| Cheshire 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 593 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Wed., 8/24 | V Football | TBA, Guilford, Shelton | Away - TBA | 3:00 p.m. | 2:30 PM | |
| Sat., 8/27 | V Football | Darien, Simsbury (Scrim.) | Home - Cheshire High Main Game field [Directions] | 9:00 a.m. | ||
| Tue., 8/30 | V Boys Soccer | Glastonbury (Scrim.) | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Tue., 8/30 | V Field Hockey | Simsbury (Scrim.) | Away - Holden Field-Turf [Directions] | 3:45 p.m. | 2:30 PM | |
| Tue., 8/30 | V Girls Soccer | Glastonbury (Scrim.) | Away - Glastonbury HS-Turf Field [Directions] | 4:15 p.m. | 2:30 PM | |
| Wed., 8/31 | V Field Hockey | Pomperaug (Scrim.) | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Wed., 8/31 | Miscellaneous Events | fall parent | Home - Cheshire HS [Directions] | 6:30 p.m. | ||
| Thu., 9/1 | V Football | Windsor (Scrim.) | Away - Windsor HS-Jack O'Brien Stadium [Directions] | 6:00 p.m. | 4:00 PM; 2 Buses | |
| Thu., 9/1 | V Boys Soccer | Naugatuck (Scrim.) | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Sat., 9/3 | V Boys Soccer | Pomperaug (Scrim.) | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Sat., 9/3 | V Field Hockey | Avon Pre Season Jamboree | Away - Avon HS-Turf Field | 8:00 a.m. | 6:45 AM | |
| Sat., 9/3 | V Girls Volleyball | Glastonbury Jamboree | Away - Glastonbury HS-Gym | 8:00 a.m. | 7:00 AM | |
| Sun., 9/4 | V Girls Soccer | Weston (Scrim.) | Home - Treadwell Park-Treadwell Town Park--Tilson Field [Directions] | 11:00 a.m. | ||
| Sun., 9/4 | V Girls Soccer | Pomperaug (Scrim.) | Home - Treadwell Park-Newtown Treadwell Park [Directions] | 11:40 a.m. | ||
| Sun., 9/4 | V Girls Soccer | Newtown (Scrim.) | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 9:00 a.m. | ||
| Mon., 9/5 | V Boys Soccer | Southington (Scrim.) | Away - Southington HS-3 TURF FIELD [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 9/6 | V Field Hockey | Glastonbury (Scrim.) | Home - Cheshire High Main Game field [Directions] | Cancelled | ||
| Tue., 9/6 | V Girls Soccer | Pomperaug (Scrim.) | Away - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | 5:00 PM | |
| Wed., 9/7 | V Girls Volleyball | Choate Rosemary Hall (Scrim.) | Away - Choate Rosemary Hall-Gym | 3:45 p.m. | 2:30 PM | |
| Thu., 9/8 | V Boys Cross Country | North Haven, Fairfield Prep, Foran | Away - Wharton Brook State Park [Directions] | 3:45 p.m. | 2:30 PM | |
| Thu., 9/8 | V Girls Cross Country | North Haven, Lauralton Hall, Foran | Away - Wharton Brook State Park [Directions] | 3:45 p.m. | 2:30 PM | |
| Thu., 9/8 | V Field Hockey | Sacred Heart Academy | Home - Cheshire High Main Game field [Directions] | W 1-0 | ||
| Thu., 9/8 | V Girls Swimming and Diving | Mercy | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | ||
| Thu., 9/8 | V Girls Volleyball | Mercy | Home - Cheshire HS-Gym West [Directions] | W 3-1 | ||
| Fri., 9/9 | V Football | New Milford | Home - Cheshire High Main Game field [Directions] | W 35-7 | ||
| Fri., 9/9 | V Girls Soccer | Amity | Away - Amity Regional HS-AHS Grass Field # 3 [Directions] | W 2-1 | 2:30 PM | |
| Sat., 9/10 | V Boys Soccer | Foran | Home - Cheshire High Main Game field [Directions] | W 3-1 | ||
| Sat., 9/10 | Miscellaneous Events | Fall festival | Home - Bartlem Park [Directions] | 8:00 a.m. | ||
| Tue., 9/13 | V Boys Soccer | Notre Dame-West Haven | Away - Veterans Memorial Park (West Haven, CT)-Field [Directions] | L 4-1 | 2:30 PM | |
| Tue., 9/13 | V Field Hockey | Lyman Hall | Home - Cheshire High Main Game field [Directions] | W 8-0 | ||
| Tue., 9/13 | V Girls Soccer | Guilford | Home - Cheshire High Main Game field [Directions] | W 2-0 | ||
| Tue., 9/13 | V Girls Swimming and Diving | Foran | Away - Foran HS -Pool [Directions] | 3:45 p.m. | 2:30 PM | |
| Wed., 9/14 | V Girls Volleyball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | W 3-1 | 2:30 PM | |
| Thu., 9/15 | V Girls Volleyball | Bristol Central | Home - Cheshire HS-Gym West [Directions] | W 3-1 | ||
| Fri., 9/16 | V Football | Hillhouse | Away - Bowen Field-Football Field [Directions] | W 30-0 | 4:00 PM; 2 Buses | |
| Fri., 9/16 | V Field Hockey | Guilford | Home - Cheshire High Main Game field [Directions] | W 2-1 | ||
| Fri., 9/16 | V Girls Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | W 5-0 | ||
| Fri., 9/16 | V Girls Swimming and Diving | Branford | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | ||
| Sat., 9/17 | V Boys Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | 7:00 AM | |
| Sat., 9/17 | V Boys Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | W 5-0 | ||
| Sat., 9/17 | V Girls Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | 7:30 AM | |
| Tue., 9/20 | V Boys Cross Country | Daniel Hand, Career Magnet, Hamden | Away - Madison Surf Club-Surf Club [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 9/20 | V Boys Soccer | Branford | Away - Branford HS-Athletic Turf Field [Directions] | W 7-0 | 4:30 PM | |
| Tue., 9/20 | V Girls Cross Country | Daniel Hand, Career Magnet, Hamden | Away - Madison Surf Club-Surf Club [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 9/20 | V Field Hockey | Mercy | Home - Cheshire High Main Game field [Directions] | W 7-0 | ||
| Tue., 9/20 | V Girls Soccer | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | W 8-0 | 2:30 PM | |
| Tue., 9/20 | V Girls Swimming and Diving | East Haven/Cross/Hillhouse/SHA | Away - Wilbur Cross HS-Swimming Pool [Directions] | 3:45 p.m. | 2:30 PM | |
| Tue., 9/20 | V Girls Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | L 2-3 | 2:30 PM | |
| Wed., 9/21 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | W 3-1 | 2:30 PM | |
| Thu., 9/22 | V Field Hockey | Farmington | Away - Farmington HS-Turf Field [Directions] | L 1-0 | 2:30 PM | |
| Thu., 9/22 | V Girls Soccer | Branford | Away - Branford HS-Athletic Turf Field [Directions] | W 2-0 | 4:30 PM | |
| Fri., 9/23 | V Football | Conard | Away - Conard HS-McKee Stadium [Directions] | W 34-7 | 4:00 PM | |
| Fri., 9/23 | V Boys Soccer | West Haven | Home - Cheshire High Main Game field [Directions] | W 4-1 | ||
| Fri., 9/23 | V Girls Swimming and Diving | Lyman Hall | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | ||
| Fri., 9/23 | V Girls Volleyball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | W 3-0 | 3:00 PM | |
| Sat., 9/24 | V Boys Cross Country | Winding Trails | Away - Winding Trails-Cross Country Course | 9:00 a.m. | 7:30 AM | |
| Sat., 9/24 | V Girls Cross Country | Farmington | Away - Winding Trails-Cross Country Course [Directions] | 9:00 a.m. | 7:30 AM | |
| Sat., 9/24 | V Field Hockey | New Canaan | Home - Cheshire High Main Game field [Directions] | L 2-0 | ||
| Sat., 9/24 | V Girls Soccer | Wilbur Cross | Home - Cheshire High Main Game field [Directions] | W 12-0 | ||
| Mon., 9/26 | Miscellaneous Events | Rosh Hashanah | Home - Cheshire HS [Directions] | 8:00 a.m. | ||
| Tue., 9/27 | V Boys Soccer | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | L 2-1 | 2:30 PM | |
| Tue., 9/27 | V Field Hockey | Amity | Home - Cheshire High Main Game field [Directions] | W 2-1 | ||
| Tue., 9/27 | V Girls Soccer | Sacred Heart Academy | Away - Sacred Heart Academy-Soccer Field [Directions] | W 2-0 | 2:30 PM | |
| Tue., 9/27 | V Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | W 3-1 | 2:30 PM | |
| Tue., 9/27 | Miscellaneous Events | Rosh Hashanah Ends | Home - Cheshire HS [Directions] | 12:00 p.m. | ||
| Wed., 9/28 | V Girls Volleyball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Thu., 9/29 | V Boys Cross Country | SCCDiv championship | Away - Guilford Fairgrounds | 5:30 p.m. | ||
| Thu., 9/29 | V Boys Cross Country | SCC Divisional Championship Boys Housatonic & Oronoque | Away - Guilford HS-Guilford Fair grounds | 5:30 p.m. | 2:30 PM | |
| Thu., 9/29 | V Girls Cross Country | SCC Div championship | Away - Guilford Fairgrounds | 5:00 p.m. | ||
