| Cheshire 2019-20 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 185 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/28 | V Boys Cross Country | Pomperaug (Scrim.) | Away - Pomperaug HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Fri., 8/30 | V Boys Cross Country | Simsbury | Away - Stratton Brook State Park [Directions] | 4:30 p.m. | ||
| Fri., 8/30 | V Girls Cross Country | Simsbury (Scrim.) | Away - Stratton Brook State Park [Directions] | 4:30 p.m. | ||
| Tue., 9/3 | V Boys Soccer | Glastonbury, Lewis Mills, Naugatuck, Wethersfield, Xavier | Away - Glastonbury HS-Field #4 | 4:00 p.m. | ||
| Tue., 9/3 | V Boys Soccer | Lewis Mills | Away - Glastonbury HS-Field #4 [Directions] | 4:45 p.m. | ||
| Thu., 9/5 | V Football | Windsor (Scrim.) | Away - Windsor HS-Jack O'Brien Stadium [Directions] | 6:00 p.m. | ||
| 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. | ||
| 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. | ||
| 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. | ||
| 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. | ||
| Tue., 9/10 | V Girls Cross Country | Lyman Hall, Mercy, West Haven | Home - Cheshire Park-Field 1 [Directions] | 4:00 p.m. | 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. | ||
| Thu., 9/12 | FR Football | Hillhouse | Away - Bowen Field-Football Field [Directions] | 6:00 p.m. | ||
| Thu., 9/12 | V Boys Soccer | Hamden | Home - Cheshire High Main Game field [Directions] | 6:30 p.m. | W 2-1 | |
| Thu., 9/12 | V Girls Soccer | North Haven | Away - North Haven MS-West Turf Field [Directions] | 7:00 p.m. | W 3-0 | |
| Fri., 9/13 | V Football | Hillhouse | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | W 35-14 | |
| Fri., 9/13 | JV Boys Soccer | Hamden | Home - Cheshire HS-Grass Fields [Directions] | 3:45 p.m. | W 3-0 | |
| Sat., 9/14 | JV Football | Hillhouse | Away - Bowen Field-Football Field [Directions] | 10:30 a.m. | ||
| Sat., 9/14 | FR Boys Soccer | Amity | Away - Amity Regional HS-Amity High School - Field # 2 [Directions] | 10:00 a.m. | W 3-0 | |
| Sat., 9/14 | JV Girls Soccer | Lauralton Hall | Away - Lauralton Hall-Soccer Field [Directions] | 2:30 p.m. | ||
| Mon., 9/16 | JV Boys Soccer | Amity | Away - Amity Regional HS-Amity High School - Field # 2 [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 9/16 | FR Boys Soccer | Guilford | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 9/16 | V Girls Volleyball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 9/16 | JV Girls Volleyball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 4:15 p.m. | W 2-0 | |
| Tue., 9/17 | V Boys Cross Country | Daniel Hand | Away - Madison Surf Club-Surf Club [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Boys Soccer | Amity | Away - Amity Regional HS-Amity High School - Field # 3 [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 9/17 | V Girls Cross Country | Daniel Hand | Away - Madison Surf Club-Surf Club [Directions] | 4:00 p.m. | Hand 26- Cheshire 29 | |
| Tue., 9/17 | V Girls Soccer | Guilford | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | L 0-1 | |
| Tue., 9/17 | FR Girls Soccer | Amity | Away - Amity Regional HS-CENTER FIELD [Directions] | 3:45 p.m. | ||
| 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. | ||
| Thu., 9/19 | JV Boys Soccer | Jonathan Law | Away - Jonathan Law HS-Grass Field [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 9/19 | V Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-1 | |
| Thu., 9/19 | JV Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | L 1-2 | |
| Fri., 9/20 | V Football | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | 7:00 p.m. | L 28-35 | |
| Fri., 9/20 | V Boys Soccer | Jonathan Law | Away - Jonathan Law HS-Lawmen Stadium [Directions] | 4:30 p.m. | W 6-0 | |
| Fri., 9/20 | FR Boys Soccer | Notre Dame-West Haven | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 9/20 | V Girls Soccer | West Haven | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 2-1 | |
| Fri., 9/20 | V Girls Volleyball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 5:00 p.m. | W 3-0 | |
