| Cheshire 2019-20 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 805 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Wed., 8/28 | V Boys Cross Country | Pomperaug (Scrim.) | Away - Pomperaug HS-Cross Country Course [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Fri., 8/30 | V Boys Cross Country | Simsbury | Away - Stratton Brook State Park [Directions] | 4:30 p.m. | 2:15 PM; 1 Bus | |
| Fri., 8/30 | V Girls Cross Country | Simsbury (Scrim.) | Away - Stratton Brook State Park [Directions] | 4:30 p.m. | 2:15 PM; 1 Bus | |
| Tue., 9/3 | V Boys Soccer | Glastonbury, Lewis Mills, Naugatuck, Wethersfield, Xavier | Away - Glastonbury HS-Field #4 | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 9/3 | V Boys Soccer | Lewis Mills | Away - Glastonbury HS-Field #4 [Directions] | 4:45 p.m. | ||
| Tue., 9/3 | V Field Hockey | Conard (Scrim.) | Home - Cheshire HS-Main Game field [Directions] | 3:45 p.m. | ||
| Thu., 9/5 | V Football | Windsor (Scrim.) | Away - Windsor HS-Jack O'Brien Stadium [Directions] | 6:00 p.m. | 4:00 PM; 2 Buses | |
| Thu., 9/5 | V Boys Soccer | Naugatuck (Scrim.) | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Thu., 9/5 | V Girls Soccer | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | 4:00 PM; 1 Bus | |
| Thu., 9/5 | JV Girls Soccer | Pomperaug (Scrim.) | Away - Pomperaug HS-PHS Soccer Field [Directions] | 6:00 p.m. | ||
| Sat., 9/7 | V Boys Cross Country | Windham Invite | Away - Windham HS | 9:30 a.m. | 7:30 AM; 1 Bus | |
| Sat., 9/7 | V Boys Soccer | Pomperaug (Scrim.) | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Sat., 9/7 | JV Boys Soccer | Pomperaug (Scrim.) | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Sat., 9/7 | V Girls Cross Country | Windham Invite | Away - Windham HS | 9:30 a.m. | 7:30 AM; 1 Bus | |
| Sat., 9/7 | V Field Hockey | Avon Field Hockey Jamboree | Away - Avon HS-Turf Field | 8:30 a.m. | 6:30 AM; 1 Bus | |
| Mon., 9/9 | V Boys Soccer | Southington (Scrim.) | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Tue., 9/10 | V Boys Cross Country | Lyman Hall, West Haven, Xavier | Home - Cheshire Park-Field 1 [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 9/10 | V Girls Cross Country | Lyman Hall, Mercy, West Haven | Home - Cheshire Park-Field 1 [Directions] | Cheshire 15 - West Haven 50 Cheshire 18 - Mercy 44 Cheshire 19 - Lyman Hall 41 | ||
| Tue., 9/10 | V Girls Soccer | Watertown (Scrim.) | Away - Watertown Veterans Field #2 [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Thu., 9/12 | FR Football | Hillhouse | Away - Bowen Field-Football Field [Directions] | 6:00 p.m. | 4:00 PM; 1 Bus | |
| Thu., 9/12 | V Boys Soccer | Hamden | Home - Cheshire High Main Game field [Directions] | W 2-1 | ||
| Thu., 9/12 | V Field Hockey | Daniel Hand | Home - Cheshire HS-Main Game field [Directions] | L 0-1 | ||
| Thu., 9/12 | V Girls Soccer | North Haven | Away - North Haven MS-West Turf Field [Directions] | W 3-0 | 5:30 PM; 1 Bus | |
| Thu., 9/12 | V Girls Swimming and Diving | Glastonbury, Sheehan | Home - Cheshire Community Pool [Directions] | CHS 88 (1-0) - SHS 83, CHS 96 (2-0) - GHS 88 | ||
| Fri., 9/13 | V Football | Hillhouse | Home - Cheshire High Main Game field [Directions] | W 35-14 | ||
| Fri., 9/13 | JV Boys Soccer | Hamden | Home - Cheshire HS-Grass Fields [Directions] | W 3-0 | ||
| Fri., 9/13 | FR Field Hockey | Amity | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 4:00 p.m. | ||
| Sat., 9/14 | JV Football | Hillhouse | Away - Bowen Field-Football Field [Directions] | 10:30 a.m. | 9:00 AM; 1 Bus | |
| Sat., 9/14 | FR Boys Soccer | Amity | Away - Amity Regional HS-Amity High School - Field # 2 [Directions] | W 3-0 | 8:30 AM; 1 Bus | |
| Sat., 9/14 | V Field Hockey | New Canaan | Home - Cheshire HS-Main Game field [Directions] | L 3-0 | ||
| Sat., 9/14 | JV Field Hockey | New Canaan | Home - Cheshire HS-Main Game field [Directions] | 12:30 p.m. | ||
| Sat., 9/14 | FR Field Hockey | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | 11:00 a.m. | 9:30 AM; 1 Bus | |
| Sat., 9/14 | JV Girls Soccer | Lauralton Hall | Away - Lauralton Hall-Soccer Field [Directions] | 2:30 p.m. | 1:00 PM; 1 Bus | |
| Mon., 9/16 | JV Boys Soccer | Amity | Away - Amity Regional HS-Amity High School - Field # 2 [Directions] | W 6-1 | 2:30 PM; 1 Bus | |
| Mon., 9/16 | FR Boys Soccer | Guilford | Home - Cheshire HS-Grass Fields [Directions] | W 2-1 | ||
| Mon., 9/16 | V Field Hockey | Shelton | Away - Shelton HS-High School - Finn Stadium [Directions] | W 6-0 | 4:00 PM; 1 Bus | |
| Mon., 9/16 | JV Field Hockey | Shelton | Away - Shelton HS-High School - Finn Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/16 | V Girls Volleyball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | W 3-0 | 3:00 PM; 1 Bus | |
| Mon., 9/16 | JV Girls Volleyball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | W 2-0 | ||
| Tue., 9/17 | V Boys Cross Country | Daniel Hand | Away - Madison Surf Club-Surf Club [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 9/17 | V Boys Soccer | Amity | Away - Amity Regional HS-Amity High School - Field # 3 [Directions] | W 2-1 | 2:30 PM; 1 Bus | |
| Tue., 9/17 | V Girls Cross Country | Daniel Hand | Away - Madison Surf Club-Surf Club [Directions] | Hand 26- Cheshire 29 | 2:30 PM; 1 Bus | |
| Tue., 9/17 | V Girls Soccer | Guilford | Home - Cheshire High Main Game field [Directions] | L 0-1 | ||
| Tue., 9/17 | FR Girls Soccer | Amity | Away - Amity Regional HS-CENTER FIELD [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Wed., 9/18 | JV Girls Soccer | Guilford | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | FR Football | Hall | Away - Hall HS-Football Practice Field [Directions] | 3:45 p.m. | 2:15 PM; 1 Bus | |
| Thu., 9/19 | JV Boys Soccer | Jonathan Law | Away - Jonathan Law HS-Grass Field [Directions] | W 7-0 | 9:00 AM; 1 Bus | |
| Thu., 9/19 | V Girls Swimming and Diving | Mercy | Away - Bad-Site Wesleyan University-Freeman Athletic Center [Directions] | Cheshire 92 (3-0) - Mercy 75 | 5:15 PM; 1 Bus | |
| Thu., 9/19 | V Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | W 3-1 | ||
| Thu., 9/19 | JV Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | L 1-2 | ||
| Fri., 9/20 | V Football | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | L 28-35 | 4:30 PM; 2 Buses | |
| Fri., 9/20 | V Boys Soccer | Jonathan Law | Away - Jonathan Law HS-Lawmen Stadium [Directions] | W 6-0 | 2:30 PM; 1 Bus | |
| Fri., 9/20 | FR Boys Soccer | Notre Dame-West Haven | Home - Cheshire HS-Grass Fields [Directions] | W 3-1 | ||
| Fri., 9/20 | V Field Hockey | Amity | Away - Amity Regional HS-Field Hockey Field [Directions] | L 2-1 | 2:30 PM; 1 Bus | |
| Fri., 9/20 | JV Field Hockey | Amity | Away - Amity Regional HS-Field Hockey Field [Directions] | 5:15 p.m. | ||
| Fri., 9/20 | V Girls Soccer | West Haven | Home - Cheshire High Main Game field [Directions] | W 2-1 | ||
| Fri., 9/20 | V Girls Volleyball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | W 3-0 | 2:30 PM; 1 Bus | |
| Fri., 9/20 | JV Girls Volleyball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | W 2-0 | ||
| Sat., 9/21 | V Boys Cross Country | Winding Trails Invite | Away - Winding Trails-Cross Country Course | 12:00 p.m. | 10:00 AM; 1 Bus | |
| Sat., 9/21 | JV Football | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | 9:00 a.m. | 7:30 AM; 1 Bus | |
| Sat., 9/21 | V Girls Cross Country | Winding trails Invite | Away - Winding Trails-Cross Country Course | 12:00 p.m. | 10:00 AM; 1 Bus | |
| Sat., 9/21 | FR Field Hockey | Sacred Heart Academy | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 10:30 a.m. | ||
| Sat., 9/21 | JV Girls Soccer | West Haven | Home - Bartlem Park [Directions] | 10:30 a.m. | ||
| Mon., 9/23 | V Girls Soccer | East Haven | Away - East Haven HS-Turf Field [Directions] | W 1-0 | 4:00 PM; 1 Bus | |
| Mon., 9/23 | FR Girls Soccer | Daniel Hand | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Mon., 9/23 | V Girls Swimming and Diving | Hamden | Home - Cheshire Community Pool [Directions] | Cheshire 92 (4-0) - Hamden 86 | ||
| Mon., 9/23 | V Girls Volleyball | West Haven | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Mon., 9/23 | JV Girls Volleyball | West Haven | Home - Cheshire HS-Gym West [Directions] | W 2-0 | ||
| Tue., 9/24 | V Boys Cross Country | Branford, East Haven, Sheehan | Home - Cheshire Park-Field 1 [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 9/24 | V Boys Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | W 6-2 | ||
| Tue., 9/24 | JV Boys Soccer | North Haven | Home - Cheshire HS-Grass Fields [Directions] | W 3-0 | ||
| Tue., 9/24 | V Girls Cross Country | Branford, East Haven, Sheehan | Home - Cheshire Park-Field 1 [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Field Hockey | Mercy | Away - Mercy HS-Field Hockey Field [Directions] | W 2-0 | 2:30 PM; 1 Bus | |
| Tue., 9/24 | JV Field Hockey | Mercy | Away - Mercy HS-Field Hockey Field [Directions] | 5:30 p.m. | ||
| Tue., 9/24 | JV Girls Soccer | East Haven, North Haven (Scrim.) | Away - East Haven HS-Grass Soccer FIeld [Directions] | 4:15 p.m. | 2:30 PM; 1 Bus | |
| Wed., 9/25 | FR Field Hockey | Guilford | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | V Girls Swimming and Diving | Lyman Hall | Away - Sheehan HS-Sheehan HS Pool [Directions] | Cheshire 96 (5-0) - Lyman Hall 82 | 4:00 PM; 1 Bus | |
| Wed., 9/25 | V Girls Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Wed., 9/25 | JV Girls Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | W 2-0 | ||
| Thu., 9/26 | FR Football | Fairfield Warde | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Thu., 9/26 | V Boys Soccer | Guilford | Home - Cheshire High Main Game field [Directions] | W 1-0 | ||
| Thu., 9/26 | FR Boys Soccer | Fairfield Prep | Home - Cheshire HS-Grass Fields [Directions] | L 1-3 | ||
| Thu., 9/26 | V Girls Soccer | Lauralton Hall | Away - Lauralton Hall-Soccer Field [Directions] | W 3-0 | 2:30 PM; 1 Bus | |
| Fri., 9/27 | V Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | W 35-20 | 4:30 PM; 2 Buses | |
| Fri., 9/27 | JV Boys Soccer | Guilford | Home - Cheshire HS-Grass Fields [Directions] | W 5-4 | ||
| Fri., 9/27 | V Field Hockey | Hamden | Home - Cheshire HS-Main Game field [Directions] | W 6-0 | ||
| Fri., 9/27 | JV Field Hockey | Hamden | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:15 p.m. | ||
| Fri., 9/27 | V Girls Volleyball | North Haven | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Fri., 9/27 | JV Girls Volleyball | North Haven | Home - Cheshire HS-Gym West [Directions] | W 2-0 | ||
| Sat., 9/28 | JV Football | Fairfield Warde | Home - Cheshire High Main Game field [Directions] | 10:30 a.m. | ||
| Sat., 9/28 | V Boys Soccer | West Haven | Home - Cheshire High Main Game field [Directions] | W 7-1 | ||
| Sat., 9/28 | JV Boys Soccer | West Haven | Home - Cheshire High Main Game field [Directions] | W 5-0 | ||
| Sat., 9/28 | V Girls Soccer | Wilbur Cross | Away - Rice Field-Rice Field 2 [Directions] | W 9-0 | 9:00 AM; 1 Bus | |
| Sat., 9/28 | JV Girls Soccer | Wilbur Cross | Away - Rice Field-Rice Field 2 [Directions] | 12:00 p.m. | 10:30 AM; 1 Bus | |
| Tue., 10/1 | V Boys Soccer | Daniel Hand | Away - Madison Surf Club-Turf Field [Directions] | T 0-0 | 4:00 PM; 1 Bus | |
