| Cheshire 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 897 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/25 | V Football | Darien (Scrim.) | Away - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 8/27, Time to 6:00 p.m. | ||||||
| Tue., 8/31 | V Boys Soccer | Glastonbury (Scrim.) | Away - Glastonbury HS-Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 8/31 | V Field Hockey | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 4:30 p.m. | ||
| Tue., 8/31 | V Girls Soccer | Pomperaug (Scrim.) | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 3-2 | |
| Wed., 9/1 | V Field Hockey | Newtown (Scrim.) | Home - Cheshire High Main Game field [Directions] | Canceled | Cancelled | |
| Thu., 9/2 | V Football | Windsor (Scrim.) | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 9/2 | V Boys Soccer | Naugatuck (Scrim.) | Away - Naugatuck HS-Veterans Field [Directions] | 3:30 p.m. | ||
| Thu., 9/2 | V Girls Soccer | Woodland (Scrim.) | Away - Woodland HS-Woodland Soccer Field [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 9/3 | V Boys Cross Country | Simsbury (Scrim.) | Away - Stratton Brook State Park [Directions] | 4:00 p.m. | ||
| Fri., 9/3 | V Girls Cross Country | Simsbury (Scrim.) | Away - Stratton Brook State Park [Directions] | 3:00 p.m. | ||
| Sat., 9/4 | V Boys Soccer | Pomperaug (Scrim.) | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Sat., 9/4 | JV Boys Soccer | Pomperaug (Scrim.) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:00 p.m. | ||
| Sat., 9/4 | V Field Hockey | Avon Pre Season Jamboree | Away - Avon HS-Turf Field | 7:00 a.m. | ||
| Sat., 9/4 | V Girls Soccer | Southington (Scrim.) | Away - Southington HS-TURF FIELD [Directions] | 10:30 a.m. | W 5-1 | |
| Sat., 9/4 | JV Girls Soccer | Southington (Scrim.) | Away - Southington HS-Soccer/Lacrosse [Directions] | 10:30 a.m. | ||
| Mon., 9/6 | V Boys Soccer | Southington (Scrim.) | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Thu., 9/9 | FR Football | Notre Dame-West Haven | Away - Veterans Field [Directions] | 3:45 p.m. | ||
| Thu., 9/9 | V Field Hockey | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 9/9 | JV Field Hockey | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | 5:15 p.m. | W 70 | |
| Thu., 9/9 | V Girls Soccer | Guilford | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 2-0 | |
| Thu., 9/9 | V Girls Volleyball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Thu., 9/9 | JV Girls Volleyball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Fri., 9/10 | V Football | Notre Dame-West Haven | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | W 26-20 (OT) | |
| Fri., 9/10 | JV Girls Soccer | Guilford | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Sat., 9/11 | JV Football | Notre Dame-West Haven | Away - Veterans Field [Directions] | 10:00 a.m. | ||
| Sat., 9/11 | FR Boys Soccer | Amity | Away - Amity Regional HS-Amity High School - Field # 2 [Directions] | 10:00 a.m. | ||
| Sat., 9/11 | FR Girls Soccer | Guilford | Away - Long Hill Park-Guilford-Soccer Field (Front) [Directions] | 10:30 a.m. | ||
| Mon., 9/13 | JV Boys Soccer | Lyman Hall | Away - Lyman Hall HS-Lyman Hall Field #1 [Directions] | 3:45 p.m. | ||
| Mon., 9/13 | FR Field Hockey | Sacred Heart Academy | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 4:00 p.m. | W 3-2 | |
| Tue., 9/14 | V Boys Soccer | Xavier | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | L 1-2 | |
| Tue., 9/14 | V Girls Soccer | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 7:00 p.m. | W 2-0 | |
| Tue., 9/14 | JV Girls Soccer | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 5:15 p.m. | ||
| Tue., 9/14 | V Girls Swimming and Diving | Foran | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Cheshire - 99 Foran- 81 | |
| Tue., 9/14 | V Girls Volleyball | Maloney | Away - Maloney HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/14 | JV Girls Volleyball | Maloney | Away - Maloney HS-Gym [Directions] | 5:00 p.m. | L 2-3 | |
| Wed., 9/15 | V Boys Cross Country | Xavier, Guilford, North Haven | Away - Mercy HS-Cross Country Course [Directions] | 3:45 p.m. | ||
| Wed., 9/15 | JV Boys Soccer | Xavier | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Wed., 9/15 | V Girls Cross Country | Mercy, Guilford, North Haven | Away - Mercy HS-Cross Country Course [Directions] | 3:45 p.m. | ||
| Wed., 9/15 | V Girls Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Wed., 9/15 | JV Girls Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | L 2-3 | |
| Thu., 9/16 | FR Football | North Haven | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Fri., 9/17 | V Football | North Haven | Away - North Haven MS-Vanacore Field [Directions] | 7:00 p.m. | W 28-0 | |
| Fri., 9/17 | V Boys Soccer | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | 3:45 p.m. | W 5-3 | |
| Fri., 9/17 | V Field Hockey | Guilford | Away - Guilford HS-New Turf field at GHS [Directions] | 3:45 p.m. | L 3-1 | |
| Fri., 9/17 | JV Field Hockey | Guilford | Away - Guilford HS-New Turf field at GHS [Directions] | 5:15 p.m. | W 2-1 | |
| Fri., 9/17 | V Girls Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 9/17 | V Girls Swimming and Diving | Branford | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | ||
| Fri., 9/17 | V Girls Volleyball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 9/17 | JV Girls Volleyball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 9/18 | V Boys Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/18 | JV Football | North Haven | Home - Cheshire High Main Game field [Directions] | 10:30 a.m. | ||
| Sat., 9/18 | FR Boys Soccer | Fairfield Prep | Home - Cheshire HS-Cheshire High School soccer field [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | V Girls Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Mon., 9/20 | V Boys Soccer | East Haven | Away - East Haven HS-EHHS Turf Field & Track [Directions] | 5:00 p.m. | W 5-0 | |
| Mon., 9/20 | V Girls Volleyball | Career Magnet | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Mon., 9/20 | JV Girls Volleyball | Career Magnet | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Tue., 9/21 | V Boys Cross Country | Jonathan Law, West Haven, Wilbur Cross | Home - Cheshire Park-Field 1 [Directions] | 5:00 p.m. | ||
| Tue., 9/21 | JV Boys Soccer | East Haven | Away - East Haven HS-Grass Soccer FIeld [Directions] | Canceled | Cancelled | |
| Tue., 9/21 | V Girls Cross Country | Jonathan Law, West Haven, Wilbur Cross | Home - Cheshire Park-Field 1 [Directions] | 5:00 p.m. | ||
| Tue., 9/21 | V Field Hockey | Mercy | Away - Mercy HS-Field Hockey Field [Directions] | 3:45 p.m. | W 3-0 | |
| Tue., 9/21 | JV Field Hockey | Mercy | Away - Mercy HS-Field Hockey Field [Directions] | 5:15 p.m. | W 6-0 | |
| Tue., 9/21 | JV Girls Soccer | Lauralton Hall | Away - Lauralton Hall-Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/21 | FR Girls Soccer | Mercy | Away - Mercy HS-Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/21 | V Girls Swimming and Diving | East Haven/Cross/Hillhouse/SHA | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | ||
| Wed., 9/22 | FR Boys Soccer | Notre Dame-West Haven | Home - Cheshire HS-Cheshire High School soccer field [Directions] | 4:00 p.m. | ||
| Wed., 9/22 | FR Field Hockey | Sacred Heart Academy | Away - Sacred Heart Academy-Field Hockey Field [Directions] | 4:00 p.m. | W 4-1 | |
| Wed., 9/22 | V Girls Volleyball | Fairfield Warde | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Wed., 9/22 | JV Girls Volleyball | Fairfield Warde | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Thu., 9/23 | FR Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 9/23 | V Boys Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 6-1 | |
| Thu., 9/23 | V Field Hockey | Branford | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 9/23 | JV Field Hockey | Branford | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:30 p.m. | W 6-0 | |
| Thu., 9/23 | V Girls Soccer | Hamden | Away - Hamden HS-HHS Turf Field #2 [Directions] | 5:00 p.m. | W 4-1 | |
| Thu., 9/23 | JV Girls Soccer | Hamden | Away - Hamden HS-HHS Turf Field #2 [Directions] | 6:30 p.m. | ||
| Thu., 9/23 | V Girls Swimming and Diving | Lyman Hall | Away - Sheehan HS-Sheehan HS Pool [Directions] | 3:45 p.m. | Cheshire - 100 Lyman Hall - 81 | |
| Fri., 9/24 | V Football | Staples | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | W 42-14 | |
| Fri., 9/24 | JV Boys Soccer | North Haven | Home - Cheshire HS-Grass Fields [Directions] | Postponed | ||
| Fri., 9/24 | V Girls Volleyball | Sacred Heart Academy | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 9/24 | JV Girls Volleyball | Sacred Heart Academy | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Sat., 9/25 | V Boys Cross Country | Winding trails invite | Away - Winding Trails-Cross Country Course | 9:00 a.m. | ||
| Sat., 9/25 | JV Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/25 | V Boys Soccer | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 4:00 p.m. | T 0-0 | |
| Sat., 9/25 | JV Boys Soccer | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 2:00 p.m. | ||
| Sat., 9/25 | FR Boys Soccer | Shelton | Away - Shelton HS-Lower Field [Directions] | 10:00 a.m. | ||
| Sat., 9/25 | V Girls Cross Country | Winding trails invite | Away - Winding Trails-Cross Country Course | 9:00 a.m. | ||
| Sat., 9/25 | FR Field Hockey | Daniel Hand | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 10:00 a.m. | L 0-4 | |
| Sat., 9/25 | V Girls Soccer | Amity | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | L 1-2 | |
| Sat., 9/25 | JV Girls Soccer | Amity | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 3:00 p.m. | ||
| Sat., 9/25 | FR Girls Soccer | Daniel Hand | Home - Cheshire HS-Bartlem Park Field 2 [Directions] | Canceled | Cancelled | |
| Mon., 9/27 | V Girls Soccer | Lauralton Hall | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 1-0 | |
| Mon., 9/27 | V Girls Volleyball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 9/27 | JV Girls Volleyball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 4:00 p.m. | L 0-2 | |
| Tue., 9/28 | V Boys Soccer | Guilford | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | L 1-2 | |
| Tue., 9/28 | FR Field Hockey | Amity | Away - Amity Regional HS-Field Hockey Field [Directions] | 3:45 p.m. | T 0-0 | |
| Tue., 9/28 | FR Girls Soccer | Amity | Away - Amity Regional HS-Amity High School - Field # 2 [Directions] | 3:45 p.m. | ||
| Wed., 9/29 | JV Boys Soccer | Guilford | Home - Cheshire HS-Grass Fields [Directions] | 5:00 p.m. | ||
| Wed., 9/29 | FR Boys Soccer | Guilford | Away - Long Hill Park-Guilford-Soccer Field (Front) [Directions] | 3:45 p.m. | ||
| Wed., 9/29 | V Field Hockey | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 9/29 | JV Field Hockey | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 5:30 p.m. | W 6-0 | |
| Wed., 9/29 | V Girls Soccer | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 6:30 p.m. | L 0-1 | |
| Wed., 9/29 | V Girls Volleyball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 5:15 p.m. | W 3-0 | |
| Wed., 9/29 | JV Girls Volleyball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 9/30 | V Boys Soccer | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 6:00 p.m. | L 5-3 | |
| Thu., 9/30 | JV Boys Soccer | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 4:00 p.m. | ||
| Thu., 9/30 | JV Girls Soccer | Sheehan | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Thu., 9/30 | V Girls Swimming and Diving | Jonathan Law | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Cheshire - 100 Law - 78 | |
| Fri., 10/1 | V Field Hockey | Sacred Heart Academy | Away - Sacred Heart Academy-Field Hockey Field [Directions] | 4:00 p.m. | T 1-1 | |
| Fri., 10/1 | JV Field Hockey | Sacred Heart Academy | Away - Sacred Heart Academy-Field Hockey Field [Directions] | 5:30 p.m. | W 2-0 | |
