| Cheshire 2020-21 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 532 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 10/1 | V Boys Cross Country | Lyman Hall, Sheehan | Away - Wharton Brook State Park [Directions] | 4:00 p.m. | ||
| Thu., 10/1 | V Girls Cross Country | Lyman Hall, Sheehan | Away - Wharton Brook State Park [Directions] | 4:00 p.m. | ||
| Thu., 10/1 | V Field Hockey | Branford | Home - Cheshire High Main Game field [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 10/1 | JV Field Hockey | Branford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 3:45 p.m. | ||
| Thu., 10/1 | V Girls Swimming and Diving | Amity | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 93 | |
| Thu., 10/1 | V Girls Swimming and Diving | Amity | Away - High Plains Community Cn [Directions] | 3:20 p.m. | Amity 88 | |
| Thu., 10/1 | V Girls Volleyball | Mercy | Away - Mercy HS-Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 10/1 | JV Girls Volleyball | Mercy | Away - Mercy HS-Gym [Directions] | 3:45 p.m. | W 2-0 | |
| Fri., 10/2 | V Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 7:00 p.m. | L 2-1 | |
| Fri., 10/2 | JV Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 3:45 p.m. | T 1-1 | |
| Fri., 10/2 | V Girls Soccer | Mercy | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | L 1-3 | |
| Sat., 10/3 | FR Boys Soccer | Amity | Home - Cheshire HS-Cheshire High School soccer field [Directions] | 10:30 a.m. | W 9-1 | |
| Sat., 10/3 | V Field Hockey | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 1:30 p.m. | W 3-1 | |
| Sat., 10/3 | JV Field Hockey | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 3:00 p.m. | ||
| Sat., 10/3 | FR Field Hockey | Amity | Away - Amity Regional HS-Field Hockey Field [Directions] | 10:30 a.m. | ||
| Sat., 10/3 | JV Girls Soccer | Mercy | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 10:30 a.m. | ||
| Sat., 10/3 | FR Girls Soccer | Amity | Away - Amity Regional HS-Amity High School - Field # 2 [Directions] | 12:30 p.m. | ||
| Mon., 10/5 | V Field Hockey | Mercy | Away - Mercy HS-Field Hockey Field [Directions] | 4:00 p.m. | W 6-0 | |
| Mon., 10/5 | JV Field Hockey | Mercy | Away - Mercy HS-Field Hockey Field [Directions] | 5:30 p.m. | ||
| Mon., 10/5 | V Girls Swimming and Diving | North Haven | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 95.5 | |
| Mon., 10/5 | V Girls Swimming and Diving | North Haven | Away - Walter Gawrych Community Pool [Directions] | 4:00 p.m. | North Haven 86.5 | |
| Mon., 10/5 | V Girls Volleyball | Lyman Hall | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 10/5 | JV Girls Volleyball | Lyman Hall | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/6 | V Boys Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | W 5-2 | |
| Tue., 10/6 | V Girls Soccer | North Haven | Away - North Haven MS-East Turf Field [Directions] | 6:00 p.m. | W 5-1 | |
| Wed., 10/7 | V Boys Cross Country | Hamden, Daniel Hand | Away - Hamden MS-Back Field [Directions] | 3:45 p.m. | ||
| Wed., 10/7 | V Girls Cross Country | Hamden, Daniel Hand | Away - Hamden MS-Back Field [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | JV Boys Soccer | North Haven | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | W 6-0 | |
| Thu., 10/8 | V Field Hockey | Guilford | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 10/8 | JV Field Hockey | Guilford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 5:30 p.m. | ||
| Thu., 10/8 | FR Girls Soccer | Shelton | Away - Shelton HS-Lower Field [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | V Girls Volleyball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Thu., 10/8 | JV Girls Volleyball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | 3:45 p.m. | W 2-0 | |
| Fri., 10/9 | JV Boys Soccer | Lyman Hall | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:00 p.m. | W 6-0 | |
| Fri., 10/9 | V Girls Soccer | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | 4:00 p.m. | W 8-0 | |
| Fri., 10/9 | V Girls Volleyball | North Haven | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | W 3-1 | |
| Fri., 10/9 | JV Girls Volleyball | North Haven | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 10/10 | V Boys Soccer | Lyman Hall | Home - Cheshire High Main Game field [Directions] | 11:00 a.m. | T 0-0 | |
| Sat., 10/10 | FR Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 10:00 a.m. | W 4-0 | |
| Sat., 10/10 | FR Field Hockey | Guilford | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 10:30 a.m. | ||
| Sat., 10/10 | JV Girls Soccer | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | Canceled | Cancelled | |
| Sat., 10/10 | FR Girls Soccer | Daniel Hand | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 2:00 p.m. | ||
| Sat., 10/10 | V Girls Swimming and Diving | Daniel Hand | Away - Cheshire Community Pool [Directions] | 5:00 p.m. | Daniel Hand 83 | |
| Sat., 10/10 | V Girls Swimming and Diving | Daniel Hand | Home - Cheshire Community Pool [Directions] | 5:45 p.m. | Cheshire 92 | |
| Tue., 10/13 | V Boys Soccer | Hamden | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | W 3-0 | |
| Tue., 10/13 | V Girls Soccer | Hamden | Away - Hamden HS-HHS Turf Field #1 [Directions] | 5:00 p.m. | W 3-1 | |
| Tue., 10/13 | JV Girls Soccer | Hamden | Away - Hamden HS-HHS Turf Field #1 [Directions] | 7:00 p.m. | ||
| Tue., 10/13 | V Girls Volleyball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 5:30 p.m. | W 3-1 | |
| Tue., 10/13 | JV Girls Volleyball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 4:30 p.m. | W 2-1 | |
| Wed., 10/14 | V Boys Cross Country | Guilford, East Haven, Xavier | Away - East River Preserve [Directions] | 3:45 p.m. | ||
| Wed., 10/14 | V Girls Cross Country | Guilford, East Haven, Mercy | Away - East River Preserve [Directions] | 3:45 p.m. | ||
| Thu., 10/15 | JV Boys Cross Country | Guilford | Home - Cheshire Park-Field 1 [Directions] | 4:00 p.m. | ||
| Thu., 10/15 | V Boys Soccer | Notre Dame-West Haven | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | W 3-1 | |
| Thu., 10/15 | JV Boys Soccer | Hamden | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | W 5-0 | |
| Thu., 10/15 | V Field Hockey | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 10/15 | JV Field Hockey | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | 5:30 p.m. | ||
| Thu., 10/15 | V Girls Swimming and Diving | Hamden | Away - Hamden HS-HHS Pool [Directions] | 3:45 p.m. | Hamden 76 | |
| Thu., 10/15 | V Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | W 3-1 | |
| Thu., 10/15 | JV Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 10/16 | V Boys Soccer | Shelton | Away - Shelton HS-Finn Stadium [Directions] | Canceled | Cancelled | |
| Fri., 10/16 | JV Boys Soccer | Shelton | Away - Shelton HS-High School - Finn Stadium [Directions] | 4:30 p.m. | Cancelled | |
| Fri., 10/16 | JV Girls Soccer | Shelton | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Canceled | Cancelled | |
| Fri., 10/16 | V Girls Swimming and Diving | Hamden | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 99 | |
| Sat., 10/17 | FR Boys Soccer | Daniel Hand | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 2:00 p.m. | W 8-1 | |
| Sat., 10/17 | FR Field Hockey | Amity | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 12:30 p.m. | ||
