 9:00 a.m. | 7:00am | 8:00am weigh in |
| Sat., 12/22 | V Girls Indoor Track | Hillhouse Qualifier | Away - Hillhouse Qualifier - Hillhouse | TBA | 8:00am | 8:00am bus to Hillhouse |
| Wed., 12/26 | V Wrestling | Northwestern | Away - NWR-7 Gym [Directions] | 6:00 p.m. | 5:30 pm weigh in | |
| Thu., 12/27 | V Girls Basketball | Torrington | Home - Gilbert [Directions] | W 42-35 | ||
| Fri., 12/28 | V Boys Basketball | O'Brien Tech | Home - Gilbert [Directions] | W 63-54 | ||
| Fri., 12/28 | JV Boys Basketball | O'Brien Tech | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Fri., 12/28 | V Boys Swimming and Diving | Lewis Mills | Home [Directions] | 7:30 p.m. | ||
| Sat., 12/29 | V Boys Swimming and Diving | Northwestern | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 12/29 | V Boys Swimming and Diving | Gilbert | Away - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 12/29 | V Wrestling | Jonathan Law Duals | Away | 9:00 a.m. | 6:30am | 7:30am Weigh In (6:30am bus departure) |
| Wed., 1/2 | V Boys Basketball | Terryville | Home - Gilbert [Directions] | W 49-45 | ||
| Wed., 1/2 | JV Boys Basketball | Terryville | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Wed., 1/2 | V Girls Basketball | Terryville | Away - Terryville HS [Directions] | W 46-37 | 4:15pm | 4:15pm Bus |
| Wed., 1/2 | JV Girls Basketball | Terryville | Away - Terryville HS [Directions] | Cancelled | ||
| Fri., 1/4 | V Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | L 42-69 | 4:15pm | 4:15pm Bus |
| Fri., 1/4 | JV Boys Basketball | Litchfield | Away - Litchfield HS [Directions] | 5:30 p.m. | ||
| Fri., 1/4 | V Boys Swimming and Diving | Litchfield | Away - CJR Pool [Directions] | 3:15 p.m. | 2:45pm | 2:45pm Bus |
| Fri., 1/4 | V Girls Basketball | Litchfield | Home - Gilbert [Directions] | W 48-27 | ||
| Fri., 1/4 | JV Girls Basketball | Litchfield | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Sat., 1/5 | V Boys Indoor Track | James Barber | Away - SCSU | TBA | shared bus with Regional 10:00am departure | |
| Sat., 1/5 | V Boys Swimming and Diving | Nonnewaug | Home - Winsted YMCA [Directions] | 4:30 p.m. | YMCA | |
| Sat., 1/5 | V Wrestling | Mt. Anthony Wrestling Tournament - Bennington, VT | Away - Mount Anthony Union HS | 8:30 a.m. | 6:15 am | 6:30 am bus??? |
| Sat., 1/5 | V Girls Indoor Track | James Barber | Away - SCSU | 11:00 a.m. | 10:00am | Shared bus with Regional 10:00am departure |
| Mon., 1/7 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Tue., 1/8 | V Girls Basketball | Housatonic Regional | Home - Gilbert [Directions] | L 38-49 | ||
| Tue., 1/8 | JV Girls Basketball | Housatonic Regional | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Wed., 1/9 | V Boys Basketball | Housatonic Regional | Away - Housatonic [Directions] | W 78-65 | 4:00pm | 4:00pm bus |
| Wed., 1/9 | JV Boys Basketball | Housatonic Regional | Away - Housatonic [Directions] | 5:30 p.m. | ||
| Wed., 1/9 | V Wrestling | Nonnewaug | Home - Gilbert [Directions] | 6:00 p.m. | 5:30pm weigh in | |
| Thu., 1/10 | JV Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | 7:00 p.m. | ||
| Thu., 1/10 | V Boys Indoor Track | Wesleyan Dev | Away - Wesleyan University | TBA | 2:15pm | 2:15pm bus departure |
| Thu., 1/10 | JV Girls Basketball | Northwestern | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Thu., 1/10 | V Girls Indoor Track | Wesleyan Dev | Away - Wesleyan University | 3:30 p.m. | 2:15pm | |