| Thu., 9/29 | V Girls Cross Country | SCC Divisional Championship Girls Housatonic & Oronoque | Away - Guilford HS-Guilford Fair grounds | 5:00 p.m. | 2:30 PM | |
| Thu., 9/29 | V Field Hockey | Branford | Away - Branford HS-Athletic Turf Field [Directions] | W 1-0 | 4:00 PM | |
| Fri., 9/30 | V Boys Cross Country | Nonnewaug | Away - Nonnewaug HS [Directions] | 3:30 p.m. | 2:00 PM | |
| Fri., 9/30 | V Football | Daniel Hand | Home - Cheshire High Main Game field [Directions] | W 28-0 | ||
| Fri., 9/30 | V Girls Cross Country | Nonnewaug | Away - Nonnewaug HS [Directions] | 5:00 p.m. | ||
| Fri., 9/30 | V Girls Soccer | Foran | Away - Foran HS -Brewster Field [Directions] | W 3-1 | 4:00 PM | |
| Fri., 9/30 | V Girls Swimming and Diving | Jonathan Law | Away - Foran HS -Pool [Directions] | 5:00 p.m. | 3:30 PM | |
| Fri., 9/30 | V Girls Volleyball | Branford | Home - Cheshire HS-Gym West [Directions] | W 3-2 | ||
| Sat., 10/1 | V Boys Soccer | Guilford | Home - Cheshire High Main Game field [Directions] | W 2-1 | ||
| Sat., 10/1 | V Girls Volleyball | RHAM | Away - RHAM HS-Gym [Directions] | L 1-3 | 7:30 AM | |
| Mon., 10/3 | V Boys Soccer | Foran | Away - Foran HS -Foran High School - Turf Field [Directions] | W 6-0 | 2:30 PM | |
| Mon., 10/3 | V Field Hockey | Shelton | Home - Cheshire High Main Game field [Directions] | W 3-0 | ||
| Mon., 10/3 | V Girls Soccer | Amity | Home - Cheshire High Main Game field [Directions] | W 8-0 | ||
| Mon., 10/3 | V Girls Swimming and Diving | Greenwich, Ridgefield | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | ||
| Mon., 10/3 | V Girls Volleyball | Mercy | Away - Mercy HS-Gym [Directions] | W 3-1 | 2:30 PM | |
| Tue., 10/4 | Miscellaneous Events | Yom Kippur | Home - Cheshire HS [Directions] | 8:00 a.m. | ||
| Wed., 10/5 | Miscellaneous Events | Yom Kippur | Home - Cheshire HS [Directions] | 8:00 a.m. | ||
| Thu., 10/6 | V Girls Volleyball | North Haven | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Fri., 10/7 | V Boys Soccer | Notre Dame-West Haven | Home - Cheshire High Main Game field [Directions] | W 4-0 | ||
| Fri., 10/7 | V Field Hockey | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | W 3-1 | 2:30 PM | |
| Fri., 10/7 | V Girls Soccer | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | W 6-2 | 5:00 PM | |
| Fri., 10/7 | V Girls Swimming and Diving | Hamden | Away - Hamden HS-HHS Pool [Directions] | 5:00 p.m. | 4:00 PM | |
| Fri., 10/7 | V Girls Volleyball | Lauralton Hall | Away - Lauralton Hall-Gym [Directions] | W 3-0 | 2:30 PM | |
| Sat., 10/8 | V Boys Cross Country | Wickham Invite | Away - Wickham Park-Manchester, Ct | 9:00 a.m. | 7:30 AM | |
| Sat., 10/8 | V Girls Cross Country | Wickham Invite | Away - Wickham Park-Manchester, Ct | 9:00 a.m. | 7:30 AM | |
| Sat., 10/8 | Miscellaneous Events | Music in Motion | Home - Cheshire High Main Game field [Directions] | 8:00 a.m. | ||
| Mon., 10/10 | Miscellaneous Events | columbus day | Home - Cheshire HS [Directions] | 8:00 a.m. | ||
| Tue., 10/11 | V Boys Cross Country | Branford, Jonathan Law, Xavier | Home - Cheshire Park-Field 1 [Directions] | 4:00 p.m. | 2:15 PM | |
| Tue., 10/11 | V Boys Soccer | North Haven | Away - North Haven MS-West Turf Field [Directions] | W 10-2 | 4:30 PM | |
| Tue., 10/11 | V Girls Cross Country | Branford, Jonathan Law, Mercy | Home - Cheshire Park-Field 1 [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Field Hockey | North Haven | Away - North Haven MS-East Turf Field [Directions] | W 6-1 | 5:00 PM | |
| Tue., 10/11 | V Girls Soccer | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | W 1-0 | 5:00 PM | |
| Tue., 10/11 | V Girls Swimming and Diving | Lauralton Hall | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | ||
| Tue., 10/11 | V Girls Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Fri., 10/14 | V Boys Cross Country | Lyman Hall | Away - Wharton Brook State Park [Directions] | 4:00 p.m. | 2:30 PM | |
| Fri., 10/14 | V Football | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | L 10-33 | 3:30 PM | |
| Fri., 10/14 | V Boys Soccer | Branford | Home - Cheshire High Main Game field [Directions] | W 8-0 | ||
| Fri., 10/14 | V Girls Cross Country | Lyman Hall | Away - Wharton Brook State Park [Directions] | 4:00 p.m. | 2:30 PM | |
| Fri., 10/14 | V Girls Soccer | Lyman Hall | Home - Cheshire High Main Game field [Directions] | W 6-0 | ||
| Fri., 10/14 | V Girls Swimming and Diving | Daniel Hand | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | ||
| Fri., 10/14 | V Girls Volleyball | Sheehan | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Sat., 10/15 | V Field Hockey | Conard | Away - Conard HS-McKee Stadium [Directions] | T 1-1 | 7:30 AM | |
| Mon., 10/17 | V Boys Soccer | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | W 6-1 | 4:30 PM | |
| Mon., 10/17 | V Field Hockey | Hamden | Away - Hamden HS-HHS Turf #2 [Directions] | W 2-0 | 4:00 PM | |
| Mon., 10/17 | V Girls Soccer | Branford | Home - Cheshire High Main Game field [Directions] | W 4-0 | ||
| Mon., 10/17 | V Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | W 3-1 | ||
| Tue., 10/18 | V Field Hockey | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | L 1-0 | 4:00 PM | |
| Tue., 10/18 | V Girls Swimming and Diving | North Haven | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | ||
| Tue., 10/18 | V Girls Volleyball | Lauralton Hall | Home - Cheshire HS-Gym West [Directions] | W 3-1 | ||
| Wed., 10/19 | V Boys Cross Country | SCC XC Championship | Away - East Shore Athletic Complex-Trail | 1:00 p.m. | 11:30 AM | |
| Wed., 10/19 | V Girls Cross Country | SCC XC Championship | Away - East Shore Athletic Complex-Trail | 1:00 p.m. | 11:30 AM | |
| Wed., 10/19 | V Girls Soccer | Wilbur Cross | Away - Bowen Field-Football Field [Directions] | W 5-0 | 5:00 PM | |
| Wed., 10/19 | Miscellaneous Events | CIAC MS Unified soccer tournament | Home - Cheshire High Main Game field [Directions] | 2:30 p.m. | ||
| Thu., 10/20 | V Girls Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | W 3-0 | 3:00 PM | |
| Fri., 10/21 | V Football | Notre Dame-West Haven | Home - Cheshire High Main Game field [Directions] | W 27-12 | ||
| Fri., 10/21 | V Girls Swimming and Diving | Amity | Away - High Plains Community Cn [Directions] | 6:45 p.m. | 5:00 PM | |
| Sat., 10/22 | V Boys Soccer | Fairfield Prep | Home - Cheshire High Main Game field [Directions] | T 2-2 | ||
| Mon., 10/24 | V Boys Soccer | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | W 3-0 | 5:00 PM | |
| Mon., 10/24 | V Field Hockey | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | W 2-1 | 2:30 PM | |
| Mon., 10/24 | V Girls Soccer | Foran | Home - Cheshire High Main Game field [Directions] | W 3-0 | ||
| Mon., 10/24 | V Girls Volleyball | Branford | Away - Branford HS-Gym [Directions] | W 3-0 | 2:30 PM | |
| Wed., 10/26 | V Field Hockey | Daniel Hand | Home - Cheshire High Main Game field [Directions] | L 3-1 | ||
| Wed., 10/26 | V Girls Soccer | Sacred Heart Academy | Home - Cheshire High Main Game field [Directions] | T 6-6 | ||
| Wed., 10/26 | V Girls Volleyball | Farmington | Away - Farmington HS [Directions] | W 3-1 | 3:30 PM | |
| Fri., 10/28 | V Football | North Haven | Home - Cheshire High Main Game field [Directions] | L 0-10 | ||
| Sat., 10/29 | V Boys Cross Country | CIAC Class L Championship | Away - Wickham Park | 9:35 a.m. | 6:45 AM | |
| Sat., 10/29 | V Boys Soccer | Guilford | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Sat., 10/29 | V Girls Cross Country | CIAC Class L Championship | Away - Wickham Park | 9:00 a.m. | 6:45 AM | |
| Sat., 10/29 | V Field Hockey | Hamden | Home - Cheshire High Main Game field [Directions] | W 4-0 [Detailed Results] | ||
| Sat., 10/29 | V Girls Soccer | Sacred Heart Academy | Home - Cheshire High Main Game field [Directions] | W 3-2 | ||
| Sat., 10/29 | V Girls Swimming and Diving | SCC Dive Championship | Home - Sheehan HS-Sheehan HS Pool [Directions] | 10:00 a.m. | ||
| Tue., 11/1 | V Boys Soccer | Fairfield Prep | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | ||