| Tue., 10/1 | JV Boys Soccer | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | L 0-2 | 2:30 PM; 1 Bus | |
| Tue., 10/1 | V Field Hockey | Sacred Heart Academy | Away - Sacred Heart Academy-Field Hockey Field [Directions] | W 3-2 | 2:30 PM; 1 Bus | |
| Tue., 10/1 | JV Field Hockey | Sacred Heart Academy | Away - Sacred Heart Academy-Field Hockey Field [Directions] | 5:30 p.m. | ||
| Tue., 10/1 | V Girls Swimming and Diving | Foran | Home - Cheshire Community Pool [Directions] | Cheshire 91 (6-0) - Foran 85 | ||
| Tue., 10/1 | V Girls Volleyball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | L 0-3 | 3:30 PM; 1 Bus | |
| Tue., 10/1 | JV Girls Volleyball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | W 2-1 | ||
| Wed., 10/2 | V Girls Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | W 2-1 | ||
| Wed., 10/2 | JV Girls Soccer | Daniel Hand | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Wed., 10/2 | V Girls Volleyball | Hamden | Away - Hamden HS-HHS Gym [Directions] | W 3-0 | 2:30 PM; 1 Bus | |
| Wed., 10/2 | JV Girls Volleyball | Hamden | Away - Hamden HS-HHS Gym [Directions] | W 2-0 | ||
| Thu., 10/3 | FR Football | Shelton | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | FR Field Hockey | Amity | Away - Amity Regional HS-Field Hockey Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Fri., 10/4 | V Football | Shelton | Away - Shelton HS-High School - Finn Stadium [Directions] | W 24-12 | 4:30 PM; 2 Buses | |
| Fri., 10/4 | V Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | L 1-0 | 2:30 PM; 1 Bus | |
| Fri., 10/4 | V Field Hockey | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | L 3-2 | 2:15 PM; 1 Bus | |
| Fri., 10/4 | JV Field Hockey | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | 5:15 p.m. | ||
| Fri., 10/4 | V Girls Soccer | Jonathan Law | Home - Cheshire High Main Game field [Directions] | W 1-0 | ||
| Fri., 10/4 | V Girls Swimming and Diving | Branford | Away - Walsh Intermediate - Branford-Pool [Directions] | Cheshire 97(7-0) - Branford 82 | 2:30 PM; 1 Bus | |
| Fri., 10/4 | V Girls Volleyball | East Haven | Away - East Haven HS-Gym [Directions] | W 3-0 | 2:30 PM; 1 Bus | |
| Fri., 10/4 | JV Girls Volleyball | East Haven | Away - East Haven HS-Gym [Directions] | W 2-0 | ||
| Sat., 10/5 | V Boys Cross Country | Nonnewaug | Away - Nonnewaug HS [Directions] | 9:00 a.m. | 7:25 AM; 1 Bus | |
| Sat., 10/5 | V Girls Cross Country | Nonnewaug | Away - Nonnewaug HS-XC Course [Directions] | 2:00 p.m. | TBA | |
| Sat., 10/5 | JV Girls Soccer | Jonathan Law | Home - Bartlem Park [Directions] | 10:30 a.m. | ||
| Mon., 10/7 | V Boys Cross Country | Shelton, Amity | Away - Shelton HS-Shelton High - Track [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Mon., 10/7 | JV Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | W 3-1 | 8:30 AM; 1 Bus | |
| Mon., 10/7 | V Girls Cross Country | Shelton, Amity | Away - Shelton HS-Shelton High - Track [Directions] | 3:45 p.m. | 2:15 PM; 1 Bus | |
| Mon., 10/7 | V Girls Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | W 2-1 | ||
| Mon., 10/7 | FR Girls Soccer | Amity | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | W 3-1 | 2:30 PM; 1 Bus | |
| Mon., 10/7 | JV Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | W 2-1 | ||
| Tue., 10/8 | FR Boys Soccer | Shelton | Away - Shelton HS-High School - Lower Field [Directions] | L 3-7 | 2:30 PM; 1 Bus | |
| Tue., 10/8 | V Field Hockey | Simsbury | Away - Holden Field-Turf [Directions] | W 2-1 | 2:30 PM; 1 Bus | |
| Tue., 10/8 | JV Field Hockey | Simsbury | Away - Simsbury HS-Holden Field (turf) [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Girls Swimming and Diving | North Haven | Home - Cheshire Community Pool [Directions] | Cheshire 94 (8-0) - North Haven 86 | ||
| Thu., 10/10 | FR Boys Soccer | Fairfield Prep | Away - Fairfield University-Barlow Field [Directions] | T 2-2 | 2:15 PM; 1 Bus | |
| Thu., 10/10 | V Girls Volleyball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | L 1-3 | 3:00 PM; 1 Bus | |
| Thu., 10/10 | JV Girls Volleyball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | L 1-2 | ||
| Fri., 10/11 | V Boys Soccer | Amity | Home - Cheshire High Main Game field [Directions] | W 5-0 | ||
| Fri., 10/11 | JV Boys Soccer | Jonathan Law | Home - Cheshire HS-Grass Fields [Directions] | W 6-0 | ||
| Fri., 10/11 | FR Boys Soccer | Notre Dame-West Haven | Away - Veterans Field [Directions] | W 5-0 | 2:30 PM; 1 Bus | |
| Fri., 10/11 | V Field Hockey | North Haven | Away - North Haven MS-East Turf Field [Directions] | W 8-0 | 2:15 PM; 1 Bus | |
| Fri., 10/11 | JV Field Hockey | North Haven | Away - North Haven MS-East Turf Field [Directions] | 5:15 p.m. | ||
| Fri., 10/11 | V Girls Soccer | Guilford | Away - Guilford HS-New Turf field at GHS [Directions] | T 0-0 | 2:15 PM; 1 Bus | |
| Fri., 10/11 | V Girls Swimming and Diving | Shelton | Away - Shelton Community Center Pool [Directions] | Cheshire 88 (9-0) - Shelton 77 | 2:15 PM; 1 Bus | |
| Sat., 10/12 | V Field Hockey | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | L 2-1 | 2:00 PM; 1 Bus | |
| Sat., 10/12 | JV Field Hockey | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:30 p.m. | ||
| Sat., 10/12 | V Girls Volleyball | Girls Volleyball Fall Brawl | Away - RHAM HS-RHAM MS | TBA | 7:00 AM; 1 Bus | |
| Mon., 10/14 | JV Boys Soccer | Amity | Home - Cheshire High Main Game field [Directions] | T 0-0 | ||
| Mon., 10/14 | FR Boys Soccer | Guilford | Away - Long Hill Park-Guilford-Soccer Field (Front) [Directions] | L 0-7 | 2:30 PM; 1 Bus | |
| Mon., 10/14 | V Field Hockey | Lyman Hall | Home - Cheshire HS-Main Game field [Directions] | W 7-0 | ||
| Mon., 10/14 | JV Field Hockey | Lyman Hall | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:15 p.m. | ||
| Tue., 10/15 | V Boys Soccer | Jonathan Law | Home - Cheshire High Main Game field [Directions] | W 5-0 | ||
| Tue., 10/15 | FR Boys Soccer | Daniel Hand | Home - Bartlem Park [Directions] | T 4-4 | ||
| Tue., 10/15 | V Field Hockey | Sheehan | Home - Cheshire HS-Main Game field [Directions] | W 6-1 | ||
| Tue., 10/15 | JV Field Hockey | Sheehan | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:15 p.m. | ||
| Tue., 10/15 | V Girls Soccer | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | T 0-0 | 3:30 PM; 1 Bus | |
| Tue., 10/15 | V Girls Volleyball | West Haven | Away - West Haven HS-Gym [Directions] | W 3-1 | 2:30 PM; 1 Bus | |
| Tue., 10/15 | JV Girls Volleyball | West Haven | Away - West Haven HS-Gym [Directions] | W 2-0 | ||
| Wed., 10/16 | JV Girls Soccer | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | Cancelled | 5:00 PM; 1 Bus | |
| Thu., 10/17 | V Boys Cross Country | SCC Championship | Away - East Shore Park Career J.V. | TBA | TBA; 1 Bus | |
| Thu., 10/17 | FR Football | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Thu., 10/17 | JV Boys Soccer | North Haven | Away - North Haven MS-West Turf Field [Directions] | W 4-0 | 9:00 AM; 1 Bus | |
| Thu., 10/17 | V Girls Cross Country | SCC championship | Away - East Shore Park Career J.V. | 1:00 p.m. | TBA; 1 Bus | |
| Thu., 10/17 | V Girls Soccer | East Haven | Home - Cheshire High Main Game field [Directions] | W 3-1 | ||
| Fri., 10/18 | V Football | Masuk | Home - Cheshire High Main Game field [Directions] | W 52-22 | ||
| Fri., 10/18 | V Boys Soccer | North Haven | Away - North Haven MS-West Turf Field [Directions] | W 3-0 | 2:30 PM; 1 Bus | |
| Fri., 10/18 | FR Field Hockey | Wethersfield | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | V Girls Swimming and Diving | Daniel Hand | Home - Cheshire Community Pool [Directions] | Cheshire 95 (10-0) - Daniel Hand 80 | ||
| Fri., 10/18 | V Girls Volleyball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | W 3-0 | 2:30 PM; 1 Bus | |
| Fri., 10/18 | JV Girls Volleyball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | W 2-0 | ||
| Sat., 10/19 | JV Football | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 11:00 a.m. | 9:30 AM; 1 Bus | |
| Mon., 10/21 | V Boys Soccer | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | L 1-0 | 4:30 PM; 1 Bus | |
| Mon., 10/21 | FR Field Hockey | Daniel Hand | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Girls Soccer | Lauralton Hall | Home - Cheshire High Main Game field [Directions] | W 3-1 | ||
| Mon., 10/21 | FR Girls Soccer | Guilford | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Girls Volleyball | Guilford | Home - Cheshire HS-Gym West [Directions] | L 2-3 | ||
| Mon., 10/21 | JV Girls Volleyball | Guilford | Home - Cheshire HS-Gym West [Directions] | L 0-2 | ||
| Tue., 10/22 | JV Boys Soccer | Guilford | Away - Long Hill Park-Guilford-Soccer Field (Front) [Directions] | W 1-0 | 2:30 PM; 1 Bus | |
| Tue., 10/22 | V Field Hockey | Lauralton Hall | Home - Cheshire HS-Main Game field [Directions] | W 5-0 | ||
| Tue., 10/22 | JV Field Hockey | Lauralton Hall | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:15 p.m. | ||
| Tue., 10/22 | JV Girls Soccer | Lauralton Hall | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Girls Swimming and Diving | Lauralton Hall | Home - Cheshire Community Pool [Directions] | Cheshire 94 (11-0) - Lauralton Hall 82 | ||
| Wed., 10/23 | V Boys Soccer | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | W 2-0 | 5:00 PM; 1 Bus | |
| Wed., 10/23 | FR Field Hockey | Guilford | Away - Guilford HS-Maturo Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Wed., 10/23 | V Girls Soccer | Wilbur Cross | Home - Cheshire High Main Game field [Directions] | W 8-0 | ||
| Wed., 10/23 | V Girls Volleyball | Foran | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Wed., 10/23 | JV Girls Volleyball | Foran | Home - Cheshire HS-Gym West [Directions] | W 2-0 | ||
| Wed., 10/23 | Miscellaneous Events | Unified soccer tournament | Home - Cheshire High Main Game field [Directions] | 2:00 p.m. | ||
| Thu., 10/24 | V Football | Wilbur Cross | Away - Bowen Field-Football Field [Directions] | W 37-0 | 4:30 PM; 2 Buses | |
| Thu., 10/24 | FR Football | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 10/24 | JV Boys Soccer | West Haven | Away - Bailey MS-Bailey MS [Directions] | T 0-0 | 5:00 PM; 1 Bus | |
| Thu., 10/24 | V Field Hockey | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | L 1-6 | 4:00 PM; 1 Bus | |
| Thu., 10/24 | JV Field Hockey | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 5:30 p.m. | ||
| Thu., 10/24 | V Girls Soccer | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | W 1-0 | 4:00 PM; 1 Bus | |
| Thu., 10/24 | JV Girls Soccer | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Fri., 10/25 | V Boys Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | L 0-2 | ||
| Fri., 10/25 | V Girls Swimming and Diving | Amity | Home - Cheshire Community Pool [Directions] | Cheshire 97 (12-0) - Amity 78 | ||
| Fri., 10/25 | V Girls Volleyball | Hamden | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Fri., 10/25 | JV Girls Volleyball | Hamden | Home - Cheshire HS-Gym West [Directions] | W 2-0 | ||
| Sat., 10/26 | V Boys Cross Country | CIAC Boys Class L Divisional Championship | Away - Wickham Park | 2:40 p.m. | ||
