| Cheshire 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 877 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. | ||
| Fri., 9/15 | Miscellaneous Events | Rosh Hashanah Begins | Home - Cheshire HS [Directions] | 4:00 p.m. | ||
| Sat., 9/16 | Miscellaneous Events | Rosh Hashanah | Home - Cheshire HS [Directions] | 7:30 a.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 | |
| Mon., 9/25 | Miscellaneous Events | YOM KIPPUR | Home - Cheshire HS [Directions] | 7:30 a.m. | ||
| 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. | ||
| Sat., 10/7 | Miscellaneous Events | Music in Motion | Home - Cheshire HS [Directions] | 1:00 p.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. | ||
| Wed., 10/18 | Miscellaneous Events | Unified Soccer tournament | Home - Cheshire High Main Game field [Directions] | 3:00 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. | ||
| Tue., 11/14 | Miscellaneous Events | CIAC Semi Field Hockey | Home - Cheshire High Main Game field [Directions] | 4:00 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. | ||
| Wed., 11/22 | V | TBA | Home - Cheshire High Main Game field [Directions] | 12:30 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 | |
| Sat., 12/2 | V Wrestling | Fitch, Glastonbury, North Haven, Xavier (Scrim.) | Home - Cheshire HS-Gym - East [Directions] | 9:30 a.m. | ||
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Mon., 12/4 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Sacred Heart University-Martire Arena [Directions] | 5:15 p.m. | W 6-2 | |
| Tue., 12/5 | V Girls Basketball | Bridgeport Central (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 4:45 p.m. | ||
| Wed., 12/6 | V Boys Basketball | Berlin (Scrim.) | Away - Berlin HS-Gibney Gymnasium [Directions] | 4:45 p.m. | ||
| Thu., 12/7 | V Boys Ice Hockey | Hamden (Scrim.) | Away - Hamden-Lou Astorino Ice Rink [Directions] | 2:50 p.m. | ||
| Thu., 12/7 | V Girls Basketball | Sheehan (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 4:45 p.m. | ||
| Fri., 12/8 | V Boys Basketball | Ellington (Scrim.) | Away - Ellington HS-Gym [Directions] | 4:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Sat., 12/9 | V Boys Ice Hockey | Newington Coop (Scrim.) | Away - Newington-Blue Rink [Directions] | 5:10 p.m. | ||
| Tue., 12/12 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | W 50-39 | |
| Tue., 12/12 | JV Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Wed., 12/13 | V Boys Ice Hockey | SCW Knights | Away - Cromwell-Upper Rink [Directions] | 4:10 p.m. | W 6-0 | |
| Wed., 12/13 | V Wrestling | Morgan | Home - Cheshire HS-Gym - East [Directions] | 6:00 p.m. | ||
| Wed., 12/13 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 12/15 | V Girls Basketball | Lyman Hall | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 59-57 | |
| Fri., 12/15 | JV Girls Basketball | Lyman Hall | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Sat., 12/16 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:15 p.m. | W 5-2 | |
| Sat., 12/16 | V Wrestling | Darien Invitational | Away - Darien HS-DHS Main Gym | 9:00 a.m. | ||
| Sun., 12/17 | V Girls Ice Hockey | Masuk Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:00 p.m. | W 3-2 | |
| Mon., 12/18 | V Boys Basketball | Career Magnet | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 63-43 | |
| Mon., 12/18 | JV Boys Basketball | Career Magnet | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 12/19 | ||||||
| Tue., 12/19 | FR Boys Basketball | Career Magnet | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Tue., 12/19 | V Boys Swimming and Diving | Notre Dame-West Haven | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Notre Dame 93 Cheshire 55 ND 1-0 C 0-1 | |
| Tue., 12/19 | V Girls Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 6:00 p.m. | L 37-62 | |
| Tue., 12/19 | JV Girls Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 4:15 p.m. | ||
| Tue., 12/19 | V Girls Indoor Track | Developmental Meet | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 5:30 p.m. | ||
| Wed., 12/20 | V Boys Indoor Track | SCC Developmental | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 5:30 p.m. | ||
| Wed., 12/20 | V Wrestling | North Haven | Away - North Haven HS-North Haven High school [Directions] | 7:00 p.m. | ||
| Wed., 12/20 | V Girls Ice Hockey | Woodstock Academy Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 5:00 p.m. | W 5-4 OT | |
| Fri., 12/22 | V Boys Basketball | Wilbur Cross | Away - Floyd Little Athletic Center-Field House [Directions] | 7:00 p.m. | L 67-46 | |
| Fri., 12/22 | JV Boys Basketball | Wilbur Cross | Away - Floyd Little Athletic Center-Field House [Directions] | 5:30 p.m. | ||
| Fri., 12/22 | FR Boys Basketball | Wilbur Cross | Away - Floyd Little Athletic Center-Field House [Directions] | 3:45 p.m. | ||
| Sat., 12/23 | V Boys Ice Hockey | Glastonbury | Away - Trinity College-Koeppel Rink [Directions] | 7:30 p.m. | W 4-3 | |
| Sat., 12/23 | V Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 12:45 p.m. | L 32-61 | |
| Sat., 12/23 | JV Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 12/23 | FR Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 9:30 a.m. | ||
| Wed., 12/27 | V Boys Basketball | Newington | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 68-51 | |
| Wed., 12/27 | JV Boys Basketball | Newington | Home - Cheshire HS-Gym West [Directions] | 4:15 p.m. | ||
| Wed., 12/27 | FR Boys Basketball | Newington | Home - Cheshire HS-Gym West [Directions] | 2:45 p.m. | ||
| Wed., 12/27 | V Wrestling | Amity, Morgan | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 12/28 | JV Boys Ice Hockey | Newington Coop | Away - Newington-Blue Rink [Directions] | 4:30 p.m. | ||
| Thu., 12/28 | V Girls Basketball | Avon | Away - Avon HS-Large Gym [Directions] | 2:00 p.m. | L 29-47 | |
| Thu., 12/28 | JV Girls Basketball | Avon | Away - Avon HS-Large Gym [Directions] | 12:30 p.m. | ||
| Thu., 12/28 | FR Girls Basketball | Avon | Away - Avon HS-Large Gym [Directions] | 11:00 a.m. | ||
| Sat., 12/30 | V Boys Ice Hockey | East Haven Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 1:00 p.m. | W Forfeit | |
| Sat., 12/30 | V Wrestling | Killingly New Year Duals | Away - Killingly HS-Gym | 9:00 a.m. | ||
| Tue., 1/2 | V Boys Basketball | Guilford | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 63-52 | |
| Tue., 1/2 | JV Boys Basketball | Guilford | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Tue., 1/2 | FR Boys Basketball | Guilford | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Tue., 1/2 | V Boys Ice Hockey | West Haven Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 6:00 p.m. | W 5-3 | |
| Tue., 1/2 | V Girls Indoor Track | Developmental Meet 2 | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | 6:30 p.m. | W 3-2 | |
| Wed., 1/3 | V Boys Indoor Track | SCC Developmental 2 | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | V Boys Swimming and Diving | Fitch/Stonington/St.Bernard/Wheeler Boys Swim | Away - UCONN Avery Point-Pool [Directions] | 3:45 p.m. | Fitch Co-op 69, Cheshire 50 0-2 | |
| Wed., 1/3 | V Wrestling | New Haven Wrestling | Home - Cheshire HS-Gym - East [Directions] | 6:00 p.m. | ||
| Wed., 1/3 | V Girls Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 7:00 p.m. | L 38-52 | |
| Wed., 1/3 | JV Girls Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/3 | V Girls Ice Hockey | New Canaan | Home - Hamden-Lou Astorino Ice Rink [Directions] | 7:00 p.m. | L 1-6 | |
| Thu., 1/4 | V Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 7:00 p.m. | L 54-33 | |
| Thu., 1/4 | JV Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 1/4 | FR Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 1/5 | V Girls Basketball | West Haven | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 45-42 | |
