| Cheshire 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 276 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 8/26 | V Football | Simsbury, Norwalk, Westfield (MA) (Scrim.) | Away - Holden Field-Turf [Directions] | 9:00 a.m. | ||
| Tue., 8/29 | V Boys Soccer | Glastonbury (Scrim.) | Away - Glastonbury HS-Turf Field [Directions] | 4:30 p.m. | ||
| Tue., 8/29 | V Field Hockey | Simsbury (Scrim.) | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 8/29 | V Girls Soccer | Glastonbury (Scrim.) | Home - Cheshire High Main Game field [Directions] | 6:30 p.m. | ||
| Tue., 8/29 | V Girls Volleyball | Simsbury (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | ||
| Thu., 8/31 | V Football | Windsor (Scrim.) | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 8/31 | V Boys Soccer | Naugatuck (Scrim.) | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Thu., 8/31 | JV Boys Soccer | Naugatuck (Scrim.) | Home - Cheshire HS-Grass Fields [Directions] | 3:45 p.m. | ||
| Thu., 8/31 | V Field Hockey | TBA | Away - Pomperaug HS-Stadium | 4:30 p.m. | ||
| Thu., 8/31 | V Girls Volleyball | Woodland (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 9/1 | V Girls Soccer | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Fri., 9/1 | JV Girls Soccer | Pomperaug (Scrim.) | Away - Pomperaug HS-PHS Soccer Field [Directions] | 6:00 p.m. | ||
| Sat., 9/2 | V Boys Soccer | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | ||
| Sat., 9/2 | JV Boys Soccer | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Sat., 9/2 | V Field Hockey | Field Hockey Play Day | Away - Avon HS-Turf Field | 8:00 a.m. | ||
| Sat., 9/2 | V Girls Volleyball | Glastonbury Volleyball Jamboree- AM wave | Away - Glastonbury HS-Gym | 8:30 a.m. | ||
| Sun., 9/3 | V Girls Soccer | Pomperaug (Scrim.) | Home - Treadwell Park-Newtown Treadwell Park [Directions] | 10:20 a.m. | ||
| Sun., 9/3 | V Girls Soccer | TBA | Away - Treadwell Park-Treadwell Town Park--Tilson Field | 11:40 a.m. | ||
| Sun., 9/3 | V Girls Soccer | Immaculate (Scrim.) | Away - Treadwell Park-Treadwell Town Park--Tilson Field [Directions] | 11:40 a.m. | ||
| Sun., 9/3 | V Girls Soccer | Newtown | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 9:00 a.m. | ||
| Mon., 9/4 | V Boys Soccer | Southington (Scrim.) | Away - Southington HS-3 TURF FIELD [Directions] | 4:00 p.m. | ||
| Mon., 9/4 | JV Boys Soccer | Southington (Scrim.) | Away - Southington HS-5 Soccer/Lacrosse [Directions] | 4:00 p.m. | ||
| Tue., 9/5 | V Field Hockey | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 6:15 p.m. | ||
| Wed., 9/6 | V Field Hockey | Glastonbury (Scrim.) | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | Cancelled | |
| Wed., 9/6 | V Girls Volleyball | Choate Rosemary Hall (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | ||
| Thu., 9/7 | FR Football | Ridgefield | Home - Cheshire High Main Game field [Directions] | Postponed | ||
| Thu., 9/7 | V Girls Soccer | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 7:00 p.m. | T 0-0 | |
| Thu., 9/7 | V Girls Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-2 | |
| Thu., 9/7 | JV Girls Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Fri., 9/8 | V Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:00 p.m. | W 39-10 | |
| Fri., 9/8 | JV Girls Soccer | Amity | Away - Amity Regional HS-CENTER FIELD [Directions] | 3:45 p.m. | ||
| Sat., 9/9 | JV Football | Ridgefield | Home - Cheshire High Main Game field [Directions] | 10:30 a.m. | ||
| Sat., 9/9 | FR Boys Soccer | Amity | Away - Amity Regional HS-AHS Grass Field # 2 [Directions] | 10:30 a.m. | ||
| Sat., 9/9 | FR Girls Soccer | Amity | Home - Cheshire HS-Grass Fields [Directions] | 10:30 a.m. | ||
| Mon., 9/11 | FR Boys Soccer | Notre Dame-West Haven | Home - Cheshire HS-Grass Fields [Directions] | Canceled | Cancelled | |
| Mon., 9/11 | FR Field Hockey | Amity | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Boys Cross Country | Guilford, Notre Dame-West Haven, Wilbur Cross | Home - Cheshire Park-Field 1 [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Boys Soccer | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 5:00 p.m. | W 2-1 | |
