| Cheshire 2020-21 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 389 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Sat., 9/26 | V Boys Soccer | Daniel Hand (Scrim.) | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Tue., 9/29 | V Girls Soccer | Woodland (Scrim.) | Home - Cheshire High Main Game field [Directions] | W 1-0 | ||
| Thu., 10/1 | V Boys Cross Country | Lyman Hall, Sheehan | Away - Wharton Brook State Park [Directions] | 4:00 p.m. | 2:30 PM | |
| Thu., 10/1 | V Girls Cross Country | Lyman Hall, Sheehan | Away - Wharton Brook State Park [Directions] | 4:00 p.m. | 2:30 PM | |
| Thu., 10/1 | V Field Hockey | Branford | Home - Cheshire High Main Game field [Directions] | W 3-0 | ||
| Thu., 10/1 | V Girls Swimming and Diving | Amity | Home - Cheshire Community Pool [Directions] | Cheshire 93 | ||
| Thu., 10/1 | V Girls Swimming and Diving | Amity | Away - High Plains Community Cn [Directions] | Amity 88 | ||
| Thu., 10/1 | V Girls Volleyball | Mercy | Away - Mercy HS-Gym [Directions] | W 3-0 | 4:00 PM | |
| Fri., 10/2 | V Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | L 2-1 | 5:00 PM | |
| Fri., 10/2 | V Girls Soccer | Mercy | Home - Cheshire High Main Game field [Directions] | L 1-3 | ||
| Sat., 10/3 | V Field Hockey | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | W 3-1 | 12:30 PM | |
| Mon., 10/5 | V Field Hockey | Mercy | Away - Mercy HS-Field Hockey Field [Directions] | W 6-0 | 2:30 PM | |
| Mon., 10/5 | V Girls Swimming and Diving | North Haven | Home - Cheshire Community Pool [Directions] | Cheshire 95.5 | ||
| Mon., 10/5 | V Girls Swimming and Diving | North Haven | Away - Walter Gawrych Community Pool [Directions] | North Haven 86.5 | ||
| Mon., 10/5 | V Girls Volleyball | Lyman Hall | Home - Cheshire HS-Gym West [Directions] | W 3-1 | ||
| Tue., 10/6 | V Boys Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | W 5-2 | ||
| Tue., 10/6 | V Girls Soccer | North Haven | Away - North Haven MS-East Turf Field [Directions] | W 5-1 | 4:30 PM | |
| Wed., 10/7 | V Boys Cross Country | Hamden, Daniel Hand | Away - Hamden MS-Back Field [Directions] | 3:45 p.m. | 2:30 PM | |
| Wed., 10/7 | V Girls Cross Country | Hamden, Daniel Hand | Away - Hamden MS-Back Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Thu., 10/8 | V Field Hockey | Guilford | Home - Cheshire High Main Game field [Directions] | W 3-1 | ||
| Thu., 10/8 | V Girls Volleyball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | W 3-1 | 4:00 PM | |
| Fri., 10/9 | V Girls Soccer | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | W 8-0 | 2:30 PM | |
| Fri., 10/9 | V Girls Volleyball | North Haven | Home - Cheshire HS-Gym West [Directions] | W 3-1 | ||
| Sat., 10/10 | V Boys Soccer | Lyman Hall | Home - Cheshire High Main Game field [Directions] | T 0-0 | ||
| Sat., 10/10 | V Girls Swimming and Diving | Daniel Hand | Away - Cheshire Community Pool [Directions] | Daniel Hand 83 | ||
| Sat., 10/10 | V Girls Swimming and Diving | Daniel Hand | Home - Cheshire Community Pool [Directions] | Cheshire 92 | ||
| Tue., 10/13 | V Boys Soccer | Hamden | Home - Cheshire High Main Game field [Directions] | W 3-0 | ||
| Tue., 10/13 | V Girls Soccer | Hamden | Away - Hamden HS-HHS Turf Field #1 [Directions] | W 3-1 | 3:30 PM | |
| Tue., 10/13 | V Girls Volleyball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | W 3-1 | 4:30 PM | |
| Wed., 10/14 | V Boys Cross Country | Guilford, East Haven, Xavier | Away - East River Preserve [Directions] | 3:45 p.m. | 2:30 PM | |