| Fri., 1/5 | JV Girls Basketball | West Haven | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Fri., 1/5 | FR Girls Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Sat., 1/6 | V Wrestling | Warrior Invitational | Away - Canton HS-Gym | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 1/6 | V Girls Ice Hockey | Hall/Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 1:30 p.m. | L 1-4 | |
| Mon., 1/8 | V Boys Basketball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 52-51 | |
| Mon., 1/8 | JV Boys Basketball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Mon., 1/8 | FR Boys Basketball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Mon., 1/8 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | L 1-4 | |
| Tue., 1/9 | V Co-ed Fencing | Guilford | Home - Cheshire HS [Directions] | 6:30 p.m. | ||
| Tue., 1/9 | V Girls Basketball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 5:00 p.m. | L 32-34 | |
| Tue., 1/9 | JV Girls Basketball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | Postponed | ||
| Wed., 1/10 | V Boys Basketball | Maloney | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 67-49 | |
| Wed., 1/10 | JV Boys Basketball | Maloney | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Wed., 1/10 | FR Boys Basketball | Maloney | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Wed., 1/10 | V Wrestling | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 1/10 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford-Red [Directions] | 8:30 p.m. | L 2-6 | |
| Thu., 1/11 | JV Boys Ice Hockey | Wethersfield | Away - Newington-Blue Rink [Directions] | 4:30 p.m. | ||
| Thu., 1/11 | V Co-ed Fencing | Morgan | Home - Cheshire HS [Directions] | 6:30 p.m. | ||
| Fri., 1/12 | V Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 7:00 p.m. | L 55-50 | |
| Fri., 1/12 | JV Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | FR Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 3:45 p.m. | ||
| Fri., 1/12 | V Boys Indoor Track | Yale Scholastic Invitational | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 1:00 p.m. | ||
| Fri., 1/12 | V Girls Basketball | East Haven | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 42-44 | |
| Fri., 1/12 | JV Girls Basketball | East Haven | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | V Girls Indoor Track | Yale Scholastic Invitational | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 1:00 p.m. | ||
| Sat., 1/13 | V Boys Ice Hockey | Wethersfield | Away - Newington-Blue Rink [Directions] | 1:10 p.m. | W 3-2 | |
| Sat., 1/13 | V Wrestling | Fairfield Ludlowe, Fairfield Warde, Joel Barlow, New Haven Wrestling | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/13 | FR Girls Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 1/13 | V Girls Ice Hockey | Suffield Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 6:00 p.m. | L 1-2 OT | |
| Mon., 1/15 | V Boys Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 51-49 | |
| Mon., 1/15 | JV Boys Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 4:15 p.m. | ||
| Mon., 1/15 | FR Boys Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 2:45 p.m. | ||
| Mon., 1/15 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-Patriot Rink [Directions] | 3:00 p.m. | W 6-3 | |
| Mon., 1/15 | V Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 3:00 p.m. | W 38-35 | |
| Mon., 1/15 | JV Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 1:00 p.m. | ||
| Mon., 1/15 | FR Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 11:00 a.m. | ||
| Tue., 1/16 | FR Girls Basketball | Wilbur Cross | Home - Cheshire HS-Gym West [Directions] | Postponed | ||
| Wed., 1/17 | V Boys Ice Hockey | Hamden | Home - Hamden-Lou Astorino Ice Rink [Directions] | 7:30 p.m. | W 2-1 | |
| Wed., 1/17 | V Boys Swimming and Diving | Fairfield Prep | Away - Fairfield University-RecPlex Pool [Directions] | 5:15 p.m. | Fairfield Prep 99, Cheshire 35 0-3 | |
| Wed., 1/17 | V Girls Basketball | Wilbur Cross | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 57-33 | |
| Wed., 1/17 | JV Girls Basketball | Wilbur Cross | Home - Cheshire HS-Gym West [Directions] | 4:15 p.m. | ||
| Wed., 1/17 | V Girls Ice Hockey | West Haven/SHA | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:00 p.m. | L 2-4 | |
| Thu., 1/18 | V Boys Basketball | East Haven | Away - East Haven HS-Gym [Directions] | 7:00 p.m. | L 62-51 | |
| Thu., 1/18 | JV Boys Basketball | East Haven | Away - East Haven HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/18 | FR Boys Basketball | East Haven | Away - East Haven HS-Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/18 | V Boys Indoor Track | SCC Novice | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 4:00 p.m. | ||
| Thu., 1/18 | V Girls Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 7:00 p.m. | L 36-41 | |
| Thu., 1/18 | JV Girls Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 1/18 | V Girls Indoor Track | SCC Novice | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 4:00 p.m. | ||
| Sat., 1/20 | V Boys Basketball | Southington | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 66-46 | |
| Sat., 1/20 | JV Boys Basketball | Southington | Home - Cheshire HS-Gym West [Directions] | 4:15 p.m. | ||
| Sat., 1/20 | FR Boys Basketball | Southington | Home - Cheshire HS-Gym West [Directions] | 2:45 p.m. | ||
| Sat., 1/20 | V Boys Ice Hockey | North Haven | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | W 5-3 | |
| Sat., 1/20 | V Boys Indoor Track | SCC Coaches Invitational | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 9:00 a.m. | ||
| Sat., 1/20 | V Wrestling | Colter Abely Midseason Classic | Away - Mercy HS-Gym | 9:00 a.m. | ||
| Sat., 1/20 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 6:00 p.m. | W 3-2 OT | |
| Sat., 1/20 | V Girls Indoor Track | SCC Coaches Invitational | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 9:00 a.m. | ||
| Mon., 1/22 | JV Boys Ice Hockey | Hamden Hall | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:30 p.m. | ||||||
| Mon., 1/22 | V Girls Basketball | Foran | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 41-44 | |
| Mon., 1/22 | JV Girls Basketball | Foran | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Mon., 1/22 | FR Girls Basketball | Bridgeport Central | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Mon., 1/22 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 5:15 p.m. | W 2-1 | |
| Tue., 1/23 | V Boys Basketball | Career Magnet | Away - Career Magnet-Gym [Directions] | 7:00 p.m. | L 53-39 | |
| Tue., 1/23 | JV Boys Basketball | Career Magnet | Away - Career Magnet-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | FR Boys Basketball | Career Magnet | Away - Career Magnet-Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/23 | V Co-ed Fencing | Daniel Hand | Home - Cheshire HS [Directions] | 6:30 p.m. | ||
| Wed., 1/24 | V Boys Ice Hockey | Daniel Hand | Home - Hamden-Lou Astorino Ice Rink [Directions] | 7:15 p.m. | W 6-2 | |
| Wed., 1/24 | V Co-ed Fencing | Morgan | Away - Morgan School-Gym [Directions] | 6:30 p.m. | ||
| Thu., 1/25 | V Boys Indoor Track | SCC East Track Championship | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 5:00 p.m. | ||
| Thu., 1/25 | V Boys Swimming and Diving | Greater New Haven | Away - Walter Gawrych Community Pool [Directions] | 4:00 p.m. | GNH 71, Cheshire 54 C 0-4 | |
| Thu., 1/25 | V Wrestling | Shelton | Home - Cheshire HS-Gym - East [Directions] | 6:00 p.m. | ||
| Thu., 1/25 | V Girls Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 38-43 | |
| Thu., 1/25 | JV Girls Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Thu., 1/25 | FR Girls Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Thu., 1/25 | V Girls Indoor Track | SCC East Track Championships | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 5:00 p.m. | ||
| Fri., 1/26 | V Boys Basketball | Wilbur Cross | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 95-61 | |