| Sat., 10/26 | JV Football | Wilbur Cross | Home - Cheshire High Main Game field [Directions] | 10:30 a.m. | ||
| Sat., 10/26 | V Girls Cross Country | CIAC Girls Class L Divisional Championship | Away - Wickham Park | 2:05 p.m. | ||
| Mon., 10/28 | V Boys Soccer | Xavier | Home - Cheshire High Main Game field [Directions] | L 1-2 | ||
| Mon., 10/28 | FR Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | L 1-3 | 2:30 PM; 1 Bus | |
| Mon., 10/28 | V Girls Soccer | Jonathan Law | Away - Jonathan Law HS-Lawmen Stadium [Directions] | L 0-3 | 4:00 PM; 1 Bus | |
| Mon., 10/28 | V Girls Volleyball | East Haven | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Mon., 10/28 | JV Girls Volleyball | East Haven | Home - Cheshire HS-Gym West [Directions] | W 2-0 | ||
| Tue., 10/29 | JV Boys Soccer | Xavier | Home - Cheshire HS-Grass Fields [Directions] | T 2-2 | ||
| Tue., 10/29 | V Field Hockey | Branford | Home - Cheshire HS-Main Game field [Directions] | W 1-0 | ||
| Tue., 10/29 | JV Field Hockey | Branford | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 4:30 p.m. | ||
| Wed., 10/30 | JV Girls Soccer | Jonathan Law | Away - Jonathan Law HS-Grass Field [Directions] | Cancelled | 2:30 PM; 1 Bus | |
| Wed., 10/30 | FR Girls Soccer | Daniel Hand | Away - Daniel Hand HS-Janssen Field #2/DHHS Campus [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Wed., 10/30 | V Girls Volleyball | Farmington | Away - Farmington HS [Directions] | L 2-3 | 2:30 PM; 1 Bus | |
| Wed., 10/30 | JV Girls Volleyball | Farmington | Away - Farmington HS [Directions] | W 2-0 | ||
| Thu., 10/31 | FR Football | East Haven | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Thu., 10/31 | FR Boys Soccer | Shelton | Home - Cheshire HS-Grass Fields [Directions] | Cancelled | ||
| Fri., 11/1 | V Boys Cross Country | CIAC Boys State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/1 | V Football | East Haven | Away - East Haven HS-Turf Field [Directions] | W 48-14 | 4:30 PM; 2 Buses | |
| Fri., 11/1 | V Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 7:00 p.m. | 5:00 PM | |
| Fri., 11/1 | V Girls Cross Country | CIAC Girls State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/1 | V Field Hockey | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | 3:45 p.m. | 1:45 PM | |
| Fri., 11/1 | JV Girls Soccer | Guilford | Away - Guilford HS-New Turf field at GHS [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Fri., 11/1 | FR Girls Soccer | Guilford | Away - Long Hill Park-Guilford-Soccer Field (Front) [Directions] | Cancelled | 2:30 PM; 1 Bus | |
| Fri., 11/1 | V Girls Swimming and Diving | Sheehan, Lauralton Hall, Amity, Branford, Career Magnet, Daniel Hand, Guilford, Hamden, Hillhouse, Jonathan Law, Foran, Lyman Hall, Mercy, TBA, North Haven, Sacred Heart Academy, West Haven, Wilbur Cross | Away - Sheehan HS-Sheehan HS Pool | Cheshire - 11th Place | TBA | |
| Sat., 11/2 | JV Football | Brookfield | Home - Cheshire High Main Game field [Directions] | 10:00 a.m. | ||
| Sat., 11/2 | V Girls Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | W 1-0 | ||
| Sat., 11/2 | V Girls Swimming and Diving | Lauralton Hall, Amity, Branford, Career Magnet, Daniel Hand, East Haven/Wilbur Cross, Guilford, Hamden, Hillhouse, Jonathan Law, Foran, Lyman Hall, Mercy, North Haven, Sacred Heart Academy, Sheehan, Shelton, West Haven, Wilbur Cross | Home - Cheshire Community Pool [Directions] | 5:00 p.m. | ||
| Sat., 11/2 | V Girls Volleyball | Hamden | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Mon., 11/4 | V Girls Soccer | Shelton | Home - Cheshire High Main Game field [Directions] | L 0-2 | ||
| Mon., 11/4 | V Girls Swimming and Diving | Lauralton Hall, Amity, Branford, Career Magnet, Daniel Hand, East Haven/Wilbur Cross, Guilford, Hamden, Hillhouse, Jonathan Law, Foran, Lyman Hall, Mercy, TBA, North Haven, Sacred Heart Academy, Sheehan, Shelton, West Haven, Wilbur Cross | Home - Southern CT State University-pool [Directions] | SCC Champions (1236) | 3:00 AM; 1 Bus | |
| Tue., 11/5 | V Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Wed., 11/6 | V Boys Soccer | scrimmage | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | ||
| Thu., 11/7 | JV Boys Soccer | scrimmage | Home - TBA [Directions] | 5:00 p.m. | ||
| Thu., 11/7 | V Girls Volleyball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 6:30 p.m. | ||
| Mon., 11/11 | V Boys Soccer | Fairfield Ludlowe | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | ||
| Mon., 11/11 | V Field Hockey | Fairfield Warde | Home - Cheshire High Main Game field [Directions] | 2:00 p.m. | ||
| Tue., 11/12 | V Girls Soccer | Danbury | Home - Cheshire High Main Game field [Directions] | W 2-1 | ||
| Wed., 11/13 | V Boys Soccer | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | 2:00 p.m. | 12:00 PM | |
| Wed., 11/13 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | 1:45 PM | |
| Wed., 11/13 | V Girls Swimming and Diving | CIAC Girls Class LL Diving Championship | Away - Middletown HS-Pool | 5:30 p.m. | ||
| Thu., 11/14 | FR Football | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Thu., 11/14 | V Girls Soccer | New Canaan | Home - Cheshire High Main Game field [Directions] | 2:00 p.m. | ||
| Thu., 11/14 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | 3:30 PM | |
| Fri., 11/15 | V Football | Sheehan | Home - Cheshire High Main Game field [Directions] | W 40-13 | ||
| Sat., 11/16 | JV Football | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 10:30 a.m. | 9:00 AM; 1 Bus | |
| Sat., 11/16 | V Girls Swimming and Diving | CIAC Girls Class LL Trials | Away - East Hartford HS-Pool | 11:30 a.m. | ||
| Tue., 11/19 | V Girls Swimming and Diving | CIAC Girls Class LL Finals | Away - Bad-Site Wesleyan University-Freeman Athletic Center | 7:00 p.m. | ||
| Thu., 11/21 | FR Football | Harding | Away - Warren Harding HS-Lewis Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Thu., 11/21 | V Girls Swimming and Diving | CIAC Girls State Open Diving | Away - Middletown HS-Pool | 5:30 p.m. | ||
| Fri., 11/22 | V Football | Harding | Home - Cheshire HS-Main Game field [Directions] | W 48-28 | ||
| Sat., 11/23 | JV Football | Harding | Away - Warren Harding HS-Lewis Field [Directions] | 10:00 a.m. | 9:30 AM; 1 Bus | |
| Sun., 11/24 | V Girls Swimming and Diving | CIAC Girls State Open Swimming | Away - Yale | 2:00 p.m. | ||
| Wed., 11/27 | V | Jr vs Sr Powderpuff | Home - Cheshire High Main Game field [Directions] | 1:00 p.m. | ||
| Thu., 11/28 | V Football | Southington | Home - Cheshire High Main Game field [Directions] | L 20-21 (OT) | ||
| Wed., 12/4 | V Football | Simsbury | Away - Holden Field-Turf [Directions] | 6:30 p.m. | 3:30 PM; 2 Buses | |
| Sat., 12/7 | V Boys Ice Hockey | Northeastern (Scrim.) | Home - Wesleyan University-Rink [Directions] | 10:00 a.m. | 8:15 AM; 1 Bus | |
| Sat., 12/7 | V Wrestling | Branford (Scrim.) | Away - Branford HS-Gym [Directions] | 9:00 a.m. | 8:00 AM | |
| Sat., 12/7 | V Girls Ice Hockey | Hamden Coop (Scrim.) | Away - Hamden-Lou Astorino Ice Rink [Directions] | 2:15 p.m. | ||
| Mon., 12/9 | V Girls Ice Hockey | Greenwich | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 1-3 | ||
| Tue., 12/10 | V Boys Basketball | Hartford Public (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | ||
| Tue., 12/10 | V Girls Basketball | Amity (Scrim.) | Home - Cheshire HS-Gym - East [Directions] | 3:30 p.m. | ||
| Thu., 12/12 | V Boys Basketball | Berlin (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Fri., 12/13 | V Girls Basketball | Newington (Scrim.) | Away - Newington HS-Newington [Directions] | 5:00 p.m. | 3:45 PM | |
| Sat., 12/14 | V Boys Ice Hockey | Newington Coop, Eastern CT Eagles, Wethersfield (Scrim.) | Away - Newington Ice Arena-Blue Rink [Directions] | 7:00 p.m. | 5:00 PM; 1 Bus | |
| Sat., 12/14 | V Wrestling | Xavier (Scrim.) | Home - Cheshire HS-Gym - East [Directions] | 9:00 a.m. | ||
| Sat., 12/14 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion-White [Directions] | W 6-2 | ||
| Mon., 12/16 | V Boys Basketball | Lyman Hall (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 3:15 p.m. | ||
| Mon., 12/16 | V Girls Ice Hockey | Hamden Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 3-2 | ||
| Wed., 12/18 | V Boys Ice Hockey | Conard | Home - Wesleyan University-Rink [Directions] | W 7-4 | 3:15 PM; 1 Bus | |
| Wed., 12/18 | V Wrestling | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | 4:30 PM; 1 Bus | |
| Wed., 12/18 | JV Wrestling | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 12/18 | V Girls Basketball | Platt | Home - Cheshire HS-Gym West [Directions] | W 56-38 | ||
| Wed., 12/18 | JV Girls Basketball | Platt | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Wed., 12/18 | FR Girls Basketball | Platt | Home - Cheshire HS-Gym - East [Directions] | 3:45 p.m. | ||
| Wed., 12/18 | V Girls Ice Hockey | Branford | Away - East Haven HS-Veterans Rink [Directions] | W 7-3 | ||
| Thu., 12/19 | V Boys Basketball | Hillhouse | Home - Cheshire HS-Gym West [Directions] | L 27-50 | ||
| Thu., 12/19 | JV Boys Basketball | Hillhouse | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | ||
| Thu., 12/19 | FR Boys Basketball | Hillhouse | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Thu., 12/19 | JV Boys Ice Hockey | Lyman Hall | Home - Wesleyan University-Rink [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Thu., 12/19 | V Boys Swimming and Diving | Sheehan | Away - Sheehan HS-Sheehan HS Pool [Directions] | Cheshire 98 Sheehan 73 | 4:00 PM; 1 Bus | |
| Thu., 12/19 | V Girls Indoor Track | SCC Girls Developmental | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | 3:30 PM; 1 Bus | |
| Fri., 12/20 | V Girls Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | L 34-37 | 4:30 PM; 1 Bus | |
| Fri., 12/20 | JV Girls Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/20 | FR Girls Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Sat., 12/21 | V Boys Basketball | Platt | Home - Cheshire HS-Gym West [Directions] | W 81-60 | ||
| Sat., 12/21 | JV Boys Basketball | Platt | Home - Cheshire HS-Gym West [Directions] | 4:15 p.m. | ||
| Sat., 12/21 | FR Boys Basketball | Platt | Home - Cheshire HS-Gym West [Directions] | 2:45 p.m. | ||
| Sat., 12/21 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavilion-Red [Directions] | W 3-2 | 1:30 PM; 1 Bus | |
| Sat., 12/21 | V Wrestling | Derby Invitational | Away - Derby HS-Gym | 9:30 a.m. | 7:30 AM; 1 Bus | |
| Mon., 12/23 | V Boys Ice Hockey | Glastonbury | Home - Wesleyan University-Rink [Directions] | W 3-2 | 11:15 AM; 1 Bus | |
| Mon., 12/23 | V Boys Indoor Track | SCC Boys Developmental | Away - New Haven Athletic Center/Hillhouse HS | 10:00 a.m. | 8:30 AM; 1 Bus | |
| Mon., 12/23 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 3-2 | ||
| Fri., 12/27 | V Boys Swimming and Diving | Holy Cross | Home - Cheshire Community Pool [Directions] | Cheshire 95 Holy Cross 85 | ||
| Fri., 12/27 | V Girls Basketball | Platt | Away - Platt HS-Gym [Directions] | W 51-30 | 11:00 AM; 1 Bus | |
| Fri., 12/27 | JV Girls Basketball | Platt | Away - Platt HS-Gym [Directions] | 12:30 p.m. | ||
| Fri., 12/27 | FR Girls Basketball | Platt | Away - Platt HS-Gym [Directions] | 11:00 a.m. | 9:30 AM; 1 Bus | |