| Fri., 1/11 | V Boys Basketball | Northwestern | Home - Gilbert Gym [Directions] | W 66-61 | ||
| Fri., 1/11 | V Boys Indoor Track | Yale Track Classic | Away - YALE | TBA | ||
| Fri., 1/11 | V Girls Basketball | Northwestern | Home - Gilbert [Directions] | L 52-30 | ||
| Fri., 1/11 | V Girls Indoor Track | Yale Track Classic | Away - YALE | TBA | Gilbert Van | |
| Sat., 1/12 | V Boys Indoor Track | Yale Track Classic | Away | TBA | ||
| Sat., 1/12 | V Boys Swimming and Diving | Shepaug Valley | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 1/12 | V Wrestling | Gilbert Duals | Home - Gilbert [Directions] | 10:00 a.m. | 9:30am weigh in | |
| Sat., 1/12 | V Girls Indoor Track | Yale Track Classic | Away - YALE | TBA | Gilbert Van | |
| Tue., 1/15 | V Boys Basketball | Shepaug Valley | Home - Gilbert [Directions] | W 76-72 | ||
| Tue., 1/15 | JV Boys Basketball | Shepaug Valley | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Tue., 1/15 | V Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | L 45-32 | 4:00pm | 4:00pm bus |
| Tue., 1/15 | JV Girls Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/16 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Pool [Directions] | 7:30 p.m. | ||
| Wed., 1/16 | V Wrestling | Derby/Oxford/Holy Cross | Home - Gilbert [Directions] | 6:00 p.m. | 5:30pm weigh in | |
| Fri., 1/18 | V Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | L 58-69 | 4:15pm | 4:15pm bus |
| Fri., 1/18 | JV Boys Basketball | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/18 | V Boys Indoor Track | HK Invite | Away - HK-Invite Hillhouse | TBA | share bus with Regional 3:00pm departure | |
| Fri., 1/18 | V Boys Swimming and Diving | Housatonic Regional | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Fri., 1/18 | V Wrestling | Avon, Farmington, Terryville-Thomaston | Away - Avon HS--Gym Two [Directions] | 4:00 p.m. | 2:45pm | 2:45pm bus |
| Fri., 1/18 | V Girls Basketball | Thomaston | Home - Gilbert [Directions] | W 45-33 | ||
| Fri., 1/18 | JV Girls Basketball | Thomaston | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Fri., 1/18 | V Girls Indoor Track | HK- Invite | Away - HillHouse | 4:00 p.m. | ||
| Sat., 1/19 | V Boys Basketball | Capital Prep | Away - Capital Preparatory Magnet School [Directions] | L 43-71 | 2:45pm | 2:45pm bus |
| Sat., 1/19 | JV Boys Basketball | Northwestern | Home - Gilbert [Directions] | 11:30 a.m. | JV/Freshman | |
| Sat., 1/19 | JV Boys Basketball | Capital Prep | Away - Capital Preparatory Magnet School [Directions] | Cancelled | ||
| Sat., 1/19 | V Boys Swimming and Diving | Litchfield | Home - Winsted YMCA [Directions] | 2:30 p.m. | ||
| Sat., 1/19 | JV Girls Basketball | Northwestern | Home - Gilbert [Directions] | 10:00 a.m. | JV/Freshman game | |
| Tue., 1/22 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | L 50-70 | 3:00pm bus | 3:00pm bus |
| Tue., 1/22 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/22 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS Pool [Directions] | 4:30 p.m. | 3:00pm | 3:00 pm bus |
| Tue., 1/22 | V Wrestling | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | 5:30 bus | 6:15pm weigh in (5:30pm bus) |
| Tue., 1/22 | V Girls Basketball | Nonnewaug | Home - Gilbert [Directions] | W 48-38 | ||
| Tue., 1/22 | JV Girls Basketball | Nonnewaug | Home - Gilbert [Directions] | 4:30 p.m. | ||
| Wed., 1/23 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss [Directions] | 5:30 p.m. | 4:00pm | 4:00pm bus |