| Wed., 10/14 | V Girls Cross Country | Guilford, East Haven, Mercy | Away - East River Preserve [Directions] | 3:45 p.m. | 2:30 PM | |
| Thu., 10/15 | V Boys Soccer | Notre Dame-West Haven | Home - Cheshire High Main Game field [Directions] | W 3-1 | ||
| Thu., 10/15 | V Field Hockey | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | W 7-0 | 2:30 PM | |
| Thu., 10/15 | V Girls Swimming and Diving | Hamden | Away - Hamden HS-HHS Pool [Directions] | Hamden 76 | ||
| Thu., 10/15 | V Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | W 3-1 | 3:30 PM | |
| Fri., 10/16 | V Boys Soccer | Shelton | Away - Shelton HS-Finn Stadium [Directions] | Cancelled | 4:00 PM | |
| Fri., 10/16 | V Girls Swimming and Diving | Hamden | Home - Cheshire Community Pool [Directions] | Cheshire 99 | ||
| Sat., 10/17 | V Girls Soccer | Shelton | Home - Cheshire High Main Game field [Directions] | W 2-1 | ||
| Mon., 10/19 | V Field Hockey | Daniel Hand | Home - Cheshire High Main Game field [Directions] | W 2-1 | ||
| Mon., 10/19 | V Girls Swimming and Diving | Mercy | Home - Cheshire Community Pool [Directions] | Cheshire 85 | ||
| Mon., 10/19 | V Girls Swimming and Diving | Virtual Meet | Away - TBA | Mercy 75 | ||
| Mon., 10/19 | V Girls Volleyball | Mercy | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Tue., 10/20 | V Boys Soccer | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | W 1-0 | 3:00 PM | |
| Tue., 10/20 | V Girls Soccer | Sheehan | Home - Cheshire High Main Game field [Directions] | L 1-0 | ||
| Thu., 10/22 | V Field Hockey | Sheehan | Home - Cheshire High Main Game field [Directions] | W 7-0 | ||
| Thu., 10/22 | V Girls Volleyball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | W 3-1 | 3:30 PM | |
| Fri., 10/23 | V Boys Cross Country | Shelton | Home - Bartlem Park [Directions] | 4:00 p.m. | 2:30 PM | |
| Fri., 10/23 | V Boys Soccer | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | T 1-1 | 2:30 PM | |
| Fri., 10/23 | V Girls Cross Country | Shelton | Home - Bartlem Park [Directions] | 4:30 p.m. | ||
| Fri., 10/23 | V Girls Soccer | Sacred Heart Academy | Home - Cheshire High Main Game field [Directions] | W 2-0 | ||
| Sat., 10/24 | V Girls Swimming and Diving | Lauralton Hall | Away - Foran HS -Pool [Directions] | LH 84.5 | ||
| Sat., 10/24 | V Girls Swimming and Diving | Lauralton Hall | Home - Cheshire Community Pool [Directions] | Cheshire 96.5 | ||
| Mon., 10/26 | V Field Hockey | Mercy | Home - Cheshire High Main Game field [Directions] | W 7-2 | ||
| Mon., 10/26 | V Girls Swimming and Diving | Amity | Away - High Plains Community Cn [Directions] | Cheshire 90.5 - Amity 87.5 | 5:30 PM | |
| Mon., 10/26 | V Girls Volleyball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | L 0-3 | 3:30 PM | |
| Tue., 10/27 | V Boys Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | L 3-0 | ||
| Tue., 10/27 | V Girls Soccer | Mercy | Away - Xavier HS-Larry McHugh Field [Directions] | L 2-1 | 3:00 PM | |
| Wed., 10/28 | V Boys Cross Country | North Haven, TBA | Away - Wharton Brook State Park [Directions] | Postponed | ||
| Wed., 10/28 | V Boys Cross Country | Branford | Home - Cheshire Park-Field 1 [Directions] | 4:30 p.m. | ||
| Wed., 10/28 | V Girls Cross Country | North Haven, TBA | Away - Wharton Brook State Park [Directions] | Postponed | ||
| Wed., 10/28 | V Girls Cross Country | Branford | Home - Cheshire Park-Field 1 [Directions] | 4:00 p.m. | 2:30 PM | |