| Fri., 10/1 | FR Field Hockey | Guilford | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 10/1 | V Girls Soccer | Mercy | Away - Xavier HS-Larry McHugh Field [Directions] | 6:30 p.m. | L 0-1 | |
| Fri., 10/1 | V Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/1 | JV Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | L 0-2 | |
| Sat., 10/2 | V Boys Cross Country | SCC Divisional Meet Boys Housatonic | Away - Guilford HS-Guilford Fair grounds | 3:50 p.m. | ||
| Sat., 10/2 | V Football | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | L 15-25 | |
| Sat., 10/2 | V Girls Cross Country | SCC Divisional Meet Girls Housatonic | Away - Guilford HS-Guilford Fair grounds | 4:25 p.m. | ||
| Sat., 10/2 | JV Girls Soccer | Mercy | Away - Mercy HS-Soccer Field [Directions] | 1:00 p.m. | ||
| Sat., 10/2 | FR Girls Soccer | Guilford | Home - Cheshire HS-Cheshire High School soccer field [Directions] | 10:00 a.m. | ||
| Mon., 10/4 | V Girls Volleyball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/4 | JV Girls Volleyball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 4:15 p.m. | W 2-0 | |
| Tue., 10/5 | JV Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Field Hockey | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 7:00 p.m. | W 7-0 | |
| Tue., 10/5 | JV Field Hockey | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 5:15 p.m. | W 4-0 | |
| Tue., 10/5 | V Girls Soccer | Guilford | Away - Bittner Park-Bittner Park Soccer [Directions] | 6:00 p.m. | T 2-2 | |
| Tue., 10/5 | JV Girls Soccer | Guilford | Away - Bittner Park-Bittner Park Soccer [Directions] | 3:45 p.m. | ||
| Tue., 10/5 | V Girls Swimming and Diving | Mercy | Away - Middletown YMCA [Directions] | 7:30 p.m. | Cheshire - 90 Mercy - 74 | |
| Wed., 10/6 | FR Boys Soccer | Xavier | Home - Cheshire HS-Cheshire High School soccer field [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | V Girls Volleyball | Shelton | Away - Shelton Intermediate School-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/6 | JV Girls Volleyball | Shelton | Away - Shelton Intermediate School-Gym [Directions] | 4:30 p.m. | W 2-1 | |
| Thu., 10/7 | JV Girls Soccer | Lauralton Hall | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Thu., 10/7 | V Girls Swimming and Diving | Glastonbury (Scrim.) | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | ||
| Fri., 10/8 | V Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 3:45 p.m. | L 1-2 | |
| Fri., 10/8 | V Field Hockey | Sheehan | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 10/8 | JV Field Hockey | Sheehan | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:15 p.m. | W 7-0 | |
| Fri., 10/8 | FR Field Hockey | Guilford | Away - Guilford HS-Maturo Field [Directions] | 5:00 p.m. | L 0-5 | |
| Fri., 10/8 | V Girls Soccer | Shelton | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 5-0 | |
| Fri., 10/8 | FR Girls Soccer | Mercy | Home - Cheshire HS-Cheshire High School soccer field [Directions] | 4:00 p.m. | ||
| Fri., 10/8 | V Girls Swimming and Diving | Hamden | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Cheshire - 103 Hamden 73 | |
| Fri., 10/8 | V Girls Volleyball | Hamden | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 10/8 | JV Girls Volleyball | Hamden | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Sat., 10/9 | V Boys Cross Country | Wickham Park | Away - Wickham Park-Manchester, Ct | 9:00 a.m. | ||
| Sat., 10/9 | V Girls Cross Country | Wickham Invite | Away - Wickham Park-Manchester, Ct | 9:00 a.m. | ||
| Sat., 10/9 | V Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 1:30 p.m. | L 0-5 | |
| Sat., 10/9 | JV Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 3:00 p.m. | L 2-1 | |
| Sat., 10/9 | JV Girls Soccer | Shelton | Home - Cheshire HS-Cheshire High School soccer field [Directions] | 10:00 a.m. | ||
| Sat., 10/9 | Miscellaneous Events | Music in Motion | Home - Cheshire High Main Game field [Directions] | 8:00 a.m. | ||
| Mon., 10/11 | V Field Hockey | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | 7:00 p.m. | W 1-0 | |
| Mon., 10/11 | JV Field Hockey | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | 5:30 p.m. | T 1-1 | |
| Mon., 10/11 | FR Field Hockey | Daniel Hand | Away - Daniel Hand HS-Polson Front Field/ DHHS Campus [Directions] | 3:45 p.m. | W 1-0 | |
| Mon., 10/11 | FR Girls Soccer | Daniel Hand | Away - Daniel Hand HS-Janssen Field #2/DHHS Campus [Directions] | Postponed | ||
| Tue., 10/12 | V Boys Cross Country | Daniel Hand, Branford, Hamden | Away - Madison Surf Club-Surf Club [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Boys Soccer | Lyman Hall | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/12 | V Girls Cross Country | Daniel Hand, Branford, Hamden | Away - Madison Surf Club-Surf Club [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Field Hockey | North Haven | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 8-0 | |
| Tue., 10/12 | JV Field Hockey | North Haven | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:30 p.m. | W 1-0 | |
| Tue., 10/12 | V Girls Soccer | North Haven | Away - North Haven MS-West Turf Field [Directions] | 6:00 p.m. | W 4-0 | |
| Tue., 10/12 | V Girls Swimming and Diving | Lauralton Hall | Away - Foran HS -Pool [Directions] | 7:30 p.m. | Cheshire - 95 LH - 80 | |
| Tue., 10/12 | V Girls Volleyball | Career Magnet | Away - Career Magnet-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 10/12 | JV Girls Volleyball | Career Magnet | Away - Career Magnet-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 10/13 | JV Boys Soccer | Lyman Hall | Home - Cheshire HS-Grass Fields [Directions] | 3:45 p.m. | ||
| Wed., 10/13 | FR Field Hockey | Amity | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 4:00 p.m. | T 2-2 | |
| Thu., 10/14 | V Boys Cross Country | Lyman Hall | Away - Wharton Brook State Park [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | FR Football | Xavier | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 10/14 | V Girls Cross Country | Lyman Hall | Away - Wharton Brook State Park [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | V Field Hockey | Hamden | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 5-0 | |
| Thu., 10/14 | JV Field Hockey | Hamden | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 2:30 p.m. | W 7-0 | |
| Fri., 10/15 | V Football | Xavier | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | L 20-21 | |
| Fri., 10/15 | FR Boys Soccer | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 4:00 p.m. | ||
| Fri., 10/15 | JV Girls Soccer | Amity | Away - Amity Regional HS-Amity High School - Field # 2 [Directions] | 3:45 p.m. | ||
| Fri., 10/15 | V Girls Swimming and Diving | Daniel Hand | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Cheshire - Hand - | |
| Fri., 10/15 | V Girls Volleyball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/15 | JV Girls Volleyball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 10/16 | JV Football | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 10:00 a.m. | ||
| Sat., 10/16 | V Boys Soccer | East Haven | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | W 6-0 | |
| Sat., 10/16 | FR Boys Soccer | Notre Dame-West Haven | Away - Veterans Field [Directions] | 10:00 a.m. | ||
| Sat., 10/16 | FR Girls Soccer | Amity | Home - Cheshire HS-Cheshire High School soccer field [Directions] | 10:00 a.m. | ||
| Mon., 10/18 | V Boys Soccer | North Haven | Away - North Haven MS-West Turf Field [Directions] | 6:00 p.m. | W 6-2 | |
| Mon., 10/18 | FR Boys Soccer | Daniel Hand | Away - Daniel Hand HS-Janssen Field #2/DHHS Campus [Directions] | 3:45 p.m. | ||
| Mon., 10/18 | V Girls Soccer | Hamden | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 5-1 | |
| Mon., 10/18 | V Girls Volleyball | Guilford | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Mon., 10/18 | JV Girls Volleyball | Guilford | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Tue., 10/19 | JV Boys Soccer | North Haven | Away - North Haven MS-West Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/19 | V Field Hockey | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 10/19 | JV Field Hockey | Daniel Hand | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:30 p.m. | W 1-0 | |
| Tue., 10/19 | JV Girls Soccer | Hamden | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Tue., 10/19 | V Girls Swimming and Diving | North Haven | Away - Walter Gawrych Community Pool [Directions] | 4:00 p.m. | Cheshire - 97 North Haven - 77 | |
| Wed., 10/20 | V Boys Cross Country | SCC Championship Meet | Away - Guilford HS-East Shore Park, New Haven | 3:00 p.m. | ||
| Wed., 10/20 | V Boys Soccer | Shelton | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 4-0 | |
| Wed., 10/20 | FR Boys Soccer | Shelton | Home - Cheshire HS-Cheshire High School soccer field [Directions] | 4:00 p.m. | ||
| Wed., 10/20 | V Girls Cross Country | SCC Championship Meet | Away - Guilford HS-East Shore Park, New Haven | 1:40 p.m. | ||
| Wed., 10/20 | FR Field Hockey | Amity | Away - Amity Regional HS-Field Hockey Field [Directions] | 3:45 p.m. | ||
| Wed., 10/20 | V Girls Soccer | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 3:45 p.m. | L 3-2 | |
| Wed., 10/20 | Miscellaneous Events | Unified soccer tournament | Home - Cheshire High Main Game field [Directions] | 2:30 p.m. | ||
| Thu., 10/21 | V Boys Cross Country | SCC Championship | Away - East Shore Park Career J.V. | 1:00 p.m. | ||
| Thu., 10/21 | FR Football | Newtown | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 10/21 | JV Boys Soccer | Shelton | Home - Cheshire HS-Grass Fields [Directions] | Postponed | ||
| Thu., 10/21 | V Girls Cross Country | SCC Championship | Away - East Shore Park Career J.V. | 1:00 p.m. | ||
| Thu., 10/21 | V Field Hockey | Conard | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 6-2 | |
| Thu., 10/21 | JV Field Hockey | Conard | Home - Cheshire HS-FIeld Hockey grass field [Directions] | 5:30 p.m. | ||
| Fri., 10/22 | V Football | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | L 13-34 | |
| Fri., 10/22 | JV Boys Soccer | Guilford | Away - Bittner Park-Bittner Park Soccer [Directions] | 3:45 p.m. | ||
| Fri., 10/22 | V Field Hockey | Simsbury | Away - Holden Field-Turf [Directions] | 3:45 p.m. | W 5-0 | |
| Fri., 10/22 | JV Field Hockey | Simsbury | Away - Simsbury HS-Grass FH Field [Directions] | 5:30 p.m. | ||
| Fri., 10/22 | V Girls Soccer | Lauralton Hall | Away - Lauralton Hall-Soccer Field [Directions] | 3:45 p.m. | W 5-1 | |
| Fri., 10/22 | V Girls Swimming and Diving | Amity | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | ||
| Fri., 10/22 | V Girls Volleyball | Jonathan Law | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 10/22 | JV Girls Volleyball | Jonathan Law | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Sat., 10/23 | JV Football | Newtown | Home - Cheshire High Main Game field [Directions] | 10:30 a.m. | ||
| Sat., 10/23 | V Boys Soccer | Guilford | Away - Bittner Park-Bittner Park Soccer [Directions] | 6:00 p.m. | W 1-0 | |
| Sat., 10/23 | FR Boys Soccer | Guilford | Home - Cheshire HS-Cheshire High School soccer field [Directions] | 10:00 a.m. | ||
| Mon., 10/25 | V Boys Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | T 1-1 | |
| Tue., 10/26 | FR Field Hockey | Branford | Home - Cheshire HS-FIeld Hockey grass field [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Tue., 10/26 | V Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-1 | |
| Tue., 10/26 | JV Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | W 2-0 | |
| Wed., 10/27 | FR Boys Soccer | Daniel Hand | Home - Cheshire HS-Bartlem Park [Directions] | Canceled | Cancelled | |
| Wed., 10/27 | V Field Hockey | Lauralton Hall | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 3-1 | |