| Fri., 1/26 | JV Boys Basketball | Wilbur Cross | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | Wilbur Cross | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Sat., 1/27 | JV Boys Ice Hockey | Xavier | Away - Wesleyan University-Freeman Athletic Center [Directions] | 6:30 p.m. | ||
| Sat., 1/27 | V Wrestling | Doc Meyers Invitational | Away - Rocky Hill HS-Gym | 9:00 a.m. | ||
| Sat., 1/27 | V Co-ed Fencing | North Branford, North Haven | Away - North Branford Intermediate School-gym [Directions] | 9:00 a.m. | ||
| Sat., 1/27 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Cromwell-Upper Rink [Directions] | 7:00 p.m. | L 1-4 | |
| Mon., 1/29 | V Boys Basketball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 7:00 p.m. | L 63-55 | |
| Mon., 1/29 | JV Boys Basketball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 5:15 p.m. | ||
| Mon., 1/29 | FR Boys Basketball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 3:45 p.m. | ||
| Mon., 1/29 | V Boys Ice Hockey | Greenwich | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | W 4-1 | |
| Tue., 1/30 | V Boys Swimming and Diving | Amity | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Amity 81, Cheshire 47 C 0-5 | |
| Tue., 1/30 | V Co-ed Fencing | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | 6:30 p.m. | ||
| Tue., 1/30 | V Girls Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 46-67 | |
| Tue., 1/30 | JV Girls Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Tue., 1/30 | V Girls Ice Hockey | Guilford Coop | Away - East Haven HS-Patsy DiLungo Rink [Directions] | 6:45 p.m. | W 5-1 | |
| Wed., 1/31 | V Boys Ice Hockey | Branford | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | W 6-2 | |
| Wed., 1/31 | V Wrestling | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 6:30 p.m. | ||
| Wed., 1/31 | V Girls Basketball | Woodland | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 57-49 | |
| Wed., 1/31 | JV Girls Basketball | Woodland | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Wed., 1/31 | FR Girls Basketball | Sacred Heart Academy | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Thu., 2/1 | JV Boys Ice Hockey | East Catholic | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | ||
| Fri., 2/2 | V Boys Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 57-48 | |
| Fri., 2/2 | JV Boys Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Fri., 2/2 | FR Boys Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Fri., 2/2 | V Girls Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 6:00 p.m. | L 44-54 | |
| Fri., 2/2 | JV Girls Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 4:15 p.m. | ||
| Sat., 2/3 | V Boys Ice Hockey | East Catholic | Away - Cromwell-Lower Rink [Directions] | 7:00 p.m. | W 6-4 | |
| Sat., 2/3 | V Boys Indoor Track | SCC Championship | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 10:00 a.m. | ||
| Sat., 2/3 | V Wrestling | East Lyme/Norwich Tech, Fairfield Prep, Montville, Woodstock Academy | Away - East Lyme HS-North Gym [Directions] | 9:30 a.m. | ||
| Sat., 2/3 | FR Girls Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 10:30 a.m. | ||
| Sat., 2/3 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | T 3-3 OT | |
| Sat., 2/3 | V Girls Indoor Track | SCC Championships | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 10:00 a.m. | ||
| Mon., 2/5 | JV Boys Ice Hockey | Wethersfield | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | ||
| Tue., 2/6 | V Boys Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 7:00 p.m. | L 73-69 | |
| Tue., 2/6 | JV Boys Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/6 | FR Boys Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 2/6 | V Boys Swimming and Diving | Hamden | Away - Hamden HS-HHS Pool [Directions] | 4:00 p.m. | Hamden 71 Cheshire 51 Cheshire 0-6 | |
| Tue., 2/6 | V Girls Basketball | Jonathan Law | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 44-42 | |
| Tue., 2/6 | JV Girls Basketball | Jonathan Law | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Tue., 2/6 | FR Girls Basketball | Jonathan Law | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Wed., 2/7 | V Boys Ice Hockey | South Windsor | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | T 4-4 | |
| Wed., 2/7 | V Wrestling | Notre Dame-West Haven | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Wed., 2/7 | V Girls Ice Hockey | Daniel Hand Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 1-5 | |
| Thu., 2/8 | V Boys Basketball | Branford | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 53-49 | |
| Thu., 2/8 | JV Boys Basketball | Branford | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Thu., 2/8 | FR Boys Basketball | Branford | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Thu., 2/8 | JV Boys Ice Hockey | Xavier | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | ||
| Thu., 2/8 | V Co-ed Fencing | North Haven | Away - North Haven HS-Auxiliary Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 2/8 | V Girls Basketball | East Haven | Away - East Haven HS-Gym [Directions] | 6:00 p.m. | L 34-41 | |
| Thu., 2/8 | JV Girls Basketball | East Haven | Away - East Haven HS-Gym [Directions] | 4:15 p.m. | ||
| Thu., 2/8 | FR Girls Basketball | Holy Cross | Away - Holy Cross-Tim McDonald Gymnasium [Directions] | 6:00 p.m. | ||
| Fri., 2/9 | V Boys Swimming and Diving | Xavier | Away - Middletown Rec Center-Pool [Directions] | 3:45 p.m. | Xavier 71 Cheshire 49 Cheshire 0-7 | |
| Fri., 2/9 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 3-0 | |
| Sat., 2/10 | V Boys Basketball | New Milford | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | ||
| Sat., 2/10 | JV Boys Basketball | New Milford | Home - Cheshire HS-Gym West [Directions] | 2:15 p.m. | ||
| Sat., 2/10 | FR Boys Basketball | New Milford | Home - Cheshire HS-Gym West [Directions] | 12:45 p.m. | ||
| Sat., 2/10 | V Boys Ice Hockey | Farmington Valley Generals | Away - Avon Old Farms-Jennings Rink [Directions] | 7:00 p.m. | W 5-1 | |
| Sat., 2/10 | V Boys Indoor Track | Class L Meet | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 10:00 a.m. | ||
| Sat., 2/10 | V Boys Indoor Track | CIAC L Divisional Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/10 | FR Girls Basketball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/10 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:15 p.m. | W 4-2 | |
| Sat., 2/10 | V Girls Indoor Track | CIAC L Divisional Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/10 | V Girls Indoor Track | Class L State Championship | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 10:00 a.m. | ||
| Mon., 2/12 | V Boys Swimming and Diving | HK-Valley | Away - Haddam Killingworth HS (HK)-HKHS Pool - no diving [Directions] | 4:00 p.m. | Hk Co-op 91 Cheshire 50 Cheshire 0-8 | |
| Mon., 2/12 | V Girls Basketball | Wilbur Cross | Away - Wilbur Cross HS-Gym [Directions] | 7:00 p.m. | W 51-39 | |
| Mon., 2/12 | JV Girls Basketball | Wilbur Cross | Away - Wilbur Cross HS-Gym [Directions] | Canceled | Cancelled | |
| Wed., 2/14 | V Boys Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 2/14 | JV Boys Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/14 | FR Boys Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 2/14 | V Boys Ice Hockey | North Branford | Home - Hamden-Lou Astorino Ice Rink [Directions] | 7:00 p.m. | W 2-0 | |
| Thu., 2/15 | JV Boys Ice Hockey | Newington Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | Canceled | Cancelled | |
| Thu., 2/15 | V Girls Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 6:30 p.m. | ||
| Thu., 2/15 | V Girls Ice Hockey | Hamden Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 2/16 | V Boys Basketball | East Haven | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | ||
| Fri., 2/16 | JV Boys Basketball | East Haven | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 2/16 | FR Boys Basketball | East Haven | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Fri., 2/16 | V Boys Swimming and Diving | Daniel Hand/Branford/Old Saybrook | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Daniel Hand Co-op 71 Cheshire 51 Cheshire 0-9 | |