| Fri., 9/20 | JV Girls Volleyball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 9/21 | V Boys Cross Country | Winding Trails Invite | Away - Winding Trails-Cross Country Course | 12:00 p.m. | ||
| Sat., 9/21 | JV Football | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | 9:00 a.m. | ||
| Sat., 9/21 | V Girls Cross Country | Winding trails Invite | Away - Winding Trails-Cross Country Course | 12:00 p.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] | 6:00 p.m. | W 1-0 | |
| Mon., 9/23 | FR Girls Soccer | Daniel Hand | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Mon., 9/23 | V Girls Volleyball | West Haven | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Mon., 9/23 | JV Girls Volleyball | West Haven | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | W 2-0 | |
| Tue., 9/24 | V Boys Cross Country | Branford, East Haven, Sheehan | Home - Cheshire Park-Field 1 [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Boys Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 6-2 | |
| Tue., 9/24 | JV Boys Soccer | North Haven | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | 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 | JV Girls Soccer | East Haven, North Haven (Scrim.) | Away - East Haven HS-Grass Soccer FIeld [Directions] | 4:15 p.m. | ||
| Wed., 9/25 | V Girls Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Wed., 9/25 | JV Girls Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | 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] | 6:30 p.m. | W 1-0 | |
| Thu., 9/26 | FR Boys Soccer | Fairfield Prep | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | L 1-3 | |
| Thu., 9/26 | V Girls Soccer | Lauralton Hall | Away - Lauralton Hall-Soccer Field [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 9/27 | V Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 7:00 p.m. | W 35-20 | |
| Fri., 9/27 | JV Boys Soccer | Guilford | Home - Cheshire HS-Grass Fields [Directions] | 3:45 p.m. | W 5-4 | |
| Fri., 9/27 | V Girls Volleyball | North Haven | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 9/27 | JV Girls Volleyball | North Haven | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | 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] | 6:00 p.m. | W 7-1 | |
| Sat., 9/28 | JV Boys Soccer | West Haven | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | W 5-0 | |
| Sat., 9/28 | V Girls Soccer | Wilbur Cross | Away - Rice Field-Rice Field 2 [Directions] | 10:30 a.m. | W 9-0 | |
| Sat., 9/28 | JV Girls Soccer | Wilbur Cross | Away - Rice Field-Rice Field 2 [Directions] | 12:00 p.m. | ||
| Tue., 10/1 | V Boys Soccer | Daniel Hand | Away - Madison Surf Club-Turf Field [Directions] | 6:00 p.m. | T 0-0 | |
| Tue., 10/1 | JV Boys Soccer | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 4:00 p.m. | L 0-2 | |
| Tue., 10/1 | V Girls Volleyball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 6:30 p.m. | L 0-3 | |
| Tue., 10/1 | JV Girls Volleyball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 5:15 p.m. | W 2-1 | |
| Wed., 10/2 | V Girls Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | 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] | 5:30 p.m. | W 3-0 | |
| Wed., 10/2 | JV Girls Volleyball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 10/3 | FR Football | Shelton | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Fri., 10/4 | V Football | Shelton | Away - Shelton HS-High School - Finn Stadium [Directions] | 7:00 p.m. | W 24-12 | |
| Fri., 10/4 | V Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 3:45 p.m. | L 1-0 | |
| Fri., 10/4 | V Girls Soccer | Jonathan Law | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 10/4 | V Girls Volleyball | East Haven | Away - East Haven HS-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/4 | JV Girls Volleyball | East Haven | Away - East Haven HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 10/5 | V Boys Cross Country | Nonnewaug | Away - Nonnewaug HS [Directions] | 9:00 a.m. | ||
| Sat., 10/5 | V Girls Cross Country | Nonnewaug | Away - Nonnewaug HS-XC Course [Directions] | 2:00 p.m. | ||