| Thu., 1/24 | V Boys Swimming and Diving | Nonnewaug | Away - Crosby HS [Directions] | 5:00 p.m. | ||
| Fri., 1/25 | V Boys Basketball | Wamogo | Home - Gilbert [Directions] | L 61-91 | ||
| Fri., 1/25 | JV Boys Basketball | Wamogo | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Fri., 1/25 | V Girls Basketball | Wamogo | Away - Wamogo Gym 1 (Large Gym) [Directions] | W 33-32 | 4:15pm | 4:15pm Bus |
| Sat., 1/26 | V Boys Indoor Track | BL Outdoor - Litchfield | Away - BL Outdoor - Litchfield | Cancelled | Van or Parent ride | |
| Sat., 1/26 | V Boys Swimming and Diving | Wamogo | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 1/26 | V Boys Swimming and Diving | Litchfield, Granby Memorial | Home - Winsted YMCA [Directions] | 6:30 p.m. | ||
| Sat., 1/26 | V Wrestling | Portland Tournament | Away | 9:00 a.m. | 7:00am | 8:00am weigh in (6:15am bus) |
| Sat., 1/26 | V Girls Indoor Track | BL - Outdoor | Away - BL Outdoor - Litchfield | Cancelled | Van or Parents | |
| Mon., 1/28 | V Boys Swimming and Diving | Lewis Mills | Home - Winsted YMCA [Directions] | 8:15 p.m. | ||
| Thu., 1/31 | V Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | L 64-61 | 4:15pm | 4:15pm bus |
| Thu., 1/31 | JV Boys Basketball | Lewis Mills | Away - Lewis Mills Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/31 | V Wrestling | Oxford | Home - Gilbert [Directions] | 6:00 p.m. | 5:30pm weigh in | |
| Fri., 2/1 | V Boys Basketball | Litchfield | Home - Gilbert [Directions] | W 68-67(OT) | ||
| Fri., 2/1 | JV Boys Basketball | Litchfield | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Fri., 2/1 | V Boys Swimming and Diving | Wamogo | Away - Shepaug Pool [Directions] | 7:30 p.m. | 6:00pm | 6:00pm Bus |
| Fri., 2/1 | V Boys Swimming and Diving | Housatonic Regional | Home - Winsted YMCA [Directions] | 7:30 p.m. | ||
| Fri., 2/1 | V Girls Basketball | Litchfield | Away - Litchfield HS [Directions] | W 42-28 | 4:15pm | 4:15pm bus |
| Fri., 2/1 | JV Girls Basketball | Litchfield | Away - Litchfield HS [Directions] | 5:30 p.m. | ||
| Sat., 2/2 | V Boys Swimming and Diving | Nonnewaug | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 2/2 | V Wrestling | TBD Tournament | Away | TBA | ?? | ?? |
| Sat., 2/2 | V Girls Basketball | Lewis Mills | Home - Gilbert [Directions] | W 30-27 | ||
| Sat., 2/2 | JV Girls Basketball | Lewis Mills | Home - Gilbert [Directions] | 4:15 p.m. | ||
| Mon., 2/4 | V Boys Indoor Track | Last Chance Meet - Hillhouse | Away - Last Chance Meet - Hillhouse | TBA | 3:00pm shared bus with regional | Share bus with Regional 3:00pm departure |
| Mon., 2/4 | V Girls Indoor Track | Last Chance Meet - Hillhouse | Away - Hillhouse | TBA | Shared bus with Regional - 3:00pm departure | |
| Tue., 2/5 | V Boys Basketball | Housatonic Regional | Home - Gilbert [Directions] | W 83-76 | ||
| Tue., 2/5 | JV Boys Basketball | Housatonic Regional | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Tue., 2/5 | V Boys Swimming and Diving | Litchfield | Away - Shepaug Pool [Directions] | 7:30 p.m. | ||
| Tue., 2/5 | V Girls Basketball | Housatonic Regional | Away - Housatonic [Directions] | L 24-48 | 4:00pm | 4:00pm bus |
| Tue., 2/5 | JV Girls Basketball | Housatonic Regional | Away - Housatonic [Directions] | 5:30 p.m. | ||
| Wed., 2/6 | V Boys Swimming and Diving | Housatonic Regional | Away - Hotchkiss [Directions] | 4:30 p.m. | ||
| Wed., 2/6 | V Wrestling | Portland/Cromwell | Home [Directions] | 6:30 p.m. | ||