| Tue., 11/1 | V Field Hockey | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | ||
| Tue., 11/1 | V Girls Soccer | Branford | Home - Cheshire High Main Game field [Directions] | W 4-0 | ||
| Tue., 11/1 | V Girls Swimming and Diving | SCC Girls swim qualifier | Home - Cheshire Community Pool [Directions] | 4:00 p.m. | ||
| Tue., 11/1 | V Girls Volleyball | West Haven | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Thu., 11/3 | V Field Hockey | Branford | Away - Amity Regional HS-Amity HS [Directions] | 7:15 p.m. | 5:00 PM | |
| Thu., 11/3 | V Girls Soccer | Mercy | Home - West Haven HS-Ken Strong Stadium [Directions] | W 2-1 | 3:30 PM | |
| Thu., 11/3 | V Girls Swimming and Diving | SCC Girls swim Championship | Home - Southern CT State University-Moore Field House [Directions] | 5:00 p.m. | 2:30 PM | |
| Thu., 11/3 | V Girls Volleyball | Guilford | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | V Football | Shelton | Away - Shelton HS-Finn Stadium [Directions] | L 14-34 | 4:30 PM | |
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Sat., 11/5 | V Girls Volleyball | Amity | Away - West Haven HS-Gym [Directions] | 1:00 p.m. | 11:00 AM | |
| Wed., 11/9 | V Boys Soccer | Avon | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Wed., 11/9 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Wed., 11/9 | V Girls Swimming and Diving | CIAC Class L Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Wed., 11/9 | Miscellaneous Events | College signing | Home - Cheshire HS [Directions] | 2:00 p.m. | ||
| Thu., 11/10 | V Girls Soccer | Darien | Home - Cheshire High Main Game field [Directions] | W 3-1 | ||
| Thu., 11/10 | V Girls Volleyball | Westhill | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Sat., 11/12 | V Football | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | W 26-0 | 11:30 AM; 2 Buses | |
| Sat., 11/12 | V Boys Soccer | Notre Dame-West Haven | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Sat., 11/12 | V Girls Soccer | Southington | Home - Cheshire High Main Game field [Directions] | W 0-0 | ||
| Sat., 11/12 | V Girls Swimming and Diving | CIAC Class L Trials | Away - Cornerstone Pool | 4:30 p.m. | ||
| Sat., 11/12 | V Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Tue., 11/15 | V Boys Soccer | Guilford | Home - Jonathan Law HS-Lawmen Stadium [Directions] | 5:30 p.m. | 3:00 PM | |
| Tue., 11/15 | V Girls Swimming and Diving | CIAC Class L Final | Away | 6:00 p.m. | ||
| Wed., 11/16 | V Girls Soccer | Ridgefield | Home - Pomperaug HS-Stadium [Directions] | W 2-1 | 5:00 PM | |
| Thu., 11/17 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sun., 11/20 | V Boys Soccer | Xavier | Home - Trinity Health Stadium-Dillon Stadium [Directions] | 6:30 p.m. | ||
| Sun., 11/20 | V Girls Soccer | Staples | Home - Trinity Health Stadium-Dillon Stadium [Directions] | 4:00 p.m. | ||
| Sun., 11/20 | V Girls Swimming and Diving | CIAC State Open Swimming Championship | Away - Yale | 2:00 p.m. | ||
| Thu., 11/24 | V Football | Southington | Home - Cheshire High Main Game field [Directions] | L 14-21 | ||
| Tue., 11/29 | V Football | St. Joseph | Away - John F Kennedy Stadium (Bridgeport, CT)-John F Kennedy Stadium [Directions] | 6:30 p.m. | 3:30 PM | |
| Sat., 12/3 | V Boys Ice Hockey | Xavier (Scrim.) | Home - Hamden-Lou Astorino Ice Rink [Directions] | 7:00 p.m. | 5:00 PM | |
| Sat., 12/3 | V Wrestling | Glastonbury (Scrim.) | Home - Cheshire HS-Gym - East [Directions] | 9:00 a.m. | ||
| Mon., 12/5 | V Girls Basketball | Bridgeport Central (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Wed., 12/7 | V Boys Basketball | Lyman Hall (Scrim.) | Away - Lyman Hall HS-Gymnasium [Directions] | 3:30 p.m. | 2:30 PM | |
| Wed., 12/7 | V Boys Ice Hockey | Hamden (Scrim.) | Home - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | 6:30 PM | |
| Wed., 12/7 | V Girls Ice Hockey | Woodstock Academy Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 1-6 | ||
| Thu., 12/8 | V Boys Basketball | Ellington (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Fri., 12/9 | V Girls Basketball | Maloney (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Sat., 12/10 | V Boys Ice Hockey | Conard (Scrim.) | Home - Hamden-Lou Astorino Ice Rink [Directions] | 5:00 p.m. | 3:15 PM | |
| Sat., 12/10 | V Boys Ice Hockey | Conard (Scrim.) | Home - Hamden-Lou Astorino Ice Rink [Directions] | 6:30 p.m. | ||
| Sat., 12/10 | V Girls Basketball | Branford (Scrim.) | Away - Branford HS-Gym [Directions] | 1:00 p.m. | 11:30 AM | |
| Sat., 12/10 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 3-7 | ||
| Mon., 12/12 | V Boys Basketball | Woodland (Scrim.) | Home - Cheshire HS-Gym West [Directions] | 3:30 p.m. | ||
| Tue., 12/13 | V Girls Basketball | Pomperaug | Home - Cheshire HS-Gym West [Directions] | L 42-57 | ||
| Tue., 12/13 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | L 3-9 | ||
| Wed., 12/14 | V Boys Ice Hockey | SCW Knights | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 4-3 | 2:00 PM | |
| Wed., 12/14 | V Wrestling | Jonathan Law | Home - Cheshire HS-Gym - East [Directions] | 5:00 p.m. | ||
| Thu., 12/15 | V Boys Basketball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | L 47-62 | 3:30 PM | |
| Fri., 12/16 | V Girls Basketball | East Haven | Away - East Haven HS-Gym [Directions] | L 41-46 | 3:00 PM | |
| Sat., 12/17 | V Boys Ice Hockey | East Haven Coop | Away - East Haven HS-Veterans Rink [Directions] | W 5-2 | 11:30 AM | |
| Sat., 12/17 | V Wrestling | Darien Invitational | Away - Darien HS-DHS Main Gym | 8:00 a.m. | 6:30 AM | |
| Sat., 12/17 | V Girls Basketball | Avon | Home - Cheshire HS-Gym West [Directions] | L 26-46 | ||
| Sat., 12/17 | V Girls Ice Hockey | Masuk Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 1-7 | ||
| Mon., 12/19 | V Boys Basketball | Branford | Home - Cheshire HS-Gym West [Directions] | W 57-47 | ||
| Mon., 12/19 | V Boys Indoor Track | SCC Developmental | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 5:30 p.m. | 4:00 PM | |
| Mon., 12/19 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | L 5-7 | 2:00 PM; 1 Bus | |
| Tue., 12/20 | V Boys Swimming and Diving | West Haven | Home - Cheshire Community Pool [Directions] | Cheshire: 92 West Haven:64 | ||
| Tue., 12/20 | V Girls Basketball | Hillhouse | Home - Cheshire HS-Gym West [Directions] | L 40-44 | ||
| Tue., 12/20 | V Girls Indoor Track | SCC Girls Developmental | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 5:30 p.m. | 4:00 PM | |
| Wed., 12/21 | V Boys Ice Hockey | Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | L 4-5 | 5:30 PM | |
| Wed., 12/21 | V Wrestling | Fairfield Prep | Away - Fairfield University-Leo T. Mahoney Arena [Directions] | 5:00 p.m. | 3:00 PM | |
| Fri., 12/23 | V Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | W 67-64(2OT) | 3:00 PM | |
| Fri., 12/23 | V Boys Ice Hockey | Lyman Hall | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 4-9 | 11:30 AM | |
| Fri., 12/23 | V Girls Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | L 35-52 | ||
| Tue., 12/27 | V Girls Basketball | Berlin | Away - Berlin HS-Gibney Gymnasium [Directions] | L 30-49 | 4:00 PM | |
| Wed., 12/28 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft School-Mays [Directions] | L 3-5 | 11:30 AM | |
| Wed., 12/28 | V Boys Swimming and Diving | Shelton | Away - Shelton Community Center Pool [Directions] | 3:30 p.m. | 2:30 PM | |
| Thu., 12/29 | V Girls Basketball | Coginchaug | Home - Cheshire HS-Gym West [Directions] | L 40-45 | ||
| Fri., 12/30 | V Boys Basketball | Maloney | Away - Maloney HS-Gym [Directions] | L 43-60 | 11:00 AM | |
| Fri., 12/30 | V Wrestling | Killingly, Gilbert, TBA, Plainville, RHAM, Shepherd Hill Regional (MA), Suffield/Windsor Locks | Away - Killingly HS-Gym | 10:00 a.m. | 7:30 AM | |
| Tue., 1/3 | V Boys Basketball | Xavier | Home - Cheshire HS-Gym West [Directions] | L 52-65 | ||
| Tue., 1/3 | V Boys Indoor Track | SCC Developmental | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 5:30 p.m. | 4:00 PM | |