| Sat., 12/28 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Wesleyan University-Rink [Directions] | L 2-3 | 4:15 PM; 1 Bus | |
| Sat., 12/28 | V Wrestling | Spartan Duals | Away - Maloney HS-Maloney Main Gym | 10:00 a.m. | 7:30 AM | |
| Sat., 12/28 | V Girls Ice Hockey | Daniel Hand Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 4-0 | ||
| Mon., 12/30 | V Boys Ice Hockey | Sheehan | Home - Wesleyan University-Rink [Directions] | W 5-4 | 4:00 PM; 1 Bus | |
| Mon., 12/30 | V Girls Basketball | Plainville | Away - Plainville HS-Wood Gymnasium [Directions] | L 34-39 | 4:00 PM; 1 Bus | |
| Mon., 12/30 | JV Girls Basketball | Plainville | Away - Plainville HS-Wood Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 12/30 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | W 9-3 | ||
| Thu., 1/2 | V Wrestling | Notre Dame-West Haven | Away - Notre Dame HS-Gym [Directions] | 7:00 p.m. | 5:00 PM; 1 Bus | |
| Fri., 1/3 | V Boys Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | L 40-44 | ||
| Fri., 1/3 | JV Boys Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Fri., 1/3 | FR Boys Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Fri., 1/3 | V Boys Swimming and Diving | Southington | Home - Cheshire Community Pool [Directions] | Cheshire 98 Southington 85 | ||
| Fri., 1/3 | V Girls Basketball | West Haven | Away - West Haven HS-Gym [Directions] | L 43-49 | 3:00 PM; 1 Bus | |
| Fri., 1/3 | JV Girls Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 4:15 p.m. | ||
| Fri., 1/3 | FR Girls Basketball | Simsbury | Away - Simsbury HS-Simsbury / Main Gym [Directions] | 3:45 p.m. | 2:30 PM | |
| Sat., 1/4 | V Boys Ice Hockey | Wethersfield | Away - Newington Ice Arena-Blue Rink [Directions] | L 0-2 | 4:15 PM; 1 Bus | |
| Sat., 1/4 | V Girls Ice Hockey | East Catholic Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | T 1-1 | ||
| Mon., 1/6 | JV Boys Ice Hockey | Xavier | Away - Wesleyan University-Rink [Directions] | 5:00 p.m. | ||
| Mon., 1/6 | V Girls Ice Hockey | Suffield Coop | Away - Enfield Twin Rinks-Rink 1 [Directions] | L 2-3 | 5:45 PM; 1 Bus (B&B - 5:45 Amity then pick up at North Haven) | |
| Mon., 1/6 | V Girls Indoor Track | SCC Girls Developmental | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | 3:30 PM; 1 Bus | |
| Tue., 1/7 | V Boys Basketball | West Haven | Away - West Haven HS-Gym [Directions] | L 56-60 | 3:45 PM; 1 Bus | |
| Tue., 1/7 | JV Boys Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/7 | FR Boys Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Tue., 1/7 | V Girls Basketball | Wilbur Cross | Home - Cheshire HS-Gym West [Directions] | L 37-53 | ||
| Tue., 1/7 | JV Girls Basketball | Wilbur Cross | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Wed., 1/8 | V Boys Ice Hockey | Branford | Away - Northford Ice Pavilion-Red [Directions] | L 0-3 | 2:30 PM; 1 Bus | |
| Thu., 1/9 | JV Boys Ice Hockey | Wethersfield (Scrim.) | Home - Wesleyan University-Rink [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Thu., 1/9 | V Boys Indoor Track | SCC Novice developmental | Away - New Haven Athletic Center/Hillhouse HS | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Thu., 1/9 | V Boys Swimming and Diving | N.Haven/E.Haven/N.Bran/Guil | Away - Walter Gawrych Community Pool [Directions] | Cheshire 97 N. Haven/E. Haven/N. Branford/Guilford 88 | 2:15 PM; 1 Bus | |
| Thu., 1/9 | V Girls Indoor Track | SCC Novice Developmental | Away - New Haven Athletic Center/Hillhouse HS | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Fri., 1/10 | V Boys Basketball | Xavier | Home - Cheshire HS-Gym West [Directions] | L 36-38 | ||
| Fri., 1/10 | JV Boys Basketball | Xavier | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 1/10 | FR Boys Basketball | Xavier | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Fri., 1/10 | V Boys Indoor Track | Yale Invite | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 1:00 p.m. | 11:30 AM | |
| Fri., 1/10 | V Girls Basketball | Shelton | Home - Cheshire HS-Gym - East [Directions] | L 20-45 | ||
| Fri., 1/10 | JV Girls Basketball | Shelton | Home - Cheshire HS-Gym - East [Directions] | 5:15 p.m. | ||
| Fri., 1/10 | FR Girls Basketball | Shelton | Home - Cheshire HS-Gym - East [Directions] | 3:45 p.m. | ||
| Fri., 1/10 | V Girls Indoor Track | Yale Invite | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 1:00 p.m. | 11:30 AM | |
| Sat., 1/11 | V Boys Ice Hockey | East Catholic | Home - Wesleyan University-Rink [Directions] | W 2-1 | 6:30 PM; 1 Bus | |
| Sat., 1/11 | V Boys Indoor Track | Yale Invite | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 9:00 a.m. | ||
| Sat., 1/11 | V Wrestling | Casey Yates Invitational | Away - Lyman Memorial HS-Gym | 9:00 a.m. | 7:30 AM | |
| Sat., 1/11 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | W 6-2 | ||
| Sat., 1/11 | V Girls Indoor Track | Yale Invite | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 9:00 a.m. | ||
| Mon., 1/13 | V Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | L 53-59 | 4:30 PM; 1 Bus | |
| Mon., 1/13 | JV Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 1/13 | FR Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Mon., 1/13 | JV Boys Ice Hockey | East Catholic | Home - Wesleyan University-Rink [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Mon., 1/13 | V Girls Basketball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | L 29-51 | ||
| Mon., 1/13 | JV Girls Basketball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Tue., 1/14 | V Boys Indoor Track | SCC Boys Developmental | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | 3:00 PM; 1 Bus | |
| Tue., 1/14 | V Boys Swimming and Diving | Hamden | Home - Cheshire Community Pool [Directions] | Cheshire 91 Hamden 81 | ||
| Tue., 1/14 | V Co-ed Fencing | Guilford | Away - Guilford HS-Aux gym at GHS [Directions] | 6:30 p.m. | ||
| Wed., 1/15 | V Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | L 60-74 | 4:00 PM; 1 Bus | |
| Wed., 1/15 | JV Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | ||
| Wed., 1/15 | FR Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 3:30 p.m. | 2:30 PM | |
| Wed., 1/15 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion-Red [Directions] | W 2-1 | 2:30 PM; 1 Bus | |
| Wed., 1/15 | V Wrestling | Branford, Morgan | Home - Cheshire HS-Gym - East [Directions] | 5:00 p.m. | ||
| Wed., 1/15 | V Co-ed Fencing | Daniel Hand | Home - Cheshire HS [Directions] | 5:30 p.m. | ||
| Wed., 1/15 | V Girls Basketball | Lauralton Hall | Away - Lauralton Hall-Gym [Directions] | W 49-32 | 3:00 PM; 1 Bus | |
| Wed., 1/15 | JV Girls Basketball | Lauralton Hall | Away - Lauralton Hall-Gym [Directions] | 4:30 p.m. | ||
| Thu., 1/16 | V Girls Ice Hockey | Guilford Coop | Away - East Haven HS-Veterans Rink [Directions] | W 6-4 | ||
| Fri., 1/17 | V Boys Basketball | Hillhouse | Away - Hillhouse HS-Gym [Directions] | L 40-47 | 4:00 PM; 1 Bus | |
| Fri., 1/17 | JV Boys Basketball | Hillhouse | Away - Hillhouse HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/17 | FR Boys Basketball | Hillhouse | Away - Hillhouse HS-Gym [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Fri., 1/17 | V Girls Basketball | Foran | Home - Cheshire HS-Gym West [Directions] | L 33-39 | ||
| Fri., 1/17 | JV Girls Basketball | Foran | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Girls Basketball | Foran | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Sat., 1/18 | V Boys Ice Hockey | West Haven Coop | Home - Wesleyan University-Rink [Directions] | W 3-1 | 8:15 AM; 1 Bus | |
| Sat., 1/18 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | Greenwich 130 Cheshire 56 | 7:15 AM; 1 Bus | |
| Sat., 1/18 | V Wrestling | The Colter Abely Mid-Season Classic | Away - Mercy HS-Gym 1 | 9:00 a.m. | 6:45 AM | |
| Sat., 1/18 | V Girls Indoor Track | SCC Coaches invite | Away - New Haven Athletic Center/Hillhouse HS | 9:00 a.m. | 7:30 AM; 1 Bus | |
| Mon., 1/20 | V Boys Ice Hockey | South Windsor | Away - South Windsor Arena-Ice Rink [Directions] | L 2-3 | 1:00 PM; 1 Bus | |
| Mon., 1/20 | V Boys Swimming and Diving | Notre Dame-West Haven | Away - Albertus Magnus College-Albertus Magnus Pool [Directions] | Cheshire 99 Notre Dame 81 | 2:00 PM; 1 Bus | |
| Tue., 1/21 | V Boys Basketball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | L 58-68 | 4:00 PM; 1 Bus | |
| Tue., 1/21 | JV Boys Basketball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 5:15 p.m. | ||
| Tue., 1/21 | FR Boys Basketball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Tue., 1/21 | V Boys Indoor Track | SCC Coaches invite | Away - New Haven Athletic Center/Hillhouse HS | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 1/21 | V Girls Basketball | Lyman Hall | Home - Cheshire HS-Gym - East [Directions] | L 44-63 | ||
| Tue., 1/21 | JV Girls Basketball | Lyman Hall | Home - Cheshire HS-Gym - East [Directions] | 5:15 p.m. | ||
| Tue., 1/21 | FR Girls Basketball | Lyman Hall | Home - Cheshire HS-Gym - East [Directions] | 3:45 p.m. | ||
| Wed., 1/22 | V Boys Ice Hockey | Immaculate | Home - Wesleyan University-Rink [Directions] | L 5-6 | 4:15 PM; 1 Bus | |
| Wed., 1/22 | V Boys Indoor Track | SCC Novice championship | Away - New Haven Athletic Center/Hillhouse HS | 3:30 p.m. | 2:15 PM; 1 Bus | |
| Wed., 1/22 | V Wrestling | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 7:00 p.m. | 5:00 PM; 1 Bus | |
| Wed., 1/22 | V Girls Indoor Track | SCC Novice championship | Away - New Haven Athletic Center/Hillhouse HS | 3:30 p.m. | 1:15 PM; 1 Bus | |
| Thu., 1/23 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | W 5-1 | 5:00 PM; 1 Bus (B&B Pick up Amity 5:00 then to Stamford) | |
| Fri., 1/24 | V Boys Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | L 63-72 | 4:00 PM; 1 Bus | |
| Fri., 1/24 | JV Boys Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/24 | FR Boys Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Fri., 1/24 | JV Boys Ice Hockey | East Catholic | Away - Cromwell - Lower-Lower Rink [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Fri., 1/24 | V Girls Basketball | West Haven | Home - Cheshire HS-Gym West [Directions] | L 45-64 | ||
| Fri., 1/24 | JV Girls Basketball | West Haven | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | ||
| Sat., 1/25 | V Boys Ice Hockey | North Haven | Home - Wesleyan University-Rink [Directions] | T 1-1 | 1:45 PM; 1 Bus | |
| Sat., 1/25 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 3-2 (OT) | ||
| Mon., 1/27 | JV Boys Ice Hockey | Hamden Hall | Away - Northford Ice Pavilion | 4:30 p.m. | 2:45 PM; 1 Bus | |
| Mon., 1/27 | V Boys Swimming and Diving | Amity | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | Cheshire 98 Amity 85 | 4:30 PM; 1 Bus | |
| Mon., 1/27 | V Co-ed Fencing | North Haven | Home - Cheshire HS-Default Facility [Directions] | 6:30 p.m. | ||
| Mon., 1/27 | FR Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 3:45 p.m. | 2:30 PM | |
| Tue., 1/28 | V Boys Basketball | Foran | Home - Cheshire HS-Gym West [Directions] | L 46-51 | ||
| Tue., 1/28 | JV Boys Basketball | Foran | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Tue., 1/28 | FR Boys Basketball | Foran | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Tue., 1/28 | V Girls Basketball | Branford | Away - Branford HS-Gym [Directions] | L 46-54 | 3:30 PM; 1 Bus | |