| Fri., 2/16 | V Wrestling | CIAC L Divisional Championship | Away - Wilton | TBA | ||
| Sat., 2/17 | V Boys Ice Hockey | Lyman Hall | Away - Northford-Red [Directions] | 5:00 p.m. | L 2-3 | |
| Sat., 2/17 | V Boys Indoor Track | State Open | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 12:00 p.m. | ||
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Ice Hockey | Guilford Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 6:30 p.m. | W 5-3 | |
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Indoor Track | State Open Championship | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 12:00 p.m. | ||
| Tue., 2/20 | V Boys Swimming and Diving | Milford Boys Swimming & Diving Team | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Milford 74 Cheshire 50 Cheshire 0-10 | |
| Wed., 2/21 | V Boys Ice Hockey | Guilford | Away - East Haven HS-Patsy DiLungo Rink [Directions] | 7:30 p.m. | W 9-3 | |
| Wed., 2/21 | V Co-ed Fencing | Guilford | Away - Guilford HS-Aux gym at GHS [Directions] | 6:30 p.m. | ||
| Wed., 2/21 | V Girls Ice Hockey | West Haven/SHA | Home - Hamden-Lou Astorino Ice Rink [Directions] | 6:00 p.m. | ||
| Thu., 2/22 | JV Boys Ice Hockey | Xavier | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | ||
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 2/24 | V Boys Ice Hockey | Trumbull | Home - Hamden-Lou Astorino Ice Rink [Directions] | 5:00 p.m. | W 5-0 | |
| Mon., 2/26 | V Girls Ice Hockey | Southington Coop | Away - Newington-Red Rink [Directions] | 6:10 p.m. | ||
| Tue., 2/27 | V Girls Basketball | Torrington | Away - Torrington HS-Connie Donahue Gymnasium [Directions] | 6:30 p.m. | L 35-49 | |
| Wed., 2/28 | V Boys Ice Hockey | West Haven Coop | Home - West Haven HS-Bennett Rink [Directions] | 6:00 p.m. | W 5-2 | |
| Fri., 3/1 | V Boys Ice Hockey | Amity | Home - West Haven HS-Bennett Rink [Directions] | 8:00 p.m. | ||
| Tue., 3/5 | V Boys Ice Hockey | Farmington Valley Generals | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | W 6-0 | |
| Tue., 3/5 | V Boys Ice Hockey | CIAC Div II First Round | Away - Higher Seed | TBA | ||
| Thu., 3/7 | V Boys Swimming and Diving | CIAC Class M Diving Championship | Away - Middletown | 5:30 p.m. | ||
| Fri., 3/8 | V Boys Ice Hockey | Watertown-Pomperaug | Home - West Haven HS-Bennett Rink [Directions] | 6:00 p.m. | W 2-1 | |
| Fri., 3/8 | V Boys Ice Hockey | CIAC Div II Quarterfinal | Away - Site TBA | TBA | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class M Qualifying Meet | Away - Cheshire Community Pool | 6:45 p.m. | ||
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class M Finals | Away - Wesleyan | 6:00 p.m. | ||
| Tue., 3/12 | V Boys Ice Hockey | Amity | Home - Quinnipiac University-TD Bank Sports Center [Directions] | 8:00 p.m. | W 3-0 | |
| Tue., 3/12 | V Boys Ice Hockey | CIAC Div II Semifinal | Away - Site TBA | TBA | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Mon., 3/18 | V Boys Ice Hockey | East Haven Coop | Home - Quinnipiac University-TD Bank Sports Center [Directions] | 7:00 p.m. | W 6-3 | |
| Mon., 3/18 | V Boys Ice Hockey | CIAC Div II Final | Away - Site TBA | TBA | ||
| Wed., 3/20 | V Boys Lacrosse | Yorktown (NY) (Scrim.) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 5:00 p.m. | ||
| Thu., 3/21 | V Boys Volleyball | Maloney (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 4:30 p.m. | ||
| Fri., 3/22 | V Baseball | Londonberry (NH) (Scrim.) | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 3/22 | FR Boys Lacrosse | Southington (Scrim.) | Home - Cheshire HS-Grass Fields [Directions] | 4:30 p.m. | ||
| Fri., 3/22 | V Softball | Maloney (Scrim.) | Home - Cheshire HS-Softball Diamond [Directions] | 3:30 p.m. | ||
| Fri., 3/22 | JV Softball | Maloney (Scrim.) | Home - Cheshire HS-Softball Diamond 2 [Directions] | 3:30 p.m. | ||
| Sat., 3/23 | V Girls Lacrosse | GIRLS LAX PLAY DAY | Away - Staples HS-Ginny Parker Field | 8:00 a.m. | Cancelled | |
| Sat., 3/23 | V Girls Lacrosse | Staples Jamboree | Away - Not Listed | 10:00 p.m. | ||
| Sun., 3/24 | V Boys Lacrosse | Andover (MA) | Home - Cheshire High Main Game field [Directions] | 12:00 p.m. | ||
| Sun., 3/24 | V Boys Lacrosse | Southington | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Mon., 3/25 | V Boys Volleyball | Bridgeport Central (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 4:45 p.m. | ||
| Mon., 3/25 | V Softball | Woodland (Scrim.) | Home - Cheshire HS-Softball Diamond [Directions] | 3:30 p.m. | ||
| Tue., 3/26 | V Girls Lacrosse | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Tue., 3/26 | JV Girls Lacrosse | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Tue., 3/26 | V Softball | Seymour (Scrim.) | Away - Seymour HS-Softball Diamond [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | V Boys Lacrosse | Darien (Scrim.) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:30 p.m. | ||
| Wed., 3/27 | JV Boys Lacrosse | Darien (Scrim.) | Home - Cheshire HS-Grass Fields [Directions] | Canceled | Cancelled | |
| Wed., 3/27 | V Boys Tennis | Hamden Hall (Scrim.) | Home - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Wed., 3/27 | V Softball | Mercy (Scrim.) | Away - Mercy HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Thu., 3/28 | V Baseball | Cheshire Academy (Scrim.) | Home - Cheshire HS-Baseball Diamond [Directions] | 3:45 p.m. | Cancelled | |
| Thu., 3/28 | V Boys Tennis | Pomperaug (Scrim.) | Home - Cheshire HS-Tennis Courts [Directions] | 3:30 p.m. | Cancelled | |
| Thu., 3/28 | V Boys Volleyball | Hall (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 4:45 p.m. | ||
| Thu., 3/28 | V Girls Lacrosse | Simsbury (Scrim.) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 3/28 | JV Girls Lacrosse | Simsbury (Scrim.) | Home - Cheshire HS-Main Game Field [Directions] | 4:30 p.m. | ||
| Sat., 3/30 | V Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | 1:00 p.m. | W 14-0 | |
| Sat., 3/30 | JV Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | 11:00 a.m. | ||
| Sat., 3/30 | FR Boys Lacrosse | Amity | Away - Amity Regional HS-AHS Grass Field # 3 [Directions] | Postponed | ||
| Sat., 3/30 | V Boys Tennis | North Haven | Home - Cheshire HS-Tennis Courts [Directions] | 1:00 p.m. | W 7-0 [Detailed Results] | |
| Sat., 3/30 | FR Girls Lacrosse | Amity | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 1:00 p.m. | ||
| Mon., 4/1 | V Baseball | Xavier | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | L 7-4 | |
| Mon., 4/1 | FR Baseball | Xavier | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Mon., 4/1 | V Boys Tennis | Shelton | Away - Shelton HS-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/1 | V Girls Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | 5:00 p.m. | W 21-1 | |
| Mon., 4/1 | JV Girls Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | 3:45 p.m. | ||
| Mon., 4/1 | V Softball | Amity | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/1 | JV Softball | Amity | Away - Amity Regional HS-CENTER FIELD [Directions] | 4:15 p.m. | ||
| Mon., 4/1 | V Girls Tennis | Foran | Home - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/2 | V Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | L 14-8 | |
| Tue., 4/2 | JV Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Tue., 4/2 | V Boys Volleyball | Conard | Away - Conard HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 4/2 | JV Boys Volleyball | Conard | Away - Conard HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 4/2 | FR Girls Lacrosse | Daniel Hand | Away - Polson MS, Madison-Polson Front Field/DHHS Campus [Directions] | Postponed | ||
| Thu., 4/4 | JV Baseball | Jonathan Law | Home - Cheshire HS-Baseball Diamond [Directions] | Postponed | ||
| Thu., 4/4 | V Boys Lacrosse | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 6:15 p.m. | W 19-3 | |