| Sat., 10/17 | V Girls Soccer | Shelton | Home - Cheshire High Main Game field [Directions] | 10:30 a.m. | W 2-1 | |
| Sat., 10/17 | FR Girls Soccer | Guilford | Away - Guilford HS-New Turf field at GHS [Directions] | 9:30 a.m. | ||
| Mon., 10/19 | V Field Hockey | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 10/19 | JV Field Hockey | Daniel Hand | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:30 p.m. | ||
| Mon., 10/19 | V Girls Swimming and Diving | Mercy | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 85 | |
| Mon., 10/19 | V Girls Swimming and Diving | Virtual Meet | Away - TBA | 7:15 p.m. | Mercy 75 | |
| Mon., 10/19 | V Girls Volleyball | Mercy | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/19 | JV Girls Volleyball | Mercy | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/20 | V Boys Soccer | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 6:30 p.m. | W 1-0 | |
| Tue., 10/20 | JV Boys Soccer | Notre Dame-West Haven | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | W 4-2 | |
| Tue., 10/20 | JV Boys Soccer | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 6:30 p.m. | ||
| Tue., 10/20 | V Girls Soccer | Sheehan | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | L 1-0 | |
| Wed., 10/21 | FR Field Hockey | Sacred Heart Academy | Away - Sacred Heart Academy-Field Hockey Field [Directions] | 4:00 p.m. | ||
| Wed., 10/21 | JV Girls Soccer | Sheehan | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:00 p.m. | ||
| Wed., 10/21 | FR Girls Soccer | Shelton | Home - Cheshire HS-Cheshire High School soccer field [Directions] | 4:00 p.m. | ||
| Thu., 10/22 | JV Boys Soccer | Guilford | Away - Bittner Park-Bittner Park Soccer [Directions] | 4:00 p.m. | L 1-3 | |
| Thu., 10/22 | V Field Hockey | Sheehan | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 10/22 | JV Field Hockey | Sheehan | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:30 p.m. | ||
| Thu., 10/22 | V Girls Volleyball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 5:15 p.m. | W 3-1 | |
| Thu., 10/22 | JV Girls Volleyball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 3:45 p.m. | W 2-1 | |
| Fri., 10/23 | V Boys Cross Country | Shelton | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Fri., 10/23 | V Boys Soccer | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 3:45 p.m. | T 1-1 | |
| Fri., 10/23 | V Girls Cross Country | Shelton | Home - Bartlem Park [Directions] | 4:30 p.m. | ||
| Fri., 10/23 | V Girls Soccer | Sacred Heart Academy | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | W 2-0 | |
| Sat., 10/24 | FR Boys Soccer | Amity | Away - Amity Regional HS-Amity High School - Field # 2 [Directions] | 10:00 a.m. | W 10-1 | |
| Sat., 10/24 | FR Field Hockey | Guilford | Away - Guilford HS-Maturo Field [Directions] | 10:00 a.m. | ||
| Sat., 10/24 | JV Girls Soccer | Sacred Heart Academy | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 10:00 a.m. | ||
| Sat., 10/24 | FR Girls Soccer | Amity | Home - Cheshire HS-Cheshire High School soccer field [Directions] | 10:30 a.m. | ||
| Sat., 10/24 | V Girls Swimming and Diving | Lauralton Hall | Away - Foran HS -Pool [Directions] | 12:30 p.m. | LH 84.5 | |
| Sat., 10/24 | V Girls Swimming and Diving | Lauralton Hall | Home - Cheshire Community Pool [Directions] | 5:45 p.m. | Cheshire 96.5 | |
| Mon., 10/26 | JV Boys Soccer | Xavier | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | L 1-2 | |
| Mon., 10/26 | V Field Hockey | Mercy | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | W 7-2 | |
| Mon., 10/26 | JV Field Hockey | Mercy | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:45 p.m. | ||
| Mon., 10/26 | V Girls Swimming and Diving | Amity | Away - High Plains Community Cn [Directions] | 6:45 p.m. | Cheshire 90.5 - Amity 87.5 | |
| Mon., 10/26 | V Girls Volleyball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 5:00 p.m. | L 0-3 | |
| Mon., 10/26 | JV Girls Volleyball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 3:45 p.m. | W 2-0 | |
| Tue., 10/27 | V Boys Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | L 3-0 | |
| Tue., 10/27 | V Girls Soccer | Mercy | Away - Xavier HS-Larry McHugh Field [Directions] | 6:30 p.m. | L 2-1 | |
| Wed., 10/28 | V Boys Cross Country | North Haven, TBA | Away - Wharton Brook State Park [Directions] | Postponed | ||
| Wed., 10/28 | V Boys Cross Country | Branford | Home - Cheshire Park-Field 1 [Directions] | 4:30 p.m. | ||
| Wed., 10/28 | V Girls Cross Country | North Haven, TBA | Away - Wharton Brook State Park [Directions] | Postponed | ||
| Wed., 10/28 | V Girls Cross Country | Branford | Home - Cheshire Park-Field 1 [Directions] | 4:00 p.m. | ||
| Wed., 10/28 | V Field Hockey | Hamden | Away - Hamden HS-HHS Turf Field #1 [Directions] | 3:45 p.m. | W 3-0 | |
| Wed., 10/28 | FR Field Hockey | Sacred Heart Academy | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 4:00 p.m. | ||
| Wed., 10/28 | JV Girls Soccer | Mercy | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 3:45 p.m. | ||
| Thu., 10/29 | JV Boys Soccer | Daniel Hand | Home - Cheshire HS-Grass Fields [Directions] | 3:45 p.m. | Cancelled | |
| Thu., 10/29 | JV Field Hockey | Hamden | Away - Hamden HS-HHS Turf Field #1 [Directions] | Canceled | Cancelled | |
| Thu., 10/29 | V Girls Swimming and Diving | Hamden | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 89 | |
| Thu., 10/29 | V Girls Swimming and Diving | Hamden | Away - Hamden HS-HHS Pool [Directions] | 3:45 p.m. | Hamden 86 | |
| Thu., 10/29 | V Girls Volleyball | Sacred Heart Academy | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/29 | JV Girls Volleyball | Sacred Heart Academy | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 10/30 | V Boys Soccer | North Haven | Away - North Haven MS-East Turf Field [Directions] | Canceled | Cancelled | |
| Fri., 10/30 | JV Boys Soccer | North Haven | Away - North Haven MS-East Turf Field [Directions] | Canceled | Cancelled | |
| Fri., 10/30 | V Girls Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | Canceled | Cancelled | |
| Sat., 10/31 | FR Boys Soccer | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 10:00 a.m. | W 3-0 | |
| Sat., 10/31 | FR Girls Soccer | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 11/2 | V Boys Soccer | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | Postponed | ||
| Tue., 11/3 | V Girls Soccer | Lyman Hall | Home - Cheshire High Main Game field [Directions] | Canceled | Cancelled | |
| Tue., 11/3 | V Girls Volleyball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 11/3 | JV Girls Volleyball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 11/4 | V Boys Soccer | Xavier | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | L 1-0 | |
| Wed., 11/4 | JV Field Hockey | Amity | Away - Amity Regional HS-Field Hockey Field [Directions] | 3:30 p.m. | ||
| Wed., 11/4 | JV Girls Soccer | Shelton | Home - Cheshire HS-Grass Fields [Directions] | 3:30 p.m. | ||
| Thu., 11/5 | JV Boys Soccer | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | Canceled | Cancelled | |
| Thu., 11/5 | FR Boys Soccer | Notre Dame-West Haven | Away - Veterans Field [Directions] | 3:45 p.m. | W 5-0 | |
| Thu., 11/5 | V Field Hockey | Amity | Away - Amity Regional HS-Field Hockey Field [Directions] | 3:15 p.m. | W 2-0 | |