| Tue., 1/28 | JV Girls Basketball | Branford | Away - Branford HS-Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/28 | V Girls Ice Hockey | New Canaan | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 2-3 | ||
| Wed., 1/29 | V Boys Ice Hockey | E.Haven Coop | Away - East Haven HS-Veterans Rink [Directions] | L 0-1 | 5:30 PM; 1 Bus | |
| Wed., 1/29 | V Boys Indoor Track | SCC East Championship | Away - New Haven Athletic Center/Hillhouse HS | 4:30 p.m. | 2:30 PM; 1 Bus | |
| Wed., 1/29 | V Wrestling | Fairfield Prep | Home - Cheshire HS-Gym - East [Directions] | 6:30 p.m. | ||
| Wed., 1/29 | V Girls Indoor Track | SCC East championship | Away - New Haven Athletic Center/Hillhouse HS | 4:30 p.m. | 2:30 PM; 1 Bus | |
| Thu., 1/30 | Miscellaneous Events | curriculum night | Home - Cheshire HS-Gym - East [Directions] | 6:30 p.m. | ||
| Fri., 1/31 | V Boys Basketball | Hamden | Home - Cheshire HS-Gym West [Directions] | L 40-70 | ||
| Fri., 1/31 | JV Boys Basketball | Hamden | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Fri., 1/31 | FR Boys Basketball | Hamden | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Fri., 1/31 | V Girls Basketball | Wilbur Cross | Away - Wilbur Cross HS-Gym [Directions] | L 39-51 | 4:00 PM; 1 Bus | |
| Fri., 1/31 | JV Girls Basketball | Wilbur Cross | Away - Wilbur Cross HS-Gym [Directions] | 5:30 p.m. | ||
| Sat., 2/1 | V Boys Ice Hockey | Daniel Hand | Away - Northford Ice Pavilion-Red [Directions] | T 1-1(OT) | 3:15 PM; 1 Bus | |
| Sat., 2/1 | V Competitive Cheerleading | SCC Cheerleading Competition | Away - North Haven HS-Fred Kelly Gymnasium | 9:00 a.m. | ||
| Sat., 2/1 | V Girls Ice Hockey | Conard | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 0-5 | ||
| Mon., 2/3 | V Boys Basketball | Xavier | Away - Xavier HS-Gym [Directions] | L 43-59 | 4:00 PM; 1 Bus | |
| Mon., 2/3 | JV Boys Basketball | Xavier | Away - Xavier HS-Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/3 | FR Boys Basketball | Xavier | Away - Xavier HS-Gym [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Mon., 2/3 | JV Boys Ice Hockey | Hamden Hall | Home - Northford Ice Pavilion-Blue [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | |
| Mon., 2/3 | V Boys Swimming and Diving | Fairfield Prep | Home - Cheshire Community Pool [Directions] | Fairfield Prep 93 Cheshire 91 | ||
| Mon., 2/3 | V Girls Basketball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | L 33-54 | 4:00 PM; 1 Bus | |
| Mon., 2/3 | JV Girls Basketball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/3 | FR Girls Basketball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Tue., 2/4 | V Boys Swimming and Diving | Xavier | Away - Wesleyan University-Pool [Directions] | Xavier 96 Cheshire 85 | 4:30 PM; 1 Bus | |
| Tue., 2/4 | V Wrestling | New Haven Wrestling | Away - Wilbur Cross HS-Little Gym [Directions] | 6:00 p.m. | 4:30 PM; 1 Bus | |
| Wed., 2/5 | V Boys Basketball | Weaver | Away - Weaver HS-Bulkeley High School [Directions] | L 41-66 | 3:00 PM; 1 Bus | |
| Wed., 2/5 | V Girls Basketball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | L 41-63 | 3:45 PM; 1 Bus | |
| Wed., 2/5 | JV Girls Basketball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/5 | FR Girls Basketball | Simsbury | Home - Cheshire HS-Gym - East [Directions] | 4:00 p.m. | ||
| Thu., 2/6 | V Girls Ice Hockey | Simsbury | Away - Simsbury ISCC-NHL [Directions] | L 0-7 | 2:00 PM; 1 Bus (B&B Pick up Amity 2:00, then Cheshire) | |
| Fri., 2/7 | V Boys Basketball | West Haven | Home - Cheshire HS-Gym West [Directions] | L 36-59 | ||
| Fri., 2/7 | JV Boys Basketball | West Haven | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | FR Boys Basketball | West Haven | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Fri., 2/7 | V Boys Indoor Track | SCC Championship | Away - New Haven Athletic Center/Hillhouse HS | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Fri., 2/7 | V Co-ed Fencing | Morgan, Marine Science Magnet | Away - Morgan HS-Gym 1 [Directions] | 6:30 p.m. | ||
| Fri., 2/7 | V Girls Basketball | Lauralton Hall | Home - Cheshire HS-Gym - East [Directions] | L 18-36 | ||
| Fri., 2/7 | JV Girls Basketball | Lauralton Hall | Home - Cheshire HS-Gym - East [Directions] | 4:15 p.m. | ||
| Fri., 2/7 | V Girls Indoor Track | SCC championship | Away - New Haven Athletic Center/Hillhouse HS | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Sat., 2/8 | V Boys Ice Hockey | Guilford | Home - Wesleyan University-Rink [Directions] | W 4-0 | 4:15 PM; 1 Bus | |
| Sat., 2/8 | V Wrestling | East Lyme Duals | Away - East Lyme HS-North Gym | 9:00 a.m. | 6:30 AM | |
| Sat., 2/8 | V Girls Ice Hockey | West Haven/SHA | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 7-6 (OT) | ||
| Tue., 2/11 | V Boys Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | W 72-45 | ||
| Tue., 2/11 | JV Boys Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Tue., 2/11 | FR Boys Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Tue., 2/11 | V Boys Swimming and Diving | Suffield | Home - Cheshire Community Pool [Directions] | Cheshire 98 Suffield Co Op 67 | ||
| Wed., 2/12 | JV Boys Ice Hockey | Wethersfield | Away - Newington Ice Arena-Blue Rink [Directions] | 3:55 p.m. | 2:30 PM; 1 Bus | |
| Wed., 2/12 | V Wrestling | Shelton | Home - Cheshire HS-Gym - East [Directions] | 6:30 p.m. | ||
| Wed., 2/12 | V Girls Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | W 37-34 | 4:15 PM; 1 Bus | |
| Wed., 2/12 | JV Girls Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/12 | FR Girls Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Wed., 2/12 | V Girls Ice Hockey | Masuk Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 6-1 | ||
| Thu., 2/13 | V Co-ed Fencing | North Haven | Away - North Haven HS-Auxiliary Gymnasium [Directions] | 6:30 p.m. | ||
| Fri., 2/14 | V Boys Swimming and Diving | Daniel Hand | Home - Cheshire Community Pool [Directions] | Cheshire 96 Hand 74 | ||
| Fri., 2/14 | JV Wrestling | Amity, Branford, Daniel Hand, East Haven, Fairfield Prep, Guilford, Jonathan Law, Foran, Morgan, Notre Dame-West Haven, Shelton, New Haven Wrestling, Xavier | Away - Mercy HS-Gym | 4:30 p.m. | 2:30 PM | |
| Fri., 2/14 | V Girls Basketball | Branford | Home - Cheshire HS-Gym West [Directions] | W 40-33 | ||
| Fri., 2/14 | JV Girls Basketball | Branford | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Sat., 2/15 | V Boys Basketball | Guilford | Home - Cheshire HS-Gym West [Directions] | W 56-55 | ||
| Sat., 2/15 | JV Boys Basketball | Guilford | Home - Cheshire HS-Gym West [Directions] | 4:15 p.m. | ||
| Sat., 2/15 | FR Boys Basketball | Guilford | Home - Cheshire HS-Gym West [Directions] | 2:45 p.m. | ||
| Sat., 2/15 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | L 0-1 | 1:00 PM; 1 Bus | |
| Sat., 2/15 | V Boys Indoor Track | CIAC Boys Class L Divisional Championship | Away - Floyd Little Athletic Center-Field House | 10:00 a.m. | ||
| Sat., 2/15 | V Wrestling | Amity, Branford, Daniel Hand, East Haven, Fairfield Prep, Guilford, Jonathan Law, Foran, Morgan, TBA, Notre Dame-West Haven, Shelton, West Haven, New Haven Wrestling, Xavier | Away - Mercy HS-Gym | 9:00 a.m. | 7:30 AM | |
| Sat., 2/15 | V Girls Indoor Track | CIAC Girls Class L Divisional Championship | Away - Floyd Little Athletic Center-FieldHouse | 10:00 a.m. | ||
| Mon., 2/17 | V Girls Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | W 47-42 OT | ||
| Mon., 2/17 | JV Girls Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 4:15 p.m. | ||
| Mon., 2/17 | V Girls Ice Hockey | Avon Coop | Away - Newington Ice Arena-Blue Rink [Directions] | L 2-3 | 11:30 AM; 1 Bus (B&B Pick up Amity 11:30 then to Cheshire) | |
| Tue., 2/18 | V Boys Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | W 55-46 | 4:00 PM; 1 Bus | |
| Tue., 2/18 | JV Boys Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/18 | FR Boys Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Tue., 2/18 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | L 5-7 | ||
| Wed., 2/19 | V Boys Ice Hockey | Farmington Valley | Home - Wesleyan University-Rink [Directions] | L 0-2 | 2:30 PM; 1 Bus | |
| Fri., 2/21 | V Boys Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | L 50-63 | 4:00 PM; 1 Bus | |
| Fri., 2/21 | JV Boys Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/21 | FR Boys Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Fri., 2/21 | V Wrestling | CIAC Class L Divisional Championship | Away - Bristol Central-Charles C. Marsh Gymnasium | 3:00 p.m. | ||
| Sat., 2/22 | V Boys Basketball | Southington | Away - Southington HS-Gym West [Directions] | W 52-48 | 4:00 PM; 1 Bus | |
| Sat., 2/22 | JV Boys Basketball | Greens Farms Academy | Away - Greens Farms Academy-Default Facility | 12:00 p.m. | ||
| Sat., 2/22 | JV Boys Basketball | Southington | Away - Southington HS-Gym West [Directions] | 5:15 p.m. | ||
| Sat., 2/22 | FR Boys Basketball | Southington | Away - Southington HS-Gym West [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Sat., 2/22 | V Boys Ice Hockey | Xavier | Home - Wesleyan University-Rink [Directions] | L 0-4 | 4:45 PM; 1 Bus | |
| Sat., 2/22 | JV Boys Ice Hockey | Xavier | Home - Wesleyan University-Rink [Directions] | 6:00 p.m. | ||
| Sat., 2/22 | V Boys Indoor Track | CIAC Boys State Open Championship | Away - Floyd Little Athletic Center-Field House | 12:00 p.m. | ||
| Sat., 2/22 | V Wrestling | CIAC Class L Divisional Championship | Away - Bristol Central-Charles C. Marsh Gymnasium | 9:00 a.m. | ||
| Sat., 2/22 | V Girls Indoor Track | CIAC Girls State Open Championship | Away - Floyd Little Athletic Center-FieldHouse | 12:00 p.m. | ||
| Tue., 2/25 | V Boys Swimming and Diving | Shelton | Home - Cheshire Community Pool [Directions] | Cheshire 101 Shelton 77 | ||
| Wed., 2/26 | V Girls Basketball | New Britain (Scrim.) | Home - Cheshire HS-Gym - East [Directions] | 4:00 p.m. | ||
| Wed., 2/26 | V Girls Ice Hockey | Hamden Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | ||
| Fri., 2/28 | V Boys Basketball | Simsbury (Scrim.) | Away - Simsbury HS-Simsbury / Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/28 | V Boys Swimming and Diving | SCC Diving Championship | Away - Sheehan HS-Sheehan HS Pool | 5:30 p.m. | ||
| Fri., 2/28 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-Field House | 3:00 p.m. | ||
| Sat., 2/29 | V Boys Ice Hockey | Eastern CT Eagles | Home - Wesleyan University-Rink [Directions] | L 0-6 | 5:05 PM; 1 Bus | |
| Sat., 2/29 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-Field House | 9:00 a.m. | ||
| Sat., 2/29 | V Girls Ice Hockey | Guilford Coop | Home - West Haven HS-Bennett Rink [Directions] | 1:00 p.m. | ||
| Mon., 3/2 | V Boys Swimming and Diving | SCC Championship Qualifying Meet | Home - Cheshire Community Pool [Directions] | Suspended | ||
| Mon., 3/2 | V Girls Basketball | Newtown | Away - Newtown HS [Directions] | 6:30 p.m. | 4:30 PM | |
| Tue., 3/3 | V Girls Ice Hockey | Guilford Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | ||
| Wed., 3/4 | V Boys Swimming and Diving | SCC Championship Meet | Away - Southern CT State University-pool | Suspended | 2:30 PM | |