| Wed., 10/27 | JV Field Hockey | Lauralton Hall | Home - Cheshire HS-FIeld Hockey grass field [Directions] | Canceled | Cancelled | |
| Wed., 10/27 | V Girls Soccer | Mercy | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | L 0-2 | |
| Wed., 10/27 | JV Girls Soccer | Mercy | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Wed., 10/27 | V Girls Volleyball | Farmington | Home - Cheshire HS-Gym West [Directions] | 6:30 p.m. | W 3-1 | |
| Wed., 10/27 | JV Girls Volleyball | Farmington | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | L 1-2 | |
| Thu., 10/28 | FR Football | Norwich Free Academy | Home - Cheshire High Main Game field [Directions] | Canceled | Cancelled | |
| Thu., 10/28 | JV Boys Soccer | Daniel Hand | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Fri., 10/29 | V Football | Norwich Free Academy | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | W 32-0 | |
| Fri., 10/29 | FR Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 5:00 p.m. | ||
| Sat., 10/30 | JV Football | Norwich Free Academy | Away - Norwich Free Academy-Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 10/30 | V Boys Soccer | Jonathan Law | Away - Jonathan Law HS-Lawmen Stadium [Directions] | 1:00 p.m. | ||
| Sat., 10/30 | FR Boys Soccer | Amity | Home - Cheshire HS-Cheshire High School soccer field [Directions] | Canceled | Cancelled | |
| Sat., 10/30 | V Field Hockey | Amity | Home - Cheshire High Main Game field [Directions] | 1:00 p.m. | W 1-0 | |
| Sat., 10/30 | V Girls Soccer | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 1:00 p.m. | L 1-0 | |
| Sat., 10/30 | V Girls Swimming and Diving | SCC Dive championship | Away - Sheehan HS-Sheehan HS Pool | 9:30 a.m. | ||
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class L Championship | Away - Wickham Park | 11:25 a.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Class L Championship | Away - Wickham Park-Manchester, Ct | 11:55 a.m. | ||
| Mon., 11/1 | V Field Hockey | Sacred Heart Academy | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 11/1 | V Girls Swimming and Diving | SCC swim Qualifying championship | Away - Cheshire Community Pool | 4:00 p.m. | ||
| Tue., 11/2 | V Boys Soccer | Notre Dame-West Haven | Away - Veterans Field [Directions] | 4:00 p.m. | ||
| Tue., 11/2 | V Girls Volleyball | Guilford | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Wed., 11/3 | V Field Hockey | Guilford | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 6:30 p.m. | L 3-0 | |
| Wed., 11/3 | V Girls Swimming and Diving | SCC swim championship | Away - Southern CT State University-pool | 5:00 p.m. | ||
| Thu., 11/4 | FR Football | West Haven | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 11/4 | V Boys Soccer | Xavier | Away - West Haven HS-Ken Strong Stadium [Directions] | 7:30 p.m. | ||
| Thu., 11/4 | V Girls Volleyball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | 7:00 p.m. | L 14-21 | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/5 | V Girls Soccer | Seymour (Scrim.) | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 7-0 | |
| Sat., 11/6 | JV Football | West Haven | Home - Cheshire High Main Game field [Directions] | 10:30 a.m. | ||
| Mon., 11/8 | V Girls Soccer | West Haven | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 11/9 | V Boys Soccer | Brien McMahon | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Wed., 11/10 | V Field Hockey | Enfield | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | W 4-0 | |
| Wed., 11/10 | V Girls Soccer | Glastonbury | Away - Glastonbury HS-Turf Field [Directions] | 2:00 p.m. | W 2-1 | |
| Wed., 11/10 | V Girls Swimming and Diving | CIAC Class L Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/11 | FR Football | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 4:30 p.m. | ||
| Thu., 11/11 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | ||
| Thu., 11/11 | V Girls Volleyball | New Canaan | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Fri., 11/12 | V Football | Shelton | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | L 0-13 | |
| Fri., 11/12 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 3:00 p.m. | L 4-0 | |
| Sat., 11/13 | JV Football | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 10:00 a.m. | ||
| Sat., 11/13 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | ||
| Sat., 11/13 | V Field Hockey | Glastonbury | Home - Cheshire High Main Game field [Directions] | 10:30 a.m. | ||
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 3:15 p.m. | ||
| Sat., 11/13 | V Girls Volleyball | Southington | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Tue., 11/16 | V Girls Swimming and Diving | CIAC Class L Swimming Championships | Away - SCSU | 6:00 p.m. | ||
| Wed., 11/17 | V Boys Soccer | Xavier | Away - Municipal Stadium (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 11/17 | V Girls Volleyball | Fairfield Ludlowe | Home - Pomperaug HS-Main Gym [Directions] | 6:00 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 11/19 | FR Football | Southington | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Sat., 11/20 | V Boys Soccer | Farmington | Away - Dillon Stadium [Directions] | 6:30 p.m. | ||
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Wed., 11/24 | V Football | Away - Cheshire HS-Main Game field | 12:45 p.m. | |||
| Wed., 11/24 | V | Red/White Bowl | Home - Cheshire High Main Game field [Directions] | 12:45 p.m. | ||
| Thu., 11/25 | V Football | Southington | Away - Southington HS-TURF FIELD [Directions] | 10:00 a.m. | L 10-17 | |
| Sat., 12/4 | V Wrestling | Glastonbury (Scrim.) | Home - Cheshire HS-Gym - East [Directions] | 8:30 a.m. | ||
| Mon., 12/6 | V Boys Basketball | Guilford (Scrim.) | Away - Guilford HS-Main gym at GHS [Directions] | 5:30 p.m. | ||
| Mon., 12/6 | V Girls Basketball | Lyman Hall (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 4:30 p.m. | ||
| Mon., 12/6 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 4:30 p.m. | L 0-3 | |
| Wed., 12/8 | V Boys Ice Hockey | St. Joseph (Scrim.) | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | ||
| Wed., 12/8 | V Girls Basketball | WCA (Scrim.) | Away - Waterbury Career Academy-Gymnasium [Directions] | 5:45 p.m. | ||
| Thu., 12/9 | V Boys Basketball | Woodland (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | ||
| Fri., 12/10 | V Girls Basketball | Avon (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 4:45 p.m. | ||
| Sat., 12/11 | V Boys Ice Hockey | Wethersfield (Scrim.) | Away - Newington Ice Arena-Blue Rink [Directions] | 8:00 p.m. | ||
| Sat., 12/11 | V Boys Ice Hockey | Wethersfield (Scrim.) | Away - Newington Ice Arena-Blue Rink [Directions] | 9:45 p.m. | ||
| Sat., 12/11 | V Girls Ice Hockey | Guilford Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | W 3-2 | |
| Mon., 12/13 | V Boys Basketball | Berlin (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 3:15 p.m. | ||
| Mon., 12/13 | V Boys Ice Hockey | East Haven Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | L 9-7 | |
| Mon., 12/13 | V Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 40-55 | |
| Mon., 12/13 | JV Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/13 | FR Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 12/15 | V Wrestling | Amity | Home - Cheshire HS-Gym - East [Directions] | Postponed | ||
| Wed., 12/15 | V Girls Ice Hockey | Masuk Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | W 3-0 | |
| Thu., 12/16 | V Boys Basketball | Xavier | Away - Xavier HS-Aurthur M. Kohs Gymnasium [Directions] | 7:00 p.m. | L 32-69 | |
| Thu., 12/16 | JV Boys Basketball | Xavier | Away - Xavier HS-Aurthur M. Kohs Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 12/16 | FR Boys Basketball | Xavier | Away - Xavier HS-Aurthur M. Kohs Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 12/16 | V Boys Indoor Track | SCC Boys Developmental 1 | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 12/22 | ||||||
| Fri., 12/17 | V Girls Basketball | Career Magnet | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 74-24 | |
| Fri., 12/17 | JV Girls Basketball | Career Magnet | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Sat., 12/18 | V Boys Basketball | Platt | Away - Platt HS-Gym [Directions] | 1:30 p.m. | L 48-82 | |
| Sat., 12/18 | JV Boys Basketball | Platt | Away - Platt HS-Gym [Directions] | 11:00 a.m. | ||
| Sat., 12/18 | FR Boys Basketball | Platt | Away - Platt HS-Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/18 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavilion-Red [Directions] | 4:45 p.m. | L 5-6 | |
| Sat., 12/18 | V Wrestling | Darien Invitational | Away - Darien HS-DHS Main Gym | Canceled | Cancelled | |
| Sat., 12/18 | V Girls Basketball | Fairfield Ludlowe | Home - Cheshire HS-Gym West [Directions] | 1:00 p.m. | L 31-49 | |
| Sat., 12/18 | JV Girls Basketball | Fairfield Ludlowe | Home - Cheshire HS-Gym West [Directions] | 11:00 a.m. | ||
| Sat., 12/18 | V Girls Ice Hockey | Hamden Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 6:30 p.m. | L 3-9 | |
| Mon., 12/20 | V Girls Indoor Track | SCC Girls Developmental 1 | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Tue., 12/21 | V Boys Ice Hockey | Conard | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | T 3-3(OT) | |
| Tue., 12/21 | V Boys Swimming and Diving | Shelton | Away - Shelton Community Center Pool [Directions] | 3:45 p.m. | ||
| Tue., 12/21 | V Girls Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 7:00 p.m. | W 49-29 | |
| Tue., 12/21 | JV Girls Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 12/21 | FR Girls Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 12/22 | V Boys Indoor Track | scc developmental | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 5:30 p.m. | ||
| Wed., 12/22 | V Wrestling | Branford | Away - Branford HS-Gym [Directions] | Postponed | ||
| Wed., 12/22 | V Co-ed Fencing | North Haven | Away - North Haven HS-Auxiliary Gymnasium [Directions] | Postponed | ||
| Thu., 12/23 | V Boys Ice Hockey | Daniel Hand | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 2-3 | |
| Mon., 12/27 | FR Girls Basketball | Foran | Home - Cheshire HS-Gym West [Directions] | Postponed | ||
| Tue., 12/28 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Hamden-Lou Astorino Ice Rink [Directions] | 1:30 p.m. | W 5-1 | |
| Tue., 12/28 | FR Girls Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | Postponed | ||
| Wed., 12/29 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall-Ice Rink [Directions] | 2:00 p.m. | L 3-5 | |
| Wed., 12/29 | V Wrestling | Notre Dame-West Haven | Home - Cheshire HS-Gym - East [Directions] | 5:00 p.m. | ||
| Thu., 12/30 | V Wrestling | Killingly, New Britain, Suffield Windsor Locks Wrestling Co Op | Away - Killingly HS-Gym [Directions] | 10:00 a.m. | ||
| Mon., 1/3 | JV Boys Ice Hockey | Xavier | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | ||
| Mon., 1/3 | V Girls Indoor Track | SCC Girls Developmental 2 | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Tue., 1/4 | V Boys Basketball | Fairfield Prep | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 28-68 | |
| Tue., 1/4 | JV Boys Basketball | Fairfield Prep | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Tue., 1/4 | FR Boys Basketball | Fairfield Prep | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Tue., 1/4 | V Boys Indoor Track | SCC Boys Developmental 2 | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Sat., 1/8 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | 3:00 p.m. | W 4-1 | |
| Sat., 1/8 | V Girls Ice Hockey | Suffield Coop | Away - Enfield Twin Rinks-Rink 1 [Directions] | 8:00 p.m. | L 1-10 | |
| Mon., 1/10 | V Boys Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 7:00 p.m. | W 58-54 | |
| Mon., 1/10 | JV Boys Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 1/10 | FR Boys Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 3:45 p.m. | ||