| Thu., 11/5 | V Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 11/5 | JV Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 11/6 | V Boys Soccer | Hamden | Away - Hamden HS-HHS Turf Field #1 [Directions] | 5:00 p.m. | W 2-1 | |
| Fri., 11/6 | JV Boys Soccer | Hamden | Away - Hamden HS-HHS Turf Field #1 [Directions] | 7:00 p.m. | T 1-1 | |
| Fri., 11/6 | V Girls Soccer | Hamden | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | W 8-0 | |
| Sat., 11/7 | V Field Hockey | Sacred Heart Academy | Home - Cheshire High Main Game field [Directions] | Canceled | Cancelled | |
| Sat., 11/7 | FR Field Hockey | Daniel Hand | Away - Daniel Hand HS-Polson Front Field/ DHHS Campus [Directions] | 10:00 a.m. | ||
| Sat., 11/7 | JV Girls Soccer | Hamden | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 10:00 a.m. | ||
| Sat., 11/7 | FR Girls Soccer | Guilford | Home - Cheshire HS-Cheshire High School soccer field [Directions] | 10:30 a.m. | ||
| Mon., 11/9 | V Girls Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | 5:30 p.m. | W 7-0 | |
| Sat., 11/14 | V Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 12:00 p.m. | ||
| Tue., 2/9 | V Boys Ice Hockey | Branford | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | ||
| Wed., 2/10 | FR Boys Basketball | Xavier | Away - Xavier HS-Aurthur M. Kohs Gymnasium [Directions] | Postponed | ||
| Wed., 2/10 | V Girls Basketball | Mercy | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 31-55 | |
| Wed., 2/10 | JV Girls Basketball | Mercy | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | ||
| Fri., 2/12 | V Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 7:00 p.m. | W 52-21 | |
| Fri., 2/12 | JV Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/12 | FR Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | Postponed | ||
| Fri., 2/12 | V Boys Swimming and Diving | Amity | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 92 - Amity 83 (1-0) | |
| Fri., 2/12 | V Boys Swimming and Diving | Amity | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | 3:20 p.m. | ||
| Fri., 2/12 | V Boys Swimming and Diving | Daniel Hand/Branford/Old Saybrook, Greater New Haven | Away - Madison Swim and Racquet [Directions] | 7:30 p.m. | ||
| Fri., 2/12 | V Girls Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 15-45 | |
| Fri., 2/12 | JV Girls Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | ||
| Sat., 2/13 | V Boys Ice Hockey | Amity | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 1-3 | |
| Mon., 2/15 | V Boys Ice Hockey | North Haven | Away - Northford Ice Pavilion-Red [Directions] | 3:15 p.m. | L 2-3 | |
| Tue., 2/16 | V Boys Basketball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 6:00 p.m. | L 47-50(OT) | |
| Tue., 2/16 | JV Boys Basketball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 4:00 p.m. | ||
| Tue., 2/16 | V Boys Swimming and Diving | Daniel Hand/Branford/Old Saybrook | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 92 - Hand 86 (2-0) | |
| Tue., 2/16 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 5:15 p.m. | L 1-4 | |
| Wed., 2/17 | V Girls Basketball | Guilford | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 46-40 | |
| Fri., 2/19 | V Boys Swimming and Diving | Xavier | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 77 - Xavier 93 (2-1) | |
| Fri., 2/19 | V Boys Swimming and Diving | Xavier | Away - Woodrow Wilson MS-Pool [Directions] | 4:00 p.m. | ||
| Sat., 2/20 | V Boys Basketball | Xavier | Away - Xavier HS-Aurthur M. Kohs Gymnasium [Directions] | 3:00 p.m. | L 40-51 | |
| Sat., 2/20 | JV Boys Basketball | Xavier | Away - Xavier HS-Aurthur M. Kohs Gymnasium [Directions] | 1:15 p.m. | ||
| Sat., 2/20 | FR Boys Basketball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 10:30 a.m. | ||
| Sat., 2/20 | V Boys Ice Hockey | Sheehan | Away - Northford Ice Pavilion-Blue [Directions] | 3:00 p.m. | L 3-7 | |
| Sat., 2/20 | V Girls Basketball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 12:00 p.m. | L 32-42 | |
| Sat., 2/20 | JV Girls Basketball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/20 | FR Girls Basketball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | Postponed | ||
| Sun., 2/21 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 2:30 p.m. | W 4-1 | |
| Mon., 2/22 | V Boys Basketball | East Haven | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 44-50 | |
| Mon., 2/22 | JV Boys Basketball | East Haven | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | ||
| Mon., 2/22 | JV Girls Basketball | East Haven | Away - East Haven HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/23 | V Boys Swimming and Diving | Fairfield Prep | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 96 - FP 90 (3-1) | |
| Tue., 2/23 | V Girls Basketball | East Haven | Away - East Haven HS-Gym [Directions] | 5:00 p.m. | W 60-56 | |
| Wed., 2/24 | V Boys Basketball | Hamden | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 58-68 | |
| Wed., 2/24 | JV Boys Basketball | Hamden | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | ||
| Wed., 2/24 | V Girls Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 6:00 p.m. | L 27-56 | |
| Wed., 2/24 | JV Girls Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/24 | V Girls Ice Hockey | Jonathan Law | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | T 1-1 | |
| Fri., 2/26 | V Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 7:00 p.m. | L 51-55 | |
| Fri., 2/26 | JV Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/26 | FR Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/26 | V Boys Swimming and Diving | Greater New Haven | Away - Walter Gawrych Community Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/26 | V Girls Basketball | Branford | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Sat., 2/27 | FR Boys Basketball | Hamden | Home - Cheshire HS-Gym West [Directions] | 10:30 a.m. | ||
| Sat., 2/27 | V Boys Ice Hockey | Daniel Hand | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | ||
| Sat., 2/27 | V Boys Swimming and Diving | Greater New Haven | Home - Cheshire Community Pool [Directions] | 5:45 p.m. | Cheshire 93.5 - GNH 92.5 (4-1) | |
| Sat., 2/27 | FR Girls Basketball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 11:30 a.m. | ||
| Sat., 2/27 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 5:00 p.m. | W 3-2 | |
| Sun., 2/28 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion-White [Directions] | 6:50 p.m. | W 5-2 | |
| Mon., 3/1 | FR Boys Basketball | Xavier | Away - Xavier HS-Aurthur M. Kohs Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 3/2 | V Boys Swimming and Diving | Amity | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 94 - Amity 80 (5-1) | |
| Tue., 3/2 | V Boys Swimming and Diving | Amity | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | 3:20 p.m. | ||
| Tue., 3/2 | V Girls Basketball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | 7:00 p.m. | L 26-61 | |
| Tue., 3/2 | JV Girls Basketball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | 5:15 p.m. | ||
| Wed., 3/3 | V Girls Ice Hockey | Jonathan Law | Away - Milford Ice Pavillion-Ice Rink [Directions] | 4:40 p.m. | W 5-2 | |
| Thu., 3/4 | JV Boys Ice Hockey | Xavier | Home - Hamden-Lou Astorino Ice Rink [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Fri., 3/5 | V Boys Basketball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 67-54 | |