| Tue., 1/3 | V Boys Swimming and Diving | Sheehan/Lyman Hall | Home - Cheshire Community Pool [Directions] | Cheshire:90 Sheehan: 67 [Detailed Results] | ||
| Tue., 1/3 | V Girls Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | L 36-41 | 2:30 PM | |
| Wed., 1/4 | V Boys Ice Hockey | Amity | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 5-1 | 2:00 PM | |
| Wed., 1/4 | V Wrestling | Shelton | Home - Cheshire HS-Gym - East [Directions] | 6:00 p.m. | ||
| Wed., 1/4 | V Girls Indoor Track | SCC Girls Developmental | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 5:30 p.m. | 4:00 PM | |
| Thu., 1/5 | V Boys Basketball | Platt | Home - Cheshire HS-Gym West [Directions] | L 46-79 | ||
| Thu., 1/5 | Miscellaneous Events | Skiing | Home - Southington Ski Mountain [Directions] | 4:45 p.m. | ||
| Fri., 1/6 | V Boys Swimming and Diving | Woodland | Away - Woodland HS-pool [Directions] | 4:30 p.m. | 3:00 PM | |
| Fri., 1/6 | V Girls Basketball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | W 48-40 | 4:00 PM | |
| Fri., 1/6 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford-Red [Directions] | L 5-9 | 2:15 PM; 1 Bus | |
| Sat., 1/7 | V Boys Basketball | Sheehan | Home - Cheshire HS-Gym West [Directions] | L 46-56 | ||
| Sat., 1/7 | V Wrestling | Warrior Invitational | Away - Canton HS-Gym | 9:30 a.m. | 7:30 AM | |
| Sat., 1/7 | V Girls Ice Hockey | Suffield Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 2-10 | ||
| Mon., 1/9 | V Boys Basketball | Career Magnet | Away - Career Magnet-Gym [Directions] | W 52-47 | 4:00 PM | |
| Mon., 1/9 | V Boys Indoor Track | SCC Novice | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 1/9 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | L 1-7 | 3:45 PM; 1 Bus | |
| Mon., 1/9 | V Girls Indoor Track | SCC Novice meet | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 1/10 | V Co-ed Fencing | Guilford | Home - Cheshire HS [Directions] | 6:30 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Mercy | Home - Cheshire HS-Gym West [Directions] | L 46-58 | ||
| Wed., 1/11 | V Boys Indoor Track | James Barber Invite | Away - Southern CT State University-Moore Field House | 4:00 p.m. | 2:30 PM | |
| Wed., 1/11 | V Girls Indoor Track | James barber invite | Away - Southern CT State University-Moore Field House | 4:00 p.m. | 2:30 PM | |
| Thu., 1/12 | V Boys Basketball | Hamden | Home - Cheshire HS-Gym West [Directions] | L 57-67 | ||
| Thu., 1/12 | V Co-ed Fencing | Daniel Hand | Home - Cheshire HS [Directions] | 6:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 6:00 p.m. | ||||||
| Thu., 1/12 | Miscellaneous Events | Skiing | Home - Southington Ski Mountain [Directions] | 4:45 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | L 25-44 | 4:00 PM | |
| Sat., 1/14 | V Boys Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | L 45-51 | 3:00 PM | |
| Sat., 1/14 | V Boys Ice Hockey | Branford | Away - Northford-Red [Directions] | L 4-6 | 1:00 PM | |
| Sat., 1/14 | V Co-ed Fencing | North Haven, Daniel Hand, Daniel Hand, Fairfield Warde, Greenwich, Old Lyme, Morgan, North Branford | Away - North Haven HS-Fred Kelly Gymnasium | 8:00 a.m. | ||
| Sat., 1/14 | V Girls Ice Hockey | Hall/Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | L 1-8 | 12:00 PM; 1 Bus (Pickup Amity first then Cheshire) | |
| Mon., 1/16 | V Girls Ice Hockey | Guilford Coop | Away - East Haven HS-Veterans Rink [Directions] | L 1-7 | ||
| Tue., 1/17 | V Boys Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | L 48-52 | ||
| Tue., 1/17 | V Boys Swimming and Diving | Greater New Haven | Away - Walter Gawrych Community Pool [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 1/17 | V Co-ed Fencing | North Haven | Home - Cheshire HS [Directions] | 6:45 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Career Magnet | Away - Career Magnet-Gym [Directions] | W 32-9 | 4:30 PM | |
| Wed., 1/18 | V Boys Ice Hockey | West Haven Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 6-5(OT) | 6:30 PM | |
| Wed., 1/18 | V Wrestling | Amity | Home - Cheshire HS-Gym - East [Directions] | 6:00 p.m. | ||
| Thu., 1/19 | Miscellaneous Events | Skiing | Home - Southington Ski Mountain [Directions] | 4:45 p.m. | ||
| Fri., 1/20 | V Girls Basketball | East Haven | Home - Cheshire HS-Gym West [Directions] | W 52-36 | ||
| Fri., 1/20 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Red Rink [Directions] | L 3-8 | 6:30 PM; 1 Bus (Pick up Amity then Cheshire) | |
| Sat., 1/21 | V Boys Basketball | Southington | Away - Southington HS-Gym West [Directions] | L 38-76 | 3:00 PM | |
| Sat., 1/21 | V Boys Ice Hockey | North Haven | Away - Northford-Red [Directions] | L 4-6 | 5:00 PM | |
| Sat., 1/21 | V Boys Indoor Track | SCC Coaches invite | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 9:00 a.m. | 7:30 AM | |
| Sat., 1/21 | V Wrestling | Colter Abely Wrestling Tournament | Away - Mercy HS-Gym | 8:00 a.m. | 7:00 AM | |
| Sat., 1/21 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | L 4-7 | ||
| Sat., 1/21 | V Girls Indoor Track | SCC Coaches invite | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 9:00 a.m. | 7:30 AM | |
| Mon., 1/23 | V Boys Swimming and Diving | Xavier | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | ||
| Mon., 1/23 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | L 2-3 | 2:45 PM; 1 Bus | |
| Tue., 1/24 | V Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | W 60-49 | 3:30 PM | |
| Tue., 1/24 | V Wrestling | Branford | Home - Cheshire HS-Gym - East [Directions] | 6:00 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Hillhouse | Away - Hillhouse HS-Gym [Directions] | L 41-58 | 4:00 PM | |
| Wed., 1/25 | V Boys Ice Hockey | Daniel Hand | Away - Northford-Red [Directions] | W 7-5 | 7:00 PM | |
| Wed., 1/25 | V Boys Indoor Track | SCC East Championship | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 5:00 p.m. | 3:30 PM | |
| Wed., 1/25 | V Girls Indoor Track | SCC East Championship | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 5:00 p.m. | 3:30 PM | |
| Wed., 1/25 | Miscellaneous Events | Curriculum night | Home - Cheshire HS [Directions] | 6:30 p.m. | ||
| Thu., 1/26 | V Girls Ice Hockey | West Haven/SHA | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 2-4 | ||
| Thu., 1/26 | Miscellaneous Events | Skiing | Home - Southington Ski Mountain [Directions] | 4:45 p.m. | ||
| Fri., 1/27 | V Boys Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | L 32-45 | ||
| Fri., 1/27 | V Girls Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | L 42-68 | 3:00 PM | |
| Sat., 1/28 | V Boys Ice Hockey | Sheehan | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 3-2 | 4:45 PM | |
| Sat., 1/28 | V Wrestling | Doc Meyers Invitational | Away - Rocky Hill HS-Gym | 9:00 a.m. | 7:15 AM | |
| Sat., 1/28 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 1-10 | ||
| Mon., 1/30 | V Boys Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 1/31 | V Boys Basketball | Xavier | Away - Xavier HS-Aurthur M. Kohs Gymnasium [Directions] | L 45-74 | 3:00 PM | |
| Tue., 1/31 | V Co-ed Fencing | Daniel Hand, North Branford | Away - Daniel Hand HS-DHHS Gym [Directions] | 6:30 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Foran | Home - Cheshire HS-Gym West [Directions] | L 33-48 | ||
| Wed., 2/1 | V Boys Ice Hockey | North Branford | Away - Northford-Red [Directions] | W 5-4 | 7:00 PM | |
| Wed., 2/1 | V Wrestling | Daniel Hand, North Haven | Away - Polson MS, Madison-Polson Big Gym/DHHS Campus [Directions] | 6:00 p.m. | 4:00 PM | |
| Wed., 2/1 | V Girls Ice Hockey | Hamden Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 1-8 | ||
| Thu., 2/2 | V Boys Swimming and Diving | Amity | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | 6:45 p.m. | 5:15 PM | |
| Thu., 2/2 | V Co-ed Fencing | North Haven | Away - North Haven HS-Auxiliary Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 2/2 | Miscellaneous Events | Skiing | Home - Southington Ski Mountain [Directions] | 4:45 p.m. | ||