| Thu., 2/7 | V Boys Indoor Track | Class S Championships | Away | TBA | ||
| Thu., 2/7 | V Boys Swimming and Diving | Nonnewaug | Away - Crosby HS [Directions] | 5:00 p.m. | 3:45pm | 3:45pm bus |
| Thu., 2/7 | V Girls Indoor Track | Class S championship | Away - Hillhouse | TBA | ||
| Fri., 2/8 | V Boys Basketball | Northwestern | Away - Northwestern Home [Directions] | W 67-51 | Students arrange own transportation to Regional | |
| Fri., 2/8 | JV Boys Basketball | Northwestern | Away - Northwestern Home [Directions] | 4:30 p.m. | Students arrange own transportation to Regional | |
| Fri., 2/8 | V Boys Swimming and Diving | Torrington | Home - Winsted YMCA [Directions] | 7:00 p.m. | ||
| Fri., 2/8 | V Girls Basketball | Northwestern | Away - NWR-7 Gym [Directions] | L 50-41 | Students arrange own transportation to Regional | |
| Fri., 2/8 | JV Girls Basketball | Northwestern | Away - NWR-7 Gym [Directions] | 3:00 p.m. | Students arrange own transportation to Regional | |
| Sat., 2/9 | V Boys Swimming and Diving | Shepaug Valley, Wamogo | Home [Directions] | 4:30 p.m. | ||
| Sat., 2/9 | V Wrestling | BL/NVL League Tournament - Gilbert School | Home - Gilbert [Directions] | 10:00 a.m. | 8:30am weigh in | |
| Wed., 2/13 | V Boys Basketball | Terryville | Away - Terryville HS [Directions] | L 61-74 | 4:15pm | 4:15pm bus |
| Wed., 2/13 | JV Boys Basketball | Terryville | Away - Terryville HS [Directions] | 5:30 p.m. | ||
| Wed., 2/13 | V Boys Swimming and Diving | Shepaug Valley | Away - Shepaug Valley HS Pool [Directions] | 4:30 p.m. | ||
| Wed., 2/13 | V Girls Basketball | Terryville | Home - Gilbert [Directions] | W 47-35 | ||
| Wed., 2/13 | JV Girls Basketball | Terryville | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Thu., 2/14 | V Girls Basketball | Shepaug Valley | Home - Gilbert [Directions] | W 42-24 | ||
| Thu., 2/14 | JV Girls Basketball | Shepaug Valley | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Fri., 2/15 | V Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | L 76-84 | 4:00pm | 4:00pm bus |
| Fri., 2/15 | JV Boys Basketball | Shepaug Valley | Away - Ted Alex Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/15 | V Wrestling | State Tournament | Away | TBA | TBD | bus time TBD |
| Sat., 2/16 | JV Boys Basketball | Northwestern | Home - Gilbert [Directions] | Cancelled | ||
| Sat., 2/16 | V Boys Swimming and Diving | Northwestern | Away - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 2/16 | V Boys Swimming and Diving | Gilbert | Home - Winsted YMCA [Directions] | 4:30 p.m. | ||
| Sat., 2/16 | V Wrestling | State Tournament | Away | TBA | TBD | bus TBD |
| Sat., 2/16 | V Girls Basketball | TBD | Home - Gilbert [Directions] | 6:00 p.m. | BL Tournament Game | |
| Thu., 2/21 | V Boys Basketball | Thomaston | Home - Gilbert [Directions] | W 90-64 | ||
| Thu., 2/21 | JV Boys Basketball | Thomaston | Home - Gilbert [Directions] | 5:30 p.m. | ||
| Fri., 2/22 | V Wrestling | State Open Tournament | Away | TBA | TBD | bus TBD |
| Sat., 2/23 | V Boys Swimming and Diving | Splash Event | Away - Planville (Splash Event) | TBA | TBA | Share bus with Regional |
| Sat., 2/23 | V Boys Swimming and Diving | Splash Classic | Away | TBA | ||
| Sat., 2/23 | V Wrestling | State Open Tournament | Away | TBA | TBD | bus TBD |
| Mon., 2/25 | V Girls Basketball | Windsor Locks | Home - Gilbert [Directions] | 7:00 p.m. | CIAC First Round | |
| Fri., 3/1 | V Boys Swimming and Diving | BL Diving | Away | TBA | ||