| Fri., 3/5 | JV Boys Basketball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 3/5 | FR Boys Basketball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Fri., 3/5 | V Boys Ice Hockey | Glastonbury | Away - Newington Ice Arena-Blue Rink [Directions] | 4:25 p.m. | L 0-4 | |
| Fri., 3/5 | V Boys Swimming and Diving | Daniel Hand/Branford/Old Saybrook | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 82 - Hand 79 (6-1) | |
| Fri., 3/5 | V Boys Swimming and Diving | Daniel Hand/Branford/Old Saybrook, Fairfield Prep | Away - Madison Swim and Racquet [Directions] | 7:30 p.m. | ||
| Fri., 3/5 | V Girls Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 7:00 p.m. | L 20-44 | |
| Fri., 3/5 | JV Girls Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 3/5 | FR Girls Basketball | Sheehan | Away - Sheehan HS [Directions] | 3:30 p.m. | ||
| Sat., 3/6 | V Boys Ice Hockey | Lyman Hall | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 1-5 | |
| Sat., 3/6 | V Girls Ice Hockey | West Haven/SHA | Home - Hamden-Lou Astorino Ice Rink [Directions] | 6:30 p.m. | L 2-3 OT | |
| Sun., 3/7 | V Boys Basketball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | 3:00 p.m. | W 59-56(2OT) | |
| Sun., 3/7 | JV Boys Basketball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | 1:30 p.m. | ||
| Sun., 3/7 | FR Boys Basketball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | 12:00 p.m. | ||
| Sun., 3/7 | V Boys Indoor Track | Amity | Away - Floyd Little Athletic Center-Field House [Directions] | 12:00 p.m. | ||
| Sun., 3/7 | V Boys Indoor Track | Amity | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 12:00 p.m. | ||
| Sun., 3/7 | V Girls Indoor Track | Amity | Away - Floyd Little Athletic Center-Field House [Directions] | 12:00 p.m. | ||
| Sun., 3/7 | V Girls Indoor Track | Amity | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 12:00 p.m. | ||
| Tue., 3/9 | V Boys Basketball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 7:00 p.m. | W 50-43 | |
| Tue., 3/9 | JV Boys Basketball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 3/9 | FR Boys Basketball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 3/9 | V Boys Swimming and Diving | Xavier | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 86 - Xavier 84 (7-1) | |
| Tue., 3/9 | V Boys Swimming and Diving | Xavier | Away - Woodrow Wilson MS-Pool [Directions] | 4:00 p.m. | ||
| Tue., 3/9 | V Girls Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 32-40 | |
| Tue., 3/9 | JV Girls Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Tue., 3/9 | FR Girls Basketball | Shelton | Home - Cheshire HS-Gym - East [Directions] | 3:45 p.m. | ||
| Wed., 3/10 | V Boys Ice Hockey | Guilford | Home - Hamden-Lou Astorino Ice Rink [Directions] | 7:30 p.m. | W 8-4 | |
| Wed., 3/10 | FR Girls Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | ||
| Wed., 3/10 | V Girls Ice Hockey | Daniel Hand Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | Postponed | ||
| Thu., 3/11 | V Boys Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 60-51 | |
| Thu., 3/11 | JV Boys Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Thu., 3/11 | FR Boys Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Thu., 3/11 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | W 4-1 | |
| Fri., 3/12 | V Boys Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 7:00 p.m. | L 40-57 | |
| Fri., 3/12 | JV Boys Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 3/12 | FR Boys Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 3/12 | V Boys Swimming and Diving | Fairfield Prep | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 93 - Fairfield Prep 88 (8-1) | |
| Fri., 3/12 | V Boys Swimming and Diving | Fairfield Prep | Away - Fairfield University-Rec Plex [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Fri., 3/12 | V Girls Basketball | Lyman Hall | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 33-32 | |
| Fri., 3/12 | JV Girls Basketball | Lyman Hall | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Fri., 3/12 | FR Girls Basketball | Lyman Hall | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Sat., 3/13 | V Boys Ice Hockey | West Haven Coop | Away - West Haven HS-Bennett Rink [Directions] | 1:00 p.m. | Cancelled | |
| Sat., 3/13 | FR Girls Basketball | Jonathan Law | Home - Cheshire HS-Gym West [Directions] | 10:30 a.m. | ||
| Sat., 3/13 | V Girls Ice Hockey | Guilford Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | Canceled | Cancelled | |
| Sun., 3/14 | V Girls Ice Hockey | Guilford Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | Canceled | Cancelled | |
| Mon., 3/15 | V Boys Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 39-43 | |
| Mon., 3/15 | JV Boys Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Mon., 3/15 | FR Boys Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Mon., 3/15 | V Boys Ice Hockey | Branford | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | W 7-5 | |
| Mon., 3/15 | V Girls Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 7:00 p.m. | L 41-64 | |
| Mon., 3/15 | JV Girls Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 3/16 | FR Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 3/16 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion-Red [Directions] | 8:50 p.m. | W 4-3 | |
| Tue., 3/16 | V Boys Swimming and Diving | Greater New Haven | Home - Cheshire Community Pool [Directions] | 3:00 p.m. | Cheshire 92 - GNH 94 (8-2) | |
| Tue., 3/16 | V Boys Swimming and Diving | Greater New Haven | Away - Walter Gawrych Community Pool [Directions] | 4:00 p.m. | ||
| Tue., 3/16 | FR Girls Basketball | Hillhouse | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Tue., 3/16 | V Girls Ice Hockey | Masuk Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | Canceled | Cancelled | |
| Wed., 3/17 | V Girls Ice Hockey | Hamden Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | Canceled | Cancelled | |
| Fri., 3/19 | V Girls Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 6:00 p.m. | ||
| Sat., 3/20 | V Boys Basketball | Daniel Hand | Away - Daniel Hand HS-Polson Gym/DHHS Campus [Directions] | 12:00 p.m. | L 54-69 | |
| Mon., 3/22 | V Girls Basketball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | 6:00 p.m. | L 50-76 | |
| Wed., 3/24 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavilion-Red [Directions] | 8:30 p.m. | W 4-3 | |
| Sat., 3/27 | V Boys Ice Hockey | North Haven | Home - West Haven HS-Bennett Rink [Directions] | 4:00 p.m. | ||
| Sat., 4/10 | V Baseball | Notre Dame-West Haven | Away - Quigley Stadium [Directions] | 11:00 a.m. | L 6-4 | |
| Sat., 4/10 | FR Baseball | Notre Dame-West Haven | Away - Painter Park-Harry Noyes Baseball Field [Directions] | 10:00 a.m. | L 14-4 | |
| Sat., 4/10 | V Boys Lacrosse | Southington | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 12:30 p.m. | W 17-6 | |
| Sat., 4/10 | JV Boys Lacrosse | Southington | Home - Cheshire HS-Main Game field [Directions] | 2:00 p.m. | W 16-2 | |
| Sat., 4/10 | V Boys Tennis | Guilford | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 1:00 p.m. | W 6-1 [Detailed Results] | |
| Sat., 4/10 | V Girls Lacrosse | Amity | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 10:00 a.m. | W 16-6 | |
| Sat., 4/10 | JV Girls Lacrosse | Amity | Home - Cheshire HS-Bartlem Park [Directions] | 11:30 a.m. | W 15-5 | |