| Tue., 9/12 | JV Boys Soccer | Fairfield Prep | Away - Fairfield University-Grauert Field [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Girls Cross Country | Guilford, Sacred Heart Academy, Wilbur Cross | Home - Cheshire Park-Field 1 [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Field Hockey | Mercy | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 5-0 | |
| Tue., 9/12 | JV Field Hockey | Mercy | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:30 p.m. | W 4-0 | |
| Tue., 9/12 | V Girls Soccer | Sheehan | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/12 | V Girls Swimming and Diving | Mercy | Away - Middletown Recreation Center-Middletwown Recreation Center [Directions] | 3:45 p.m. | Cheshire 94 - Mercy 64 | |
| Wed., 9/13 | FR Boys Soccer | Wilbur Cross | Away - Wilbur Cross HS-Rice Field 1 [Directions] | Postponed | ||
| Wed., 9/13 | FR Field Hockey | Sacred Heart Academy | Away - Sacred Heart Academy-Field Hockey Field [Directions] | Postponed | ||
| Wed., 9/13 | JV Girls Soccer | Sheehan | Home - Cheshire HS-Grass Fields [Directions] | Postponed | ||
| Wed., 9/13 | V Girls Volleyball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 5:45 p.m. | W 3-2 | |
| Wed., 9/13 | JV Girls Volleyball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 4:30 p.m. | W 2-1 | |
| Thu., 9/14 | V Football | Shelton | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 21-14 (OT) | |
| Thu., 9/14 | FR Football | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | FR Field Hockey | Daniel Hand | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 3:45 p.m. | ||
| Thu., 9/14 | V Girls Soccer | Hamden | Away - Hamden HS-HHS Turf #2 [Directions] | 5:00 p.m. | W 8-2 | |
| Thu., 9/14 | JV Girls Soccer | Hamden | Away - Hamden HS-HHS Turf #2 [Directions] | 6:30 p.m. | ||
| Thu., 9/14 | V Girls Volleyball | Foran | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Thu., 9/14 | JV Girls Volleyball | Foran | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Fri., 9/15 | JV Football | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 3:00 p.m. | ||
| Mon., 9/18 | V Girls Soccer | Wilbur Cross | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 6-0 | |
| Mon., 9/18 | V Girls Swimming and Diving | Lyman Hall | Away - Sheehan HS-Sheehan HS Pool [Directions] | 5:30 p.m. | Cheshire 101 - Lyman Hall 77 | |
| Mon., 9/18 | V Girls Volleyball | East Haven | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Mon., 9/18 | JV Girls Volleyball | East Haven | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Tue., 9/19 | V Boys Cross Country | Branford, Hamden, Hillhouse | Away - Branford Supply Pond [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | V Boys Soccer | Career/Hillhouse | Away - Bowen Field-Football Field [Directions] | 6:00 p.m. | W 7-0 | |
| Tue., 9/19 | V Girls Cross Country | Branford, Hamden, Hillhouse | Away - Branford Supply Pond [Directions] | 3:30 p.m. | ||
| Tue., 9/19 | V Field Hockey | Branford | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 9/19 | JV Field Hockey | Branford | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:30 p.m. | L 0-1 | |
| Wed., 9/20 | JV Boys Soccer | Career/Hillhouse | Away - Boulevard Field [Directions] | Postponed | ||
| Wed., 9/20 | FR Boys Soccer | Shelton | Away - Shelton HS-Lower Field [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | FR Field Hockey | Guilford | Away - Guilford HS-Maturo Field [Directions] | 5:15 p.m. | ||
| Wed., 9/20 | JV Girls Soccer | Wilbur Cross | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | V Girls Volleyball | Fairfield Warde | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | L 1-3 | |
| Wed., 9/20 | JV Girls Volleyball | Fairfield Warde | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Thu., 9/21 | FR Football | Glastonbury | Away - Glastonbury HS-Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/21 | V Field Hockey | Farmington | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 9/21 | JV Field Hockey | Farmington | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:30 p.m. | ||
| Thu., 9/21 | V Girls Soccer | Foran | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 2-1 | |