| Fri., 3/1 | V Wrestling | New England Tournament | Away | TBA | ||
| Sat., 3/2 | V Boys Swimming and Diving | Berkshire League Championship | Away - Hotchkiss | TBA | TBA | TBA bus time |
| Sun., 3/3 | V Boys Swimming and Diving | BL Swim Championships | Away - Hotchkiss | 1:00 p.m. | ||
| Thu., 3/7 | V Boys Swimming and Diving | State Diving | Away | TBA | ||
| Sat., 3/9 | V Boys Swimming and Diving | State Trials | Away | TBA | ||
| Mon., 3/11 | V Boys Swimming and Diving | Tournament Game - Opponent Not Known | Away | 5:00 p.m. | ||
| Thu., 3/14 | V Boys Swimming and Diving | Opens | Away - Yale | 7:00 p.m. | ||
| Tue., 3/26 | V Baseball | Avon (Scrim.) | Away - Avon HS [Directions] | 3:45 p.m. | 2:30pm | 2:30pm bus departs bottom of the hill |
| Thu., 3/28 | V Baseball | Naugatuck (Scrim.) | Away - Naugatuck HS [Directions] | 3:45 p.m. | ||
| Mon., 4/1 | V Baseball | Shepaug Valley | Away - Ted Alex Field [Directions] | L 3-2 | 2:30pm | 2:30pm bus departs bottom of the hill |
| Mon., 4/1 | V Softball | Shepaug Valley | Home - Rowley Field [Directions] | L 21-4 | ||
| Tue., 4/2 | V Boys Outdoor Track | Thomaston, Shepaug Valley | Away - Nystroms Park [Directions] | 4:00 p.m. | 2:45pm | 2:45pm Departure |
| Tue., 4/2 | V Girls Outdoor Track | Thomaston, Shepaug Valley | Away - Nystroms Park [Directions] | 4:00 p.m. | 2:45pm | 2:45pm pickup |
| Wed., 4/3 | V Baseball | Wamogo | Home - Walker Field [Directions] | W 7-6(8) | ||
| Wed., 4/3 | V Boys Golf | Lewis Mills | Away - Fairview [Directions] | Lewis Mills 195 Gilbert 233 | 2:15pm departure - School Van | |
| Wed., 4/3 | V Boys Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | L 1-4 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Wed., 4/3 | V Softball | Wamogo/Litchfield | Home - Rowley Field [Directions] | L 20-1 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Wed., 4/3 | V Girls Tennis | Lewis Mills | Home - Gilbert [Directions] | L 0-7 | ||
| Sat., 4/6 | V Baseball | Northwestern | Home - Walker Field [Directions] | L 2-4 | ||
| Tue., 4/9 | V Baseball | Nonnewaug | Away - Nonnewaug Varsity Baseball Field [Directions] | L 11-0(5) | 2:30pm | 2:30 pm bus departs bottom of the hill |
| Tue., 4/9 | V Boys Outdoor Track | Terryville | Away [Directions] | 4:00 p.m. | 2:45pm | 2:45pm departure |
| Tue., 4/9 | V Girls Outdoor Track | Terryville | Away [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Baseball | Housatonic Regional | Home - Walker Field Winsted [Directions] | L 3-9 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Wed., 4/10 | V Boys Golf | Northwestern | Home - Greenwood Country Club [Directions] | Gilbert 188 NW 7 213 | non-league match | |
| Wed., 4/10 | V Boys Tennis | Housatonic Regional | Away - Housatonic [Directions] | L 2-3 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Wed., 4/10 | V Softball | Housatonic Regional | Home - Rowley Field [Directions] | W 17-6 | ||
| Wed., 4/10 | V Girls Tennis | Housatonic Regional | Home - Gilbert [Directions] | L 3-4 | ||
| Thu., 4/11 | V Softball | Northwestern | Away - Northwestern Varsity Field [Directions] | L 0-16 | 2:45pm | Bus Drop off only - |
| Thu., 4/11 | JV Softball | Northwestern | Away - Northwestern Field [Directions] | 3:45 p.m. | ||
| Fri., 4/12 | V Baseball | Terryville | Away - Terryville HS [Directions] | L 1-2 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Fri., 4/12 | V Boys Tennis | Litchfield | Home - Gilbert [Directions] | L 0-5 [Detailed Results] | ||