| Fri., 2/3 | V Boys Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | W 60-54 | 4:00 PM | |
| Fri., 2/3 | V Girls Basketball | Jonathan Law | Home - Cheshire HS-Gym West [Directions] | W 44-42 | ||
| Fri., 2/3 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | L 2-3 | ||
| Sat., 2/4 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | W 3-0 | 5:30 PM | |
| Sat., 2/4 | V Boys Indoor Track | SCC Championship | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 10:00 a.m. | 8:00 AM | |
| Sat., 2/4 | V Wrestling | Fairfield Ludlowe, Greenwich, New Milford, Norwalk, Shelton | Away - Fairfield Ludlowe HS-Main Gym | 9:00 a.m. | 7:00 AM | |
| Sat., 2/4 | V Girls Indoor Track | SCC Championship | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 10:00 a.m. | 8:00 AM | |
| Tue., 2/7 | V Boys Basketball | Career Magnet | Home - Cheshire HS-Gym West [Directions] | W 69-40 | ||
| Tue., 2/7 | V Boys Swimming and Diving | Fairfield Prep | Home - Cheshire Community Pool [Directions] | Fairfield Prep 97 Cheshire 62 | ||
| Tue., 2/7 | V Girls Basketball | Mercy | Away - Mercy HS-Gym [Directions] | L 30-61 | 4:00 PM | |
| Tue., 2/7 | V Girls Ice Hockey | Greenwich | Home - Hamden-Lou Astorino Ice Rink [Directions] | T 3-3 | ||
| Wed., 2/8 | V Boys Ice Hockey | East Catholic | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 5-2 | 6:30 PM | |
| Wed., 2/8 | V Wrestling | New Haven Wrestling | Away - Wilbur Cross HS-Little Gym [Directions] | 6:00 p.m. | 4:00 PM | |
| Wed., 2/8 | V Co-ed Fencing | Guilford | Away - Guilford HS-Aux gym at GHS [Directions] | 6:30 p.m. | ||
| Thu., 2/9 | V Boys Swimming and Diving | Hamden | Away - Hamden HS-HHS Pool [Directions] | 4:00 p.m. | 2:30 PM | |
| Thu., 2/9 | Miscellaneous Events | Skiing | Home - Southington Ski Mountain [Directions] | 4:45 p.m. | ||
| Fri., 2/10 | V Boys Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | L 46-73 | 5:30 PM | |
| Fri., 2/10 | V Boys Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/10 | V Girls Basketball | Amity | Home - Cheshire HS-Gym West [Directions] | W 49-44 | ||
| Fri., 2/10 | V Girls Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | Farmington Valley Generals | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 5-4 | 2:30 PM | |
| Sat., 2/11 | V Wrestling | Branford, Amity, Daniel Hand, East Haven, Fairfield Prep, Guilford, Jonathan Law, Foran, Morgan, North Haven, Notre Dame-West Haven, Shelton, New Haven Wrestling, Xavier | Away - Branford HS-Gym | 10:00 a.m. | 7:30 AM | |
| Sat., 2/11 | V Co-ed Fencing | Morgan | Away - TBA [Directions] | 6:30 p.m. | ||
| Sat., 2/11 | V Girls Ice Hockey | Guilford Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 2-3 | ||
| Mon., 2/13 | V Boys Swimming and Diving | Daniel Hand/Branford/Old Saybrook, TBA | Home - Cheshire Community Pool [Directions] | 7:00 p.m. | ||
| Mon., 2/13 | V Girls Basketball | Career Magnet | Home - Cheshire HS-Gym West [Directions] | W 50-13 | ||
| Tue., 2/14 | V Boys Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | W 62-51 | 3:30 PM | |
| Wed., 2/15 | V Boys Ice Hockey | Wethersfield | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 3-2 | 6:30 PM | |
| Wed., 2/15 | V Girls Ice Hockey | Daniel Hand Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 4-7 | ||
| Thu., 2/16 | V Girls Basketball | Mercy | Away - Mercy HS-Gym [Directions] | 6:30 p.m. | 4:30 PM | |
| Fri., 2/17 | V Boys Basketball | Jonathan Law | Home - Cheshire HS-Gym West [Directions] | L 39-54 | ||
| Fri., 2/17 | V Wrestling | CIAC L Championship | Away - Guilford | 4:00 p.m. | ||
| Sat., 2/18 | V Boys Ice Hockey | Eastern CT Eagles | Away - Norwich - Rose Garden-RoseGarden Arena [Directions] | W 8-5 | 3:00 PM | |
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Wrestling | CIAC L Championship | Away - Guilford | 10:30 a.m. | ||
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/20 | V Boys Ice Hockey | South Windsor | Away - South Windsor Arena-Ice Rink [Directions] | W 6-0 | 12:00 PM | |
| Mon., 2/20 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 5:00 p.m. | ||
| Wed., 2/22 | V Boys Ice Hockey | Guilford | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 7-5 | 6:30 PM | |
| Fri., 2/24 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/25 | V Boys Ice Hockey | JBWA | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 4-2 | 5:30 PM | |
| Sat., 2/25 | V Boys Swimming and Diving | SCC Dive Championship | Away - Sheehan HS-Sheehan HS Pool | 9:00 a.m. | ||
| Sat., 2/25 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/27 | V Boys Swimming and Diving | SCC Qualifying Meet | Home - Cheshire Community Pool [Directions] | 4:00 p.m. | ||
| Wed., 3/1 | V Boys Swimming and Diving | SCC Championship Meet | Home - SCSU-Field House [Directions] | 4:30 p.m. | 2:30 PM | |
| Wed., 3/1 | V Girls Basketball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | 6:30 p.m. | 5:00 PM | |
| Wed., 3/1 | Unified Sports Basketball | Amity, Jonathan Law, Shelton, West Haven | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 3:00 p.m. | ||
| Tue., 3/7 | V Boys Ice Hockey | Trumbull | Home - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | ||
| Wed., 3/8 | V Boys Swimming and Diving | CIAC Class M Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class M Trials | Away - Cheshire Community Pool | 6:15 p.m. | ||
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Class M Finals | Away - SCSU | 6:00 p.m. | ||
| Fri., 3/17 | V Boys Swimming and Diving | CIAC Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC State Open Championship | Away - Yale | 1:00 p.m. | ||
| Wed., 3/22 | V Softball | Masuk (Scrim.) | Away - Masuk HS-Masuk High School Softball Field [Directions] | 4:15 p.m. | 2:30 PM | |
| Fri., 3/24 | V Baseball | Londonberry (NH) (Scrim.) | Home - Cheshire HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Sat., 3/25 | V Boys Lacrosse | Wilton (Scrim.) | Away - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:15 p.m. | ||
| Sat., 3/25 | V Girls Lacrosse | Play Day - Girls Lax | Away - Staples HS-Ginny Parker Field | 9:00 a.m. | 7:30 AM | |
| Sun., 3/26 | V Boys Lacrosse | Ridgefield (Scrim.) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 12:30 p.m. | ||
| Sun., 3/26 | V Boys Lacrosse | Wilton (Scrim.) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:15 p.m. | ||
| Mon., 3/27 | V Softball | Southington (Scrim.) | Away - Southington HS-1 Softball Varsity Field [Directions] | Cancelled | 3:00 PM | |
| Tue., 3/28 | V Baseball | Middletown (Scrim.) | Home - Cheshire HS-Baseball Diamond [Directions] | Cancelled | ||
| Tue., 3/28 | V Boys Volleyball | Maloney (Scrim.) | Away - Maloney HS-Gym [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 3/28 | V Girls Lacrosse | Pomperaug (Scrim.) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | ||
| Wed., 3/29 | V Baseball | North Haven (Scrim.) | Home - Cheshire HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Wed., 3/29 | V Boys Lacrosse | Darien (Scrim.) | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | 3:30 PM | |
| Wed., 3/29 | V Boys Tennis | Hamden Hall (Scrim.) | Home - Cheshire HS-Tennis Courts [Directions] | W 9-1 [Detailed Results] | ||
| Wed., 3/29 | V Softball | Seymour (Scrim.) | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Thu., 3/30 | V Girls Lacrosse | Simsbury (Scrim.) | Away - Holden Field-Turf [Directions] | 4:30 p.m. | 2:15 PM | |
| Thu., 3/30 | V Softball | Woodland (Scrim.) | Away - Woodland HS-Softball Diamond [Directions] | Cancelled | 2:15 PM | |
| Fri., 3/31 | V Boys Tennis | Pomperaug (Scrim.) | Home - Cheshire HS-Tennis Courts [Directions] | W 10-0 [Detailed Results] | ||
| Sat., 4/1 | V Boys Lacrosse | LaSalle Academy (RI) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 17-8 | ||
| Sun., 4/2 | V Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | W 1-0 | 12:00 PM | |
| Mon., 4/3 | V Boys Tennis | North Haven | Away - North Haven Athletic Complex-Tennis Courts [Directions] | W 6-1 [Detailed Results] | 2:30 PM | |