| Fri., 9/22 | V Football | Glastonbury | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | W 27-0 | |
| Fri., 9/22 | JV Boys Soccer | Hamden | Home - Cheshire HS-Grass Fields [Directions] | 3:45 p.m. | ||
| Fri., 9/22 | V Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | L 0-3 | |
| Fri., 9/22 | FR Girls Soccer | Shelton | Away - Shelton HS-Upper Field [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | V Girls Volleyball | Hamden | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 9/22 | JV Girls Volleyball | Hamden | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 9/23 | JV Football | Glastonbury | Away - Glastonbury HS-Turf Field [Directions] | 9:30 a.m. | ||
| Sat., 9/23 | V Boys Soccer | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 12:30 p.m. | T 1-1 | |
| Sat., 9/23 | FR Boys Soccer | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 10:30 a.m. | ||
| Sat., 9/23 | V Girls Soccer | Mercy | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | L 0-1 | |
| Tue., 9/26 | V Boys Soccer | Jonathan Law | Away - Jonathan Law HS-Lawmen Stadium [Directions] | 6:00 p.m. | W 1-0 | |
| Tue., 9/26 | JV Boys Soccer | Jonathan Law | Away - Jonathan Law HS-New Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Girls Soccer | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 6:30 p.m. | W 2-0 | |
| Tue., 9/26 | JV Girls Soccer | Mercy | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | FR Girls Soccer | Amity | Away - Amity Regional HS-CENTER FIELD [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Girls Swimming and Diving | Guilford | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Cheshire 100 - Guilford 77 | |
| Tue., 9/26 | V Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 9/26 | JV Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 9/27 | V Boys Cross Country | SCC Divisional Race | Away - Guilford HS-Guilford Fair grounds | 4:00 p.m. | ||
| Wed., 9/27 | FR Boys Soccer | Daniel Hand | Away - Daniel Hand HS-Janssen Field #2/DHHS Campus [Directions] | 3:45 p.m. | ||
| Wed., 9/27 | V Girls Cross Country | SCC Divisional Race | Away - Guilford HS-Guilford Fair grounds | 4:00 p.m. | ||
| Wed., 9/27 | V Field Hockey | Lauralton Hall | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 3-2 | |
| Wed., 9/27 | JV Field Hockey | Lauralton Hall | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:30 p.m. | ||
| Wed., 9/27 | FR Field Hockey | Amity | Away - Amity Regional HS-Field Hockey Field [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | JV Girls Soccer | Branford | Away - Branford HS-Grass Field [Directions] | 3:45 p.m. | ||
| Wed., 9/27 | V Girls Volleyball | Mercy | Away - Mercy HS-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 9/27 | JV Girls Volleyball | Mercy | Away - Mercy HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 9/28 | V Boys Cross Country | SCC Division championship | Away - Guilford Fairgrounds | TBA | ||
| Thu., 9/28 | FR Football | Fairfield Prep | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 9/28 | V Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 7:00 p.m. | W 3-2 | |
| Thu., 9/28 | JV Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | V Girls Cross Country | SCC Division championship | Away - Guilford Fairgrounds | TBA | ||
| Thu., 9/28 | V Field Hockey | Sacred Heart Academy | Away - Sacred Heart Academy-Field Hockey Field [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 9/28 | JV Field Hockey | Sacred Heart Academy | Away - Sacred Heart Academy-Field Hockey Field [Directions] | 5:30 p.m. | ||
| Fri., 9/29 | V Football | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 6:00 p.m. | W 14-0 | |
| Fri., 9/29 | FR Boys Soccer | Fairfield Prep | Away - Fairfield University-Grauert Field [Directions] | Postponed | ||
| Fri., 9/29 | V Girls Soccer | Daniel Hand | Away - Madison Surf Club-Surf Club [Directions] | 6:00 p.m. | L 0-2 | |
| Fri., 9/29 | JV Girls Soccer | Daniel Hand | Away - Madison Surf Club-Surf Club [Directions] | 4:00 p.m. | ||
| Fri., 9/29 | V Girls Volleyball | North Haven | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 9/29 | JV Girls Volleyball | North Haven | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Sat., 9/30 | JV Football | Fairfield Prep | Home - Cheshire High Main Game field [Directions] | 10:30 a.m. | ||