| Fri., 4/12 | V Girls Tennis | Litchfield | Away - Litchfield HS [Directions] | L 0-7 | 2:45pm | 2:45pm bus departs student lot |
| Sat., 4/13 | V Girls Tennis | Shepaug Valley | Home - Gilbert [Directions] | L 0-7 | ||
| Tue., 4/16 | V Baseball | Wolcott Tech | Home - Walker Field [Directions] | W 11-1 (6) | ||
| Tue., 4/16 | JV Baseball | Wolcott Tech | Home - Walker Field [Directions] | 3:30 p.m. | JV game to be played after the Varsity Game | |
| Tue., 4/16 | V Boys Outdoor Track | Lewis Mills, Shepaug Valley | Away - Lewis Mills Track [Directions] | 3:00 p.m. | 2:45pm | 2:45pm Departure |
| Tue., 4/16 | V Girls Outdoor Track | Lewis Mills, Shepaug Valley | Away - Lewis Mills Track [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Baseball | Lewis Mills | Home - Walker Field [Directions] | L 8-1 | ||
| Wed., 4/17 | V Girls Tennis | Wamogo | Home - Gilbert [Directions] | L 3-4 | ||
| Thu., 4/18 | V Baseball | Litchfield | Away - Litchfield HS Baseball Field [Directions] | L 6-8 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Thu., 4/18 | V Boys Golf | Northwestern | Away - Greenwood Country Club [Directions] | 11:00 a.m. | NON-League Match | |
| Tue., 4/23 | V Baseball | Thomaston | Home - Walker Field [Directions] | L 2-12 (10) | ||
| Tue., 4/23 | V Boys Outdoor Track | Thomaston, Litchfield | Away - Nystroms Park [Directions] | 4:00 p.m. | 2:45pm | 2:45pm Departure |
| Tue., 4/23 | V Boys Tennis | Thomaston | Home - Gilbert [Directions] | W 3-2 [Detailed Results] | ||
| Tue., 4/23 | V Girls Outdoor Track | Thomaston, Litchfield | Away - Nystroms Park [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Softball | Thomaston | Away - Bev Lowden Softball Field (T.H.S.) [Directions] | L 5-12 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Tue., 4/23 | V Girls Tennis | Thomaston | Away - Nystroms Park [Directions] | W 6-1 | 2:45pm | 2:45pm pickup bottom of the hill |
| Wed., 4/24 | V Boys Golf | Terryville, Lewis Mills | Away [Directions] | Gilbert 180 Mills 173 Terry/Thom 204 | ||
| Thu., 4/25 | V Baseball | Shepaug Valley | Home - Walker Field [Directions] | L 15-0 (5) | ||
| Thu., 4/25 | V Boys Golf | Litchfield | Away - Litchfield Country Club [Directions] | Gilbert 182 Litchfield 220 | ||
| Thu., 4/25 | V Softball | Shepaug Valley | Away - Dick Ayer Field [Directions] | L 1-16 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Thu., 4/25 | V Girls Tennis | Nonnewaug | Away - Edgewood Tennis and Bath [Directions] | L 1-6 | 8:30am | 8:30am bus departs Gilbert |
| Mon., 4/29 | V Baseball | Wamogo | Away - New Britain Stadium [Directions] | L 4-0 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Mon., 4/29 | V Boys Golf | Housatonic Regional, Wolcott Tech | Home - Greenwood Country Club [Directions] | Gilbert 178 Housatonic 203 | ||
| Mon., 4/29 | V Boys Tennis | Shepaug Valley | Home - Gilbert [Directions] | L 0-5 [Detailed Results] | ||
| Mon., 4/29 | V Softball | Wamogo/Litchfield | Away - Wamogo HS [Directions] | L 0-15 | ||
| Mon., 4/29 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS Courts [Directions] | L 0-7 | 2:30pm | Student Dismiss 2:15pm bus departs 2:30pm bottom of the hill |
| Tue., 4/30 | V Boys Outdoor Track | Nonnewaug | Home - Regional 7 [Directions] | 4:00 p.m. | 2:45pm | 2:45pm Departure - Drop only |
| Tue., 4/30 | V Boys Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | L 2-3 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Tue., 4/30 | V Girls Outdoor Track | Nonnewaug | Home - Regional 7 [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Softball | Terryville | Home - Rowley Field [Directions] | L 11-7 | ||