| Mon., 1/10 | JV Boys Ice Hockey | Wethersfield | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | ||
| Mon., 1/10 | V Girls Basketball | West Haven | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 29-60 | |
| Mon., 1/10 | JV Girls Basketball | West Haven | Home - Cheshire HS-Gym West [Directions] | 4:00 p.m. | ||
| Mon., 1/10 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 4:00 p.m. | L 2-7 | |
| Tue., 1/11 | V Boys Indoor Track | SCC Novice Meet | Away - TBA | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Tue., 1/11 | V Girls Indoor Track | SCC Novice Meet | Away - TBA | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Wed., 1/12 | V Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 7:00 p.m. | W 43-37 | |
| Wed., 1/12 | JV Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/12 | FR Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 1/13 | V Boys Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 7:00 p.m. | L 39-62 | |
| Thu., 1/13 | JV Boys Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 1/13 | FR Boys Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 1/13 | V Boys Ice Hockey | Wethersfield | Away - Newington Ice Arena-Blue Rink [Directions] | 6:05 p.m. | T 2-2 | |
| Thu., 1/13 | V Wrestling | Morgan | Away - Morgan School-Gym [Directions] | 7:00 p.m. | ||
| Thu., 1/13 | V Girls Ice Hockey | New Canaan | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 0-8 | |
| Fri., 1/14 | V Boys Basketball | Xavier | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 42-51 | |
| Fri., 1/14 | JV Boys Basketball | Xavier | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 1/14 | FR Boys Basketball | Xavier | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Fri., 1/14 | JV Boys Ice Hockey | Northwest Catholic | Away - Simsbury - ISCC-NHL [Directions] | 7:20 p.m. | ||
| Fri., 1/14 | JV Girls Basketball | Career Magnet | Away - Career Magnet-Gym [Directions] | Canceled | Cancelled | |
| Sat., 1/15 | V Boys Ice Hockey | Branford | Home - Hamden-Lou Astorino Ice Rink [Directions] | 6:00 p.m. | W 5-4(OT) | |
| Sat., 1/15 | V Wrestling | Platt, Amity, Brien McMahon | Away - Platt HS-Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/15 | V Girls Basketball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 4:30 p.m. | W 49-30 | |
| Sat., 1/15 | JV Girls Basketball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 3:00 p.m. | ||
| Sun., 1/16 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 6:30 p.m. | L 1-5 | |
| Mon., 1/17 | V Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 3:00 p.m. | L 35-55 | |
| Mon., 1/17 | V Boys Ice Hockey | South Windsor | Home - Hamden-Lou Astorino Ice Rink [Directions] | 2:30 p.m. | L 1-2 | |
| Tue., 1/18 | V Boys Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 7:00 p.m. | L 44-57 | |
| Tue., 1/18 | JV Boys Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/18 | FR Boys Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 1/18 | V Boys Swimming and Diving | Oxford | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Final: Cheshire 94 Oxford 82 [Detailed Results] | |
| Tue., 1/18 | V Wrestling | Jonathan Law | Home - Cheshire HS-Gym - East [Directions] | 5:00 p.m. | ||
| Tue., 1/18 | V Girls Basketball | Guilford | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 24-41 | |
| Tue., 1/18 | JV Girls Basketball | Guilford | Home - Cheshire HS-Gym West [Directions] | 4:30 p.m. | ||
| Tue., 1/18 | FR Girls Basketball | Guilford | Home - Cheshire HS-Gym West [Directions] | Canceled | Cancelled | |
| Wed., 1/19 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | L 5-7 | |
| Wed., 1/19 | Miscellaneous Events | curriculum night | Home - Cheshire HS [Directions] | 6:00 p.m. | ||
| Thu., 1/20 | V Girls Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 6:00 p.m. | W 53-48 | |
| Thu., 1/20 | JV Girls Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 4:15 p.m. | ||
| Fri., 1/21 | V Boys Basketball | Career Magnet | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 54-28 | |
| Fri., 1/21 | JV Boys Basketball | Career Magnet | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 1/21 | FR Boys Basketball | Career Magnet | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Fri., 1/21 | JV Boys Ice Hockey | Northwest Catholic | Away - Simsbury - ISCC-NHL [Directions] | 7:20 p.m. | ||
| Fri., 1/21 | V Boys Swimming and Diving | Daniel Hand/Branford/Old Saybrook | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Final: Hand 97 Cheshire 81 [Detailed Results] | |
| Fri., 1/21 | V Co-ed Fencing | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | 6:30 p.m. | ||
| Sat., 1/22 | V Boys Ice Hockey | North Haven | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | L 1-7 | |
| Sat., 1/22 | V Boys Indoor Track | SCC Coaches Invite | Away - TBA-Floyd Little Athletic Center | 9:00 a.m. | ||
| Sat., 1/22 | V Wrestling | Xavier, Bristol Central, Bristol Eastern, Burlington (MA), Fitch, Guilford, Joel Barlow, TBA, Pomperaug, Ridgefield, Simsbury, Trumbull, Hall, Xaverian Brothers (MA) | Away - Xavier HS-Gym | 9:00 a.m. | ||
| Sat., 1/22 | V Girls Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 49-31 | |
| Sat., 1/22 | JV Girls Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 4:15 p.m. | ||
| Sat., 1/22 | FR Girls Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 2:45 p.m. | ||
| Sat., 1/22 | V Girls Indoor Track | SCC Coaches Invite | Away - TBA-Floyd Little Athletic Center | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Sun., 1/23 | V Girls Ice Hockey | Avon | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 1-6 | |
| Mon., 1/24 | V Boys Swimming and Diving | HK-Valley | Away - Haddam Killingworth HS (HK)-HKHS Pool - no diving [Directions] | 4:00 p.m. | Final: Cheshire 78 H-K 64 | |
| Mon., 1/24 | JV Wrestling | Simsbury | Away - Simsbury HS-Gym 2 [Directions] | 4:00 p.m. | ||
| Mon., 1/24 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 7:15 p.m. | L 1-4 | |
| Tue., 1/25 | V Boys Basketball | Lyman Hall | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 50-39 | |
| Tue., 1/25 | JV Boys Basketball | Lyman Hall | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Tue., 1/25 | FR Boys Basketball | Lyman Hall | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Tue., 1/25 | V Girls Basketball | Mercy | Away - Mercy HS-Gym [Directions] | 7:00 p.m. | L 43-63 | |
| Tue., 1/25 | JV Girls Basketball | Mercy | Away - Mercy HS-Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/26 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 8:00 p.m. | L 0-8 | |
| Wed., 1/26 | V Boys Indoor Track | SCC Sectional East Championships | Away - TBA-Floyd Little Athletic Center | 5:00 p.m. | ||
| Wed., 1/26 | V Wrestling | Fairfield Prep | Away - Fairfield University-Brissette Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 1/26 | V Co-ed Fencing | Guilford | Away - Guilford HS-Aux gym at GHS [Directions] | 6:30 p.m. | ||
| Wed., 1/26 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:50 p.m. | L 2-9 | |
| Wed., 1/26 | V Girls Indoor Track | SCC Sectional East Championships | Away - TBA-connell memorial rink | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to New Haven Athletic Center/Hillhouse HS | ||||||
| Thu., 1/27 | V Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 7:00 p.m. | L 46-55 | |
| Thu., 1/27 | JV Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/27 | FR Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/27 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | ||
| Thu., 1/27 | V Girls Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 6:00 p.m. | L 45-59 | |
| Thu., 1/27 | JV Girls Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 4:15 p.m. | ||
| Sat., 1/29 | V Wrestling | Portland, Avon, Coventry, Daniel Hand, East Haven, Gilbert, Glastonbury, Griswold/Wheeler, Morgan, TBA, TBA, New Britain, Nonnewaug, Plainville, Somers, St. Paul Catholic, Terryville/Thomaston, Thomaston, New Haven Wrestling | Away - Portland HS-Portland HS | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Mon., 1/31 | V Girls Basketball | Lauralton Hall | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 60-51 | |
| Mon., 1/31 | JV Girls Basketball | Lauralton Hall | Home - Cheshire HS-Gym West [Directions] | Canceled | Cancelled | |
| Mon., 1/31 | Miscellaneous Events | Unified basketball | Home - HAMDEN [Directions] | 3:00 p.m. | ||
| Tue., 2/1 | V Boys Swimming and Diving | Hamden, Sheehan/Lyman Hall | Away - Hamden HS-HHS Pool [Directions] | 4:00 p.m. | Final: Hamden 95 Cheshire 83 Final: Cheshire 91 Sheehan 67 | |
| Tue., 2/1 | V Wrestling | New Haven Wrestling | Home - Cheshire HS-Gym - East [Directions] | 6:00 p.m. | ||
| Tue., 2/1 | V Girls Ice Hockey | West Haven/SHA | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 2-4 | |
| Wed., 2/2 | V Boys Basketball | Southington | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 48-31 | |
| Wed., 2/2 | JV Boys Basketball | Southington | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Wed., 2/2 | FR Boys Basketball | Southington | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Wed., 2/2 | V Boys Ice Hockey | North Branford | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:00 p.m. | W 3-1 | |
| Wed., 2/2 | JV Boys Ice Hockey | Xavier | Away - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 8:00 p.m. | ||
| Wed., 2/2 | V Girls Basketball | Lauralton Hall | Away - Lauralton Hall-Gym [Directions] | 6:15 p.m. | L 56-63 | |
| Wed., 2/2 | JV Girls Basketball | Lauralton Hall | Away - Lauralton Hall-Gym [Directions] | Canceled | Cancelled | |
| Thu., 2/3 | V Wrestling | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 2/4 | V Boys Indoor Track | SCC Championship Meet | Away - TBA-Floyd Little Athletic Center | 4:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 2/6, Time to 10:00 a.m. | ||||||
| Fri., 2/4 | V Girls Indoor Track | SCC Championships | Away - TBA | 4:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 2/6, Time to 10:00 a.m. | ||||||
| Sat., 2/5 | V Boys Basketball | Fairfield Prep | Away - Fairfield Warde HS-Gym [Directions] | 1:00 p.m. | L 49-72 | |
| Sat., 2/5 | JV Boys Basketball | Fairfield Prep | Away - Fairfield Warde HS-Gym [Directions] | 11:15 a.m. | ||
| Sat., 2/5 | FR Boys Basketball | Fairfield Prep | Away - Fairfield Warde HS-Gym [Directions] | 9:30 a.m. | ||
| Sat., 2/5 | V Boys Ice Hockey | West Haven Coop | Away - West Haven HS-Bennett Rink [Directions] | 1:00 p.m. | W 5-2 | |
| Sat., 2/5 | V Boys Swimming and Diving | Greater New Haven | Away - Walter Gawrych Community Pool [Directions] | 5:00 p.m. | Final: GNH 101 Cheshire 76 | |
| Sun., 2/6 | V Girls Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 3:15 p.m. | L 28-72 | |
| Sun., 2/6 | JV Girls Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 1:15 p.m. | ||
| Mon., 2/7 | V Girls Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 63-44 | |
| Mon., 2/7 | JV Girls Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Mon., 2/7 | FR Girls Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Tue., 2/8 | V Boys Basketball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 57-61 | |
| Tue., 2/8 | JV Boys Basketball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Tue., 2/8 | FR Boys Basketball | Sheehan | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Tue., 2/8 | V Boys Ice Hockey | Immaculate | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | L 2-4 | |
| Tue., 2/8 | V Boys Swimming and Diving | Glastonbury | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Final: Glastonbury 92 Cheshire 85 | |
| Wed., 2/9 | V Girls Basketball | Mercy | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | L 24-52 | |
| Wed., 2/9 | JV Girls Basketball | Mercy | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Wed., 2/9 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Hamden-Lou Astorino Ice Rink [Directions] | 6:00 p.m. | W 5-4 | |