| Mon., 4/3 | V Girls Lacrosse | North Haven | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 19-1 | ||
| Mon., 4/3 | V Softball | Shelton | Home - Cheshire HS-Softball Diamond [Directions] | W 10-0 | ||
| Mon., 4/3 | V Girls Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | L 3-4 [Detailed Results] | 2:30 PM | |
| Tue., 4/4 | V Boys Golf | Amity | Away - Race Brook C.C. [Directions] | 3:15 p.m. | 1:30 PM | |
| Tue., 4/4 | V Boys Lacrosse | New Canaan | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | L 6-7 | ||
| Tue., 4/4 | V Boys Outdoor Track | Hamden, East Haven | Away - Hamden HS-HHS Turf #1 [Directions] | 3:45 p.m. | 2:30 PM | |
| Tue., 4/4 | V Girls Outdoor Track | Hamden, East Haven | Away - Hamden HS-HHS Turf #1 [Directions] | 3:45 p.m. | 2:30 PM | |
| Tue., 4/4 | V Softball | Enfield | Home - Cheshire HS-Softball Diamond [Directions] | W 12-6 | ||
| Wed., 4/5 | V Baseball | Branford | Away - Branford HS-Baseball Diamond [Directions] | W 9-2 | 2:30 PM | |
| Wed., 4/5 | V Boys Tennis | Hamden | Home - Cheshire HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Wed., 4/5 | V Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | W 3-0 | 2:30 PM | |
| Wed., 4/5 | V Girls Lacrosse | Lauralton Hall | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 19-4 | ||
| Wed., 4/5 | V Softball | Lauralton Hall | Away - Lauralton Hall-Softball Varsity Diamond [Directions] | W 16-0 | 2:15 PM | |
| Wed., 4/5 | V Girls Tennis | Daniel Hand | Away - Daniel Hand HS-Polson Tennis Courts/DHHS Campus [Directions] | W 4-3 | 2:30 PM | |
| Thu., 4/6 | V Baseball | Southington | Home - Cheshire HS-Baseball Diamond [Directions] | L 12-7 | ||
| Thu., 4/6 | V Boys Golf | Cromwell | Away - TPC River Highlands [Directions] | 2:40 p.m. | 1:30 PM | |
| Thu., 4/6 | V Boys Tennis | Branford | Away - Branford HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | 2:00 PM | |
| Thu., 4/6 | V Boys Volleyball | Simsbury | Home - Cheshire HS-Gym West [Directions] | W 3-2 | ||
| Sat., 4/8 | V Boys Lacrosse | Southington | Away - Southington HS-3 TURF FIELD [Directions] | W 19-2 | 2:00 PM | |
| Sat., 4/8 | V Girls Lacrosse | Conard | Away - Conard HS-McKee Stadium [Directions] | W 13-8 | 8:45 AM | |
| Sat., 4/8 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | L 0-13 | 10:30 AM | |
| Mon., 4/10 | V Baseball | Fairfield Prep | Home - Cheshire HS-Baseball Diamond [Directions] | W 6-5 | ||
| Mon., 4/10 | V Boys Tennis | Sheehan | Away - Sheehan HS-Sheehan HS Tennis Courts [Directions] | W 7-0 [Detailed Results] | 2:30 PM | |
| Mon., 4/10 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 0-3 | 2:30 PM | |
| Mon., 4/10 | V Softball | Wilbur Cross | Home - Cheshire HS-Softball Diamond [Directions] | W 13-0 | ||
| Mon., 4/10 | V Girls Tennis | Guilford | Home - Cheshire HS-Tennis Courts [Directions] | L 2-5 [Detailed Results] | ||
| Tue., 4/11 | V Boys Lacrosse | Notre Dame-West Haven | Away - Notre Dame HS-Veteran's Stadium [Directions] | W 18-3 | 3:30 PM | |
| Tue., 4/11 | V Girls Lacrosse | Sacred Heart Academy | Away - Sacred Heart Academy-Lacrosse Field [Directions] | W 15-5 | 2:15 PM | |
| Tue., 4/11 | V Girls Tennis | Lauralton Hall | Away - Eisenhower Park-Eisenhower [Directions] | W 7-0 [Detailed Results] | 2:30 PM | |
| Wed., 4/12 | V Baseball | Shelton | Away - Shelton HS-Baseball Diamond - N Constitution Blvd [Directions] | W 9-5 | 2:30 PM | |
| Wed., 4/12 | V Boys Tennis | Jonathan Law | Home - Cheshire HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Wed., 4/12 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | L 0-3 | 2:30 PM | |
| Wed., 4/12 | V Softball | Jonathan Law | Home - Cheshire HS-Softball Diamond [Directions] | L 8-1 | ||
| Fri., 4/14 | V Baseball | Guilford | Home - Dunkin Donuts Park [Directions] | L 3-7 | 1:30 PM | |
| Fri., 4/14 | V Boys Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Fri., 4/14 | V Girls Lacrosse | Newtown | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | L 11-12 | ||
| Fri., 4/14 | V Softball | Foran | Away - Foran HS -Danielle Kemp Memorial Field [Directions] | L 5-4 | 8:45 AM | |
| Fri., 4/14 | V Girls Tennis | North Haven | Home - Cheshire HS-Tennis Courts [Directions] | W 6-1 | ||
| Sat., 4/15 | V Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | W 14-5 | 9:00 AM | |
| Sat., 4/15 | V Boys Outdoor Track | Record Journal Meet | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) | 10:00 a.m. | 8:00 AM | |
| Sat., 4/15 | V Girls Outdoor Track | Record Journal Meet | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) | 10:00 a.m. | 8:00 AM | |
| Mon., 4/17 | V Baseball | Hillhouse/Career | Away - West Rock Park - Amhryn Field [Directions] | W 10-2 | 2:30 PM | |
| Mon., 4/17 | V Girls Lacrosse | Branford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 19-7 | ||
| Mon., 4/17 | V Softball | East Haven | Away - East Haven HS-Softball Diamond [Directions] | W 13-1 | 2:15 PM | |
| Tue., 4/18 | V Boys Golf | Hamden | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Tue., 4/18 | V Boys Lacrosse | Mahwah (NJ) | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 17-7 | ||
| Tue., 4/18 | V Boys Outdoor Track | Branford, Shelton | Away - Branford HS-Athletic Turf Field [Directions] | 3:45 p.m. | 2:30 PM | |
| Tue., 4/18 | V Boys Tennis | Xavier | Home - Cheshire HS-Tennis Courts [Directions] | W 5-2 [Detailed Results] | ||
| Tue., 4/18 | V Girls Golf | St. Paul Catholic | Home - Southington Country Club [Directions] | 2:45 p.m. | ||
| Tue., 4/18 | V Girls Outdoor Track | Branford, Shelton | Away - Branford HS-Athletic Turf Field [Directions] | 3:45 p.m. | 2:30 PM | |
| Tue., 4/18 | V Girls Tennis | Sacred Heart Academy | Away - Hamden MS-Tennis Courts [Directions] | W 5-2 [Detailed Results] | 2:15 PM | |
| Wed., 4/19 | V Baseball | Sheehan | Home - Cheshire HS-Baseball Diamond [Directions] | L 5-2 | ||
| Wed., 4/19 | V Boys Volleyball | Xavier | Home - Cheshire HS-Gym West [Directions] | W 3-1 | ||
| Wed., 4/19 | V Girls Golf | Newington | Away - Indian Hill Country Club [Directions] | 3:00 p.m. | 1:30 PM | |
| Wed., 4/19 | V Softball | Amity | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | W 9-6 | 2:15 PM | |
| Wed., 4/19 | V Girls Tennis | Shelton | Home - Cheshire HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Thu., 4/20 | V Boys Lacrosse | Xavier | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 16-4 | ||
| Thu., 4/20 | V Boys Volleyball | Masuk | Home - Cheshire HS-Gym West [Directions] | L 0-3 | ||
| Thu., 4/20 | V Softball | West Haven | Home - Cheshire HS-Softball Diamond [Directions] | W 7-0 | ||
| Fri., 4/21 | V Baseball | East Haven | Home - Cheshire HS-Baseball Diamond [Directions] | W 14-4 | ||
| Fri., 4/21 | V Boys Tennis | Daniel Hand | Home - Cheshire HS-Tennis Courts [Directions] | L 2-5 [Detailed Results] | ||
| Fri., 4/21 | V Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | W 3-2 | 3:00 PM | |
| Fri., 4/21 | V Girls Lacrosse | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | L 11-12 | 2:15 PM | |
| Fri., 4/21 | Miscellaneous Events | Dodd Track Meet | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | ||
| Sat., 4/22 | V Boys Lacrosse | Simsbury | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 19-6 | ||
| Sat., 4/22 | V Girls Tennis | Jonathan Law | Home - Cheshire HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Sun., 4/23 | Miscellaneous Events | 1/2 marathon | Home - Cheshire HS [Directions] | 8:00 a.m. | ||
| Mon., 4/24 | V Baseball | Foran | Away - Foran HS -Ken Walker FIeld [Directions] | W 2-0 | 2:30 PM | |
| Mon., 4/24 | V Boys Golf | Guilford | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Mon., 4/24 | V Boys Tennis | Notre Dame-West Haven | Home - Cheshire HS-Tennis Courts [Directions] | L 2-5 [Detailed Results] | ||
| Mon., 4/24 | V Boys Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | W 3-0 | 2:30 PM | |
| Mon., 4/24 | V Girls Lacrosse | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | W 18-1 | 3:00 PM | |
| Mon., 4/24 | V Softball | Waterford | Home - Cheshire HS-Softball Diamond [Directions] | W 6-2 | ||