| Sat., 4/10 | V Softball | Guilford | Away - Guilford HS-Varsity softball field [Directions] | 11:00 a.m. | W 9-0 | |
| Sat., 4/10 | JV Softball | Guilford | Away - Guilford HS-Varsity softball field [Directions] | 12:30 p.m. | ||
| Sat., 4/10 | V Girls Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | 11:00 a.m. | L 0-7 | |
| Mon., 4/12 | V Baseball | Sheehan | Away - Sheehan HS-Neubauer Baseball Field @ Sheehan HS [Directions] | 3:00 p.m. | L 4-3(8) | |
| Mon., 4/12 | FR Baseball | Sheehan | Away - Moran MS-Baseball Field [Directions] | 11:00 a.m. | L 6-4 | |
| Mon., 4/12 | V Boys Lacrosse | Daniel Hand | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 13-4 | |
| Mon., 4/12 | JV Boys Lacrosse | Daniel Hand | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | W 14-4 | |
| Mon., 4/12 | V Boys Tennis | Branford | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 12:30 p.m. | W 6-1 [Detailed Results] | |
| Mon., 4/12 | V Boys Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-2 | |
| Mon., 4/12 | JV Boys Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | L 2-1 | |
| Mon., 4/12 | V Softball | Hamden | Away - Hamden HS-HHS Softball Field [Directions] | 3:45 p.m. | W 17-1 | |
| Mon., 4/12 | V Girls Tennis | Lauralton Hall | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Tue., 4/13 | JV Baseball | Sheehan | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | L 2-6 | |
| Wed., 4/14 | V Baseball | Hamden | Away - Hamden HS-HHS Baseball Field [Directions] | 4:00 p.m. | L 4-0 | |
| Wed., 4/14 | FR Baseball | Hamden | Away - Legion Field - Hamden-Legion Baseball Field [Directions] | 4:00 p.m. | L 16-10 | |
| Wed., 4/14 | V Boys Golf | Hamden | Away - Laurel View Golf Course [Directions] | 2:30 p.m. | Cheshire 168 Hamden 192 | |
| Wed., 4/14 | V Boys Tennis | Shelton | Away - Shelton HS-High School - Tennis Courts [Directions] | 10:00 a.m. | W 6-1 [Detailed Results] | |
| Wed., 4/14 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 4/14 | JV Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:00 p.m. | L 2-1 | |
| Wed., 4/14 | V Softball | Daniel Hand | Away - Daniel Hand HS-Green Hill Softball Turf Field [Directions] | 3:45 p.m. | W 16-1 | |
| Wed., 4/14 | JV Softball | Daniel Hand | Away - Daniel Hand HS-Green Hill Grass Diamond [Directions] | Canceled | Cancelled | |
| Wed., 4/14 | V Girls Tennis | Mercy | Away - Wesleyan University-Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Thu., 4/15 | JV Baseball | Hamden | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 4/15 | JV Softball | Maloney | Home - Cheshire HS-Softball Diamond 2 [Directions] | Postponed | ||
| Fri., 4/16 | V Girls Lacrosse | Lauralton Hall | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:00 p.m. | W 13-4 | |
| Fri., 4/16 | JV Girls Lacrosse | Lauralton Hall | Home - Cheshire High Main Game field [Directions] | 5:30 p.m. | W 22-2 | |
| Sat., 4/17 | V Baseball | Amity | Home - Cheshire HS-Baseball Diamond [Directions] | 2:00 p.m. | L 9-0 | |
| Sat., 4/17 | JV Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | 10:30 a.m. | W 5-3 | |
| Sat., 4/17 | FR Baseball | Amity | Home - Bartlem Park [Directions] | 2:00 p.m. | ||
| Sat., 4/17 | V Boys Lacrosse | Sheehan | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 10:00 a.m. | W 15-2 | |
| Sat., 4/17 | V Boys Tennis | North Haven | Away - North Haven Athletic Complex-Tennis Courts [Directions] | 12:00 p.m. | W 7-0 [Detailed Results] | |
| Sat., 4/17 | V Girls Lacrosse | North Branford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 1:00 p.m. | W 16-4 | |
| Sat., 4/17 | V Softball | Amity | Home - Cheshire HS-Softball Diamond [Directions] | 2:30 p.m. | W 4-0 | |
| Sat., 4/17 | JV Softball | Amity | Home - Cheshire HS-Softball Diamond 2 [Directions] | 4:00 p.m. | ||
| Mon., 4/19 | V Baseball | North Haven | Away - North Haven Athletic Complex-Robert E. DeMayo Field [Directions] | 3:45 p.m. | L 12-11 | |
| Mon., 4/19 | FR Baseball | North Haven | Away - North Haven Athletic Complex-Brook Field-Baseball [Directions] | 3:45 p.m. | W 10-3 | |
| Mon., 4/19 | FR Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | Canceled | Cancelled | |
| Mon., 4/19 | V Boys Tennis | Fairfield Prep | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 2:30 p.m. | W 4-3 [Detailed Results] | |
| Mon., 4/19 | JV Girls Lacrosse | North Branford | Home - Bartlem Park [Directions] | 4:30 p.m. | W 17-1 | |
| Mon., 4/19 | V Softball | Sheehan | Home - Cheshire HS-Softball Diamond [Directions] | 4:00 p.m. | W 13-0 | |
| Mon., 4/19 | V Girls Tennis | Daniel Hand | Away - Polson MS, Madison-Polson Tennis Courts/DHHS Campus [Directions] | 3:45 p.m. | L 2-5 | |
| Tue., 4/20 | JV Baseball | North Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | L 13-15 | |
| Tue., 4/20 | V Boys Golf | Guilford | Home - Farms Country club [Directions] | 2:30 p.m. | Cheshire 169 Guilford 182 | |
| Tue., 4/20 | V Boys Lacrosse | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 6:00 p.m. | W 9-7 | |
| Tue., 4/20 | V Boys Volleyball | Masuk | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 2-3 | |
| Tue., 4/20 | JV Boys Volleyball | Masuk | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Tue., 4/20 | V Girls Golf | Lauralton Hall | Home - Southington Country Club [Directions] | 2:30 p.m. | CHS 185 Lauralton Hall 213 | |
| Tue., 4/20 | V Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 3:45 p.m. | L 10-17 | |
| Tue., 4/20 | FR Girls Lacrosse | Glastonbury | Away - Glastonbury HS-Field 13 [Directions] | 4:00 p.m. | W 11-2 | |
| Tue., 4/20 | V Softball | East Haven | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | W 7-0 | |
| Tue., 4/20 | V Girls Tennis | Guilford | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Wed., 4/21 | V Boys Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | 4:15 p.m. | W 3-0 | |
| Wed., 4/21 | JV Boys Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | 5:30 p.m. | W 2-0 | |
| Wed., 4/21 | JV Softball | East Haven | Home - Cheshire HS-Softball Diamond 2 [Directions] | Canceled | Cancelled | |
| Thu., 4/22 | JV Baseball | Daniel Hand | Away - Town Campus - Madison-Baseball Field [Directions] | 3:45 p.m. | L 5-6 | |
| Thu., 4/22 | V Boys Golf | Jonathan Law | Away - Orange Hills Country Club [Directions] | 2:45 p.m. | Cheshire 172 Law 208 | |
| Thu., 4/22 | V Boys Outdoor Track | Guilford | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | Cheshire 99 Guilford 28 [Detailed Results] | |
| Thu., 4/22 | V Boys Volleyball | Pomperaug | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 4/22 | JV Boys Volleyball | Pomperaug | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Thu., 4/22 | V Girls Outdoor Track | Guilford | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Fri., 4/23 | V Baseball | Lyman Hall | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | W 11-10(8) | |
| Fri., 4/23 | V Girls Lacrosse | Daniel Hand | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 17-10 | |
| Fri., 4/23 | JV Girls Lacrosse | Daniel Hand | Home - Cheshire HS-Bartlem Park [Directions] | 4:30 p.m. | L 4-7 | |
| Fri., 4/23 | JV Softball | North Haven | Away - North Haven Athletic Complex-Brook Field-Softball [Directions] | Canceled | Cancelled | |
| Fri., 4/23 | JV Softball | Newtown | Home - Cheshire HS-Softball Diamond 2 [Directions] | 4:00 p.m. | ||