| Thu., 2/10 | JV Boys Ice Hockey | Wethersfield | Away - Newington Ice Arena-Blue Rink [Directions] | 4:30 p.m. | ||
| Thu., 2/10 | V Co-ed Fencing | Old Lyme | Away - Old Lyme MS-Lyme-Old Lyme Middle School Gym [Directions] | Canceled | Cancelled | |
| Fri., 2/11 | V Boys Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 46-47 | |
| Fri., 2/11 | JV Boys Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 2/11 | FR Boys Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Fri., 2/11 | V Boys Swimming and Diving | Amity | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | 6:45 p.m. | Final: Amity 96 Cheshire 77 | |
| Fri., 2/11 | V Girls Basketball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 7:00 p.m. | L 40-53 | |
| Fri., 2/11 | JV Girls Basketball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 5:15 p.m. | ||
| Fri., 2/11 | FR Girls Basketball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | Canceled | Cancelled | |
| Sat., 2/12 | V Boys Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 1:00 p.m. | W 47-41 | |
| Sat., 2/12 | V Boys Ice Hockey | East Catholic | Away - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 7:00 p.m. | L 4-7 | |
| Sat., 2/12 | V Boys Indoor Track | Class L Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/12 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 3:30 p.m. | W 51-45 | |
| Sat., 2/12 | JV Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 2:00 p.m. | ||
| Sat., 2/12 | V Girls Ice Hockey | Guilford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:40 p.m. | L 3-9 | |
| Sat., 2/12 | V Girls Indoor Track | Class L Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/14 | V Girls Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 50-34 | |
| Mon., 2/14 | JV Girls Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | 4:15 p.m. | ||
| Tue., 2/15 | V Boys Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 7:00 p.m. | L 38-51 | |
| Tue., 2/15 | JV Boys Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/15 | FR Boys Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 2/16 | V Boys Basketball | Career Magnet | Away - Career Magnet-Gym [Directions] | 7:00 p.m. | W 58-49 | |
| Wed., 2/16 | JV Boys Basketball | Career Magnet | Away - Career Magnet-Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/16 | FR Boys Basketball | Career Magnet | Away - Career Magnet-Gym [Directions] | 3:45 p.m. | ||
| Wed., 2/16 | V Boys Ice Hockey | Farmington Valley Generals | Away - Avon Old Farms-Jennings Rink [Directions] | 8:00 p.m. | L 0-6 | |
| Wed., 2/16 | FR Girls Basketball | Foran | Home - Cheshire HS-Gym West [Directions] | 3:30 p.m. | ||
| Wed., 2/16 | V Girls Ice Hockey | Daniel Hand Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 1-2 | |
| Fri., 2/18 | V Boys Basketball | Branford | Home - Cheshire HS-Gym West [Directions] | 7:00 p.m. | L 47-62 | |
| Fri., 2/18 | JV Boys Basketball | Branford | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 2/18 | FR Boys Basketball | Branford | Home - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Fri., 2/18 | JV Boys Ice Hockey | East Catholic | Away - Champions Skating Rink - Cromwell-Lower Rink [Directions] | Canceled | Cancelled | |
| Fri., 2/18 | V Boys Swimming and Diving | Xavier | Away - Middletown YMCA [Directions] | 7:15 p.m. | ||
| Fri., 2/18 | V Wrestling | Class L Championship - Day 1 | Away - Wilton | 3:00 p.m. | ||
| Fri., 2/18 | V Girls Basketball | Guilford | Away - Guilford HS-Aux gym at GHS [Directions] | 5:00 p.m. | ||
| Sat., 2/19 | V Boys Ice Hockey | Eastern CT Eagles | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 4-6 | |
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class L Championship - Day 2 | Away - Wilton | 9:00 a.m. | ||
| Sat., 2/19 | V Girls Ice Hockey | Simsbury | Away - Simsbury - ISCC-NHL [Directions] | 6:10 p.m. | L 3-10 | |
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sun., 2/20 | JV Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | Canceled | Cancelled | |
| Mon., 2/21 | V Boys Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | L 52-65 | |
| Mon., 2/21 | JV Boys Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | 3:15 p.m. | ||
| Mon., 2/21 | FR Boys Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | 1:30 p.m. | ||
| Mon., 2/21 | V Boys Swimming and Diving | Fairfield Prep | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | Final: Fairfield Prep 97 Cheshire 83 | |
| Mon., 2/21 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion-Red [Directions] | 12:30 p.m. | W 9-5 | |
| Wed., 2/23 | V Boys Ice Hockey | Trumbull | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | L 1-5 | |
| Wed., 2/23 | V Boys Swimming and Diving | Greenwich | Home - Cheshire Community Pool [Directions] | Canceled | Cancelled | |
| Wed., 2/23 | V Girls Ice Hockey | Guilford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:30 p.m. | ||
| Sat., 2/26 | V Boys Ice Hockey | Guilford | Away - West Haven HS-Bennett Rink [Directions] | 3:30 p.m. | L 2-4 | |
| Sat., 2/26 | V Boys Swimming and Diving | SCC Dive Championship | Away - Sheehan HS-Sheehan HS Pool | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 12:00 p.m. | ||||||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/28 | JV Boys Ice Hockey | Hamden Hall | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | ||
| Mon., 2/28 | V Boys Swimming and Diving | Amity, Daniel Hand, Fairfield Prep, H-K/Morgan/Valley, Hamden, Foran/Law, Lyman Hall/Coginchaug, N.Haven/E.Haven/N.Bran/Guil, Notre Dame-West Haven, Sheehan, Shelton, West Haven, Xavier | Home - Cheshire Community Pool [Directions] | 4:00 p.m. | ||
| Mon., 2/28 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 6:30 p.m. | ||
| Wed., 3/2 | V Boys Swimming and Diving | SCC Championship Meet | Away - Southern CT State University-pool | 4:30 p.m. | ||
| Wed., 3/2 | Miscellaneous Events | SCC Unified basketball | Home - TBA [Directions] | 3:00 p.m. | ||
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class L Diving Championships | Away - Sheehan | 6:30 p.m. | ||
| Fri., 3/11 | V Boys Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 6:30 p.m. | ||
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class L Swimming Championships | Away - Cornerstone Pool | 1:30 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Wed., 3/23 | V Softball | Seymour (Scrim.) | Away - Seymour HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Thu., 3/24 | JV Softball | Seymour (Scrim.) | Away - Seymour HS-Bungay Field [Directions] | Canceled | Cancelled | |
| Fri., 3/25 | V Baseball | East Haven (Scrim.) | Home - Cheshire HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Sat., 3/26 | V Boys Lacrosse | St. Joseph, New Milford (Scrim.) | Away - St. Joseph HS-Upper Turf [Directions] | 10:00 a.m. | ||
| Sat., 3/26 | V Girls Lacrosse | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | ||
| Sat., 3/26 | JV Girls Lacrosse | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 11:30 a.m. | ||
| Sat., 3/26 | V Softball | Woodland (Scrim.) | Home - Cheshire HS-Softball Diamond [Directions] | 12:30 p.m. | ||
| Tue., 3/29 | V Baseball | Southington (Scrim.) | Away - Southington HS-Baseball Varsity Field [Directions] | Canceled | Cancelled | |
| Tue., 3/29 | V Boys Lacrosse | Trumbull (Scrim.) | Away - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Tue., 3/29 | JV Boys Lacrosse | Trumbull (Scrim.) | Away - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | V Boys Volleyball | Ridgefield (Scrim.) | Away - Ridgefield HS-Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 3/29 | V Girls Lacrosse | Staples (Scrim.) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 5:00 p.m. | ||
| Tue., 3/29 | JV Girls Lacrosse | Staples (Scrim.) | Home - Cheshire HS-Bartlem Park [Directions] | 4:30 p.m. | Cancelled | |
| Tue., 3/29 | V Softball | Fairfield Ludlowe (Scrim.) | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 3/30 | V Softball | Maloney (Scrim.) | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Thu., 3/31 | V Boys Volleyball | Bridgeport Central (Scrim.) | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 5:30 p.m. | ||
| Thu., 3/31 | JV Boys Volleyball | Bridgeport Central (Scrim.) | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Girls Lacrosse | Simsbury (Scrim.) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 3/31 | JV Girls Lacrosse | Simsbury (Scrim.) | Home - Cheshire HS-Bartlem Park [Directions] | 5:00 p.m. | ||
| Thu., 3/31 | V Softball | Masuk (Scrim.) | Home - Cheshire HS-Softball Diamond [Directions] | 5:00 p.m. | ||
| Thu., 3/31 | JV Softball | Masuk (Scrim.) | Home - Cheshire HS-Softball Diamond 2 [Directions] | Canceled | Cancelled | |
| Fri., 4/1 | V Baseball | Maloney (Scrim.) | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Sat., 4/2 | V Boys Lacrosse | LaSalle Academy (RI) | Away - La Salle Academy-Cimini Stadium | 12:00 p.m. | L 9-7 | |
| Sat., 4/2 | FR Boys Lacrosse | Amity, Notre Dame-West Haven | Home - Cheshire High Main Game field [Directions] | 2:00 p.m. | ||
| Sat., 4/2 | V Boys Volleyball | Simsbury | Away - Simsbury HS-Simsbury / Main Gym [Directions] | 11:00 a.m. | W 3-1 | |
| Sat., 4/2 | JV Boys Volleyball | Simsbury | Away - Simsbury HS-Simsbury / Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 4/2 | V Girls Lacrosse | Amity | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 10:00 a.m. | W 9-8 OT | |
| Sat., 4/2 | JV Girls Lacrosse | Amity | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 11:30 a.m. | W 15-1 | |
| Sat., 4/2 | V Softball | Hamden | Home - Cheshire HS-Softball Diamond [Directions] | 12:00 p.m. | W 15-0 | |
| Sat., 4/2 | JV Softball | Hamden | Home - Cheshire HS-Softball Diamond 2 [Directions] | Canceled | Cancelled | |
| Sat., 4/2 | JV Softball | Woodland | Home - Cheshire HS-Softball Diamond 2 [Directions] | 2:30 p.m. | ||
| Mon., 4/4 | V Baseball | Amity | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | L 6-15 | |
| Mon., 4/4 | FR Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | 4:00 p.m. | L 15-3 | |
| Mon., 4/4 | V Boys Tennis | Guilford | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Mon., 4/4 | V Softball | East Haven | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | L 2-5 | |
| Mon., 4/4 | JV Softball | East Haven | Home - Cheshire HS-Softball Diamond 2 [Directions] | Canceled | Cancelled | |
| Mon., 4/4 | V Girls Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/5 | JV Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | 4:00 p.m. | L 4-3 | |
| Tue., 4/5 | V Boys Lacrosse | Southington | Away - Southington HS-TURF FIELD [Directions] | 6:00 p.m. | W 17-4 | |
| Tue., 4/5 | JV Boys Lacrosse | Southington | Away - Southington HS-SubVLacrosse/Soccer [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Boys Volleyball | Newtown | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 4/5 | JV Boys Volleyball | Newtown | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Tue., 4/5 | V Girls Lacrosse | Conard | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:30 p.m. | W 9-7 | |
| Tue., 4/5 | JV Girls Lacrosse | Conard | Home - Cheshire HS-Bartlem Park [Directions] | 5:30 p.m. | W 14-0 | |
| Tue., 4/5 | V Softball | North Haven | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | W 7-6 | |
| Tue., 4/5 | JV Softball | North Haven | Home - Cheshire HS-Softball Diamond 2 [Directions] | 5:30 p.m. | ||
| Tue., 4/5 | V Girls Tennis | North Haven | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | L 2-6 [Detailed Results] | |
| Wed., 4/6 | FR Boys Lacrosse | Guilford | Home - Cheshire HS-Grass Fields [Directions] | Postponed | ||
| Wed., 4/6 | V Boys Outdoor Track | Guilford, Foran | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Wed., 4/6 | V Boys Volleyball | Kolbe Cathedral | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-1 | |