| Thu., 4/4 | JV Boys Lacrosse | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 4:30 p.m. | ||
| Thu., 4/4 | V Boys Volleyball | Brookfield | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Thu., 4/4 | JV Boys Volleyball | Brookfield | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Thu., 4/4 | V Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | 5:15 p.m. | W 16-7 | |
| Thu., 4/4 | JV Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 4/4 | FR Girls Lacrosse | East Lyme | Home - Cheshire HS-Bartlem Park [Directions] | 5:00 p.m. | ||
| Fri., 4/5 | V Baseball | Jonathan Law | Away - Jonathan Law HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/5 | FR Boys Lacrosse | Notre Dame-West Haven | Home - Cheshire HS-Grass Fields [Directions] | 4:30 p.m. | ||
| Fri., 4/5 | V Boys Tennis | Trumbull | Home - Cheshire HS-Tennis Courts [Directions] | 3:00 p.m. | L 3-4 [Detailed Results] | |
| Fri., 4/5 | V Boys Volleyball | Xavier | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Fri., 4/5 | JV Boys Volleyball | Xavier | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 4/5 | V Girls Lacrosse | Wilton | Home - Cheshire HS-Main Game Field [Directions] | 6:00 p.m. | ||
| Fri., 4/5 | JV Girls Lacrosse | Wilton | Home - Cheshire HS-Main Game Field [Directions] | Postponed | ||
| Fri., 4/5 | V Girls Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Sat., 4/6 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 1:00 p.m. | ||
| Sat., 4/6 | JV Baseball | Ridgefield | Home - Cheshire HS-Baseball Diamond [Directions] | 1:00 p.m. | ||
| Sat., 4/6 | FR Baseball | Ridgefield | Away - Playground Field [Directions] | 1:00 p.m. | ||
| Sat., 4/6 | V Boys Lacrosse | LaSalle Academy (RI) | Away - La Salle Academy-Cimini Stadium | 1:00 p.m. | W 14-13 | |
| Sat., 4/6 | JV Boys Lacrosse | LaSalle Academy (RI) | Away - La Salle Academy-Cimini Stadium | 11:00 a.m. | ||
| Sat., 4/6 | V Softball | Fairfield Warde | Home - Cheshire HS-Softball Diamond [Directions] | 1:00 p.m. | ||
| Mon., 4/8 | V Baseball | West Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/8 | V Boys Tennis | Guilford | Home - Cheshire HS-Tennis Courts [Directions] | 11:00 a.m. | W 5-2 [Detailed Results] | |
| Mon., 4/8 | V Girls Lacrosse | Sacred Heart Academy | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | ||
| Mon., 4/8 | JV Girls Lacrosse | Sacred Heart Academy | Home - Cheshire HS-Main Game Field [Directions] | 4:30 p.m. | ||
| Mon., 4/8 | V Softball | Career Magnet | Home - Cheshire HS-Softball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/8 | JV Softball | Career Magnet | Home - Cheshire HS-Softball Diamond 2 [Directions] | Canceled | Cancelled | |
| Mon., 4/8 | V Girls Tennis | Shelton | Away - Shelton HS-Tennis Courts [Directions] | 11:00 a.m. | W 6-1 | |
| Tue., 4/9 | JV Baseball | West Haven | Away - West Haven HS-Whitey Piurek Field [Directions] | 4:30 p.m. | ||
| Tue., 4/9 | V Boys Lacrosse | Notre Dame-West Haven | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:30 p.m. | W 17-10 | |
| Tue., 4/9 | JV Boys Lacrosse | Notre Dame-West Haven | Home - Cheshire HS-Main Game Field [Directions] | 4:30 p.m. | ||
| Tue., 4/9 | V Boys Volleyball | Darien | Home - Cheshire HS-Gym West [Directions] | 4:30 p.m. | ||
| Tue., 4/9 | JV Boys Volleyball | Darien | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | ||
| Wed., 4/10 | V Baseball | Notre Dame-West Haven | Away - Quigley Stadium-Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 4/10 | FR Baseball | Notre Dame-West Haven | Away - Painter Park-Harry Noyes Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 4/10 | V Boys Outdoor Track | Amity, Fairfield Prep | Away - Amity Regional HS-Amity HS Track [Directions] | 3:45 p.m. | ||
| Wed., 4/10 | JV Boys Outdoor Track | Amity, Fairfield Prep | Away - Amity Regional HS-Amity HS Track [Directions] | 3:45 p.m. | ||
| Wed., 4/10 | V Boys Tennis | Lyman Hall | Home - Cheshire HS-Tennis Courts [Directions] | 1:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/10 | V Girls Lacrosse | Amity | Home - Cheshire HS-Main Game Field [Directions] | 6:00 p.m. | ||
| Wed., 4/10 | JV Girls Lacrosse | Amity | Home - Cheshire HS-Main Game Field [Directions] | 4:30 p.m. | ||
| Wed., 4/10 | V Girls Outdoor Track | Amity, Lauralton Hall | Away - Amity Regional HS-Amity HS Track [Directions] | 3:45 p.m. | ||
| Wed., 4/10 | V Softball | Jonathan Law | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Wed., 4/10 | JV Softball | Jonathan Law | Home - Cheshire HS-Softball Diamond 2 [Directions] | Postponed | ||
| Fri., 4/12 | V Boys Volleyball | Southington | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Fri., 4/12 | JV Boys Volleyball | Southington | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 4/12 | V Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 6:00 p.m. | ||
| Fri., 4/12 | JV Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:30 p.m. | ||
| Fri., 4/12 | JV Softball | Masuk | Home - Cheshire HS-Softball Diamond 2 [Directions] | Canceled | Cancelled | |
| Sat., 4/13 | JV Baseball | Sheehan | Home - Cheshire HS-Baseball Diamond [Directions] | 2:00 p.m. | ||
| Sat., 4/13 | V Boys Lacrosse | Stepinac (NY) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 1:00 p.m. | W 17-9 | |
| Sat., 4/13 | JV Boys Lacrosse | Stepinac (NY) | Home - Cheshire HS-Grass Fields [Directions] | 11:00 a.m. | ||
| Sat., 4/13 | V Boys Outdoor Track | YMCA Meet | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 10:00 a.m. | ||
| Sat., 4/13 | V Girls Outdoor Track | YMCA Meet | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 10:00 a.m. | ||
| Sat., 4/13 | V Softball | Masuk | Home - Cheshire HS-Softball Diamond [Directions] | 2:00 p.m. | ||
| Sat., 4/13 | JV Softball | Maloney | Away - North End Field [Directions] | 11:00 a.m. | ||
| Sat., 4/13 | JV Softball | Fairfield Warde | Home - Cheshire HS-Softball Diamond 2 [Directions] | Postponed | ||
| Mon., 4/15 | FR Baseball | Cheshire Academy | Home - Cheshire HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/15 | FR Boys Lacrosse | Guilford | Away - Guilford HS-Maturo Field [Directions] | 3:45 p.m. | ||
| Mon., 4/15 | JV Boys Volleyball | Platt | Away - Platt HS-Gym [Directions] | 5:00 p.m. | ||
| Mon., 4/15 | V Girls Golf | Lauralton Hall | Home - Southington Country Club [Directions] | 2:30 p.m. | ||
| Mon., 4/15 | V Girls Lacrosse | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 4/15 | V Softball | West Haven | Away - West Haven HS-Frank Biondi Softball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/15 | V Girls Tennis | Guilford | Home - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 4/16 | V Baseball | Sheehan | Away - Sheehan HS-Neubauer Baseball Field @ Sheehan HS [Directions] | 3:45 p.m. | ||
| Tue., 4/16 | FR Baseball | Sheehan | Away - West Side Field [Directions] | 3:45 p.m. | ||
| Tue., 4/16 | V Boys Tennis | Xavier | Away - Wesleyan University-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Tue., 4/16 | FR Girls Lacrosse | Hall | Home - Cheshire HS-Bartlem Park [Directions] | 5:30 p.m. | ||
| Tue., 4/16 | JV Softball | West Haven | Away - West Haven HS-Frank Biondi Field [Directions] | 4:30 p.m. | ||
| Wed., 4/17 | V Baseball | East Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Boys Golf | Xavier | Away - Portland Golf Course [Directions] | 2:30 p.m. | ||
| Wed., 4/17 | FR Boys Lacrosse | Trumbull | Home - Cheshire HS-Grass Fields [Directions] | 4:30 p.m. | ||
| Wed., 4/17 | JV Boys Outdoor Track | Quinnipiac Outdoor Track Classic | Away - Hamden HS-HHS Turf #1 | 3:45 p.m. | ||
| Wed., 4/17 | V Boys Tennis | Notre Dame-West Haven | Away - U New Haven-UNH Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 4/17 | V Boys Volleyball | New Milford | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Wed., 4/17 | JV Boys Volleyball | New Milford | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Wed., 4/17 | V Girls Golf | St. Paul Catholic | Away - Westwoods Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 4/17 | JV Girls Lacrosse | Sheehan | Home - Cheshire HS-Bartlem Park [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Girls Outdoor Track | Quinnipiac Outdoor Track Classic | Away - Hamden HS-HHS Turf #1 | 3:45 p.m. | ||