| 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. | ||
| Mon., 10/7 | JV Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 4:00 p.m. | W 3-1 | |
| Mon., 10/7 | V Girls Cross Country | Shelton, Amity | Away - Shelton HS-Shelton High - Track [Directions] | 3:45 p.m. | ||
| Mon., 10/7 | V Girls Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | 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] | 5:30 p.m. | W 3-1 | |
| Mon., 10/7 | JV Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 10/8 | FR Boys Soccer | Shelton | Away - Shelton HS-High School - Lower Field [Directions] | 4:00 p.m. | L 3-7 | |
| Thu., 10/10 | FR Boys Soccer | Fairfield Prep | Away - Fairfield University-Barlow Field [Directions] | 3:30 p.m. | T 2-2 | |
| Thu., 10/10 | V Girls Volleyball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 6:00 p.m. | L 1-3 | |
| Thu., 10/10 | JV Girls Volleyball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 4:30 p.m. | L 1-2 | |
| Fri., 10/11 | V Boys Soccer | Amity | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 5-0 | |
| Fri., 10/11 | JV Boys Soccer | Jonathan Law | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | W 6-0 | |
| Fri., 10/11 | FR Boys Soccer | Notre Dame-West Haven | Away - Veterans Field [Directions] | 3:45 p.m. | W 5-0 | |
| Fri., 10/11 | V Girls Soccer | Guilford | Away - Guilford HS-New Turf field at GHS [Directions] | 3:45 p.m. | T 0-0 | |
| Sat., 10/12 | V Girls Volleyball | Girls Volleyball Fall Brawl | Away - RHAM HS-RHAM MS | TBA | ||
| Mon., 10/14 | JV Boys Soccer | Amity | Home - Cheshire High Main Game field [Directions] | 11:00 a.m. | T 0-0 | |
| Mon., 10/14 | FR Boys Soccer | Guilford | Away - Long Hill Park-Guilford-Soccer Field (Front) [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 10/15 | V Boys Soccer | Jonathan Law | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 5-0 | |
| Tue., 10/15 | FR Boys Soccer | Daniel Hand | Home - Bartlem Park [Directions] | 4:00 p.m. | T 4-4 | |
| Tue., 10/15 | V Girls Soccer | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | 5:00 p.m. | T 0-0 | |
| Tue., 10/15 | V Girls Volleyball | West Haven | Away - West Haven HS-Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Tue., 10/15 | JV Girls Volleyball | West Haven | Away - West Haven HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 10/16 | JV Girls Soccer | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | Canceled | Cancelled | |
| Thu., 10/17 | V Boys Cross Country | SCC Championship | Away - East Shore Park Career J.V. | TBA | ||
| Thu., 10/17 | FR Football | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | JV Boys Soccer | North Haven | Away - North Haven MS-West Turf Field [Directions] | 3:45 p.m. | W 4-0 | |
| Thu., 10/17 | V Girls Cross Country | SCC championship | Away - East Shore Park Career J.V. | 1:00 p.m. | ||
| Thu., 10/17 | V Girls Soccer | East Haven | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 10/18 | V Football | Masuk | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | W 52-22 | |
| Fri., 10/18 | V Boys Soccer | North Haven | Away - North Haven MS-West Turf Field [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 10/18 | V Girls Volleyball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/18 | JV Girls Volleyball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 3:45 p.m. | W 2-0 | |
| Sat., 10/19 | JV Football | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 11:00 a.m. | ||
| Mon., 10/21 | V Boys Soccer | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 6:00 p.m. | L 1-0 | |
| Mon., 10/21 | V Girls Soccer | Lauralton Hall | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | 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] | 6:30 p.m. | L 2-3 | |
| Mon., 10/21 | JV Girls Volleyball | Guilford | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | L 0-2 | |
| Tue., 10/22 | JV Boys Soccer | Guilford | Away - Long Hill Park-Guilford-Soccer Field (Front) [Directions] | 3:45 p.m. | W 1-0 | |