| Wed., 5/1 | V Baseball | Nonnewaug | Home - Walker Field [Directions] | L 14-2 (6) | ||
| Wed., 5/1 | V Boys Tennis | Thomaston | Away - Nystroms Park [Directions] | W 3-2 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Wed., 5/1 | V Softball | Nonnewaug | Away - Nonnewaug Varsity Softball Field [Directions] | L 0-12 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Wed., 5/1 | V Girls Tennis | Thomaston | Home - Gilbert [Directions] | W 6-1 | ||
| Thu., 5/2 | V Softball | Litchfield | Home - Rowley Field [Directions] | W 12-6 | ||
| Fri., 5/3 | V Boys Tennis | Housatonic Regional | Home - Gilbert [Directions] | L 1-4 [Detailed Results] | ||
| Fri., 5/3 | V Girls Tennis | Housatonic Regional | Away - Housatonic [Directions] | L 3-4 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Sat., 5/4 | V Boys Tennis | Shepaug Valley | Away - Shepaug Valley HS Courts [Directions] | L 2-3 | 2:30pm | 2:30pm bus departs bottom of the hill |
| Mon., 5/6 | V Baseball | Housatonic Regional | Away - Housatonic [Directions] | L 6-5 (10) | ||
| Mon., 5/6 | V Boys Golf | Nonnewaug, Wamogo | Away - Heritage Village CC [Directions] | Gilbert 183 Nonnewaug 239 Wamogo 223 | ||
| Mon., 5/6 | V Boys Tennis | Litchfield | Away - Litchfield HS [Directions] | L 0-5 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Mon., 5/6 | V Softball | Housatonic Regional | Away - Housatonic [Directions] | W 10-2 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Mon., 5/6 | V Girls Tennis | Litchfield | Home - Gilbert [Directions] | L 0-7 | ||
| Tue., 5/7 | V Boys Outdoor Track | Litchfield, Housatonic Regional | Away - Plumb Hill Field Complex, Litchfield [Directions] | 4:00 p.m. | 2:45pm | 2:45pm Departure |
| Tue., 5/7 | V Girls Outdoor Track | Litchfield, Housatonic Regional | Away - Plumb Hill Field Complex, Litchfield [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Softball | Wolcott Tech | Away - Wolcott Tech Softball Field [Directions] | W 15-7 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Wed., 5/8 | V Baseball | Terryville | Home - Walker Field [Directions] | L 11-4 | ||
| Wed., 5/8 | V Boys Golf | Tournament Game - Opponent Not Known | Away | TBA | Stigberg Tournament | |
| Wed., 5/8 | V Boys Tennis | Nonnewaug | Away - Edgewood Tennis & Bath [Directions] | L 0-5 | 2:30pm | 2:30pm bus departs bottom of the hill |
| Wed., 5/8 | V Boys Tennis | Nonnewaug | Home - Edgewood Tennis & Bath [Directions] | L 0-5 | ||
| Wed., 5/8 | V Softball | Terryville | Away - Terryville HS [Directions] | W 24-10 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Wed., 5/8 | V Girls Tennis | Nonnewaug | Home - Gilbert [Directions] | L 1-6 | ||
| Thu., 5/9 | V Boys Golf | Housatonic Regional, Wamogo | Away - Sharon CC [Directions] | Gilbert 188 Housatonic 194 Wamogo 235 | ||
| Thu., 5/9 | V Boys Tennis | Lewis Mills | Home - Gilbert [Directions] | L 0-5 [Detailed Results] | ||
| Thu., 5/9 | V Softball | Nonnewaug | Home - Rowley Field [Directions] | L 14-0 | ||
| Thu., 5/9 | V Girls Tennis | Lewis Mills | Away - Lewis Mills Tennis Courts [Directions] | L 1-6 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Fri., 5/10 | V Boys Tennis | Wamogo | Home - Gilbert [Directions] | L 0-5 [Detailed Results] | ||