| Mon., 3/9 | V Boys Ice Hockey | Westhill-Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 6:40 p.m. | ||
| Thu., 3/12 | V Boys Swimming and Diving | CIAC Boys Class L Diving Championship | Away - Middletown HS-MHS Pool | Cancelled | ||
| Sat., 3/14 | V Boys Swimming and Diving | CIAC Boys Class L Trials | Away - Cornerstone Aquatics Center-Pool | Cancelled | ||
| Tue., 3/17 | V Boys Swimming and Diving | CIAC Boys Class L Finals | Away - Wesleyan University-Pool | Cancelled | ||
| Thu., 3/19 | V Boys Swimming and Diving | CIAC Boys State Open Diving | Away - Bulkeley HS-Pool | Cancelled | ||
| Sat., 3/21 | V Boys Swimming and Diving | CIAC Boys State Open Swimming | Away - Yale | Cancelled | ||
| Thu., 3/26 | V Softball | Masuk (Scrim.) | Away - Masuk HS-Masuk High School Softball Field [Directions] | Cancelled | 2:15 PM | |
| Sat., 3/28 | V Boys Lacrosse | Brien McMahon, Minnechaug (MA) (Scrim.) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Sat., 3/28 | V Girls Lacrosse | Staples, Bishop Guertin (NH), Fairfield Ludlowe, Greenwich, TBA, Pleasantville (NY), Weston | Away - Staples HS-Ginny Parker Field | Cancelled | 7:45 AM | |
| Sat., 3/28 | V Softball | Norwich Free Academy | Home - Cheshire HS-Softball Diamond [Directions] | Cancelled | ||
| Sat., 3/28 | JV Softball | Norwich Free Academy | Home - Cheshire HS-Softball Diamond 2 [Directions] | Cancelled | ||
| Sat., 3/28 | V Girls Tennis | Lauralton Hall, Southington (Scrim.) | Away - Tennis Central [Directions] | Cancelled | ||
| Mon., 3/30 | V Softball | Seymour (Scrim.) | Away - Seymour HS-Softball Diamond [Directions] | Cancelled | 2:15 PM | |
| Tue., 3/31 | V Baseball | Southington (Scrim.) | Away - Southington HS-Baseball Varsity Field [Directions] | Cancelled | 2:15 PM | |
| Tue., 3/31 | V Girls Lacrosse | Wilton (Scrim.) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Wed., 4/1 | V Baseball | West Haven (Scrim.) | Away - West Haven HS-Whitey Piurek Field [Directions] | Cancelled | 2:30 PM | |
| Wed., 4/1 | V Boys Lacrosse | Newtown (Scrim.) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Wed., 4/1 | V Softball | Fairfield Ludlowe (Scrim.) | Home - Cheshire HS-Softball Diamond [Directions] | Cancelled | ||
| Wed., 4/1 | JV Softball | Fairfield Ludlowe (Scrim.) | Home - Cheshire HS-Softball Diamond 2 [Directions] | Cancelled | ||
| Thu., 4/2 | V Girls Lacrosse | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | Cancelled | 3:15 PM | |
| Thu., 4/2 | JV Girls Lacrosse | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | Cancelled | 3:15 PM | |
| Fri., 4/3 | V Baseball | East Haven (Scrim.) | Away - East Haven HS-Baseball Field [Directions] | Cancelled | 2:30 PM | |
| Fri., 4/3 | V Softball | Immaculate Conception (NJ) | Away - Seton Hall (HS Teams) | Cancelled | ||
| Sat., 4/4 | V Boys Lacrosse | Crestwood (PA) | Home - Western CT State University [Directions] | Cancelled | 1:00 PM; 1 Bus | |
| Sat., 4/4 | JV Boys Lacrosse | Crestwood (PA) | Home - Western CT State University [Directions] | Cancelled | 2:00 PM | |
| Sat., 4/4 | V Boys Tennis | Pomperaug | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Sat., 4/4 | V Boys Volleyball | Glastonbury | Away - Glastonbury HS-Gym [Directions] | Cancelled | 7:30 AM | |
| Sat., 4/4 | V Softball | Blair Academy (NJ) | Home - Branch Brook Park-Field #1-Turf [Directions] | Cancelled | ||
| Sat., 4/4 | V Softball | Sussex Tech (DE) | Home - Branch Brook Park-Field #1-Turf [Directions] | Cancelled | ||
| Sun., 4/5 | V Softball | Morris Knolls (NJ) | Home - Branch Brook Park-Field #1-Turf [Directions] | Cancelled | ||
| Mon., 4/6 | V Baseball | Guilford | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Mon., 4/6 | FR Baseball | Guilford | Home - Bartlem Park [Directions] | Cancelled | ||
| Mon., 4/6 | V Girls Lacrosse | Hall | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Mon., 4/6 | JV Girls Lacrosse | Hall | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Mon., 4/6 | FR Girls Lacrosse | Amity | Away - Amity Regional HS-Amity High School - Field # 3 [Directions] | Cancelled | 2:30 PM | |
| Mon., 4/6 | V Softball | Amity | Home - Cheshire HS-Softball Diamond [Directions] | Cancelled | ||
| Mon., 4/6 | JV Softball | Amity | Home - Cheshire HS-Softball Diamond 2 [Directions] | Cancelled | ||
| Mon., 4/6 | V Girls Tennis | Foran | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Tue., 4/7 | JV Baseball | Guilford | Away - Guilford HS-Baseball Diamond [Directions] | Cancelled | 2:30 PM | |
| Tue., 4/7 | V Boys Golf | Notre Dame-West Haven | Away - Race Brook C.C. [Directions] | Postponed | ||
| Tue., 4/7 | V Boys Lacrosse | Conard | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Tue., 4/7 | JV Boys Lacrosse | Conard | Home - Cheshire HS-Grass Fields [Directions] | Cancelled | ||
| Tue., 4/7 | V Boys Outdoor Track | Amity | Home - Cheshire High Main Game field [Directions] | Cancelled | ||
| Tue., 4/7 | V Boys Tennis | East Haven | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Tue., 4/7 | V Girls Outdoor Track | Amity | Home - Cheshire High Main Game field [Directions] | Cancelled | ||
| Wed., 4/8 | V Baseball | Sheehan | Away - Sheehan HS-Neubauer Baseball Field @ Sheehan HS [Directions] | Cancelled | 2:30 PM | |
| Wed., 4/8 | FR Baseball | Sheehan | Away - West Side Field-Baseball Field [Directions] | Cancelled | ||
| Wed., 4/8 | FR Boys Lacrosse | East Lyme | Away - East Lyme HS-Frosh Lacrosse Field [Directions] | Cancelled | 2:15 PM | |
| Wed., 4/8 | V Boys Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Wed., 4/8 | JV Boys Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Wed., 4/8 | V Girls Golf | Farmington, Northwest Catholic | Away - Tunxis Country Club [Directions] | Cancelled | 1:45 PM | |
| Wed., 4/8 | V Girls Lacrosse | Conard | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Wed., 4/8 | JV Girls Lacrosse | Conard | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Wed., 4/8 | V Softball | Hamden | Away - Hamden HS-HHS Softball Field [Directions] | Cancelled | 2:15 PM | |
| Wed., 4/8 | V Girls Tennis | Mercy | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Thu., 4/9 | V Boys Tennis | Lyman Hall | Away - Doolittle Park-Doolittle Tennis Courts [Directions] | Cancelled | 2:30 PM | |
| Thu., 4/9 | V Boys Volleyball | Farmington | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Thu., 4/9 | JV Boys Volleyball | Farmington | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Thu., 4/9 | FR Girls Lacrosse | Daniel Hand | Away - Polson MS, Madison-Polson Front Field/DHHS Campus [Directions] | Cancelled | 2:30 PM | |
| Sat., 4/11 | V Baseball | Darien | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Sat., 4/11 | FR Baseball | Darien | Home - Bartlem Park [Directions] | Cancelled | ||
| Sat., 4/11 | V Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | Cancelled | 9:00 AM | |
| Sat., 4/11 | JV Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 11 [Directions] | Cancelled | 11:00 AM | |
| Mon., 4/13 | V Boys Golf | Hamden | Away - Laurel View Golf Course [Directions] | Postponed | 1:30 PM; 1 Van | |
| Mon., 4/13 | V Girls Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | Cancelled | 2:30 PM | |
| Mon., 4/13 | JV Girls Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | Cancelled | ||
| Mon., 4/13 | V Girls Tennis | Pomperaug | Away - Edgewood Bath and Tennis Club [Directions] | Cancelled | 9:00 AM | |
| Tue., 4/14 | JV Baseball | Sheehan | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Tue., 4/14 | V Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | Cancelled | 1:30 PM | |
| Tue., 4/14 | JV Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | Cancelled | 3:30 PM | |
| Tue., 4/14 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | Cancelled | ||
| Tue., 4/14 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | Cancelled | 2:30 PM | |
| Wed., 4/15 | V Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | Cancelled | 2:30 PM | |
| Wed., 4/15 | FR Boys Lacrosse | Fairfield Prep | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Wed., 4/15 | V Boys Tennis | Hamden | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Wed., 4/15 | V Softball | Daniel Hand | Away - Daniel Hand HS-Green Hill Softball Turf Field [Directions] | Cancelled | 2:00 PM | |
| Wed., 4/15 | JV Softball | Daniel Hand | Away - Daniel Hand HS-Green Hill Grass Diamond [Directions] | Cancelled | ||
| Thu., 4/16 | JV Baseball | Amity | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Thu., 4/16 | FR Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | Cancelled | ||
| Thu., 4/16 | V Boys Tennis | Foran | Away - Foran HS -Foran Tennis Courts [Directions] | Cancelled | 2:15 PM | |
| Thu., 4/16 | V Girls Lacrosse | South Windsor | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Thu., 4/16 | JV Girls Lacrosse | South Windsor | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Thu., 4/16 | V Girls Tennis | Lyman Hall | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Fri., 4/17 | V Baseball | North Haven | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Fri., 4/17 | FR Baseball | North Haven | Home - Bartlem Park [Directions] | Cancelled | ||
| Fri., 4/17 | FR Boys Lacrosse | Glastonbury | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Fri., 4/17 | V Boys Tennis | Xavier | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Fri., 4/17 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | Cancelled | 2:15 PM | |
| Fri., 4/17 | JV Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | Cancelled | ||
| Fri., 4/17 | V Girls Outdoor Track | Record Journal Meet | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | Cancelled | 2:15 PM | |
| Fri., 4/17 | V Softball | Guilford | Away - Guilford HS-Varsity softball field [Directions] | Cancelled | 9:00 AM | |
| Sat., 4/18 | JV Baseball | North Haven | Away - North Haven Athletic Complex-Brook Field-Baseball [Directions] | Cancelled | 9:00 AM | |
| Sat., 4/18 | V Boys Lacrosse | Amity | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Sat., 4/18 | JV Boys Lacrosse | Amity | Home - Cheshire HS-Grass Fields [Directions] | Cancelled | ||
| Mon., 4/20 | V Baseball | Lyman Hall | Away - Pat Wall Field-Baseball Field [Directions] | Cancelled | 2:30 PM | |
| Mon., 4/20 | FR Baseball | Lyman Hall | Away - Doolittle Park-Baseball Field [Directions] | Cancelled | ||
| Mon., 4/20 | V Boys Golf | Jonathan Law | Home - Farms Country club [Directions] | Postponed | ||
| Mon., 4/20 | V Boys Lacrosse | Foran | Away - Foran HS -Foran High School - Turf Field [Directions] | Cancelled | 3:00 PM | |
| Mon., 4/20 | JV Boys Lacrosse | Foran | Away - Foran HS -Foran High School - Turf Field [Directions] | Cancelled | 5:00 PM | |
| Mon., 4/20 | V Boys Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | Cancelled | 2:15 PM | |
| Mon., 4/20 | V Boys Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | Cancelled | 2:30 PM | |
| Mon., 4/20 | JV Boys Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | Cancelled | ||
| Mon., 4/20 | V Girls Lacrosse | Mercy | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Mon., 4/20 | JV Girls Lacrosse | Mercy | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Mon., 4/20 | V Softball | Sheehan | Home - Cheshire HS-Softball Diamond [Directions] | Cancelled | ||