| Wed., 4/17 | V Softball | Guilford | Away - Guilford HS-Varsity softball field [Directions] | 4:15 p.m. | ||
| Wed., 4/17 | V Girls Tennis | Branford | Home - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | W 6-0 | |
| Thu., 4/18 | V Boys Golf | Branford, Portland | Home - Farms Country club [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Thu., 4/18 | V Boys Lacrosse | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 6:00 p.m. | ||
| Thu., 4/18 | JV Boys Lacrosse | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 4:30 p.m. | ||
| Thu., 4/18 | V Boys Outdoor Track | Wilbur Cross, East Haven | Away - Wilbur Cross HS-Wilbur Cross Athletic Complex [Directions] | 4:00 p.m. | ||
| Thu., 4/18 | V Girls Outdoor Track | Wilbur Cross, East Haven | Away - Wilbur Cross HS-Wilbur Cross Athletic Complex [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | V Baseball | Lyman Hall | Away - Pat Wall Field-Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 4/19 | V Boys Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Fri., 4/19 | JV Boys Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 4/19 | V Girls Lacrosse | Conard | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | ||
| Fri., 4/19 | JV Girls Lacrosse | Conard | Home - Cheshire HS-Bartlem Park [Directions] | 4:30 p.m. | ||
| Fri., 4/19 | V Softball | Sacred Heart Academy | Home - Cheshire HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | V Girls Tennis | Lauralton Hall | Away - Eisenhower Park-Eisenhower [Directions] | 3:45 p.m. | W 4-3 | |
| Sat., 4/20 | JV Baseball | Cheshire Academy | Home - Cheshire HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Sat., 4/20 | V Boys Lacrosse | Glastonbury | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 1:00 p.m. | ||
| Sat., 4/20 | JV Boys Lacrosse | Glastonbury | Home - Cheshire HS-Main Game Field [Directions] | 11:00 a.m. | ||
| Sat., 4/20 | V Boys Tennis | Fairfield Prep | Home - Cheshire HS-Tennis Courts [Directions] | 1:00 p.m. | ||
| Sat., 4/20 | V Girls Outdoor Track | Monogovan Girls Invitational - Bethel HS | Away - Not Listed | 9:00 a.m. | ||
| Sat., 4/20 | JV Softball | Guilford | Away - Guilford HS-Varsity softball field [Directions] | 11:00 a.m. | ||
| Sat., 4/20 | JV Softball | West Haven | Home - Guilford HS-JV softball field [Directions] | 12:30 p.m. | ||
| Mon., 4/22 | V Baseball | Guilford | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | FR Baseball | Guilford | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 5/10 | ||||||
| Mon., 4/22 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | V Boys Tennis | North Haven | Away - North Haven Athletic Complex-Tennis Courts [Directions] | 3:45 p.m. | ||
| Mon., 4/22 | V Boys Volleyball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:15 p.m. | ||||||
| Mon., 4/22 | JV Boys Volleyball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | V Girls Golf | Newington, Wethersfield | Away - Indian Hill Country Club [Directions] | 3:00 p.m. | ||
| Mon., 4/22 | V Girls Lacrosse | Sheehan | Home - Cheshire HS-Main Game Field [Directions] | 3:30 p.m. | ||
| Mon., 4/22 | JV Girls Lacrosse | Sheehan | Home - Cheshire HS-Bartlem Park [Directions] | Postponed | ||
| Mon., 4/22 | V Softball | Amity | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Mon., 4/22 | JV Softball | Amity | Home - Cheshire HS-Softball Diamond 2 [Directions] | 4:15 p.m. | ||
| Mon., 4/22 | V Girls Tennis | Daniel Hand | Away - Polson MS, Madison-Polson Tennis Courts/DHHS Campus [Directions] | 3:45 p.m. | W 4-3 | |
| Tue., 4/23 | JV Baseball | Guilford | Away - Guilford HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Golf | Amity | Home - Farms Country club [Directions] | 2:15 p.m. | ||
| Tue., 4/23 | V Boys Lacrosse | Guilford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:30 p.m. | ||
| Tue., 4/23 | JV Boys Lacrosse | Guilford | Home - Cheshire HS-Grass Fields [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Branford | Home - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 4/24 | V Baseball | Xavier | Away - Palmer Field-Baseball Diamond [Directions] | 7:00 p.m. | ||
| Wed., 4/24 | FR Baseball | Xavier | Away - Xavier HS-Richard Magner Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Boys Golf | Guilford | Away - Madison Country Club [Directions] | 2:15 p.m. | ||
| Wed., 4/24 | V Boys Outdoor Track | Lyman Hall, Shelton | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Wed., 4/24 | V Boys Tennis | Shelton | Home - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 4/24 | V Boys Volleyball | Xavier | Away - Xavier HS-Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | JV Boys Volleyball | Xavier | Away - Xavier HS-Gym [Directions] | 5:00 p.m. | ||
| Wed., 4/24 | V Girls Outdoor Track | Lyman Hall, Shelton | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Wed., 4/24 | V Softball | Wilbur Cross | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Thu., 4/25 | JV Baseball | Xavier | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Golf | Notre Dame-West Haven | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Thu., 4/25 | FR Boys Lacrosse | Daniel Hand | Away - Daniel Hand HS-Janssen Field #2/DHHS Campus [Directions] | 4:30 p.m. | ||
| Thu., 4/25 | V Boys Volleyball | Masuk | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Thu., 4/25 | JV Boys Volleyball | Masuk | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Thu., 4/25 | V Girls Golf | Berlin | Home - Southington Country Club [Directions] | 2:30 p.m. | ||
| Thu., 4/25 | V Girls Lacrosse | Glastonbury | Home - Cheshire HS-Main Game Field [Directions] | 6:00 p.m. | ||
| Thu., 4/25 | JV Girls Lacrosse | Glastonbury | Home - Cheshire HS-Bartlem Park [Directions] | 4:30 p.m. | ||
| Thu., 4/25 | FR Girls Lacrosse | Conard | Away - Conard HS-North Field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Softball | Southington | Away - Southington HS-1 Softball Varsity Field [Directions] | 4:30 p.m. | ||
| Thu., 4/25 | JV Softball | Southington | Away - Southington HS-9 Softball JV Field [Directions] | Postponed | ||
| Fri., 4/26 | V Baseball | Jonathan Law | Home - Cheshire HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Fri., 4/26 | FR Baseball | Jonathan Law | Home - Bartlem Park [Directions] | Canceled | Cancelled | |
| Fri., 4/26 | V Boys Tennis | Xavier | Home - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 4/26 | V Softball | Career Magnet | Away - East Shore Athletic Complex-Softball Field 2 [Directions] | 3:45 p.m. | ||
| Fri., 4/26 | JV Softball | North Haven | Away - North Haven MS-North Haven Middle School Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 4/27 | JV Baseball | Jonathan Law | Away - Jonathan Law HS-Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | FR Baseball | St. Paul Catholic | Home - Cheshire HS-Baseball Diamond [Directions] | 10:30 a.m. | ||
| Sat., 4/27 | V Boys Lacrosse | Simsbury | Away - Holden Field-Turf [Directions] | 12:00 p.m. | ||
| Sat., 4/27 | JV Boys Lacrosse | Simsbury | Away - Simsbury HS-Simsbury Grass Field [Directions] | 10:00 a.m. | ||
| Mon., 4/29 | V Baseball | Southington | Away - Southington HS-4 Baseball Varsity Field [Directions] | 6:00 p.m. | ||
| Mon., 4/29 | FR Baseball | North Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Boys Golf | Cromwell, Shelton | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Mon., 4/29 | FR Boys Lacrosse | Conard | Away - Conard HS-North Field [Directions] | 5:15 p.m. | ||
| Mon., 4/29 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 6:00 p.m. | ||
| Mon., 4/29 | JV Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | V Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 6:00 p.m. | ||