| Wed., 10/28 | V Field Hockey | Hamden | Away - Hamden HS-HHS Turf Field #1 [Directions] | W 3-0 | 2:30 PM | |
| Thu., 10/29 | V Girls Swimming and Diving | Hamden | Home - Cheshire Community Pool [Directions] | Cheshire 89 | ||
| Thu., 10/29 | V Girls Swimming and Diving | Hamden | Away - Hamden HS-HHS Pool [Directions] | Hamden 86 | ||
| Thu., 10/29 | V Girls Volleyball | Sacred Heart Academy | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Fri., 10/30 | V Boys Soccer | North Haven | Away - North Haven MS-East Turf Field [Directions] | Cancelled | 4:30 PM | |
| Fri., 10/30 | V Girls Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | Cancelled | ||
| Mon., 11/2 | V Boys Soccer | Lyman Hall | Away - Lyman Hall HS-Fitzgerald Field [Directions] | Postponed | 2:30 PM | |
| Tue., 11/3 | V Girls Soccer | Lyman Hall | Home - Cheshire High Main Game field [Directions] | Cancelled | ||
| Tue., 11/3 | V Girls Volleyball | Sheehan | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Wed., 11/4 | V Boys Soccer | Xavier | Home - Cheshire High Main Game field [Directions] | L 1-0 | ||
| Thu., 11/5 | V Field Hockey | Amity | Away - Amity Regional HS-Field Hockey Field [Directions] | W 2-0 | 2:30 PM | |
| Thu., 11/5 | V Girls Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Fri., 11/6 | V Boys Soccer | Hamden | Away - Hamden HS-HHS Turf Field #1 [Directions] | W 2-1 | 3:30 PM | |
| Fri., 11/6 | V Girls Soccer | Hamden | Home - Cheshire High Main Game field [Directions] | W 8-0 | ||
| Sat., 11/7 | V Field Hockey | Sacred Heart Academy | Home - Cheshire High Main Game field [Directions] | Cancelled | ||
| Mon., 11/9 | V Field Hockey | Branford | Home - Cheshire High Main Game field [Directions] | W 3-1 | ||
| Mon., 11/9 | V Girls Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | W 7-0 | ||
| Wed., 11/11 | V Field Hockey | Guilford | Home - Cheshire High Main Game field [Directions] | 2:00 p.m. | ||
| Wed., 11/11 | V Girls Soccer | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | W 3-0 | 12:30 PM | |
| Wed., 11/11 | V Girls Volleyball | Sheehan | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Thu., 11/12 | V Boys Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | ||
| Fri., 11/13 | V Girls Soccer | Mercy | Away - Xavier HS-Larry McHugh Field [Directions] | L 1-0 | 3:45 PM | |
| Fri., 11/13 | V Girls Volleyball | North Haven | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Sat., 11/14 | V Boys Soccer | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 12:00 p.m. | 10:00 AM | |
| Fri., 12/11 | V Girls Basketball | Daniel Hand (Scrim.) | Away - Daniel Hand HS-DHHS Gym [Directions] | Cancelled | ||
| Sat., 12/19 | V Wrestling | Daniel Hand (Scrim.) | Away - Polson MS, Madison-Polson Big Gym/DHHS Campus [Directions] | Suspended | ||
| Thu., 2/4 | V Boys Ice Hockey | Glastonbury (Scrim.) | Away - Newington Ice Arena-Blue Rink [Directions] | 4:00 p.m. | 2:30 PM | |
| Fri., 2/5 | V Boys Basketball | Jonathan Law (Scrim.) | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 6:00 p.m. | 4:30 PM | |
| Fri., 2/5 | V Girls Basketball | Lauralton Hall (Scrim.) | Away - Lauralton Hall-Gym [Directions] | 5:00 p.m. | 3:45 PM | |
| Sat., 2/6 | V Boys Ice Hockey | Newington Coop (Scrim.) | Away - Newington Ice Arena-Blue Rink [Directions] | 6:55 p.m. | 6:00 PM | |
| Tue., 2/9 | V Boys Ice Hockey | Branford | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | 2:45 PM | |
| Wed., 2/10 | V Girls Basketball | Mercy | Home - Cheshire HS-Gym West [Directions] | L 31-55 | ||