| Fri., 4/23 | V Girls Tennis | Sacred Heart Academy | Away - Hamden MS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Sat., 4/24 | V Baseball | Daniel Hand | Home - Cheshire HS-Baseball Diamond [Directions] | 10:30 a.m. | L 12-3 | |
| Sat., 4/24 | JV Baseball | Lyman Hall | Away - Pat Wall Field-Baseball Field [Directions] | 10:00 a.m. | W 12-9 | |
| Sat., 4/24 | FR Baseball | Daniel Hand | Home - Bartlem Park [Directions] | 10:30 a.m. | W 13-13 | |
| Sat., 4/24 | JV Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | 11:00 a.m. | W 7-5 | |
| Sat., 4/24 | V Boys Tennis | Xavier | Away - Wesleyan University-Tennis Courts [Directions] | 12:00 p.m. | W 4-3 [Detailed Results] | |
| Sat., 4/24 | FR Girls Lacrosse | Daniel Hand | Away - Daniel Hand HS-Polson Front Field/ DHHS Campus [Directions] | 11:00 a.m. | L 10-5 | |
| Mon., 4/26 | V Baseball | Guilford | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | W 10-9 | |
| Mon., 4/26 | FR Baseball | Guilford | Home - Bartlem Park [Directions] | 4:00 p.m. | L 19-4 | |
| Mon., 4/26 | JV Boys Lacrosse | Guilford | Away - Guilford HS-Maturo Field [Directions] | 4:00 p.m. | W 10-2 | |
| Mon., 4/26 | V Boys Tennis | Daniel Hand | Away - Polson MS, Madison-Polson Tennis Courts/DHHS Campus [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Mon., 4/26 | V Boys Volleyball | Kolbe Cathedral | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 4/26 | JV Boys Volleyball | Kolbe Cathedral | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Mon., 4/26 | V Girls Golf | Mercy | Away - Lyman Orchards [Directions] | 3:10 p.m. | CHS 195 Mercy 259 | |
| Mon., 4/26 | V Girls Lacrosse | Trumbull | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 20-4 | |
| Mon., 4/26 | JV Girls Lacrosse | Trumbull | Home - Cheshire HS-Bartlem Park [Directions] | 4:30 p.m. | W 20-0 | |
| Mon., 4/26 | V Softball | West Haven | Home - Cheshire HS-Softball Diamond [Directions] | 4:00 p.m. | W 7-4 | |
| Mon., 4/26 | JV Softball | West Haven | Home - Cheshire HS-Softball Diamond 2 [Directions] | 5:30 p.m. | ||
| Mon., 4/26 | V Girls Tennis | North Haven | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Tue., 4/27 | JV | Staples | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | L 5-7 | |
| Tue., 4/27 | JV Baseball | Guilford | Away - Guilford HS-@ Long Hill Road [Directions] | 4:00 p.m. | W 11-1 | |
| Tue., 4/27 | V Boys Golf | Jonathan Law | Home - Farms Country club [Directions] | 2:30 p.m. | Cheshire 167 Law 205 | |
| Tue., 4/27 | V Boys Lacrosse | Staples | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | L 9-12 | |
| Tue., 4/27 | V Boys Outdoor Track | Hillhouse | Away - Bowen Field-Football Field [Directions] | 4:00 p.m. | ||
| Tue., 4/27 | V Girls Lacrosse | Mercy | Away - Mercy HS-Lacrosse Field [Directions] | 4:00 p.m. | W 20-8 | |
| Tue., 4/27 | JV Girls Lacrosse | Mercy | Away - Mercy HS-Lacrosse Field [Directions] | 5:30 p.m. | W 20-2 | |
| Tue., 4/27 | V Girls Outdoor Track | Hillhouse | Away - Bowen Field-Football Field [Directions] | Postponed | ||
| Wed., 4/28 | V Baseball | Fairfield Prep | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | L 13-3 | |
| Wed., 4/28 | FR Baseball | Fairfield Prep | Home - Bartlem Park [Directions] | 4:00 p.m. | L 6-5 | |
| Wed., 4/28 | V Boys Golf | Fairfield Prep | Away - Brooklawn Country Club [Directions] | 3:00 p.m. | Cheshire 173 Fairfield Prep 157 | |
| Wed., 4/28 | V Boys Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 4/28 | JV Boys Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 4/28 | V Girls Golf | Amity | Home - Southington Country Club [Directions] | 3:00 p.m. | CHS 189 Amity 197 | |
| Wed., 4/28 | FR Girls Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | 5:00 p.m. | W 7-6 | |
| Wed., 4/28 | V Softball | Lyman Hall | Away - Lyman Hall HS-Varsity Softball Field [Directions] | 3:45 p.m. | W 11-2 | |
| Wed., 4/28 | JV Softball | Lyman Hall | Away - Lyman Hall HS-JV Softball Field [Directions] | 5:15 p.m. | ||
| Thu., 4/29 | JV Baseball | Fairfield Prep | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 5/18, Time to 5:30 p.m. | ||||||
| Thu., 4/29 | V Boys Golf | Xavier | Home - Farms Country club [Directions] | 2:30 p.m. | Cheshire 174 Xavier 183 | |
| Thu., 4/29 | V Boys Lacrosse | Notre Dame-West Haven | Away - Notre Dame HS-Veteran's Stadium [Directions] | 6:00 p.m. | W 18-7 | |
| Thu., 4/29 | JV Boys Lacrosse | Notre Dame-West Haven | Away - Notre Dame HS-Veteran's Stadium [Directions] | 4:00 p.m. | W 6-4 | |
| Thu., 4/29 | V Girls Lacrosse | North Haven | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 5:00 p.m. | W 21-2 | |
| Fri., 4/30 | V Baseball | Sheehan | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | L 6-3 | |
| Fri., 4/30 | FR Baseball | Sheehan | Home - Bartlem Park [Directions] | 4:00 p.m. | L 20-12 | |
| Fri., 4/30 | V Boys Volleyball | Norwich Free Academy | Away - Norwich Free Academy-Alumni Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 4/30 | JV Boys Volleyball | Norwich Free Academy | Away - Norwich Free Academy-Alumni Gym [Directions] | 4:15 p.m. | L 1-2 | |
| Fri., 4/30 | FR Girls Lacrosse | Amity | Home - Bartlem Park [Directions] | 4:00 p.m. | W 10-5 | |
| Fri., 4/30 | V Softball | Hamden | Home - Cheshire HS-Softball Diamond [Directions] | 4:00 p.m. | W 16-4 | |
| Fri., 4/30 | V Girls Tennis | Amity | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Sat., 5/1 | JV Baseball | Sheehan | Away - Sheehan HS-Neubauer Baseball Field @ Sheehan HS [Directions] | 10:00 a.m. | W 4-2 | |
| Sat., 5/1 | V Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 6:00 p.m. | L 5-15 | |
| Sat., 5/1 | JV Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Barlow Field [Directions] | 4:00 p.m. | L 6-10 | |
| Sat., 5/1 | V Boys Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | 12:00 p.m. | W 4-3 [Detailed Results] | |
| Sat., 5/1 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 1:00 p.m. | L 5-15 | |
| Sat., 5/1 | V Girls Tennis | Foran | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 10:00 a.m. | W 6-1 | |
| Mon., 5/3 | JV | Shelton | Away - Shelton HS-Finn Stadium [Directions] | Postponed | ||
| Mon., 5/3 | V Baseball | Hamden | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | L 6-2 | |
| Mon., 5/3 | FR Baseball | Hamden | Home - Bartlem Park [Directions] | 4:00 p.m. | L 15-5 | |
| Mon., 5/3 | V Boys Golf | Guilford | Away - Madison Country Club [Directions] | 2:00 p.m. | Cheshire 171 Guilford 173 | |
| Mon., 5/3 | V Boys Tennis | Branford | Away - Branford HS-Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Mon., 5/3 | V Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 5/3 | JV Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 4:30 p.m. | L 02 | |
| Mon., 5/3 | V Softball | Sheehan | Away - Sheehan HS-Sheehan HS Softball Field [Directions] | 3:30 p.m. | W 7-2 | |
| Mon., 5/3 | Miscellaneous Events | cheer tryout | Home - Cheshire HS-Gym West [Directions] | 6:15 p.m. | ||
| Tue., 5/4 | JV Baseball | Hamden | Away - Legion Field - Hamden-Legion Baseball Field [Directions] | 4:00 p.m. | L 2-3 | |
| Tue., 5/4 | V Boys Golf | Hamden | Home - Farms Country club [Directions] | 2:30 p.m. | Cheshire 167 Hamden 206 | |
| Tue., 5/4 | V Boys Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | 6:00 p.m. | W 20-7 | |