| Mon., 4/20 | JV Softball | Sheehan | Home - Cheshire HS-Softball Diamond 2 [Directions] | Cancelled | ||
| Mon., 4/20 | V Girls Tennis | Career Magnet | Away - East Shore Athletic Complex-Tennis Courts [Directions] | Cancelled | 2:30 PM | |
| Tue., 4/21 | JV Baseball | Lyman Hall | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Tue., 4/21 | V Boys Golf | Guilford | Home - Farms Country club [Directions] | Postponed | ||
| Tue., 4/21 | FR Girls Lacrosse | East Lyme | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Tue., 4/21 | V Girls Outdoor Track | Lauralton Hall, East Haven, Foran | Home - Cheshire High Main Game field [Directions] | Cancelled | ||
| Tue., 4/21 | V Girls Tennis | East Haven | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Wed., 4/22 | V Baseball | Hamden | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 4/22 | FR Baseball | Hamden | Home - Bartlem Park [Directions] | Cancelled | ||
| Wed., 4/22 | FR Boys Lacrosse | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | Cancelled | 2:30 PM | |
| Wed., 4/22 | V Boys Outdoor Track | Foran, East Haven, Fairfield Prep | Away - Foran HS -Foran High School Track [Directions] | Cancelled | 2:15 PM | |
| Wed., 4/22 | V Boys Tennis | Fairfield Prep | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Wed., 4/22 | V Boys Volleyball | Xavier | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Wed., 4/22 | JV Boys Volleyball | Xavier | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Wed., 4/22 | V Girls Golf | Lauralton Hall | Away - Oronoque Country Club [Directions] | Cancelled | 1:45 PM; 1 Van | |
| Wed., 4/22 | V Girls Lacrosse | Amity | Away - Amity Regional HS-Amity High School - Field # 3 [Directions] | Cancelled | 2:15 PM | |
| Wed., 4/22 | JV Girls Lacrosse | Amity | Away - Amity Regional HS-Amity High School - Field # 3 [Directions] | Cancelled | ||
| Wed., 4/22 | V Softball | East Haven | Home - Cheshire HS-Softball Diamond [Directions] | Cancelled | ||
| Wed., 4/22 | JV Softball | East Haven | Home - Cheshire HS-Softball Diamond 2 [Directions] | Cancelled | ||
| Thu., 4/23 | JV Baseball | Hamden | Away - Legion Field - Hamden-Legion Baseball Field [Directions] | Cancelled | 2:30 PM | |
| Thu., 4/23 | V Boys Golf | Foran | Home - Farms Country club [Directions] | Postponed | ||
| Thu., 4/23 | V Boys Lacrosse | North Haven | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Thu., 4/23 | JV Boys Lacrosse | North Haven | Home - Cheshire HS-Grass Fields [Directions] | Cancelled | ||
| Thu., 4/23 | V Girls Golf | Canton | Home - Southington Country Club [Directions] | Cancelled | ||
| Thu., 4/23 | V Girls Tennis | West Haven | Away - Painter Park-Painter park tennis courts [Directions] | Cancelled | 2:30 PM | |
| Fri., 4/24 | V Baseball | East Haven | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Fri., 4/24 | FR Baseball | East Haven | Home - Bartlem Park [Directions] | Cancelled | ||
| Fri., 4/24 | FR Boys Lacrosse | Daniel Hand | Away - Daniel Hand HS-Janssen Field #2/DHHS Campus [Directions] | Cancelled | 2:15 PM | |
| Fri., 4/24 | V Boys Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | Cancelled | 2:30 PM | |
| Fri., 4/24 | V Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | Cancelled | 2:15 PM | |
| Fri., 4/24 | JV Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | Cancelled | ||
| Fri., 4/24 | V Softball | North Haven | Away - North Haven Athletic Complex-Varsity Softball Field [Directions] | Cancelled | 5:00 PM | |
| Fri., 4/24 | JV Softball | North Haven | Away - North Haven Athletic Complex-Brook Field-Softball [Directions] | Cancelled | 2:30 PM | |
| Sat., 4/25 | V Baseball | Taconic (MA) | Away - Taconic HS-Baseball | Cancelled | 7:00 AM | |
| Sat., 4/25 | FR Baseball | Taconic (MA) | Away - Taconic HS-Baseball | Cancelled | ||
| Sat., 4/25 | V Boys Lacrosse | Simsbury | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Sat., 4/25 | JV Boys Lacrosse | Simsbury | Home - Cheshire HS-Grass Fields [Directions] | Cancelled | ||
| Mon., 4/27 | V Baseball | Daniel Hand | Away - Daniel Hand HS-Polson Baseball Field /DHHS Campus [Directions] | Cancelled | 2:30 PM | |
| Mon., 4/27 | FR Baseball | Daniel Hand | Away - Town Campus - Madison-Baseball Field [Directions] | Cancelled | 2:30 PM | |
| Mon., 4/27 | V Boys Golf | Guilford | Away - Madison Country Club [Directions] | Postponed | 1:00 PM; 1 Van | |
| Mon., 4/27 | V Boys Tennis | Daniel Hand | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Mon., 4/27 | V Boys Volleyball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | Cancelled | 3:00 PM | |
| Mon., 4/27 | JV Boys Volleyball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | Cancelled | ||
| Mon., 4/27 | V Girls Golf | Suffield | Home - Southington Country Club [Directions] | Cancelled | ||
| Mon., 4/27 | V Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | Cancelled | 4:00 PM | |
| Mon., 4/27 | JV Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | Cancelled | ||
| Mon., 4/27 | FR Girls Lacrosse | Guilford | Away - Guilford HS-@ Long Hill Road [Directions] | Cancelled | 2:30 PM | |
| Mon., 4/27 | V Softball | West Haven | Home - Cheshire HS-Softball Diamond [Directions] | Cancelled | ||
| Mon., 4/27 | V Girls Tennis | North Haven | Away - North Haven Athletic Complex-Tennis Courts [Directions] | Cancelled | 2:30 PM | |
| Mon., 4/27 | Miscellaneous Events | Dodd track meet | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Tue., 4/28 | JV Baseball | Daniel Hand | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Tue., 4/28 | V Boys Outdoor Track | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | Cancelled | 2:30 PM | |
| Tue., 4/28 | V Boys Tennis | Wilbur Cross | Away - Wilbur Cross HS-Wilbur Cross Tennis Courts [Directions] | Cancelled | 2:30 PM | |
| Tue., 4/28 | V Girls Golf | Amity | Away - Race Brook C.C. [Directions] | Cancelled | 1:45 PM; 1 Van | |
| Tue., 4/28 | V Girls Outdoor Track | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | Cancelled | 2:30 PM | |
| Tue., 4/28 | JV Softball | West Haven | Home - Cheshire HS-Softball Diamond 2 [Directions] | Cancelled | ||
| Wed., 4/29 | V Baseball | Conard | Away - Conard HS-Baseball Diamond [Directions] | Cancelled | 2:30 PM | |
| Wed., 4/29 | FR Baseball | Conard | Away - Sedgwick MS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 4/29 | FR Boys Lacrosse | Guilford | Away - Guilford HS-Maturo Field [Directions] | Cancelled | 2:15 PM | |
| Wed., 4/29 | V Boys Volleyball | Kolbe Cathedral | Away - Kolbe-cathedral HS-Gym [Directions] | Cancelled | 2:30 PM | |
| Wed., 4/29 | JV Boys Volleyball | Kolbe Cathedral | Away - Kolbe-cathedral HS-Gym [Directions] | Cancelled | ||
| Wed., 4/29 | FR Girls Lacrosse | Conard | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Thu., 4/30 | JV Baseball | Conard | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Thu., 4/30 | V Boys Golf | Fairfield Prep, Shelton | Away - Brooklawn Country Club [Directions] | Postponed | 1:45 PM; 1 Van | |
| Thu., 4/30 | V Boys Lacrosse | Notre Dame-West Haven | Away - Notre Dame HS-Veteran's Stadium [Directions] | Cancelled | 4:00 PM | |
| Thu., 4/30 | JV Boys Lacrosse | Notre Dame-West Haven | Away - Notre Dame HS-Veteran's Stadium [Directions] | Cancelled | 2:15 PM | |
| Thu., 4/30 | V Girls Golf | Mercy | Home - Southington Country Club [Directions] | Cancelled | ||
| Thu., 4/30 | V Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | Cancelled | 2:30 PM | |
| Thu., 4/30 | JV Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | Cancelled | ||
| Fri., 5/1 | V Baseball | Fairfield Prep | Away - Fairfield University-Alumni Diamond [Directions] | Cancelled | 2:30 PM | |
| Fri., 5/1 | FR Baseball | Fairfield Prep | Away - Owen Fish Park-Owen Fish [Directions] | Cancelled | 2:30 PM | |
| Fri., 5/1 | FR Boys Lacrosse | Notre Dame-West Haven | Away - Notre Dame HS-Veteran's Stadium [Directions] | Cancelled | 2:15 PM | |
| Fri., 5/1 | V Girls Outdoor Track | Middletown JV Invite | Away - Middletown HS-MHS Stadium | Cancelled | 1:30 PM | |
| Fri., 5/1 | V Softball | Hamden | Home - Cheshire HS-Softball Diamond [Directions] | Cancelled | ||
| Fri., 5/1 | V Girls Tennis | North Haven | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Sat., 5/2 | JV Baseball | Fairfield Prep | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Sat., 5/2 | V Boys Lacrosse | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | Cancelled | 4:00 PM | |
| Sat., 5/2 | JV Boys Lacrosse | East Lyme | Away - East Lyme HS-JV Lacrosse Field [Directions] | Cancelled | 2:30 PM | |
| Sat., 5/2 | V Boys Tennis | Avon | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Sat., 5/2 | V Girls Outdoor Track | Middletown Invite | Away - Middletown HS-MHS Stadium | Cancelled | 11:30 AM | |
| Mon., 5/4 | V Baseball | Sheehan | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Mon., 5/4 | FR Baseball | Sheehan | Home - Bartlem Park [Directions] | Cancelled | ||
| Mon., 5/4 | V Boys Golf | Daniel Hand | Away - Madison Country Club [Directions] | Postponed | 1:00 PM | |
| Mon., 5/4 | V Boys Tennis | Foran | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Mon., 5/4 | V Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | Cancelled | 2:30 PM | |
| Mon., 5/4 | JV Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | Cancelled | ||
| Mon., 5/4 | V Girls Golf | St. Paul Catholic | Away - Westwoods Golf Course [Directions] | Cancelled | ||
| Mon., 5/4 | V Girls Lacrosse | Lauralton Hall | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Mon., 5/4 | JV Girls Lacrosse | Lauralton Hall | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Mon., 5/4 | V Softball | Sheehan | Away - Sheehan HS-Sheehan HS Softball Field [Directions] | Cancelled | 2:15 PM | |
| Mon., 5/4 | JV Softball | Sheehan | Away - Sheehan HS-Sheehan HS Softball Field [Directions] | Cancelled | ||
| Mon., 5/4 | V Girls Tennis | Sacred Heart Academy | Away - Hamden MS-Tennis Courts [Directions] | Cancelled | 2:30 PM | |
| Tue., 5/5 | JV Baseball | Sheehan | Away - Sheehan HS-Neubauer Baseball Field @ Sheehan HS [Directions] | Cancelled | 2:30 PM | |
| Tue., 5/5 | V Boys Golf | Hamden | Home - Farms Country club [Directions] | Postponed | ||
| Tue., 5/5 | V Boys Lacrosse | Daniel Hand | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Tue., 5/5 | JV Boys Lacrosse | Daniel Hand | Home - Cheshire HS-Grass Fields [Directions] | Cancelled | ||
| Tue., 5/5 | V Boys Tennis | Hamden | Away - Tennis Courts- Hamden HS [Directions] | Cancelled | 2:30 PM | |
| Tue., 5/5 | V Girls Tennis | Guilford | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Wed., 5/6 | V Baseball | Lyman Hall | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 5/6 | FR Baseball | Lyman Hall | Home - Bartlem Park [Directions] | Cancelled | ||
| Wed., 5/6 | FR Boys Lacrosse | Xavier | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Wed., 5/6 | V Boys Outdoor Track | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | Cancelled | 2:30 PM | |