| Wed., 4/6 | JV Boys Volleyball | Kolbe Cathedral | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Wed., 4/6 | V Girls Outdoor Track | Guilford, Foran | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Thu., 4/7 | JV Baseball | Shelton | Home - Cheshire HS-Baseball Diamond [Directions] | Postponed | ||
| Thu., 4/7 | JV Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/7 | V Girls Lacrosse | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 6:30 p.m. | W 10-5 | |
| Thu., 4/7 | JV Girls Lacrosse | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 5:00 p.m. | W 11-7 | |
| Fri., 4/8 | V Baseball | North Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | W 10-2 | |
| Fri., 4/8 | FR Baseball | North Haven | Away - North Haven MS-Bailey Road Baseball Field [Directions] | 4:00 p.m. | L 9-3 | |
| Fri., 4/8 | V Boys Tennis | Xavier | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Fri., 4/8 | V Boys Volleyball | Darien | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 4/8 | JV Boys Volleyball | Darien | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 4/8 | FR Girls Lacrosse | East Lyme | Home - Cheshire High Main Game field [Directions] | 4:30 p.m. | W 9-8 | |
| Fri., 4/8 | V Softball | Shelton | Away - Shelton HS-Softball Diamond [Directions] | 4:15 p.m. | L 5-1 | |
| Fri., 4/8 | JV Softball | Shelton | Away - Shelton HS-Upper Field [Directions] | 5:45 p.m. | ||
| Sat., 4/9 | JV Baseball | North Haven | Away - North Haven MS-Bailey Road Baseball Field [Directions] | 10:30 a.m. | ||
| Sat., 4/9 | V Boys Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 6:00 p.m. | W 15-0 | |
| Sat., 4/9 | JV Boys Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | ||
| Sat., 4/9 | V Girls Lacrosse | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | 10:30 a.m. | W 19-5 | |
| Sat., 4/9 | JV Girls Lacrosse | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | 9:00 a.m. | W 14-0 | |
| Sun., 4/10 | Miscellaneous Events | 1/2 marathon | Home - Cheshire HS [Directions] | 7:00 a.m. | ||
| Mon., 4/11 | V Boys Lacrosse | Shelton | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 18-1 | |
| Mon., 4/11 | JV Boys Lacrosse | Shelton | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | V Boys Tennis | Fairfield Prep | Away - Fairfield University-Walsh Athletic Center - Tennis Courts [Directions] | 3:45 p.m. | L 2-5 [Detailed Results] | |
| Mon., 4/11 | V Boys Volleyball | Joel Barlow | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 4/11 | JV Boys Volleyball | Joel Barlow | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Mon., 4/11 | V Softball | Guilford | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | W 5-1 | |
| Mon., 4/11 | JV Softball | Guilford | Home - Cheshire HS-Softball Diamond 2 [Directions] | 5:45 p.m. | ||
| Mon., 4/11 | V Girls Tennis | Lauralton Hall | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Tue., 4/12 | V Baseball | Darien | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 4/12 | V Softball | Waterford | Away - Waterford HS-Lancer Softball Field [Directions] | 4:30 p.m. | W 5-4 | |
| Tue., 4/12 | JV Softball | Waterford | Away - Waterford HS-Veterans Softball Field - off campus [Directions] | 4:30 p.m. | ||
| Wed., 4/13 | V Baseball | Sheehan | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | W 7-2 | |
| Wed., 4/13 | FR Baseball | Sheehan | Home - Bartlem Park [Directions] | 4:00 p.m. | L 10-0 | |
| Wed., 4/13 | V Boys Tennis | Daniel Hand | Away - Polson MS, Madison-Polson Tennis Courts/DHHS Campus [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Wed., 4/13 | V Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | W 3-2 | |
| Wed., 4/13 | JV Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Softball | Lauralton Hall | Away - Lauralton Hall-Softball Varsity Diamond [Directions] | 4:15 p.m. | W 6-4 | |
| Wed., 4/13 | V Girls Tennis | Guilford | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Thu., 4/14 | V Baseball | Guilford | Home - Cheshire HS-Baseball Diamond [Directions] | 3:00 p.m. | W 5-4 | |
| Thu., 4/14 | JV Baseball | Sheehan | Away - Sheehan HS-Neubauer Baseball Field @ Sheehan HS [Directions] | 3:45 p.m. | ||
| Thu., 4/14 | FR Baseball | Guilford | Home - Bartlem Park [Directions] | 3:00 p.m. | W 13-3 | |
| Thu., 4/14 | FR Boys Lacrosse | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | V Boys Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | 1:00 p.m. | L 3-4 [Detailed Results] | |
| Thu., 4/14 | V Girls Lacrosse | Glastonbury | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 10:00 a.m. | W 15-7 | |
| Thu., 4/14 | JV Girls Lacrosse | Glastonbury | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 11:30 a.m. | W 14-1 | |
| Fri., 4/15 | V Boys Outdoor Track | Record Journal Track Meet | Away - Platt HS-Track | 11:00 a.m. | ||
| Fri., 4/15 | V Girls Outdoor Track | Record Journal Track Meet | Away - Platt HS-Track | 11:00 a.m. | ||
| Fri., 4/15 | Miscellaneous Events | Good Friday | Home - Cheshire HS [Directions] | 8:00 a.m. | ||
| Sat., 4/16 | JV Baseball | Guilford | Away - Guilford HS-Baseball Diamond [Directions] | 10:30 a.m. | L 7-6 | |
| Sat., 4/16 | V Boys Lacrosse | Glastonbury | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 1:00 p.m. | W 16-4 | |
| Sat., 4/16 | JV Boys Lacrosse | Glastonbury | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 11:00 a.m. | ||
| Sat., 4/16 | V Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 10:00 a.m. | L 13-14 | |
| Sat., 4/16 | JV Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 11:30 a.m. | W 13-3 | |
| Sun., 4/17 | Miscellaneous Events | Easter | Home - Cheshire HS [Directions] | 8:00 a.m. | ||
| Mon., 4/18 | V Baseball | Notre Dame-West Haven | Away - Quigley Stadium [Directions] | 3:45 p.m. | L 9-7 | |
| Mon., 4/18 | FR Baseball | Notre Dame-West Haven | Away - Painter Park-Harry Noyes Baseball Field [Directions] | 4:00 p.m. | L 5-4 (8) | |
| Mon., 4/18 | V Boys Golf | Hamden | Away - Laurel View Golf Course [Directions] | 2:15 p.m. | Cheshire 162 Hamden 191 | |
| Mon., 4/18 | FR Girls Lacrosse | Amity | Home - Bartlem Park [Directions] | 4:00 p.m. | W 16-1 | |
| Mon., 4/18 | V Softball | Lyman Hall | Away - Lyman Hall HS-Varsity Softball Field [Directions] | 3:45 p.m. | W 13-1 | |
| Mon., 4/18 | JV Softball | Lyman Hall | Away - Lyman Hall HS-JV Softball Field [Directions] | 5:15 p.m. | ||
| Tue., 4/19 | V Boys Lacrosse | Notre Dame-West Haven | Away - Notre Dame HS-Veteran's Stadium [Directions] | 6:00 p.m. | W 20-9 | |
| Tue., 4/19 | JV Boys Lacrosse | Notre Dame-West Haven | Away - Notre Dame HS-Veteran's Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/19 | V Girls Lacrosse | Guilford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | L 12-14 | |
| Tue., 4/19 | JV Girls Lacrosse | Guilford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:30 p.m. | W 17-1 | |
| Tue., 4/19 | FR Girls Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | 5:00 p.m. | W 15-5 | |
| Wed., 4/20 | V Baseball | Lyman Hall | Away - Pat Wall Field-Baseball Field [Directions] | 3:45 p.m. | L 4-3 | |
| Wed., 4/20 | JV Baseball | Notre Dame-West Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:15 p.m. | L 11-3 | |
| Wed., 4/20 | V Boys Outdoor Track | Hamden, Hillhouse | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Wed., 4/20 | V Boys Tennis | Branford | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Wed., 4/20 | V Boys Volleyball | Xavier | Away - Xavier HS-Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Wed., 4/20 | JV Boys Volleyball | Xavier | Away - Xavier HS-Gym [Directions] | 5:00 p.m. | ||
| Wed., 4/20 | V Girls Outdoor Track | Hamden, Hillhouse | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Wed., 4/20 | V Softball | Sheehan | Away - Sheehan HS-Sheehan HS Softball Field [Directions] | 3:45 p.m. | W 12-0 | |
| Wed., 4/20 | JV Softball | Sheehan | Away - Sheehan HS-Sheehan HS Softball Field [Directions] | Canceled | Cancelled | |
| Wed., 4/20 | V Girls Tennis | Shelton | Away - Shelton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/21 | V Baseball | West Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | W 6-5 | |
| Thu., 4/21 | V Boys Golf | Amity | Home - Farms Country club [Directions] | 2:30 p.m. | Cheshire 165 Amity 172 | |
| Thu., 4/21 | V Boys Lacrosse | Amity | Away - Amity Regional HS-Amity High School - Field # 3 [Directions] | 5:30 p.m. | W 16-3 | |
| Thu., 4/21 | JV Boys Lacrosse | Amity | Away - Amity Regional HS-Amity High School - Field # 3 [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Boys Tennis | Shelton | Away - Shelton HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 [Detailed Results] | |
| Fri., 4/22 | V Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:00 p.m. | W 3-1 | |
| Fri., 4/22 | JV Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 3:45 p.m. | ||
| Fri., 4/22 | V Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 5:45 p.m. | W 11-8 | |
| Fri., 4/22 | JV Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 4:00 p.m. | W 7-6 | |
| Fri., 4/22 | FR Girls Lacrosse | Glastonbury | Away - Glastonbury HS-Field 13 [Directions] | 4:00 p.m. | W 15-5 | |
| Fri., 4/22 | V Softball | Amity | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | 4:00 p.m. | W 14-5 | |
| Fri., 4/22 | JV Softball | Amity | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | 5:30 p.m. | ||
| Fri., 4/22 | V Girls Tennis | Sacred Heart Academy | Away - Hamden MS-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Sat., 4/23 | V Baseball | Guilford | Away - Guilford HS-Baseball Diamond [Directions] | 10:30 a.m. | L 3-1 | |
| Sat., 4/23 | JV Baseball | West Haven | Away - West Haven HS-Whitey Piurek Field [Directions] | 10:30 a.m. | L 8-7 | |
| Sat., 4/23 | FR Baseball | Guilford | Away - Long Hill Park-Guilford-Baseball Field [Directions] | 10:30 a.m. | W 7-2 | |
| Sat., 4/23 | V Boys Lacrosse | Simsbury | Away - Holden Field-Turf [Directions] | 1:00 p.m. | W 18-11 | |
| Sat., 4/23 | JV Boys Lacrosse | Simsbury | Away - Simsbury HS-Simsbury Grass Field [Directions] | 11:00 a.m. | ||
| Sun., 4/24 | Miscellaneous Events | Alumni banquet | Home - Cheshire HS [Directions] | 6:00 p.m. | ||
| Mon., 4/25 | V Baseball | Holy Cross | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | W 8-5 | |
| Mon., 4/25 | V Boys Golf | Sheehan | Away - Farms Country club [Directions] | 2:45 p.m. | Cheshire 154 Sheehan 189 | |
| Mon., 4/25 | FR Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Tennis | North Haven | Away - North Haven Athletic Complex-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Mon., 4/25 | V Boys Volleyball | Oxford | Home - Cheshire HS-Gym West [Directions] | 6:15 p.m. | W 3-0 | |
| Mon., 4/25 | JV Boys Volleyball | Oxford | Home - Cheshire HS-Gym West [Directions] | 5:30 p.m. | ||
| Mon., 4/25 | V Girls Golf | Mercy | Home - Southington Country Club [Directions] | 3:00 p.m. | CHS 192 Mercy 238 | |
| Mon., 4/25 | FR Girls Lacrosse | Hall | Away - Hall HS-Field Hockey Stadium [Directions] | 4:00 p.m. | W 13-1 | |
| Mon., 4/25 | V Girls Tennis | Mercy | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/26 | V Baseball | Shelton | Away - Shelton HS-Baseball Diamond - N Constitution Blvd [Directions] | 4:15 p.m. | L 5-1 | |
| Tue., 4/26 | FR Baseball | Shelton | Away - Nike Site - Shelton-Baseball FIeld [Directions] | 4:15 p.m. | W 7-5 | |
| Tue., 4/26 | FR Boys Lacrosse | Daniel Hand | Home - Cheshire HS-Bartlem Park [Directions] | Postponed | ||
| Tue., 4/26 | V Boys Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 4/26 | V Girls Lacrosse | Lauralton Hall | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 17-8 | |
| Tue., 4/26 | JV Girls Lacrosse | Lauralton Hall | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:30 p.m. | W 8-0 | |
| Wed., 4/27 | V Baseball | Branford | Away - Branford HS-Baseball Diamond [Directions] | 4:00 p.m. | W 11-1 | |