| Tue., 5/4 | V Boys Tennis | Shelton | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 5:30 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/4 | V Girls Golf | Mercy | Home - Southington Country Club [Directions] | 3:00 p.m. | ||
| Tue., 5/4 | V Girls Lacrosse | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 6:00 p.m. | W 17-3 | |
| Tue., 5/4 | JV Girls Lacrosse | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 4:30 p.m. | W 5-4 | |
| Wed., 5/5 | V Boys Golf | Daniel Hand | Away - Madison Country Club [Directions] | 2:30 p.m. | Cheshire 168 Hand 145 | |
| Wed., 5/5 | V Boys Volleyball | Newtown | Away - Newtown HS-Newtown High School Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 5/5 | JV Boys Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 5/5 | V Girls Golf | Daniel Hand | Away - Madison Country Club [Directions] | 3:00 p.m. | CHS 179 Hand 226 | |
| Wed., 5/5 | JV Softball | East Haven | Away - East Haven HS-Softball Diamond [Directions] | Canceled | Cancelled | |
| Wed., 5/5 | Miscellaneous Events | cheer tryout | Home - Cheshire HS-Gym West [Directions] | 6:15 p.m. | ||
| Thu., 5/6 | V Baseball | Daniel Hand | Away - Daniel Hand HS-Polson Baseball Field /DHHS Campus [Directions] | 3:45 p.m. | L 7-6 | |
| Thu., 5/6 | JV Baseball | Daniel Hand | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 5/6 | V Boys Golf | Notre Dame-West Haven | Away - Race Brook C.C. [Directions] | 2:45 p.m. | Cheshire 164 Notre Dame 150 | |
| Thu., 5/6 | V Girls Golf | St. Paul Catholic | Home - Southington Country Club [Directions] | 3:00 p.m. | CHS 190 St. Paul 201 | |
| Thu., 5/6 | V Girls Lacrosse | Glastonbury | Away - Glastonbury HS-Field 12 [Directions] | 4:15 p.m. | W 14-9 | |
| Thu., 5/6 | JV Girls Lacrosse | Glastonbury | Away - Glastonbury HS-Field 12 [Directions] | 5:45 p.m. | W 12-4 | |
| Thu., 5/6 | JV Softball | North Haven | Home - Cheshire HS-Softball Diamond 2 [Directions] | 4:00 p.m. | ||
| Thu., 5/6 | V Girls Tennis | Foran | Away - Foran HS -Foran Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Thu., 5/6 | Miscellaneous Events | Dodd track meet | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | ||
| Fri., 5/7 | V | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | 5:00 p.m. | W 11-8 | |
| Fri., 5/7 | V Baseball | Guilford | Away - Guilford HS-Baseball Diamond [Directions] | 4:00 p.m. | L 6-1 | |
| Fri., 5/7 | FR Baseball | Guilford | Away - Long Hill Park-Guilford-Baseball Field [Directions] | 4:00 p.m. | L 7-4 | |
| Fri., 5/7 | V Boys Outdoor Track | Amity | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | Cheshire 74 Amity 76 | |
| Fri., 5/7 | V Boys Tennis | North Haven | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Fri., 5/7 | V Boys Volleyball | Xavier | Away - Xavier HS-Gym [Directions] | 5:00 p.m. | W 3-1 | |
| Fri., 5/7 | JV Boys Volleyball | Xavier | Away - Xavier HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 5/7 | V Girls Outdoor Track | Amity | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Fri., 5/7 | V Softball | North Haven | Home - Cheshire HS-Softball Diamond [Directions] | 3:30 p.m. | W 12-0 | |
| Fri., 5/7 | V Softball | North Haven | Home - Cheshire HS-Softball Diamond [Directions] | 5:15 p.m. | W 8-4 | |
| Fri., 5/7 | V Girls Tennis | Lauralton Hall | Away - Eisenhower Park [Directions] | 3:45 p.m. | L 2-5 | |
| Fri., 5/7 | Miscellaneous Events | cheer tryout | Home - Cheshire HS-Gym West [Directions] | 6:15 p.m. | ||
| Sat., 5/8 | JV Baseball | Guilford | Home - Cheshire HS-Baseball Diamond [Directions] | 10:30 a.m. | L 4-10 | |
| Sat., 5/8 | V Boys Lacrosse | Xavier | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:00 p.m. | W 17-4 | |
| Sat., 5/8 | JV Boys Lacrosse | Xavier | Home - Cheshire HS-Main Game field [Directions] | 2:00 p.m. | W 16-3 | |
| Sat., 5/8 | V Boys Tennis | Southington | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 2:00 p.m. | W 6-1 [Detailed Results] | |
| Sat., 5/8 | V Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | L 4-13 | |
| Sat., 5/8 | V Girls Tennis | Mercy | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 5:00 p.m. | W 7-0 | |
| Mon., 5/10 | V Baseball | Amity | Away - Old Tavern Road Complex-Brinley Field [Directions] | 7:00 p.m. | L 12-0 | |
| Mon., 5/10 | V Boys Golf | Shelton | Away - Brownson Country Club [Directions] | 2:45 p.m. | Cheshire 160 Shelton 157 | |
| Mon., 5/10 | V Boys Lacrosse | North Haven | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 19-2 | |
| Mon., 5/10 | JV Boys Lacrosse | North Haven | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | W 12-2 | |
| Mon., 5/10 | V Boys Outdoor Track | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 3:45 p.m. | ||
| Mon., 5/10 | V Boys Tennis | Fairfield Prep | Away - Fairfield University-Walsh Athletic Center - Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Mon., 5/10 | V Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 5/10 | JV Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | L 0-2 | |
| Mon., 5/10 | V Girls Golf | Lauralton Hall | Home - Southington Country Club [Directions] | 3:00 p.m. | CHS 208 Lauralton Hall 206 | |
| Mon., 5/10 | V Girls Outdoor Track | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 3:45 p.m. | ||
| Mon., 5/10 | V Girls Tennis | Daniel Hand | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Tue., 5/11 | JV Baseball | Amity | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | L 6-13 | |
| Tue., 5/11 | FR Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 5/11 | FR Boys Lacrosse | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | Canceled | Cancelled | |
| Tue., 5/11 | V Girls Golf | Amity | Away - Race Brook C.C. [Directions] | 3:30 p.m. | CHS 185 Amity 193 | |
| Tue., 5/11 | V Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 5:30 p.m. | W 10-6 | |
| Tue., 5/11 | V Softball | East Haven | Away - East Haven HS-Softball Diamond [Directions] | 4:15 p.m. | W 3-0 | |
| Tue., 5/11 | Miscellaneous Events | Dodd track meet | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | ||
| Wed., 5/12 | V Baseball | North Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | W 11-4 | |
| Wed., 5/12 | FR Baseball | North Haven | Home - Bartlem Park [Directions] | 4:00 p.m. | L 13-3 | |
| Wed., 5/12 | V Boys Outdoor Track | Shelton | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | Cheshire 65 Shelton 85 | |
| Wed., 5/12 | V Boys Tennis | Xavier | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | W 5-2 [Detailed Results] | |
| Wed., 5/12 | V Boys Volleyball | Norwich Free Academy | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 5/12 | JV Boys Volleyball | Norwich Free Academy | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Wed., 5/12 | V Girls Golf | Newington, Berlin | Away - Indian Hill Country Club [Directions] | 3:00 p.m. | CHS 190 Newington 232 Berlin 202 | |
| Wed., 5/12 | V Girls Outdoor Track | Shelton | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Wed., 5/12 | V Softball | Lyman Hall | Home - Cheshire HS-Softball Diamond [Directions] | 4:00 p.m. | W 5-3 | |
| Wed., 5/12 | JV Softball | Lyman Hall | Home - Cheshire HS-Softball Diamond 2 [Directions] | 5:30 p.m. | ||
| Wed., 5/12 | V Girls Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | 5:30 p.m. | L 1-6 | |
| Thu., 5/13 | V | Shelton | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 5:00 p.m. | W 21-6 | |