| Sat., 9/30 | V Boys Soccer | Sheehan | Away - Choate Rosemary Hall-Choate-Hartevelt Field [Directions] | 7:00 p.m. | W 5-1 | |
| Sat., 9/30 | V Field Hockey | North Haven | Away - North Haven MS-East Turf Field [Directions] | 7:00 p.m. | W 3-0 | |
| Sat., 9/30 | JV Field Hockey | North Haven | Away - North Haven MS-East Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 10/2 | V Girls Soccer | Amity | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 2-1 | |
| Mon., 10/2 | V Girls Swimming and Diving | Jonathan Law | Away - Foran HS -Pool [Directions] | 5:00 p.m. | Cheshire 96 - Law 79 | |
| Mon., 10/2 | V Girls Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 6:00 p.m. | L 2-3 | |
| Mon., 10/2 | JV Girls Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 4:30 p.m. | L 0-2 | |
| Tue., 10/3 | V Boys Soccer | Hamden | Home - Cheshire High Main Game field [Directions] | 6:30 p.m. | L 2-0 | |
| Tue., 10/3 | V Field Hockey | Lyman Hall | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/3 | JV Field Hockey | Lyman Hall | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:30 p.m. | ||
| Tue., 10/3 | JV Girls Soccer | Amity | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | FR Girls Soccer | Daniel Hand | Away - Daniel Hand HS-Janssen Field #2/DHHS Campus [Directions] | 3:45 p.m. | ||
| Wed., 10/4 | FR Boys Soccer | Amity | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | FR Field Hockey | Daniel Hand | Away - Daniel Hand HS-Polson Front Field/ DHHS Campus [Directions] | 3:45 p.m. | ||
| Wed., 10/4 | V Girls Volleyball | Guilford | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-1 | |
| Wed., 10/4 | JV Girls Volleyball | Guilford | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Thu., 10/5 | FR Football | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | V Boys Soccer | Fairfield Prep | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | L 2-1 | |
| Thu., 10/5 | FR Boys Soccer | Fairfield Prep | Home - Cheshire HS-Grass Fields [Directions] | 3:30 p.m. | ||
| Thu., 10/5 | V Field Hockey | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 6:30 p.m. | L 1-2 | |
| Thu., 10/5 | JV Field Hockey | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 5:00 p.m. | ||
| Thu., 10/5 | FR Field Hockey | Sacred Heart Academy | Home - Cheshire HS-FIeld Hockey grass field [Directions] | Postponed | ||
| Thu., 10/5 | V Girls Soccer | Sheehan | Away - Lyman Hall HS-Fitzgerald Field [Directions] | 7:00 p.m. | W 1-0 | |
| Thu., 10/5 | V Girls Swimming and Diving | North Haven | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Cheshire 88 - NH 77 | |
| Fri., 10/6 | V Football | Amity | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | W 41-6 | |
| Fri., 10/6 | JV Boys Soccer | Fairfield Prep | Home - Cheshire HS-Grass Fields [Directions] | 3:45 p.m. | ||
| Fri., 10/6 | JV Girls Soccer | Sheehan | Away - PRAGEMANN PARK [Directions] | 3:45 p.m. | ||
| Fri., 10/6 | V Girls Volleyball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 5:00 p.m. | W 3-1 | |
| Fri., 10/6 | JV Girls Volleyball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 10/7 | JV Football | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 10:00 a.m. | ||
| Mon., 10/9 | V Girls Soccer | Hamden | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | W 5-0 | |
| Mon., 10/9 | V Girls Volleyball | Platt | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Mon., 10/9 | JV Girls Volleyball | Platt | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Tue., 10/10 | V Boys Cross Country | Foran, East Haven, Fairfield Prep | Away - EISENHOWER PARK [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Sheehan | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 1-0 | |
| Tue., 10/10 | V Girls Cross Country | Lauralton Hall, East Haven, Foran | Away - Eisenhower Park [Directions] | 3:45 p.m. | ||
| Tue., 10/10 | JV Field Hockey | Daniel Hand | Home - Cheshire HS-FIeld Hockey grass field [Directions] | Postponed | ||
| Tue., 10/10 | JV Girls Soccer | Hamden | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | FR Boys Soccer | Wilbur Cross | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | V Field Hockey | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 6:30 p.m. | L 0-1 | |