| Wed., 4/27 | V Boys Golf | Xavier | Home - Farms Country club [Directions] | 2:15 p.m. | Cheshire 173 Xavier 185 | |
| Wed., 4/27 | V Boys Outdoor Track | Career Magnet, Jonathan Law | Away - Bowen Field-Track [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Girls Golf | St. Paul Catholic, Suffield | Away - Westwoods Golf Course [Directions] | 2:45 p.m. | CHS 156 St. Paul 165 Suffield 221 | |
| Wed., 4/27 | V Girls Outdoor Track | Career Magnet, Jonathan Law | Away - Bowen Field-Track [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Softball | Southington | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | L 1-14 | |
| Wed., 4/27 | JV Softball | Southington | Home - Cheshire HS-Softball Diamond 2 [Directions] | 5:45 p.m. | ||
| Wed., 4/27 | V Girls Tennis | Foran | Away - Foran HS -Richard A. Herman Memorial Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/27 | Miscellaneous Events | Dodd track | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Thu., 4/28 | JV Baseball | Branford | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | W 18-16 | |
| Thu., 4/28 | V Boys Golf | Shelton | Away - Highland Golf Club [Directions] | 2:45 p.m. | Cheshire 180 Shelton 176 | |
| Thu., 4/28 | V Boys Lacrosse | Fairfield Prep | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | L 11-12 | |
| Thu., 4/28 | JV Boys Lacrosse | Fairfield Prep | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Girls Golf | Newington, Conard | Away - Indian Hill Country Club [Directions] | 3:00 p.m. | CHS 210 Newington 217 Conard 203 | |
| Thu., 4/28 | V Softball | Guilford | Away - Guilford HS-Varsity softball field [Directions] | 4:15 p.m. | L 5-6 | |
| Thu., 4/28 | JV Softball | Guilford | Away - Guilford HS-Varsity softball field [Directions] | 5:30 p.m. | ||
| Fri., 4/29 | FR Boys Lacrosse | Guilford | Away - Guilford HS-Maturo Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Boys Tennis | Sheehan | Away - Sheehan HS-Sheehan HS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 [Detailed Results] | |
| Fri., 4/29 | V Girls Lacrosse | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 4:15 p.m. | L 10-11 | |
| Fri., 4/29 | JV Girls Lacrosse | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 6:00 p.m. | W 15-2 | |
| Sat., 4/30 | Miscellaneous Events | jr prom | Home - Cheshire HS [Directions] | 5:00 p.m. | ||
| Mon., 5/2 | V Boys Lacrosse | Daniel Hand | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 15-13 | |
| Mon., 5/2 | V Boys Tennis | Notre Dame-West Haven | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Mon., 5/2 | V Boys Volleyball | Brookfield | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 5/2 | JV Boys Volleyball | Brookfield | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Mon., 5/2 | V Girls Golf | Daniel Hand, Glastonbury | Home - Southington Country Club [Directions] | 2:30 p.m. | CHS 186 Hand 243 Glastonbury 194 | |
| Mon., 5/2 | FR Girls Lacrosse | Conard | Away - Conard HS-North Field [Directions] | 4:00 p.m. | W 11-0 | |
| Tue., 5/3 | V Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | 3:45 p.m. | L 2-1 | |
| Tue., 5/3 | JV Baseball | Amity | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | L 5-1 | |
| Tue., 5/3 | FR Baseball | Amity | Away - Old Tavern Road Complex-Brinley Field [Directions] | 3:45 p.m. | W 3-2 | |
| Tue., 5/3 | V Boys Golf | Fairfield Prep | Home - Farms Country club [Directions] | 2:15 p.m. | Cheshire 159 Fairfield Prep 151 | |
| Tue., 5/3 | V Boys Tennis | Jonathan Law | Away - Jonathan Law HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Tue., 5/3 | V Softball | Mercy | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | W 13-1 | |
| Tue., 5/3 | JV Softball | Mercy | Home - Cheshire HS-Softball Diamond 2 [Directions] | 5:45 p.m. | ||
| Tue., 5/3 | Miscellaneous Events | Dodd track | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Wed., 5/4 | JV Boys Lacrosse | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | 6:15 p.m. | ||
| Wed., 5/4 | V Boys Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 5/4 | JV Boys Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Thu., 5/5 | JV Baseball | Shelton | Away - Riverview Park - Shelton-Baseball Field [Directions] | 4:00 p.m. | L 20-10 | |
| Thu., 5/5 | FR Baseball | Shelton | Home - Bartlem Park [Directions] | 4:00 p.m. | W 14-1 | |
| Thu., 5/5 | V Boys Golf | Guilford | Away - Madison Country Club [Directions] | 2:00 p.m. | Cheshire 153 Guilford 168 | |
| Thu., 5/5 | V Boys Lacrosse | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 6:00 p.m. | W 17-6 | |
| Thu., 5/5 | JV Boys Lacrosse | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Boys Outdoor Track | Lyman Hall | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Thu., 5/5 | V Girls Golf | Canton | Home - Southington Country Club [Directions] | 3:00 p.m. | CHS 186 Canton 253 | |
| Thu., 5/5 | V Girls Lacrosse | Sacred Heart Academy | Away - Sacred Heart Academy-Lacrosse Field [Directions] | 4:15 p.m. | W 17-5 | |
| Thu., 5/5 | JV Girls Lacrosse | Sacred Heart Academy | Away - Sacred Heart Academy-Lacrosse Field [Directions] | 5:45 p.m. | ||
| Thu., 5/5 | FR Girls Lacrosse | Guilford | Home - Bartlem Park [Directions] | 4:00 p.m. | W 15-6 | |
| Thu., 5/5 | V Girls Outdoor Track | Lyman Hall | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Thu., 5/5 | V Softball | Lauralton Hall | Home - Cheshire HS-Softball Diamond [Directions] | 5:00 p.m. | W 4-1 | |
| Fri., 5/6 | V Baseball | North Haven | Away - North Haven Athletic Complex-Robert E. DeMayo Field [Directions] | 3:30 p.m. | L 6-1 | |
| Fri., 5/6 | FR Baseball | North Haven | Away - North Haven MS-Bailey Road Baseball Field [Directions] | 3:45 p.m. | L 8-3 | |
| Fri., 5/6 | FR Boys Lacrosse | Daniel Hand | Away - Daniel Hand HS-Janssen Field #2/DHHS Campus [Directions] | 5:00 p.m. | ||
| Fri., 5/6 | V Boys Outdoor Track | Middletown | Away - Middletown HS-MHS Stadium [Directions] | 4:00 p.m. | ||
| Fri., 5/6 | V Boys Volleyball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 5/6 | FR Girls Lacrosse | Glastonbury | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Fri., 5/6 | V Girls Outdoor Track | Middletown | Away - Middletown HS-MHS Stadium [Directions] | 4:00 p.m. | ||
| Sat., 5/7 | JV Baseball | North Haven | Home - Cheshire HS-Baseball Diamond [Directions] | Postponed | ||
| Sat., 5/7 | V Boys Outdoor Track | Middletown | Away - Middletown HS-MHS Stadium [Directions] | 12:00 p.m. | ||
| Sat., 5/7 | V Girls Lacrosse | Wilton | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | L 7-15 | |
| Sat., 5/7 | JV Girls Lacrosse | Wilton | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:30 p.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Middletown | Away - Middletown HS-MHS Stadium [Directions] | 12:00 p.m. | ||
| Sat., 5/7 | JV Softball | Woodland | Away - Woodland HS-Softball Diamond [Directions] | Canceled | Cancelled | |
| Mon., 5/9 | V Baseball | Sheehan | Away - Sheehan HS-Neubauer Baseball Field @ Sheehan HS [Directions] | 3:45 p.m. | W 14-4 | |
| Mon., 5/9 | FR Baseball | Sheehan | Away - West Side Field-Baseball Field [Directions] | 4:00 p.m. | W 15-2 | |
| Mon., 5/9 | V Boys Golf | Notre Dame-West Haven | Home - Farms Country club [Directions] | 2:15 p.m. | Cheshire 167 Notre Dame 187 | |
| Mon., 5/9 | V Boys Lacrosse | Guilford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 18-7 | |
| Mon., 5/9 | JV Boys Lacrosse | Guilford | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Tennis | Amity | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | L 2-5 [Detailed Results] | |
| Mon., 5/9 | V Boys Volleyball | Norwich Free Academy | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 5/9 | JV Boys Volleyball | Norwich Free Academy | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Mon., 5/9 | FR Girls Lacrosse | East Lyme | Away - East Lyme HS-Back Field Hockey Field [Directions] | 4:30 p.m. | L 6-11 | |
| Mon., 5/9 | V Softball | Mercy | Away - Mercy HS-Softball Diamond [Directions] | 4:15 p.m. | W 19-9 | |
| Mon., 5/9 | JV Softball | Mercy | Away - Mercy HS-Softball Diamond [Directions] | 5:45 p.m. | ||
| Mon., 5/9 | V Girls Tennis | North Haven | Away - North Haven Athletic Complex-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Tue., 5/10 | JV Baseball | Sheehan | Home - Cheshire HS-Baseball Diamond [Directions] | 3:30 p.m. | L 11-1 | |
| Tue., 5/10 | V Boys Golf | East Haven | Home - Farms Country club [Directions] | 2:30 p.m. | Cheshire 165 East Haven 203 | |
| Tue., 5/10 | FR Boys Lacrosse | Fairfield Prep | Home - Bartlem Park [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Boys Outdoor Track | West Haven, Shelton | Away - West Haven HS-Ken Strong Stadium [Directions] | 3:45 p.m. | ||
| Tue., 5/10 | V Boys Volleyball | Xavier | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 5/10 | JV Boys Volleyball | Xavier | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Tue., 5/10 | V Girls Golf | Hall | Away - Rockledge Golf Club West Hartford [Directions] | 3:00 p.m. | CHS 209 Hall 188 | |
| Tue., 5/10 | V Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 6:00 p.m. | L 9-18 | |
| Tue., 5/10 | JV Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 4:30 p.m. | ||
| Tue., 5/10 | V Girls Outdoor Track | West Haven, Shelton | Away - West Haven HS-Ken Strong Stadium [Directions] | 3:45 p.m. | ||
| Tue., 5/10 | V Girls Tennis | Sheehan | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/10 | Miscellaneous Events | Dodd track | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Wed., 5/11 | V Baseball | Notre Dame-West Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | L 10-0 | |
| Wed., 5/11 | FR Baseball | Notre Dame-West Haven | Home - Bartlem Park [Directions] | 4:00 p.m. | W 5-4 | |
| Wed., 5/11 | V Boys Tennis | Xavier | Away - Wesleyan University-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Wed., 5/11 | V Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 6:00 p.m. | W 3-1 | |
| Wed., 5/11 | JV Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 5/11 | V Girls Golf | St. Paul Catholic | Home - Southington Country Club [Directions] | 3:00 p.m. | CHS 189 St. Paul 190 | |
| Wed., 5/11 | FR Girls Lacrosse | Amity | Away - Amity Regional HS-Amity High School - Field # 3 [Directions] | 3:45 p.m. | W 12-0 | |
| Wed., 5/11 | V Girls Tennis | Daniel Hand | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 4:00 p.m. | L 2-5 [Detailed Results] | |
| Thu., 5/12 | V Baseball | Shelton | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | W 7-6 | |
| Thu., 5/12 | JV Baseball | Notre Dame-West Haven | Away - Quigley Stadium [Directions] | 4:00 p.m. | W 7-5 | |
| Thu., 5/12 | FR Baseball | Wolcott | Away - BAW 90' Sr. Field [Directions] | 3:45 p.m. | ||
| Thu., 5/12 | FR Baseball | Wolcott | Away - BAW 90' Sr. Field [Directions] | 4:00 p.m. | L 11-6 | |
| Thu., 5/12 | V Boys Golf | Hamden | Home - Southington Country Club [Directions] | 2:15 p.m. | Cheshire 156 Hamden 199 | |
| Thu., 5/12 | V Boys Lacrosse | Lyman Hall | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 25-10 | |
| Thu., 5/12 | JV Boys Lacrosse | Lyman Hall | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Girls Golf | Berlin | Home - Southington Country Club [Directions] | 3:00 p.m. | CHS 194 Berlin 176 | |
| Thu., 5/12 | V Softball | Lyman Hall | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | W 9-0 | |
| Thu., 5/12 | JV Softball | Lyman Hall | Home - Cheshire HS-Softball Diamond 2 [Directions] | 5:45 p.m. | ||
| Fri., 5/13 | V Baseball | Lyman Hall | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | L 8-16 | |
| Fri., 5/13 | V Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 5:30 p.m. | W 10-8 | |
| Fri., 5/13 | JV Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 7:00 p.m. | ||
| Fri., 5/13 | V Boys Tennis | Fairfield Prep | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Fri., 5/13 | V Girls Lacrosse | Daniel Hand | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 11-9 | |