| Thu., 5/13 | JV Baseball | North Haven | Away - North Haven Athletic Complex-Brook Field-Baseball [Directions] | 4:00 p.m. | L 3-11 | |
| Thu., 5/13 | JV Boys Lacrosse | Shelton | Home - Cheshire HS-Grass Fields [Directions] | 7:00 p.m. | W 16-3 | |
| Thu., 5/13 | V Girls Golf | Lauralton Hall | Away - Oronoque Country Club [Directions] | 2:30 p.m. | CHS 184 Lauralton Hall 212 | |
| Thu., 5/13 | FR Girls Lacrosse | Hall | Away - Hall HS-Field Hockey Stadium [Directions] | 3:30 p.m. | W 5-4 | |
| Thu., 5/13 | JV Softball | West Haven | Away - West Haven HS-Frank Biondi Field [Directions] | 3:45 p.m. | ||
| Fri., 5/14 | V Baseball | Lyman Hall | Away - Pat Wall Field-Baseball Field [Directions] | 3:45 p.m. | W 9-6 | |
| Fri., 5/14 | V Boys Tennis | Notre Dame-West Haven | Away - U New Haven-UNH Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Fri., 5/14 | V Boys Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 5/14 | JV Boys Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Fri., 5/14 | V Girls Lacrosse | Guilford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | L 3-17 | |
| Fri., 5/14 | V Softball | Amity | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | 4:15 p.m. | L 4-3 | |
| Fri., 5/14 | V Girls Tennis | Sacred Heart Academy | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Sat., 5/15 | JV | Simsbury | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | W 15-6 | |
| Sat., 5/15 | JV Baseball | Lyman Hall | Home - Cheshire HS-Baseball Diamond [Directions] | 10:30 a.m. | L 7-14 | |
| Sat., 5/15 | V Boys Lacrosse | Simsbury | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 18-4 | |
| Sat., 5/15 | V Softball | West Haven | Away - West Haven HS-Frank Biondi Field [Directions] | 2:00 p.m. | W 7-3 | |
| Mon., 5/17 | V | NotreDame | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 16-9 | |
| Mon., 5/17 | V Baseball | Fairfield Prep | Away - Fairfield University-Alumni Diamond [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/17 | FR Baseball | Fairfield Prep | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/17 | V Boys Golf | Southington, Conard | Away - Southington HS-Hawk's Landing Country Club [Directions] | 3:00 p.m. | Cheshire 154 Southington 158 | |
| Mon., 5/17 | V Boys Outdoor Track | SCC East Sectional Track & Field Qualifier | Away - Bowen Field-Track | 2:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 5/19 | ||||||
| Mon., 5/17 | V Boys Volleyball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-1 | |
| Mon., 5/17 | JV Boys Volleyball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-1 | |
| Mon., 5/17 | V Girls Golf | Amity | Home - Southington Country Club [Directions] | 3:00 p.m. | CHS 187 Amity 196 | |
| Mon., 5/17 | V Girls Outdoor Track | SCC East Sectional Track & Field Qualifier | Away - Bowen Field-Track | 2:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 5/19 | ||||||
| Mon., 5/17 | JV Softball | Daniel Hand | Home - Cheshire HS-Softball Diamond 2 [Directions] | Canceled | Cancelled | |
| Mon., 5/17 | V Girls Tennis | North Haven | Away - North Haven Athletic Complex-Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Tue., 5/18 | JV Baseball | Fairfield Prep | Home - Cheshire HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Tue., 5/18 | JV Baseball | Fairfield Prep | Home - Cheshire HS-Baseball Diamond [Directions] | 5:30 p.m. | ||
| Tue., 5/18 | V Boys Golf | Notre Dame-West Haven | Home - Farms Country club [Directions] | 2:15 p.m. | Cheshire 173 Notre Dame 167 | |
| Tue., 5/18 | V Boys Tennis | Daniel Hand | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Tue., 5/18 | V Boys Volleyball | Xavier | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 5/18 | JV Boys Volleyball | Xavier | Home - Cheshire HS-Gym West [Directions] | 4:30 p.m. | ||
| Tue., 5/18 | V Girls Lacrosse | Branford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 18-3 | |
| Tue., 5/18 | V Softball | Daniel Hand | Home - Cheshire HS-Softball Diamond [Directions] | 4:00 p.m. | W 14-2 | |
| Tue., 5/18 | JV Softball | Amity | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | Postponed | ||
| Wed., 5/19 | V Baseball | Notre Dame-West Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | W 5-4 | |
| Wed., 5/19 | FR Baseball | Notre Dame-West Haven | Home - Bartlem Park [Directions] | 4:00 p.m. | L 8-4 | |
| Wed., 5/19 | V Boys Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 4:00 p.m. | W 13-8 | |
| Wed., 5/19 | V Boys Tennis | Notre Dame-West Haven | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Wed., 5/19 | V Girls Golf | Daniel Hand | Away - Madison Country Club [Directions] | 2:30 p.m. | CHS 171 Hand 225 | |
| Wed., 5/19 | V Softball | Guilford | Home - Cheshire HS-Softball Diamond [Directions] | 4:00 p.m. | W 12-0 | |
| Wed., 5/19 | JV Softball | Guilford | Home - Cheshire HS-Softball Diamond 2 [Directions] | 5:30 p.m. | ||
| Wed., 5/19 | Miscellaneous Events | Dodd Track meet | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Thu., 5/20 | JV Baseball | Notre Dame-West Haven | Away - Quigley Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/20 | V Boys Golf | Shelton | Home - Farms Country club [Directions] | 2:30 p.m. | Cheshire 181 Shelton 168 | |
| Thu., 5/20 | V Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | L 10-9 | |
| Thu., 5/20 | JV Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | W 11-7 | |
| Thu., 5/20 | V Boys Outdoor Track | Amity, Lyman Hall, Sheehan, Shelton | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | ||
| Thu., 5/20 | V Girls Outdoor Track | Amity, Lyman Hall, Sheehan, Shelton | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | ||
| Thu., 5/20 | V Softball | Southington | Away - Southington HS-Softball Varsity Field [Directions] | 4:00 p.m. | L 3-2 | |
| Fri., 5/21 | FR Baseball | Daniel Hand | Away - Town Campus - Madison-Baseball Field [Directions] | 3:45 p.m. | L 11-1 | |
| Fri., 5/21 | V Boys Outdoor Track | Lyman Hall | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Fri., 5/21 | JV Softball | Seymour | Home - Cheshire HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:15 p.m. | ||||||
| Sat., 5/22 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | 11:30 a.m. | ||
| Mon., 5/24 | Miscellaneous Events | Dodd track meet | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Tue., 5/25 | V Girls Golf | Mercy | Away - Lyman Orchards [Directions] | 3:10 p.m. | CHS 168 Mercy 234 | |
| Tue., 5/25 | V Girls Outdoor Track | SCC Championship Meet | Away - Hillhouse HS-Bowen Field | 1:30 p.m. | ||
| Wed., 5/26 | V Boys Golf | Sheehan | Home - Farms Country club [Directions] | 2:30 p.m. | Cheshire 167 Sheehan 189 | |
| Wed., 5/26 | V Girls Golf | Daniel Hand | Home - Southington Country Club [Directions] | 3:00 p.m. | CHS 172 Hand 237 | |
| Thu., 5/27 | V Girls Golf | St. Paul Catholic | Away - Westwoods Golf Course [Directions] | 3:00 p.m. | CHS 148 St. Paul 164 | |
| Tue., 6/1 | V Girls Golf | Newington, St. Paul Catholic | Home - Southington Country Club [Directions] | 3:00 p.m. | CHS 170 Newington 206 St. Paul 187 | |
| Wed., 6/2 | Miscellaneous Events | SCC Girls Golf tournament | Home - TBA [Directions] | 8:00 a.m. | ||
| Mon., 6/7 | Miscellaneous Events | Senior Walk concert | Home - Cheshire HS [Directions] | 3:00 p.m. | ||
| Thu., 6/10 | Miscellaneous Events | Band concert | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||