| Mon., 4/29 | JV Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | FR Girls Lacrosse | Amity | Away - Amity Regional HS-AHS Grass Field # 3 [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | V Softball | Jonathan Law | Away - Jonathan Law HS-Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Girls Tennis | Amity | Home - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | L 4-3 | |
| Tue., 4/30 | JV Baseball | Southington | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Lacrosse | Daniel Hand | Home - Cheshire HS-Main Game Field [Directions] | 6:30 p.m. | ||
| Tue., 4/30 | JV Boys Lacrosse | Daniel Hand | Home - Cheshire HS-Grass Fields [Directions] | 4:30 p.m. | ||
| Tue., 4/30 | V Girls Golf | Amity | Away - Race Brook C.C. [Directions] | 3:15 p.m. | ||
| Tue., 4/30 | FR Girls Lacrosse | North Haven | Home - Cheshire HS-Bartlem Park [Directions] | 4:30 p.m. | ||
| Tue., 4/30 | V Girls Tennis | Foran | Away - Foran HS -Richard A. Herman Memorial Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/1 | V Baseball | West Haven | Away - West Haven HS-Whitey Piurek Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | JV Baseball | Fairfield Prep | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Baseball | Fairfield Prep | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Boys Golf | Notre Dame-West Haven | Away - Race Brook C.C. [Directions] | 2:00 p.m. | ||
| Wed., 5/1 | FR Boys Lacrosse | Amity | Home - Cheshire HS-Grass Fields [Directions] | Canceled | Cancelled | |
| Wed., 5/1 | V Boys Outdoor Track | Guilford, Daniel Hand | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Boys Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | V Boys Volleyball | Kolbe Cathedral | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Wed., 5/1 | JV Boys Volleyball | Kolbe Cathedral | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Wed., 5/1 | V Girls Outdoor Track | Guilford, Daniel Hand | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Softball | Daniel Hand | Away - Polson MS, Madison-DHHS SB Turf [Directions] | 4:15 p.m. | ||
| Thu., 5/2 | JV Baseball | West Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Golf | Daniel Hand | Away - Madison Country Club [Directions] | 2:30 p.m. | ||
| Thu., 5/2 | V Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 7:00 p.m. | ||
| Thu., 5/2 | JV Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Barlow Field [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Girls Golf | Berlin, Plainville | Away - Timberlin Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/2 | V Girls Lacrosse | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 6:30 p.m. | ||
| Thu., 5/2 | JV Girls Lacrosse | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 5/2 | FR Girls Lacrosse | North Haven | Away - North Haven MS-West Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 5/2 | JV Softball | North Haven | Home - Cheshire HS-Softball Diamond 2 [Directions] | 4:15 p.m. | ||
| Fri., 5/3 | V Baseball | Notre Dame-West Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | FR Baseball | Notre Dame-West Haven | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | FR Boys Lacrosse | Guilford | Home - Cheshire HS-Grass Fields [Directions] | 4:30 p.m. | ||
| Fri., 5/3 | V Boys Outdoor Track | Middletown Invitational - Middletown HS (JV) | Away - Not Listed | 3:30 p.m. | ||
| Fri., 5/3 | V Boys Tennis | Lyman Hall | Away - Doolittle Park-Doolittle Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 5/3 | V Boys Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | V Girls Outdoor Track | Middletown Invitational - Middletown HS (Fresh/Soph) | Away - Not Listed | 3:30 p.m. | ||
| Fri., 5/3 | JV Softball | Jonathan Law | Away - Jonathan Law HS-Softball Field [Directions] | 4:15 p.m. | ||
| Fri., 5/3 | V Girls Tennis | Shelton | Home - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Sat., 5/4 | JV Baseball | Notre Dame-West Haven | Away - Quigley Stadium-Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 5/4 | V Boys Outdoor Track | Middletown Invitational - Middletown HS | Away - Not Listed | 12:00 p.m. | ||
| Sat., 5/4 | V Girls Outdoor Track | Middletown Invitational - Varsity | Away - Not Listed | 12:00 p.m. | ||
| Sat., 5/4 | JV Softball | Woodland | Home - Derby HS-Payden Park [Directions] | 1:00 p.m. | ||
| Mon., 5/6 | V Baseball | Sheehan | Home - University of Connecticut - Elliott Ballpark-Elliot Ballpark [Directions] | 5:00 p.m. | ||
| Mon., 5/6 | FR Baseball | Sheehan | Home - Bartlem Park [Directions] | Postponed | ||
| Mon., 5/6 | V Boys Golf | Hamden | Away - Laurel View Golf Course [Directions] | 2:30 p.m. | ||
| Mon., 5/6 | FR Boys Lacrosse | Notre Dame-West Haven | Away - Notre Dame HS-Veteran's Stadium [Directions] | 3:45 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Branford | Away - Branford HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Mon., 5/6 | V Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 6:00 p.m. | ||
| Mon., 5/6 | JV Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 5/6 | V Girls Golf | 2024 CIAC Spring Girls Classic | Away - [CIAC] Grassy Hills Country Club | 3:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-[CIAC] Grassy Hills Country Club | ||||||
| Mon., 5/6 | V Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 6:00 p.m. | ||
| Mon., 5/6 | JV Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 4:30 p.m. | ||
| Mon., 5/6 | FR Girls Lacrosse | Glastonbury | Away - Glastonbury HS-Field 13 [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | West Haven | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Mon., 5/6 | JV Softball | West Haven | Home - Cheshire HS-Softball Diamond 2 [Directions] | 4:15 p.m. | ||
| Mon., 5/6 | V Girls Tennis | Daniel Hand | Home - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Baseball | Holy Cross | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Baseball | Sheehan | Away - Sheehan HS-Neubauer Baseball Field @ Sheehan HS [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Boys Golf | Branford | Away - Pine Orchard Country Club [Directions] | 3:00 p.m. | ||
| Tue., 5/7 | V Boys Lacrosse | Iona Prep (NY) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 7:00 p.m. | ||
| Tue., 5/7 | JV Boys Lacrosse | Iona Prep (NY) | Home - Cheshire HS-Grass Fields [Directions] | 5:00 p.m. | ||
| Tue., 5/7 | V Boys Tennis | Amity | Home - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | FR Baseball | St. Paul Catholic | Away - St. Paul Catholic HS -St. Paul Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | V Boys Outdoor Track | Sheehan | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | V Boys Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Wed., 5/8 | JV Boys Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Wed., 5/8 | V Girls Golf | Mercy | Away - Lyman Orchards -Jones Course [Directions] | 2:25 p.m. | ||
| Wed., 5/8 | JV Girls Lacrosse | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Girls Outdoor Track | Sheehan | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | V Softball | Guilford | Away - Cheshire HS-Softball Diamond [Directions] | 3:00 p.m. | ||
| Wed., 5/8 | V Softball | Guilford | Home - Cheshire HS-Softball Diamond [Directions] | 4:45 p.m. | ||
| Wed., 5/8 | JV Softball | Guilford | Home - Cheshire HS-Softball Diamond 2 [Directions] | 5:30 p.m. | ||
| Wed., 5/8 | V Girls Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Thu., 5/9 | JV Baseball | Xavier | Away - Xavier HS-Richard Magner Field [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Boys Golf | Guilford | Home - Farms Country club [Directions] | 2:15 p.m. | ||
| Thu., 5/9 | V Girls Golf | Newington | Home - Southington Country Club [Directions] | 2:30 p.m. | ||
| Thu., 5/9 | V Girls Lacrosse | Staples | Home - Cheshire HS-Main Game Field [Directions] | 6:00 p.m. | ||
| Thu., 5/9 | JV Girls Lacrosse | Staples | Home - Cheshire HS-Bartlem Park [Directions] | 4:30 p.m. | ||