| Fri., 5/10 | V Softball | Lewis Mills | Away - Lewis Mills Softball Field [Directions] | L 1-16 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Fri., 5/10 | JV Softball | Lewis Mills | Away - Lewis Mills Softball Field [Directions] | 3:45 p.m. | ||
| Fri., 5/10 | V Girls Tennis | Wamogo | Away - Wamogo Tennis Courts [Directions] | L 3-4 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Sat., 5/11 | V Baseball | Canton | Away - Bowdoin Field [Directions] | W 5-2 | 8:30am | Pickup at Gilbert |
| Sat., 5/11 | JV Baseball | Canton | Away - Bowdoin Field [Directions] | 12:30 p.m. | ||
| Sat., 5/11 | JV Softball | Regional Jamboree | Away - Northwestern Regional 7 | 10:00 a.m. | JV Jamboree 10:00am start (2 5 inning games) | |
| Mon., 5/13 | V Boys Tennis | Northwestern | Away - NWR-7 Tennis Courts [Directions] | L 0-5 | 2:45pm | Activity bus- drop off only |
| Mon., 5/13 | V Girls Tennis | Northwestern | Home - Gilbert [Directions] | L 2-5 | ||
| Tue., 5/14 | V Baseball | Lewis Mills | Away - Walker Field, Gilbert [Directions] | L 7-4 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Tue., 5/14 | V Boys Golf | Shepaug Valley, Lewis Mills | Away - Lake Waramaug Country Club [Directions] | Gilbert 187 Lewis Mills 170 Sheoaug 219 | ||
| Tue., 5/14 | V Boys Outdoor Track | Northwestern, Thomaston, Wamogo | Away - Northwestern HS [Directions] | 4:00 p.m. | 2:45pm | 2:45pm Departure- Drop only |
| Tue., 5/14 | V Girls Outdoor Track | Northwestern, Thomaston, Wamogo | Away - Northwestern HS [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Softball | Lewis Mills | Home - Rowley Field [Directions] | L 9-2 | ||
| Tue., 5/14 | JV Softball | Lewis Mills | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Wed., 5/15 | V Boys Golf | Northwestern, Litchfield, Terryville | Away - Norfolk CC [Directions] | Gilbert 182 NW #7 194 Litchfield 234 Terry/ Thom 199 | ||
| Wed., 5/15 | V Softball | Northwestern | Home - Rowley Field [Directions] | L 15-4 | ||
| Wed., 5/15 | JV Softball | Northwestern | Home - Rowley Field [Directions] | 3:45 p.m. | ||
| Thu., 5/16 | V Baseball | Northwestern | Away - Northwestern Varsity Field [Directions] | L 1-10 | 2:45pm | Activity bus drop only |
| Thu., 5/16 | V Boys Golf | Northwestern | Home - Greenwood Country Club [Directions] | Gilbert 180 NW # 7 210 | ||
| Thu., 5/16 | V Softball | Cheney Tech | Home - Rowley Field [Directions] | W 19-2 | ||
| Thu., 5/16 | V Girls Tennis | Northwestern | Away - NWR-7 Tennis Courts [Directions] | L 1-6 | 2:45pm | Activity bus- drop off only |
| Fri., 5/17 | V Baseball | Litchfield | Home - Walker Field [Directions] | L 8-6 (9) | ||
| Sat., 5/18 | JV Baseball | Litchfield | Home - Walker Field [Directions] | 10:00 a.m. | ||
| Mon., 5/20 | V Boys Golf | Wolcott Tech | Home - Fairview CC [Directions] | Gilbert 187 OWTS 226 | NON-League Match | |
| Tue., 5/21 | V Baseball | Thomaston | Away - Thomaston H.S. Field [Directions] | W 5-1 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Tue., 5/21 | V Boys Golf | Shepaug Valley, Nonnewaug | Home - Greenwood Country Club [Directions] | Gilbert 201 Shepaug 224 Nonnewaug 225 | ||
| Tue., 5/21 | V Softball | Litchfield | Away - Plumb Hill Field Complex [Directions] | L 12-14 | 2:45pm | 2:45pm bus departs bottom of the hill |
| Thu., 5/23 | V Boys Golf | Chappa Golf Tournament | Away - Chappa Golf Tournament | 8:00 a.m. | ||
| Thu., 5/23 | V Softball | Thomaston | Home - Rowley Field [Directions] | L 0-11 | ||
| Sat., 6/1 | JV Softball | JV Jamboree | Away - Northwestern Regional 7 | 10:00 a.m. | 10:00am Start JV Jamboree | |