| Wed., 5/6 | V Boys Volleyball | Newtown | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Wed., 5/6 | JV Boys Volleyball | Newtown | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Wed., 5/6 | V Girls Golf | Daniel Hand | Home - Southington Country Club [Directions] | Cancelled | ||
| Wed., 5/6 | V Girls Lacrosse | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | Cancelled | 5:00 PM | |
| Wed., 5/6 | JV Girls Lacrosse | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | Cancelled | ||
| Wed., 5/6 | FR Girls Lacrosse | Amity | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Wed., 5/6 | V Girls Outdoor Track | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | Cancelled | 2:30 PM | |
| Wed., 5/6 | V Softball | East Haven | Away - East Haven HS-Softball Diamond [Directions] | Cancelled | 2:15 PM | |
| Wed., 5/6 | JV Softball | East Haven | Away - Deer Run Field [Directions] | Cancelled | ||
| Thu., 5/7 | V Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | Cancelled | 3:00 PM | |
| Thu., 5/7 | JV Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Barlow Field [Directions] | Cancelled | 2:15 PM | |
| Thu., 5/7 | V Girls Tennis | Daniel Hand | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Thu., 5/7 | Miscellaneous Events | Dodd track meet | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Fri., 5/8 | V Baseball | Hamden | Away - Hamden HS-HHS Baseball Field [Directions] | Cancelled | 2:30 PM | |
| Fri., 5/8 | FR Baseball | Hamden | Away - Legion Field - Hamden-Legion Baseball Field [Directions] | Cancelled | ||
| Fri., 5/8 | FR Boys Lacrosse | Daniel Hand | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Fri., 5/8 | V Boys Tennis | Jonathan Law | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Fri., 5/8 | V Boys Volleyball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Fri., 5/8 | JV Boys Volleyball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Fri., 5/8 | V Girls Lacrosse | Pomperaug | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Fri., 5/8 | JV Girls Lacrosse | Pomperaug | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Fri., 5/8 | FR Girls Lacrosse | Glastonbury | Away - Glastonbury HS-Field 13 [Directions] | Cancelled | 2:30 PM | |
| Fri., 5/8 | V Softball | North Haven | Home - Cheshire HS-Softball Diamond [Directions] | Cancelled | ||
| Fri., 5/8 | JV Softball | North Haven | Home - Cheshire HS-Softball Diamond 2 [Directions] | Cancelled | ||
| Sat., 5/9 | JV Baseball | Hamden | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Mon., 5/11 | V Baseball | Daniel Hand | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Mon., 5/11 | FR Baseball | Daniel Hand | Home - Bartlem Park [Directions] | Cancelled | ||
| Mon., 5/11 | V Boys Tennis | Career Magnet | Away - Edgewood Park-Tennis Courts [Directions] | Cancelled | 2:30 PM | |
| Mon., 5/11 | V Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | Cancelled | 2:30 PM | |
| Mon., 5/11 | JV Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | Cancelled | ||
| Mon., 5/11 | V Girls Golf | Lauralton Hall | Home - Southington Country Club [Directions] | Cancelled | ||
| Mon., 5/11 | V Girls Lacrosse | Branford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Mon., 5/11 | JV Girls Lacrosse | Branford | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Mon., 5/11 | V Softball | West Haven | Away - West Haven HS-Frank Biondi Field [Directions] | Cancelled | 4:30 PM | |
| Mon., 5/11 | JV Softball | West Haven | Away - West Haven HS-Frank Biondi Field [Directions] | Cancelled | 2:30 PM | |
| Mon., 5/11 | V Girls Tennis | Foran | Away - Foran HS -Foran Tennis Courts [Directions] | Cancelled | 2:15 PM | |
| Tue., 5/12 | JV Baseball | Daniel Hand | Away - Town Campus - Madison-Baseball Field [Directions] | Cancelled | 2:30 PM | |
| Tue., 5/12 | V Boys Golf | Jonathan Law | Away - Orange Hills Country Club [Directions] | Postponed | 1:00 PM | |
| Tue., 5/12 | V Boys Lacrosse | Shelton | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Tue., 5/12 | V Boys Outdoor Track | Guilford, Shelton | Home - Cheshire High Main Game field [Directions] | Cancelled | ||
| Tue., 5/12 | V Boys Tennis | Lyman Hall | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Tue., 5/12 | V Girls Outdoor Track | Shelton | Home - Cheshire High Main Game field [Directions] | Cancelled | ||
| Tue., 5/12 | V Softball | St. Joseph | Home - Cheshire HS-Softball Diamond [Directions] | Cancelled | ||
| Tue., 5/12 | JV Softball | St. Joseph | Home - Cheshire HS-Softball Diamond 2 [Directions] | Cancelled | ||
| Tue., 5/12 | V Girls Tennis | Mercy | Away - Wesleyan University-Tennis Courts - Vine Street, Middletown [Directions] | Cancelled | 2:35 PM | |
| Wed., 5/13 | V Baseball | Fairfield Prep | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Wed., 5/13 | FR Baseball | Fairfield Prep | Home - Bartlem Park [Directions] | Cancelled | ||
| Wed., 5/13 | JV Boys Lacrosse | Shelton | Home - Cheshire HS-Grass Fields [Directions] | Cancelled | ||
| Wed., 5/13 | FR Boys Lacrosse | Notre Dame-West Haven | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Wed., 5/13 | V Boys Volleyball | Putnam | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Wed., 5/13 | JV Boys Volleyball | Putnam | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Wed., 5/13 | V Girls Golf | Newington | Away - Indian Hill Country Club [Directions] | Cancelled | 1:45 PM | |
| Wed., 5/13 | FR Girls Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | Cancelled | 4:00 PM | |
| Thu., 5/14 | V Boys Lacrosse | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | Cancelled | 4:30 PM | |
| Thu., 5/14 | JV Boys Lacrosse | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | Cancelled | 3:00 PM | |
| Thu., 5/14 | V Girls Golf | Mercy | Away - Lyman Orchards [Directions] | Cancelled | 1:45 PM | |
| Thu., 5/14 | V Girls Lacrosse | Glastonbury | Away - Glastonbury HS-Field 12 [Directions] | Cancelled | 2:30 PM | |
| Thu., 5/14 | JV Girls Lacrosse | Glastonbury | Away - Glastonbury HS-Field 12 [Directions] | Cancelled | ||
| Thu., 5/14 | Miscellaneous Events | Dodd track meet | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Fri., 5/15 | V Baseball | Amity | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Fri., 5/15 | FR Baseball | Amity | Home - Bartlem Park [Directions] | Cancelled | ||
| Fri., 5/15 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | Cancelled | 2:15 PM | |
| Fri., 5/15 | V Boys Tennis | East Haven | Away - East Haven HS-Tennis Court [Directions] | Cancelled | 2:30 PM | |
| Fri., 5/15 | V Boys Volleyball | Xavier | Away - Xavier HS-Gym [Directions] | Cancelled | 2:30 PM | |
| Fri., 5/15 | JV Boys Volleyball | Xavier | Away - Xavier HS-Gym [Directions] | Cancelled | ||
| Fri., 5/15 | FR Girls Lacrosse | Daniel Hand | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Fri., 5/15 | V Girls Outdoor Track | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | Cancelled | 3:30 PM | |
| Fri., 5/15 | V Softball | Amity | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | Cancelled | 2:15 PM | |
| Fri., 5/15 | JV Softball | Amity | Away - Center Field [Directions] | Cancelled | ||
| Fri., 5/15 | V Girls Tennis | Lauralton Hall | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | Cancelled | ||
| Sat., 5/16 | JV Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | Cancelled | 9:00 AM | |
| Sat., 5/16 | V Boys Lacrosse | Trumbull | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Sat., 5/16 | JV Boys Lacrosse | Trumbull | Home - Cheshire HS-Grass Fields [Directions] | Cancelled | ||
| Sat., 5/16 | V Boys Tennis | Amity (Scrim.) | Away - Amity Regional HS-Tennis Courts [Directions] | Cancelled | 8:00 AM | |
| Sat., 5/16 | V Girls Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | Cancelled | 8:00 AM | |
| Mon., 5/18 | V Baseball | North Haven | Away - North Haven Athletic Complex-Robert E. DeMayo Field [Directions] | Cancelled | 5:30 PM | |
| Mon., 5/18 | JV Baseball | Fairfield Prep | Away - Tunxis Hill Park [Directions] | Cancelled | 2:30 PM | |
| Mon., 5/18 | FR Baseball | North Haven | Away - North Haven MS-Bailey Road Baseball Field [Directions] | Cancelled | 2:30 PM | |
| Mon., 5/18 | V Boys Golf | Shelton | Home - Southington Country Club [Directions] | Postponed | ||
| Mon., 5/18 | V Boys Tennis | Sheehan | Away - Sheehan HS-Sheehan HS Tennis Courts [Directions] | Cancelled | 2:45 PM | |
| Mon., 5/18 | V Girls Golf | Amity | Home - Southington Country Club [Directions] | Cancelled | ||
| Mon., 5/18 | V Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | Cancelled | 2:30 PM | |
| Mon., 5/18 | JV Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | Cancelled | ||
| Mon., 5/18 | V Softball | Daniel Hand | Home - Cheshire HS-Softball Diamond [Directions] | Cancelled | ||
| Mon., 5/18 | JV Softball | Daniel Hand | Home - Cheshire HS-Softball Diamond 2 [Directions] | Cancelled | ||
| Tue., 5/19 | JV Baseball | North Haven | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Tue., 5/19 | V Boys Golf | Notre Dame-West Haven | Home - Farms Country club [Directions] | Postponed | ||
| Tue., 5/19 | V Boys Lacrosse | Guilford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Tue., 5/19 | JV Boys Lacrosse | Guilford | Home - Cheshire HS-Grass Fields [Directions] | Cancelled | ||
| Tue., 5/19 | V Boys Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Tue., 5/19 | JV Boys Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Tue., 5/19 | V Girls Golf | Suffield | Away - Copper Hill Golf Course [Directions] | Cancelled | 1:30 PM | |
| Tue., 5/19 | FR Girls Lacrosse | East Lyme | Away - East Lyme HS-Frosh Lacrosse Field [Directions] | Cancelled | 2:30 PM | |
| Tue., 5/19 | V Girls Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | Cancelled | 2:30 PM | |
| Wed., 5/20 | V Baseball | Guilford | Away - Guilford HS-Baseball Diamond [Directions] | Cancelled | 2:30 PM | |
| Wed., 5/20 | FR Baseball | Guilford | Away - Long Hill Park-Guilford-Baseball Field [Directions] | Cancelled | 2:30 PM | |
| Wed., 5/20 | FR Boys Lacrosse | Guilford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Wed., 5/20 | V Softball | Guilford | Home - Cheshire HS-Softball Diamond [Directions] | Cancelled | ||
| Wed., 5/20 | JV Softball | Guilford | Home - Cheshire HS-Softball Diamond 2 [Directions] | Cancelled | ||
| Thu., 5/21 | JV Baseball | Guilford | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Thu., 5/21 | V Boys Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | Cancelled | 2:30 PM | |
| Thu., 5/21 | JV Boys Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | Cancelled | ||
| Thu., 5/21 | V Girls Golf | Daniel Hand | Away - Madison Country Club [Directions] | Cancelled | 1:00 PM | |
| Thu., 5/21 | V Girls Lacrosse | Jonathan Law | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | ||
| Thu., 5/21 | JV Girls Lacrosse | Jonathan Law | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Fri., 5/22 | FR Girls Lacrosse | Guilford | Home - Cheshire HS-Bartlem Park [Directions] | Cancelled | ||
| Thu., 5/28 | V Boys Volleyball | Rockville | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Thu., 5/28 | JV Boys Volleyball | Rockville | Home - Cheshire HS-Gym West [Directions] | Cancelled | ||
| Tue., 6/2 | V Girls Golf | Newington | Home - Southington Country Club [Directions] | Cancelled | ||