| Wed., 10/11 | V Girls Volleyball | East Haven | Away - East Haven HS-Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Wed., 10/11 | JV Girls Volleyball | East Haven | Away - East Haven HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 10/12 | FR Football | Hamden | Away - Hamden HS-HHS Turf #1 [Directions] | 5:30 p.m. | ||
| Thu., 10/12 | V Boys Soccer | Jonathan Law | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 1-0 | |
| Thu., 10/12 | JV Boys Soccer | Guilford | Away - Long Hill Park-Guilford-Soccer Field (Front) [Directions] | 3:45 p.m. | ||
| Thu., 10/12 | FR Boys Soccer | Notre Dame-West Haven | Away - Veterans Memorial Park (West Haven, CT)-Field [Directions] | Canceled | Cancelled | |
| Thu., 10/12 | FR Field Hockey | Guilford | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 3:45 p.m. | ||
| Thu., 10/12 | FR Girls Soccer | Shelton | Home - Cheshire HS-Grass Fields [Directions] | Postponed | ||
| Fri., 10/13 | V Boys Cross Country | Lyman Hall | Home - Cheshire Park-Field 1 [Directions] | 4:30 p.m. | ||
| Fri., 10/13 | V Football | Hamden | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | W 41-0 | |
| Fri., 10/13 | FR Boys Soccer | Xavier | Home - Cheshire HS-Grass Fields [Directions] | 3:30 p.m. | ||
| Fri., 10/13 | V Girls Cross Country | Lyman Hall | Home - Cheshire Park-Field 1 [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Field Hockey | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 4:00 p.m. | OT-L 2-1 | |
| Fri., 10/13 | JV Field Hockey | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 10/13 | V Girls Soccer | Wilbur Cross | Away - Wilbur Cross HS-Wilbur Cross Athletic Complex [Directions] | 6:30 p.m. | W 8-0 | |
| Fri., 10/13 | JV Girls Soccer | Wilbur Cross | Away - Wilbur Cross HS-Wilbur Cross Athletic Complex [Directions] | 4:30 p.m. | ||
| Fri., 10/13 | V Girls Volleyball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 10/13 | JV Girls Volleyball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 10/14 | JV Football | Hamden | Away - Hamden HS-HHS Turf #1 [Directions] | 10:00 a.m. | ||
| Sat., 10/14 | V Boys Soccer | Simsbury | Home - Cheshire High Main Game field [Directions] | 10:30 a.m. | W 3-1 | |
| Sat., 10/14 | FR Boys Soccer | Shelton | Home - Cheshire HS-Grass Fields [Directions] | Postponed | ||
| Mon., 10/16 | V Boys Soccer | Hamden | Away - Hamden HS-HHS Turf #1 [Directions] | 5:00 p.m. | W 1-0 | |
| Mon., 10/16 | JV Boys Soccer | Hamden | Away - Hamden HS-HHS Turf #2 [Directions] | 6:30 p.m. | ||
| Mon., 10/16 | FR Field Hockey | Shelton | Home - Cheshire HS-FIeld Hockey grass field [Directions] | Canceled | Cancelled | |
| Mon., 10/16 | V Girls Soccer | Foran | Away - Foran HS -Foran High School - Turf Field [Directions] | 5:30 p.m. | W 5-1 | |
| Mon., 10/16 | JV Girls Soccer | Foran | Away - Foran HS -Foran High School - Turf Field [Directions] | 7:15 p.m. | ||
| Mon., 10/16 | V Girls Swimming and Diving | Daniel Hand | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Cheshire 93 - Hand 85 | |
| Mon., 10/16 | V Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | L 0-3 | |
| Mon., 10/16 | JV Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | L 1-2 | |
| Tue., 10/17 | V Field Hockey | Hamden | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 2-1 | |
| Tue., 10/17 | JV Field Hockey | Hamden | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | V Boys Cross Country | SCC Conference Championship Race | Away - East Shore Athletic Complex-Trail | 1:00 p.m. | ||
| Wed., 10/18 | V Boys Cross Country | SCC Championship | Away - East Shore Park Career J.V. | 1:00 p.m. | ||
| Wed., 10/18 | V Boys Soccer | Guilford | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 2-1 | |
| Wed., 10/18 | FR Boys Soccer | Guilford | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | V Girls Cross Country | SCC Conference Championship Race | Away - East Shore Athletic Complex-Trail | 1:00 p.m. | ||
| Wed., 10/18 | V Girls Cross Country | SCC Championship | Away - East Shore Park Career J.V. | 1:00 p.m. | ||