| Mon., 4/24 | V Girls Tennis | Branford | Away - Branford HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | 2:30 PM | |
| Tue., 4/25 | V Boys Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | W 14-4 | 4:30 PM | |
| Tue., 4/25 | V Boys Tennis | Fairfield Prep | Away - Fairfield University-Walsh Athletic Center - Tennis Courts [Directions] | L 1-6 [Detailed Results] | 2:15 PM | |
| Tue., 4/25 | V Girls Golf | Lauralton Hall | Away - Lauralton Hall-Oronoque CC [Directions] | 2:30 p.m. | 1:00 PM | |
| Wed., 4/26 | V Boys Golf | Notre Dame-West Haven | Away - Race Brook C.C. [Directions] | 2:45 p.m. | 1:30 PM | |
| Wed., 4/26 | V Boys Outdoor Track | Sheehan, West Haven | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 3:45 p.m. | ||
| Wed., 4/26 | V Boys Volleyball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | W 3-1 | ||
| Wed., 4/26 | V Girls Outdoor Track | Sheehan, West Haven | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Wed., 4/26 | V Softball | Shelton | Away - Shelton HS-Softball Diamond [Directions] | W 15-0 | 2:15 PM | |
| Wed., 4/26 | V Girls Tennis | Mercy | Home - Cheshire HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Thu., 4/27 | V Boys Golf | Daniel Hand | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Thu., 4/27 | V Boys Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | W 4-3 [Detailed Results] | 3:30 PM | |
| Thu., 4/27 | V Girls Golf | Canton | Home - Southington Country Club [Directions] | 2:45 p.m. | ||
| Thu., 4/27 | V Girls Lacrosse | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | W 16-5 | 4:15 PM | |
| Fri., 4/28 | V Baseball | Branford | Home - Cheshire HS-Baseball Diamond [Directions] | W 1-0 | ||
| Fri., 4/28 | V Boys Volleyball | Xavier | Away - Xavier HS-Gym [Directions] | W 3-0 | 2:30 PM | |
| Fri., 4/28 | V Girls Tennis | Sheehan | Away - Sheehan HS-Sheehan HS Tennis Courts [Directions] | W 6-1 | 2:30 PM | |
| Sat., 4/29 | V Boys Lacrosse | Amity | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 19-2 | ||
| Sat., 4/29 | Miscellaneous Events | Jr Prom | Home - Cheshire HS [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Baseball | Fairfield Prep | Away - Fairfield University-Alumni Diamond [Directions] | L 4-1 | 2:15 PM | |
| Mon., 5/1 | V Boys Lacrosse | Daniel Hand | Away - Madison Surf Club-Turf Field [Directions] | W 14-9 | 4:30 PM | |
| Mon., 5/1 | V Boys Tennis | Amity | Home - Cheshire HS-Tennis Courts [Directions] | L 1-6 [Detailed Results] | ||
| Mon., 5/1 | V Boys Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | W 3-0 | 4:30 PM | |
| Mon., 5/1 | V Girls Golf | Daniel Hand | Away - Madison Country Club [Directions] | 3:00 p.m. | 1:45 PM | |
| Mon., 5/1 | V Girls Lacrosse | Daniel Hand | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 15-9 | ||
| Tue., 5/2 | V Boys Golf | Shelton | Away - Brownson Country Club [Directions] | 2:45 p.m. | 1:30 PM | |
| Tue., 5/2 | V Boys Outdoor Track | Daniel Hand | Away - Daniel Hand HS-DHHS Track [Directions] | 3:45 p.m. | 2:15 PM | |
| Tue., 5/2 | V Girls Outdoor Track | Daniel Hand | Away - Daniel Hand HS-DHHS Track [Directions] | 3:45 p.m. | 2:30 PM | |
| Tue., 5/2 | Miscellaneous Events | Dodd track meet | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Wed., 5/3 | V Baseball | Shelton | Home - Cheshire HS-Baseball Diamond [Directions] | W 2-1 | ||
| Wed., 5/3 | V Boys Golf | Cromwell | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Wed., 5/3 | V Boys Tennis | Hall | Home - Cheshire HS-Tennis Courts [Directions] | L 1-6 [Detailed Results] | ||
| Wed., 5/3 | V Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | W 3-0 | 2:00 PM | |
| Wed., 5/3 | V Girls Golf | Glastonbury | Away - Glastonbury Hills Country Club [Directions] | 3:00 p.m. | 1:30 PM | |
| Wed., 5/3 | V Girls Lacrosse | East Lyme | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 12-7 | ||
| Wed., 5/3 | V Softball | Jonathan Law | Away - Jonathan Law HS-Softball Field [Directions] | L 2-1 | 2:15 PM | |
| Wed., 5/3 | Miscellaneous Events | College Signing | Home - Cheshire HS [Directions] | 2:00 p.m. | ||
| Thu., 5/4 | V Boys Golf | Notre Dame-West Haven | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Thu., 5/4 | V Boys Lacrosse | Fairfield Prep | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | L 13-12 | ||
| Thu., 5/4 | V Boys Volleyball | Southington | Home - Cheshire HS-Gym West [Directions] | W 3-1 | ||
| Thu., 5/4 | V Girls Golf | Amity | Home - Southington Country Club [Directions] | 2:45 p.m. | ||
| Fri., 5/5 | V Baseball | Guilford | Away - Guilford HS-Baseball Diamond [Directions] | L 12-6 | 2:15 PM | |
| Fri., 5/5 | V Softball | Foran | Home - Cheshire HS-Softball Diamond [Directions] | W 6-1 | ||
| Fri., 5/5 | V Girls Tennis | Daniel Hand | Home - Cheshire HS-Tennis Courts [Directions] | L 3-4 [Detailed Results] | ||
| Sat., 5/6 | V Baseball | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | W 5-3 | 9:00 AM | |
| Sat., 5/6 | V Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | L 4-18 | 2:30 PM | |
| Mon., 5/8 | V Baseball | Hillhouse/Career | Home - Cheshire HS-Baseball Diamond [Directions] | W 4-0 | ||
| Mon., 5/8 | V Boys Golf | Guilford | Away - Madison Country Club [Directions] | 2:00 p.m. | 12:30 PM | |
| Mon., 5/8 | V Girls Golf | Hall, Northwest Catholic | Away - Rockledge Golf Club West Hartford [Directions] | 3:00 p.m. | 1:30 PM | |
| Mon., 5/8 | V Softball | East Haven | Home - Cheshire HS-Softball Diamond [Directions] | W 16-3 | ||
| Mon., 5/8 | V Girls Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | L 1-6 [Detailed Results] | 2:30 PM | |
| Tue., 5/9 | V Boys Golf | Amity | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Tue., 5/9 | V Boys Lacrosse | Iona Prep (NY) | Away - IONA PREP-Lacrosse Field | L 12-18 | 12:00 PM | |
| Tue., 5/9 | V Boys Tennis | Notre Dame-West Haven | Away - U New Haven-UNH Tennis Courts [Directions] | L 2-5 [Detailed Results] | 2:30 PM | |
| Tue., 5/9 | V Boys Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | W 3-0 | 3:00 PM | |
| Tue., 5/9 | V Girls Golf | Glastonbury | Home - Southington Country Club [Directions] | 2:45 p.m. | ||
| Tue., 5/9 | V Girls Lacrosse | Guilford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 12-7 | ||
| Tue., 5/9 | V Girls Tennis | Amity | Home - Cheshire HS-Tennis Courts [Directions] | L 3-4 [Detailed Results] | ||
| Wed., 5/10 | V Baseball | Sheehan | Away - Sheehan HS-Neubauer Baseball Field @ Sheehan HS [Directions] | L 12-2 | 2:30 PM | |
| Wed., 5/10 | V Boys Outdoor Track | Wilbur Cross, Xavier | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 3:45 p.m. | ||
| Wed., 5/10 | V Boys Tennis | Daniel Hand | Away - Polson MS, Madison-Polson Tennis Courts/DHHS Campus [Directions] | L 1-6 [Detailed Results] | 2:30 PM | |
| Wed., 5/10 | V Boys Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | W 3-1 | ||
| Wed., 5/10 | V Girls Golf | Mercy | Home - Southington Country Club [Directions] | 2:45 p.m. | ||
| Wed., 5/10 | V Girls Outdoor Track | Mercy, Wilbur Cross | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Wed., 5/10 | V Softball | Amity | Home - Cheshire HS-Softball Diamond [Directions] | W 3-0 | ||
| Wed., 5/10 | V Girls Tennis | Lauralton Hall | Home - Cheshire HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Thu., 5/11 | V Baseball | East Haven | Away - East Haven HS-Baseball Field [Directions] | W 11-7 | 2:30 PM | |
| Thu., 5/11 | V Boys Golf | Branford | Home - Farms Country club [Directions] | 2:00 p.m. | ||
| Thu., 5/11 | V Boys Tennis | Fairfield Prep | Home - Cheshire HS-Tennis Courts [Directions] | L 0-7 | ||
| Thu., 5/11 | V Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | W 11-7 | 2:30 PM | |
| Thu., 5/11 | V Softball | Lauralton Hall | Home - Cheshire HS-Softball Diamond [Directions] | W 13-0 | ||
| Thu., 5/11 | V Girls Tennis | North Haven | Away - North Haven Athletic Complex-Tennis Courts [Directions] | W 6-1 [Detailed Results] | 2:30 PM | |