| Fri., 2/12 | V Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | W 52-21 | 3:45 PM | |
| Fri., 2/12 | V Boys Swimming and Diving | Amity | Home - Cheshire Community Pool [Directions] | Cheshire 92 - Amity 83 (1-0) | ||
| Fri., 2/12 | V Boys Swimming and Diving | Amity | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | 3:20 p.m. | ||
| Fri., 2/12 | V Boys Swimming and Diving | Daniel Hand/Branford/Old Saybrook, Greater New Haven | Away - Madison Swim and Racquet [Directions] | 7:30 p.m. | ||
| Fri., 2/12 | V Girls Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | L 15-45 | ||
| Sat., 2/13 | V Boys Ice Hockey | Amity | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 1-3 | 2:45 PM | |
| Mon., 2/15 | V Boys Ice Hockey | North Haven | Away - Northford Ice Pavilion-Red [Directions] | L 2-3 | 1:30 PM | |
| Mon., 2/15 | V Girls Ice Hockey | West Haven/SHA (Scrim.) | Away - West Haven HS-Bennett Rink [Directions] | 12:00 p.m. | ||
| Tue., 2/16 | V Boys Basketball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | L 47-50(OT) | 2:30 PM | |
| Tue., 2/16 | V Boys Swimming and Diving | Daniel Hand/Branford/Old Saybrook | Home - Cheshire Community Pool [Directions] | Cheshire 92 - Hand 86 (2-0) | ||
| Tue., 2/16 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | L 1-4 | ||
| Wed., 2/17 | V Girls Basketball | Guilford | Home - Cheshire HS-Gym West [Directions] | W 46-40 | ||
| Fri., 2/19 | V Boys Swimming and Diving | Xavier | Home - Cheshire Community Pool [Directions] | Cheshire 77 - Xavier 93 (2-1) | ||
| Fri., 2/19 | V Boys Swimming and Diving | Xavier | Away - Woodrow Wilson MS-Pool [Directions] | 4:00 p.m. | ||
| Sat., 2/20 | V Boys Basketball | Xavier | Away - Xavier HS-Aurthur M. Kohs Gymnasium [Directions] | L 40-51 | 11:30 AM | |
| Sat., 2/20 | V Boys Ice Hockey | Sheehan | Away - Northford Ice Pavilion-Blue [Directions] | L 3-7 | 1:30 PM | |
| Sat., 2/20 | V Girls Basketball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | L 32-42 | 8:45 AM | |
| Sun., 2/21 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | W 4-1 | ||
| Mon., 2/22 | V Boys Basketball | East Haven | Home - Cheshire HS-Gym West [Directions] | L 44-50 | ||
| Tue., 2/23 | V Boys Swimming and Diving | Fairfield Prep | Home - Cheshire Community Pool [Directions] | Cheshire 96 - FP 90 (3-1) | ||
| Tue., 2/23 | V Girls Basketball | East Haven | Away - East Haven HS-Gym [Directions] | W 60-56 | 3:30 PM | |
| Wed., 2/24 | V Boys Basketball | Hamden | Home - Cheshire HS-Gym West [Directions] | L 58-68 | ||
| Wed., 2/24 | V Girls Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | L 27-56 | ||
| Wed., 2/24 | V Girls Ice Hockey | Jonathan Law | Home - Hamden-Lou Astorino Ice Rink [Directions] | T 1-1 | ||
| Fri., 2/26 | V Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | L 51-55 | 3:30 PM | |
| Fri., 2/26 | V Boys Swimming and Diving | Greater New Haven | Away - Walter Gawrych Community Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/26 | V Girls Basketball | Branford | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Sat., 2/27 | V Boys Ice Hockey | Daniel Hand | Home - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | 2:45 PM | |
| Sat., 2/27 | V Boys Swimming and Diving | Greater New Haven | Home - Cheshire Community Pool [Directions] | Cheshire 93.5 - GNH 92.5 (4-1) | ||
| Sat., 2/27 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | W 3-2 | ||
| Sun., 2/28 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion-White [Directions] | W 5-2 | ||