| Thu., 5/9 | FR Girls Lacrosse | Sheehan | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | JV Softball | Foran | Home - Cheshire HS-Softball Diamond 2 [Directions] | 4:15 p.m. | ||
| Fri., 5/10 | V Baseball | East Haven | Away - East Haven HS-Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Boys Lacrosse | Mahwah (NJ) | Away - Mahwah HS | 6:30 p.m. | ||
| Fri., 5/10 | JV Boys Lacrosse | Mahwah (NJ) | Away - Mahwah HS-Stadium Turf | 4:30 p.m. | ||
| Fri., 5/10 | V Boys Tennis | Fairfield Prep | Away - Fairfield University-Walsh Athletic Center - Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 5/10 | V Boys Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 6:00 p.m. | ||
| Fri., 5/10 | JV Boys Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 5/10 | FR Girls Lacrosse | Conard | Home - Cheshire HS-Bartlem Park [Directions] | 5:00 p.m. | ||
| Fri., 5/10 | V Softball | Sheehan | Home - [CIAC] Burrill Family Field at UConn Softball Comp-[CIAC] Burrill Family Field at UConn [Directions] | 5:30 p.m. | ||
| Fri., 5/10 | V Girls Tennis | Branford | Away - Branford HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Sat., 5/11 | JV Baseball | East Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 10:30 a.m. | ||
| Mon., 5/13 | V Baseball | Lyman Hall | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | FR Baseball | North Haven | Away - North Haven MS-Bailey Road Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 5/13 | FR Boys Lacrosse | Daniel Hand | Home - Cheshire HS-Main Game Field [Directions] | 4:30 p.m. | ||
| Mon., 5/13 | V Boys Volleyball | Bunnell | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Mon., 5/13 | JV Boys Volleyball | Bunnell | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Mon., 5/13 | V Girls Golf | St. Paul Catholic, Suffield | Home - Southington Country Club [Directions] | 2:30 p.m. | ||
| Mon., 5/13 | V Girls Lacrosse | Farmington | Home - Cheshire HS-Main Game Field [Directions] | 6:00 p.m. | ||
| Mon., 5/13 | JV Girls Lacrosse | Farmington | Home - Cheshire HS-Bartlem Park [Directions] | 4:30 p.m. | ||
| Mon., 5/13 | FR Girls Lacrosse | East Lyme | Away - East Lyme HS-Back Field Hockey Field [Directions] | 4:30 p.m. | ||
| Mon., 5/13 | V Girls Outdoor Track | SCC East Division Championship | Away - Not Listed | TBA | ||
| Mon., 5/13 | V Softball | Sacred Heart Academy | Away - Sacred Heart Academy-Softball Diamond [Directions] | 4:15 p.m. | ||
| Mon., 5/13 | V Girls Tennis | Lauralton Hall | Home - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 5/14 | JV Baseball | Lyman Hall | Away - Pat Wall Field-Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 5/14 | V Boys Golf | Shelton | Away - Brownson Country Club [Directions] | 2:45 p.m. | ||
| Tue., 5/14 | V Boys Lacrosse | North Haven | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:30 p.m. | ||
| Tue., 5/14 | JV Boys Lacrosse | North Haven | Home - Cheshire HS-Grass Fields [Directions] | 4:30 p.m. | ||
| Tue., 5/14 | V Boys Outdoor Track | SCC East Sectional | Away - Not Listed | TBA | ||
| Tue., 5/14 | V Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 5/14 | JV Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | JV Boys Volleyball | Platt | Home - Cheshire HS-Gym West [Directions] | Postponed | ||
| Tue., 5/14 | V Softball | Wilbur Cross | Away - Blake Field - New Haven-Blake Field 1 [Directions] | 3:45 p.m. | ||
| Tue., 5/14 | JV Softball | Southington | Home - Cheshire HS-Softball Diamond [Directions] | 4:30 p.m. | ||
| Wed., 5/15 | V Baseball | Guilford | Away - Guilford HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | FR Baseball | Guilford | Away - Long Hill Park-Guilford-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Boys Golf | North Haven | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Wed., 5/15 | FR Boys Lacrosse | Fairfield Prep | Home - Cheshire HS-Grass Fields [Directions] | 4:30 p.m. | ||
| Wed., 5/15 | V Boys Tennis | Notre Dame-West Haven | Home - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/15 | V Girls Golf | Daniel Hand | Away - Madison Country Club [Directions] | 2:30 p.m. | ||
| Wed., 5/15 | V Girls Lacrosse | Mercy | Home - Cheshire HS-Main Game Field [Directions] | 6:00 p.m. | ||
| Wed., 5/15 | JV Girls Lacrosse | Mercy | Home - Cheshire HS-Main Game Field [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Boys Lacrosse | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 7:00 p.m. | ||
| Thu., 5/16 | JV Boys Lacrosse | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 5:15 p.m. | ||
| Thu., 5/16 | V Boys Outdoor Track | SCC BOYS NOVICE | Away - Daniel Hand HS-DHHS Track | 3:45 p.m. | ||
| Thu., 5/16 | V Girls Golf | Amity | Home - Southington Country Club [Directions] | 2:30 p.m. | ||
| Thu., 5/16 | FR Girls Lacrosse | Daniel Hand | Home - Cheshire HS-Bartlem Park [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Softball | Daniel Hand | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Thu., 5/16 | JV Softball | Daniel Hand | Home - Cheshire HS-Softball Diamond 2 [Directions] | 4:15 p.m. | ||
| Fri., 5/17 | FR Boys Lacrosse | Joel Barlow | Home - Cheshire HS-Grass Fields [Directions] | 4:30 p.m. | ||
| Fri., 5/17 | V Boys Outdoor Track | SCC Novice Championship - Hamden High School | Away - Not Listed | TBA | ||
| Fri., 5/17 | V Boys Volleyball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Fri., 5/17 | V Girls Outdoor Track | SCC Girls Novice Meet | Away - Hamden HS-HHS Turf #1 | 3:45 p.m. | ||
| Fri., 5/17 | V Girls Outdoor Track | SCC Girls Novice - Hamden High School | Away - Not Listed | TBA | ||
| Sat., 5/18 | V Baseball | Daniel Hand | Home - Cheshire HS-Baseball Diamond [Directions] | 1:00 p.m. | ||
| Sat., 5/18 | JV Baseball | Amity | Away - Old Tavern Road Complex-Brinley Field [Directions] | 1:00 p.m. | ||
| Sat., 5/18 | FR Baseball | Daniel Hand | Home - Cheshire HS-Baseball Diamond [Directions] | 9:00 a.m. | ||
| Mon., 5/20 | JV Baseball | Notre Dame-West Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/20 | V Boys Volleyball | South Windsor | Away - South Windsor HS-Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/20 | JV Boys Volleyball | South Windsor | Away - South Windsor HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 5/21 | V Boys Golf | Foran | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Tue., 5/21 | V Boys Outdoor Track | SCC Championship - Amity High School | Away - Not Listed | TBA | ||
| Tue., 5/21 | V Girls Golf | Lauralton Hall | Away - Lauralton Hall-Oronoque CC [Directions] | 2:30 p.m. | ||
| Tue., 5/21 | V Girls Outdoor Track | SCC Varsity Championship - Amity High School | Away - Not Listed | TBA | ||
| Wed., 5/22 | V Boys Golf | Hamden | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Wed., 5/22 | V Boys Tennis | Daniel Hand (Scrim.) | Away - Polson MS, Madison-Polson Tennis Courts/DHHS Campus [Directions] | 3:45 p.m. | ||
| Wed., 5/22 | V Girls Golf | Mercy | Home - Southington Country Club [Directions] | 2:30 p.m. | ||
| Wed., 5/22 | V Girls Outdoor Track | Last Chance Meet - Cheshire or Lyman Hall | Away - Not Listed | TBA | ||
| Thu., 5/23 | V Boys Golf | Sheehan | Home - Farms Country club [Directions] | 2:15 p.m. | ||
| Thu., 5/23 | V Girls Golf | Glastonbury | Home - Southington Country Club [Directions] | 2:30 p.m. | ||
| Tue., 5/28 | V Girls Golf | Daniel Hand | Home - Southington Country Club [Directions] | 2:30 p.m. | ||
| Thu., 5/30 | V Boys Outdoor Track | Class L State Championship - Willowbrook Park, New Britain | Away - Not Listed | 3:00 p.m. | ||
| Thu., 5/30 | V Girls Outdoor Track | Class L Championship - Willowbrook Park, New Britain | Away - Not Listed | 3:00 p.m. | ||
| Mon., 6/3 | V Boys Outdoor Track | State Open Championship | Away - Not Listed | 1:30 p.m. | ||
| Mon., 6/3 | V Girls Outdoor Track | State Open - Willowbrook Park, New Britain | Away - Not Listed | 1:30 p.m. | ||