| Wed., 10/18 | V Girls Soccer | Mercy | Away - Xavier HS-Larry McHugh Field [Directions] | 4:30 p.m. | L 0-4 | |
| Wed., 10/18 | JV Girls Soccer | Amity | Away - Amity Regional HS-AHS Grass Field # 3 [Directions] | 3:45 p.m. | ||
| Thu., 10/19 | JV Boys Soccer | Guilford | Home - Cheshire HS-Grass Fields [Directions] | 3:45 p.m. | ||
| Thu., 10/19 | V Field Hockey | Conard | Home - Cheshire High Main Game field [Directions] | 5:30 p.m. | W 1-0 | |
| Thu., 10/19 | JV Field Hockey | Conard | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 7:00 p.m. | ||
| Thu., 10/19 | FR Field Hockey | Shelton | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 3:45 p.m. | ||
| Thu., 10/19 | JV Girls Soccer | Mercy | Away - Mercy HS-Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/19 | V Girls Swimming and Diving | Lauralton Hall | Away - Foran HS -Pool [Directions] | 7:00 p.m. | Cheshire 103 - Lauralton 72 | |
| Fri., 10/20 | JV Boys Soccer | Jonathan Law | Home - Cheshire HS-Grass Fields [Directions] | 3:45 p.m. | ||
| Fri., 10/20 | FR Field Hockey | Shelton, Sacred Heart Academy (Scrim.) | Away - Shelton HS-Finn Stadium [Directions] | 3:30 p.m. | ||
| Fri., 10/20 | V Girls Soccer | Branford | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/20 | V Girls Volleyball | Mercy | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 10/20 | JV Girls Volleyball | Mercy | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Sat., 10/21 | V Boys Soccer | Career/Hillhouse | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | W 4-0 | |
| Sat., 10/21 | FR Boys Soccer | Daniel Hand | Home - Cheshire HS-Main Game Field [Directions] | 10:30 a.m. | ||
| Sat., 10/21 | V Field Hockey | Sheehan | Away - Lyman Hall HS-Fitzgerald Field [Directions] | 1:00 p.m. | W 1-0 | |
| Sat., 10/21 | JV Field Hockey | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | Canceled | Cancelled | |
| Sat., 10/21 | JV Girls Soccer | Branford | Home - Cheshire HS-Main Game Field [Directions] | 12:45 p.m. | ||
| Mon., 10/23 | V Girls Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 1-0 | |
| Mon., 10/23 | FR Girls Soccer | Daniel Hand | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | V Girls Swimming and Diving | Amity | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Cheshire 95 - Amity 83 | |
| Mon., 10/23 | V Girls Volleyball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/23 | JV Girls Volleyball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 4:30 p.m. | W 2-0 | |
| Tue., 10/24 | V Boys Soccer | Xavier | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 3-1 | |
| Tue., 10/24 | JV Boys Soccer | Xavier | Home - Cheshire HS-Grass Fields [Directions] | 3:45 p.m. | ||
| Tue., 10/24 | V Field Hockey | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 7:00 p.m. | W 3-0 | |
| Tue., 10/24 | JV Field Hockey | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/24 | FR Field Hockey | Shelton | Away - Shelton Intermediate School-Shelton Intermediate [Directions] | 3:45 p.m. | ||
| Wed., 10/25 | FR Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 4:00 p.m. | ||
| Wed., 10/25 | V Field Hockey | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | 6:00 p.m. | T 0-0 | |
| Wed., 10/25 | JV Field Hockey | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 10/25 | V Girls Volleyball | Bristol Central | Away - Bristol Central HS-Charles C. Marsh Gymnasium [Directions] | 6:30 p.m. | W 3-1 | |
| Wed., 10/25 | JV Girls Volleyball | Bristol Central | Away - Bristol Central HS-Charles C. Marsh Gymnasium [Directions] | 5:00 p.m. | L 1-2 | |
| Thu., 10/26 | FR Football | Notre Dame-West Haven | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 10/26 | V Girls Volleyball | Farmington | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | L 2-3 | |
| Thu., 10/26 | JV Girls Volleyball | Farmington | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | L 0-2 | |
| Fri., 10/27 | V Football | Notre Dame-West Haven | Away - Veterans Memorial Park (West Haven, CT)-Field [Directions] | 7:00 p.m. | W 28-3 | |
| Sat., 10/28 | V Boys Cross Country | CIAC Class L Championship | Away - Wickham Park | 2:40 p.m. | ||
| Sat., 10/28 | JV Football | Notre Dame-West Haven | Home - Cheshire High Main Game field [Directions] | 9:00 a.m. | ||