| Fri., 5/12 | V Boys Lacrosse | Joel Barlow | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 18-3 | ||
| Fri., 5/12 | V Boys Volleyball | Simsbury | Away - Simsbury HS-Simsbury / Main Gym [Directions] | L 0-3 | 2:15 PM | |
| Sat., 5/13 | Miscellaneous Events | Senior Prom | Home - Cheshire HS [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Baseball | Foran | Home - Cheshire HS-Baseball Diamond [Directions] | L 6-4 | ||
| Mon., 5/15 | V Boys Tennis | Guilford | Home - Cheshire HS-Tennis Courts [Directions] | W 5-2 [Detailed Results] | ||
| Mon., 5/15 | V Boys Volleyball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | W 3-2 | 2:30 PM | |
| Mon., 5/15 | V Girls Golf | Lauralton Hall | Home - Southington Country Club [Directions] | 2:45 p.m. | ||
| Mon., 5/15 | V Girls Lacrosse | Mercy | Away - Mercy HS-Lacrosse Field [Directions] | W 19-1 | 2:15 PM | |
| Mon., 5/15 | V Softball | West Haven | Away - West Haven HS-Frank Biondi Softball Field [Directions] | L 4-5 | 2:15 PM | |
| Tue., 5/16 | V Boys Golf | Xavier | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Tue., 5/16 | V Boys Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | W 24-4 | 5:30 PM | |
| Tue., 5/16 | V Boys Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | L 1-6 [Detailed Results] | 2:30 PM | |
| Tue., 5/16 | V Boys Volleyball | Southington | Away - Southington HS-Gym West [Directions] | W 3-2 | 3:45 PM | |
| Tue., 5/16 | Miscellaneous Events | Dodd Track Meet | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | ||
| Wed., 5/17 | V Baseball | Daniel Hand | Away - Daniel Hand HS-Polson Baseball Field /DHHS Campus [Directions] | L 8-6 | 2:15 PM | |
| Wed., 5/17 | V Girls Golf | Amity | Away - Race Brook C.C. [Directions] | 3:15 p.m. | 1:30 PM | |
| Wed., 5/17 | V Girls Lacrosse | Farmington | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 12-9 | ||
| Wed., 5/17 | V Softball | Sheehan | Home - Cheshire HS-Softball Diamond [Directions] | W 3-0 | ||
| Thu., 5/18 | V Boys Golf | Shelton | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Thu., 5/18 | V Boys Lacrosse | Shelton | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 16-1 | ||
| Thu., 5/18 | V Boys Volleyball | Newtown | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Thu., 5/18 | V Girls Golf | St. Paul Catholic | Away - Westwoods Golf Course [Directions] | 3:00 p.m. | 1:30 PM | |
| Fri., 5/19 | V Boys Tennis | Notre Dame-West Haven | Away - U New Haven-UNH Tennis Courts [Directions] | L 3-4 [Detailed Results] | 2:30 PM | |
| Fri., 5/19 | V Softball | Wilbur Cross | Away - Blake Field - New Haven-Blake Field 1 [Directions] | W 13-0 | 2:30 PM | |
| Sat., 5/20 | V Girls Tennis | North Haven | Home - North Haven Health & Racquet [Directions] | W 6-1 | 4:15 PM | |
| Mon., 5/22 | V Boys Golf | Hamden | Away - Laurel View Golf Course [Directions] | 2:30 p.m. | 1:00 PM | |
| Mon., 5/22 | V Boys Lacrosse | Daniel Hand | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 15-5 | ||
| Mon., 5/22 | V Girls Golf | Mercy | Away - Lyman Orchards -Jones Course [Directions] | 2:25 p.m. | 1:00 PM | |
| Mon., 5/22 | V Girls Lacrosse | Amity | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 13-6 | ||
| Mon., 5/22 | V Softball | Guilford | Away - Guilford HS-Varsity softball field [Directions] | 4:15 p.m. | 2:15 PM | |
| Mon., 5/22 | V Girls Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | 3:45 p.m. | 2:30 PM | |
| Tue., 5/23 | V Softball | North Haven | Away - North Haven Athletic Complex-Varsity Softball Field [Directions] | 5:00 p.m. | 3:15 PM | |
| Wed., 5/24 | V Baseball | North Haven (Scrim.) | Away - North Haven Athletic Complex-Robert E. DeMayo Field [Directions] | 3:45 p.m. | 2:30 PM | |
| Wed., 5/24 | V Boys Lacrosse | Fairfield Prep | Away - Foran HS -Foran High School - Turf Field [Directions] | 6:30 p.m. | ||
| Wed., 5/24 | V Boys Lacrosse | Fairfield Prep | Away - Foran HS -Foran High School - Turf Field [Directions] | 6:30 p.m. | 4:00 PM | |
| Wed., 5/24 | V Boys Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Wed., 5/24 | V Girls Golf | Daniel Hand, Suffield | Home - Southington Country Club [Directions] | 2:30 p.m. | ||
| Wed., 5/24 | V Girls Lacrosse | Guilford | Home - Foran HS -Foran High School - Turf Field [Directions] | W 14-7 | 2:15 PM | |
| Wed., 5/24 | V Girls Outdoor Track | Last chance meet | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Thu., 5/25 | V Boys Golf | Sheehan | Home - Farms Country club [Directions] | 2:30 p.m. | ||
| Fri., 5/26 | V Boys Tennis | Newtown | Away - Newtown HS-NHS Tennis Courts [Directions] | W 5-2 [Detailed Results] | 1:15 PM | |
| Fri., 5/26 | V Boys Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | W 3-1 | ||
| Fri., 5/26 | V Girls Tennis | Shelton | Home - Cheshire HS-Tennis Courts [Directions] | 2:00 p.m. | ||
| Sat., 5/27 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 11:00 a.m. | 9:30 AM | |
| Sun., 5/28 | V Softball | TBA | Home - Cheshire HS-Softball Diamond [Directions] | Cancelled | ||
| Tue., 5/30 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 3:30 p.m. | 1:15 PM | |
| Tue., 5/30 | V Boys Golf | 2023 SCC Boys Golf Championship | Away - Farms Country club | 8:00 a.m. | ||
| Tue., 5/30 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 3:00 p.m. [Detailed Results] | 1:15 PM | |
| Tue., 5/30 | V Girls Lacrosse | Southington | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 14-10 | ||
| Tue., 5/30 | V Softball | Westhill | Home - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Wed., 5/31 | V Boys Lacrosse | Newington | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | ||
| Wed., 5/31 | V Boys Outdoor Track | CIAC Class L Championships | Away - Willow Brook Park | 4:00 p.m. | ||
| Wed., 5/31 | V Boys Volleyball | Putnam | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Wed., 5/31 | V Girls Golf | Newington | Home - Southington Country Club [Directions] | 2:45 p.m. | ||
| Wed., 5/31 | V Girls Outdoor Track | CIAC Class L Championships | Away - Willow Brook Park | 4:00 p.m. | ||
| Wed., 5/31 | V Softball | Trumbull | Home - Cheshire HS-Softball Diamond [Directions] | 4:30 p.m. | ||
| Fri., 6/2 | V Boys Volleyball | Rockville | Away - Rockville HS-Main gymnasium [Directions] | W 3-0 | 4:00 PM | |
| Fri., 6/2 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | 2:15 PM | |
| Fri., 6/2 | V Softball | Newtown | Away - Newtown HS-Lindell A. Hertberg Softball Field [Directions] | 4:15 p.m. | ||
| Sat., 6/3 | V Boys Lacrosse | Joel Barlow | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | ||
| Sat., 6/3 | Miscellaneous Events | CIAC kids marathon | Home - Cheshire High Main Game field [Directions] | 8:00 a.m. | ||
| Sun., 6/4 | Miscellaneous Events | Youth Lax Fest | Home - Cheshire High Main Game field [Directions] | 8:00 a.m. | ||
| Mon., 6/5 | V Boys Golf | CIAC Division I Championship | Away - Tallwood CC | 7:30 a.m. | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Tue., 6/6 | V Boys Volleyball | Farmington | Home - SMSA-Gym [Directions] | 7:00 p.m. | 4:30 PM | |
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Boys Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Girls Golf | CIAC Division I Championship | Away - Timberlin GC | 8:30 a.m. | ||
| Wed., 6/7 | V Girls Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Girls Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Fri., 6/9 | V Boys Lacrosse | Guilford | Home - Cheshire HS-Main Game field [Directions] | 6:00 p.m. | ||
| Fri., 6/9 | V Boys Volleyball | Masuk | Away - SMSA HS-Main Gym [Directions] | 6:00 p.m. | 4:30 PM | |
| Sat., 6/10 | V Boys Golf | CIAC State Open Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/10 | V Girls Golf | CIAC State Open Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Sun., 6/11 | V Boys Lacrosse | Daniel Hand | Home - Sacred Heart University [Directions] | 12:30 p.m. | ||
| Mon., 6/12 | V Boys Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 2:00 p.m. | ||
| Mon., 6/12 | V Girls Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||