| Fri., 5/13 | JV Girls Lacrosse | Daniel Hand | Home - Cheshire HS-Bartlem Park [Directions] | 4:30 p.m. | ||
| Fri., 5/13 | V Softball | East Haven | Away - East Haven HS-Softball Diamond [Directions] | 4:30 p.m. | L 2-15 | |
| Fri., 5/13 | JV Softball | East Haven | Away - East Haven HS-Softball Diamond [Directions] | Canceled | Cancelled | |
| Fri., 5/13 | V Girls Tennis | Lauralton Hall | Away - Eisenhower Park-Eisenhower [Directions] | 5:00 p.m. | W 5-2 [Detailed Results] | |
| Sat., 5/14 | JV Baseball | Lyman Hall | Away - Pat Wall Field-Baseball Field [Directions] | 10:00 a.m. | W 12-2 | |
| Sat., 5/14 | FR Girls Lacrosse | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 10:00 a.m. | L 2-11 | |
| Sat., 5/14 | Miscellaneous Events | senior prom | Home - Cheshire HS [Directions] | 5:00 p.m. | ||
| Mon., 5/16 | V Baseball | West Haven | Away - West Haven HS-Whitey Piurek Field [Directions] | 3:15 p.m. | L 4-3 | |
| Mon., 5/16 | V Boys Golf | Coginchaug | Away - Coginchaug-Lyman Orchards Golf course [Directions] | 3:00 p.m. | Cheshire 158 Coginchaug 191 | |
| Mon., 5/16 | FR Boys Lacrosse | Xavier | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | V Boys Tennis | Daniel Hand | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 2:00 p.m. | L 0-7 [Detailed Results] | |
| Mon., 5/16 | V Girls Golf | Mercy | Away - Lyman Orchards -Jones Course [Directions] | 2:20 p.m. | CHS 178 Mercy 212 | |
| Mon., 5/16 | V Girls Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | 1:45 p.m. | L 3-4 [Detailed Results] | |
| Tue., 5/17 | JV Baseball | West Haven | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Boys Golf | Amity | Away - The Tradition Golf Club at Oak Lane [Directions] | 2:40 p.m. | Cheshire 161 Amity 171 | |
| Tue., 5/17 | V Boys Lacrosse | New Fairfield | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 19-5 | |
| Tue., 5/17 | JV Boys Lacrosse | New Fairfield | Home - Cheshire HS-Grass Fields [Directions] | Canceled | Cancelled | |
| Tue., 5/17 | FR Boys Lacrosse | Amity | Away - Amity Regional HS-Amity High School - Field # 3 [Directions] | Canceled | Cancelled | |
| Tue., 5/17 | V Boys Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 5/17 | V Boys Volleyball | Simsbury | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 1-3 | |
| Tue., 5/17 | JV Boys Volleyball | Simsbury | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Tue., 5/17 | V Girls Golf | Amity | Home - Southington Country Club [Directions] | 3:00 p.m. | CHS 178 Amity 202 | |
| Tue., 5/17 | V Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | 3:45 p.m. | W 20-10 | |
| Tue., 5/17 | JV Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | 5:15 p.m. | ||
| Tue., 5/17 | V Softball | Amity | Home - Cheshire HS-Softball Diamond [Directions] | 4:30 p.m. | W 4-3 | |
| Tue., 5/17 | JV Softball | Amity | Home - Cheshire HS-Softball Diamond 2 [Directions] | 6:00 p.m. | ||
| Tue., 5/17 | V Girls Tennis | Amity | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. | L 2-5 [Detailed Results] | |
| Wed., 5/18 | V Baseball | Branford | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | W 8-7 | |
| Wed., 5/18 | FR Baseball | Coginchaug | Home - Bartlem Park [Directions] | 3:30 p.m. | L 15-11 | |
| Wed., 5/18 | FR Baseball | Branford | Home - Bartlem Park [Directions] | Canceled | Cancelled | |
| Wed., 5/18 | V Boys Outdoor Track | SCC West Division Championship | Away - Bowen Field-Track | 12:30 p.m. | ||
| Wed., 5/18 | V Boys Volleyball | Southington | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 1-3 | |
| Wed., 5/18 | JV Boys Volleyball | Southington | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Wed., 5/18 | V Girls Golf | Daniel Hand | Away - Madison Country Club [Directions] | 2:30 p.m. | CHS 194 Hand 214 | |
| Wed., 5/18 | FR Girls Lacrosse | North Haven | Home - Bartlem Park [Directions] | 4:00 p.m. | W 16-2 | |
| Wed., 5/18 | V Girls Outdoor Track | SCC West Div Championship | Away - Bowen Field-Track | 12:30 p.m. | ||
| Wed., 5/18 | V Softball | North Haven | Away - North Haven Athletic Complex-Varsity Softball Field [Directions] | 4:15 p.m. | W 15-3 | |
| Wed., 5/18 | V Girls Tennis | Daniel Hand | Away - Polson MS, Madison-Polson Tennis Courts/DHHS Campus [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Wed., 5/18 | Miscellaneous Events | Dodd track | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Thu., 5/19 | JV Baseball | Branford | Away - Branford HS-Baseball Diamond [Directions] | Postponed | ||
| Thu., 5/19 | V Boys Golf | Xavier | Away - Portland Golf Course [Directions] | 2:00 p.m. | Cheshire 159 Xavier 163 | |
| Thu., 5/19 | V Boys Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | 7:00 p.m. | W 21-8 | |
| Thu., 5/19 | JV Boys Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Boys Outdoor Track | SCC Boys Novice Meet | Away - Daniel Hand HS-DHHS Track | 3:30 p.m. | ||
| Thu., 5/19 | V Boys Tennis | Southington | Away - Southington HS-Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Thu., 5/19 | V Girls Lacrosse | Sacred Heart Academy | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 14-6 | |
| Thu., 5/19 | JV Girls Lacrosse | Sacred Heart Academy | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:00 p.m. | ||
| Fri., 5/20 | FR Boys Lacrosse | Notre Dame-West Haven | Home - Cheshire HS [Directions] | 5:00 p.m. | ||
| Fri., 5/20 | V Boys Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 1-3 | |
| Fri., 5/20 | JV Boys Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 5/20 | V Girls Golf | Amity | Away - Race Brook C.C. [Directions] | 2:45 p.m. | CHS 195 Amity 186 | |
| Fri., 5/20 | FR Girls Lacrosse | Guilford | Away - Guilford HS-@ Long Hill Road [Directions] | 4:00 p.m. | ||
| Fri., 5/20 | V Girls Outdoor Track | SCC Novice Championship | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) | 3:45 p.m. | ||
| Fri., 5/20 | V Softball | Shelton | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | W 4-3 | |
| Fri., 5/20 | JV Softball | Shelton | Home - Cheshire HS-Softball Diamond 2 [Directions] | 5:30 p.m. | ||
| Fri., 5/20 | V Girls Tennis | Jonathan Law | Away - Jonathan Law HS-Tennis Courts [Directions] | 12:00 p.m. | W 6-1 [Detailed Results] | |
| Sat., 5/21 | JV Baseball | Holy Cross | Away - Holy Cross-Alumni Field [Directions] | Canceled | Cancelled | |
| Sat., 5/21 | JV Baseball | Amity | Away - Old Tavern Road Complex-Brinley Field [Directions] | 3:00 p.m. | ||
| Sat., 5/21 | V Boys Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | 12:00 p.m. | ||
| Sat., 5/21 | V Girls Tennis | North Haven | Away - North Haven Athletic Complex-Tennis Courts [Directions] | 3:45 p.m. | ||
| Mon., 5/23 | V Boys Golf | Daniel Hand | Away - Madison Country Club [Directions] | 2:00 p.m. | Cheshire 158 Hand 168 | |
| Mon., 5/23 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | Canceled | Cancelled | |
| Mon., 5/23 | V Boys Volleyball | Pomperaug | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | W 3-2 | |
| Mon., 5/23 | JV Boys Volleyball | Pomperaug | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Mon., 5/23 | V Softball | West Haven | Away - West Haven HS-Frank Biondi Field [Directions] | 7:00 p.m. | ||
| Mon., 5/23 | Miscellaneous Events | Signing day | Home - Cheshire HS [Directions] | 2:00 p.m. | ||
| Tue., 5/24 | V Boys Golf | Guilford | Home - Farms Country club [Directions] | 2:30 p.m. | Cheshire 159 Guilford 161 | |
| Tue., 5/24 | V Boys Lacrosse | Daniel Hand | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:30 p.m. | ||
| Tue., 5/24 | V Boys Outdoor Track | SCC Championship | Away - Bowen Field-Track | 3:00 p.m. | ||
| Tue., 5/24 | V Girls Golf | Newington | Home - Southington Country Club [Directions] | 3:00 p.m. | CHS 184 Newington 212 | |
| Tue., 5/24 | V Girls Lacrosse | Amity | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:00 p.m. | W 20-8 | |
| Tue., 5/24 | V Girls Outdoor Track | SCC Championship | Away - Bowen Field-Track | 2:00 p.m. | ||
| Tue., 5/24 | Miscellaneous Events | Senior awards night | Home - Cheshire HS [Directions] | 6:00 p.m. | ||
| Wed., 5/25 | V Baseball | North Haven (Scrim.) | Away - North Haven Athletic Complex-Robert E. DeMayo Field [Directions] | 4:15 p.m. | ||
| Wed., 5/25 | V Boys Golf | Fairfield Prep | Away - Patterson Club [Directions] | 3:00 p.m. | Cheshire 159 Fairfield Prep 168 | |
| Wed., 5/25 | FR Boys Lacrosse | Southington | Home - Cheshire High Main Game field [Directions] | Canceled | Cancelled | |
| Wed., 5/25 | V Boys Volleyball | Xavier | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Wed., 5/25 | V Girls Golf | Lauralton Hall | Away - Oronoque Country Club [Directions] | 2:30 p.m. | CHS 183 Lauralton 213 | |
| Wed., 5/25 | V Girls Outdoor Track | Amity, Lyman Hall, Sheehan, Shelton | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Thu., 5/26 | V Boys Lacrosse | Fairfield Prep | Away - West Haven HS-Ken Strong Stadium [Directions] | 7:30 p.m. | ||
| Thu., 5/26 | V Girls Lacrosse | Guilford | Away - West Haven HS-Frank Biondi Field [Directions] | 5:30 p.m. | L 6-12 | |
| Fri., 5/27 | V Boys Tennis | Naugatuck | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:00 p.m. | W 7-0 [Detailed Results] | |
| Fri., 5/27 | V Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 6:00 p.m. | ||
| Fri., 5/27 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 2:00 p.m. | ||
| Sat., 5/28 | V Girls Lacrosse | Conard | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 11:30 a.m. | W 14-11 | |
| Mon., 5/30 | Miscellaneous Events | Memorial Day | Home - Cheshire HS [Directions] | 8:00 a.m. | ||
| Tue., 5/31 | V Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Boys Tennis | East Lyme | Away - East Lyme HS-Tennis Court 6 [Directions] | 3:00 p.m. | ||
| Tue., 5/31 | V Girls Golf | Canton | Away - Blue Fox Run Golf Course [Directions] | 3:00 p.m. | CHS 175 Canton 250 | |
| Tue., 5/31 | V Girls Lacrosse | Farmington | Away - Farmington HS-Turf Field [Directions] | 5:00 p.m. | W 12-7 | |
| Tue., 5/31 | V Softball | Simsbury | Home - Cheshire HS-Softball Diamond [Directions] | 3:30 p.m. | ||
| Wed., 6/1 | V Boys Lacrosse | Xavier | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | ||
| Wed., 6/1 | V Boys Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/1 | V Boys Volleyball | Maloney | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Wed., 6/1 | V Girls Golf | Lauralton Hall | Home - Southington Country Club [Directions] | 3:00 p.m. | ||
| Wed., 6/1 | V Girls Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/1 | V Softball | Bristol Central | Away - Bristol Central HS-Softball Field [Directions] | Postponed | ||
| Thu., 6/2 | V Girls Golf | SCC Girls Golf Championship | Away - Lauralton Hall-Oronoque CC | 8:00 a.m. | ||
| Thu., 6/2 | V Softball | Bristol Central | Away - Casey Field-Softball Field [Directions] | Suspended | ||
| Fri., 6/3 | V Boys Volleyball | Xavier | Away - Xavier HS-Gym [Directions] | 6:00 p.m. | ||
| Fri., 6/3 | V Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | ||
| Fri., 6/3 | V Softball | Bristol Central | Away - Casey Field-Softball Field [Directions] | 10:00 a.m. | ||
| Sat., 6/4 | V Boys Lacrosse | Joel Barlow | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 3:00 p.m. | ||
| Mon., 6/6 | V Boys Golf | CIAC Division I Spring Championship | Away - Stanley GC | 8:00 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Golf | CIAC Division I Championship | Away - Tashua Knolls GC | 8:30 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Lacrosse | Wilton | Home - Jonathan Law HS-Lawmen Stadium [Directions] | 7:30 p.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Boys Golf | CIAC State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/11 | V Girls Golf | CIAC Girls State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||