| Sat., 10/28 | V Boys Soccer | West Haven | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | W 2-2 | Would like 3 officials |
| Sat., 10/28 | V Girls Cross Country | CIAC Class L Championship | Away - Wickham Park | 2:05 p.m. | ||
| Sat., 10/28 | V Field Hockey | Branford | Home - Cheshire High Main Game field [Directions] | 11:30 a.m. | L 1-2 | |
| Sat., 10/28 | V Girls Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 1:30 p.m. | W 6-5 pks | Would like 3 officials |
| Sat., 10/28 | V Girls Swimming and Diving | SCC Girls Dive Trials/Finals | Home - Sheehan HS-Sheehan HS Pool [Directions] | 10:00 a.m. | ||
| Mon., 10/30 | V Boys Soccer | Xavier | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | L 3-2 | |
| Mon., 10/30 | V Girls Soccer | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 5:00 p.m. | W 2-1 | |
| Mon., 10/30 | V Girls Swimming and Diving | SCC Girls Swim Trials | Home - Cheshire Community Pool [Directions] | 4:00 p.m. | ||
| Mon., 10/30 | V Girls Volleyball | Branford | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Wed., 11/1 | V Girls Swimming and Diving | Lauralton Hall, Amity, Branford, Daniel Hand, East Haven/Cross/Hillhouse/SHA, Guilford, Hamden, Jonathan Law, Foran, Lyman Hall, Mercy, North Haven, Sacred Heart Academy, Sheehan, Shelton, West Haven | Home - Southern CT State University-pool [Directions] | 6:00 p.m. | ||
| Wed., 11/1 | V Girls Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Thu., 11/2 | FR Football | North Haven | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 11/2 | V Girls Soccer | Mercy | Away - West Haven HS-Ken Strong Stadium [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 11/3 | V Football | North Haven | Away - North Haven MS-Vanacore Field [Directions] | 7:00 p.m. | L 7-24 | |
| Sat., 11/4 | JV Football | North Haven | Home - Cheshire High Main Game field [Directions] | 10:30 a.m. | ||
| Sat., 11/4 | V Girls Volleyball | Amity | Away - West Haven HS-Gym [Directions] | 1:00 p.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/6 | V Girls Soccer | Stamford | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 5-0 | |
| Tue., 11/7 | V Boys Soccer | Berlin | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 3-1 | |
| Tue., 11/7 | V Girls Volleyball | Stamford | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Wed., 11/8 | V Field Hockey | Conard | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 11/8 | V Girls Soccer | Ridgefield | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | L 0-1 | |
| Wed., 11/8 | V Girls Swimming and Diving | CIAC Class L Diving Championship | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/9 | V Boys Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 1-0 | |
| Thu., 11/9 | V Girls Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Fri., 11/10 | V Football | West Haven | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | L 14-25 | |
| Sat., 11/11 | V Boys Soccer | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 1:00 p.m. | W 1-0 | |
| Sat., 11/11 | V Field Hockey | Glastonbury | Away - Glastonbury HS-Turf Field [Directions] | 1:00 p.m. | ||
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 11:15 a.m. | ||
| Sat., 11/11 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 1:00 p.m. | ||
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class L Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Wed., 11/15 | V Boys Soccer | East Lyme | Away - Guilford HS-New Turf field at GHS [Directions] | 7:00 p.m. | ||
| Thu., 11/16 | JV Football | Southington | Away - Southington HS-3 TURF FIELD [Directions] | 6:00 p.m. | ||
| Thu., 11/16 | FR Football | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/18 | JV Football | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | Canceled | Cancelled | |
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Thu., 11/23 | V Football | Southington | Away - Southington HS-3 TURF FIELD [Directions] | 10:00 a.m. | W 34-20 | |
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Tue., 11/28 | V Football | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 6:30 p.m. | L 21-42 | |
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||