| Tue., 10/22 | JV Girls Soccer | Lauralton Hall | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | V Boys Soccer | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | 6:30 p.m. | W 2-0 | |
| Wed., 10/23 | V Girls Soccer | Wilbur Cross | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 8-0 | |
| Wed., 10/23 | V Girls Volleyball | Foran | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Wed., 10/23 | JV Girls Volleyball | Foran | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | W 2-0 | |
| Thu., 10/24 | V Football | Wilbur Cross | Away - Bowen Field-Football Field [Directions] | 7:00 p.m. | W 37-0 | |
| 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] | 3:45 p.m. | T 0-0 | |
| Thu., 10/24 | V Girls Soccer | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 6:00 p.m. | W 1-0 | |
| Thu., 10/24 | JV Girls Soccer | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | V Boys Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | L 0-2 | |
| Fri., 10/25 | V Girls Volleyball | Hamden | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 10/25 | JV Girls Volleyball | Hamden | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | 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] | 6:00 p.m. | L 1-2 | |
| Mon., 10/28 | FR Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 3:45 p.m. | L 1-3 | |
| Mon., 10/28 | V Girls Soccer | Jonathan Law | Away - Jonathan Law HS-Lawmen Stadium [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 10/28 | V Girls Volleyball | East Haven | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Mon., 10/28 | JV Girls Volleyball | East Haven | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | W 2-0 | |
| Tue., 10/29 | JV Boys Soccer | Xavier | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | T 2-2 | |
| Wed., 10/30 | JV Girls Soccer | Jonathan Law | Away - Jonathan Law HS-Grass Field [Directions] | Canceled | Cancelled | |
| Wed., 10/30 | FR Girls Soccer | Daniel Hand | Away - Daniel Hand HS-Janssen Field #2/DHHS Campus [Directions] | 3:45 p.m. | ||
| Wed., 10/30 | V Girls Volleyball | Farmington | Away - Farmington HS [Directions] | 5:00 p.m. | L 2-3 | |
| Wed., 10/30 | JV Girls Volleyball | Farmington | Away - Farmington HS [Directions] | 4:00 p.m. | 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] | Canceled | 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] | 7:00 p.m. | W 48-14 | |
| Fri., 11/1 | V Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 7:00 p.m. | ||
| Fri., 11/1 | V Girls Cross Country | CIAC Girls State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/1 | JV Girls Soccer | Guilford | Away - Guilford HS-New Turf field at GHS [Directions] | 4:00 p.m. | ||
| Fri., 11/1 | FR Girls Soccer | Guilford | Away - Long Hill Park-Guilford-Soccer Field (Front) [Directions] | Canceled | Cancelled | |
| 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] | 6:00 p.m. | W 1-0 | |
| 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] | 6:00 p.m. | L 0-2 | |
| 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. | ||
| Tue., 11/12 | V Girls Soccer | Danbury | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | W 2-1 | |
| Wed., 11/13 | V Boys Soccer | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | 2:00 p.m. | ||
| Thu., 11/14 | FR Football | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 4:00 p.m. | ||
| 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. | ||
| Fri., 11/15 | V Football | Sheehan | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | W 40-13 | |
| Sat., 11/16 | JV Football | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 10:30 a.m. | ||
| Thu., 11/21 | FR Football | Harding | Away - Warren Harding HS-Lewis Field [Directions] | 4:00 p.m. | ||
| Fri., 11/22 | V Football | Harding | Home - Cheshire HS-Main Game field [Directions] | 7:00 p.m. | W 48-28 | |
| Sat., 11/23 | JV Football | Harding | Away - Warren Harding HS-Lewis Field [Directions] | 10:00 a.m. | ||
| Thu., 11/28 | V Football | Southington | Home - Cheshire High Main Game field [Directions] | 10:00 a.m. | L 20-21 (OT) | |
| Wed., 12/4 | V Football | Simsbury | Away - Holden Field-Turf [Directions] | 6:30 p.m. | ||