| Tue., 3/2 | V Boys Swimming and Diving | Amity | Home - Cheshire Community Pool [Directions] | Cheshire 94 - Amity 80 (5-1) | ||
| Tue., 3/2 | V Boys Swimming and Diving | Amity | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | 3:20 p.m. | ||
| Tue., 3/2 | V Girls Basketball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | L 26-61 | 3:45 PM | |
| Wed., 3/3 | V Girls Ice Hockey | Jonathan Law | Away - Milford Ice Pavillion-Ice Rink [Directions] | W 5-2 | ||
| Fri., 3/5 | V Boys Basketball | Sheehan | Home - Cheshire HS-Gym West [Directions] | W 67-54 | ||
| Fri., 3/5 | V Boys Ice Hockey | Glastonbury | Away - Newington Ice Arena-Blue Rink [Directions] | L 0-4 | 2:45 PM | |
| Fri., 3/5 | V Boys Swimming and Diving | Daniel Hand/Branford/Old Saybrook | Home - Cheshire Community Pool [Directions] | Cheshire 82 - Hand 79 (6-1) | ||
| Fri., 3/5 | V Boys Swimming and Diving | Daniel Hand/Branford/Old Saybrook, Fairfield Prep | Away - Madison Swim and Racquet [Directions] | 7:30 p.m. | ||
| Fri., 3/5 | V Girls Basketball | Sheehan | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | L 20-44 | 4:00 PM | |
| Sat., 3/6 | V Boys Ice Hockey | Lyman Hall | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 1-5 | 2:45 PM | |
| Sat., 3/6 | V Girls Ice Hockey | West Haven/SHA | Home - Hamden-Lou Astorino Ice Rink [Directions] | L 2-3 OT | ||
| Sun., 3/7 | V Boys Basketball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | W 59-56(2OT) | ||
| Sun., 3/7 | V Boys Indoor Track | Amity | Away - Floyd Little Athletic Center-Field House [Directions] | 12:00 p.m. | ||
| Sun., 3/7 | V Boys Indoor Track | Amity | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 12:00 p.m. | 10:45 AM | |
| Sun., 3/7 | V Girls Indoor Track | Amity | Away - Floyd Little Athletic Center-Field House [Directions] | 12:00 p.m. | ||
| Sun., 3/7 | V Girls Indoor Track | Amity | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 12:00 p.m. | 10:45 AM | |
| Tue., 3/9 | V Boys Basketball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | W 50-43 | 3:45 PM | |
| Tue., 3/9 | V Boys Swimming and Diving | Xavier | Home - Cheshire Community Pool [Directions] | Cheshire 86 - Xavier 84 (7-1) | ||
| Tue., 3/9 | V Boys Swimming and Diving | Xavier | Away - Woodrow Wilson MS-Pool [Directions] | 4:00 p.m. | ||
| Tue., 3/9 | V Girls Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | L 32-40 | ||
| Wed., 3/10 | V Boys Ice Hockey | Guilford | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 8-4 | 6:00 PM | |
| Wed., 3/10 | V Girls Ice Hockey | Daniel Hand Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | Postponed | ||
| Thu., 3/11 | V Boys Basketball | Shelton | Home - Cheshire HS-Gym West [Directions] | W 60-51 | ||
| Thu., 3/11 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | W 4-1 | 6:15 PM | |
| Fri., 3/12 | V Boys Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | L 40-57 | 4:00 PM | |
| Fri., 3/12 | V Boys Swimming and Diving | Fairfield Prep | Home - Cheshire Community Pool [Directions] | Cheshire 93 - Fairfield Prep 88 (8-1) | ||
| Fri., 3/12 | V Boys Swimming and Diving | Fairfield Prep | Away - Fairfield University-Rec Plex [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Fri., 3/12 | V Girls Basketball | Lyman Hall | Home - Cheshire HS-Gym West [Directions] | W 33-32 | ||
| Sat., 3/13 | V Boys Ice Hockey | West Haven Coop | Away - West Haven HS-Bennett Rink [Directions] | Cancelled | 11:15 AM | |
| Sat., 3/13 | V Girls Ice Hockey | Guilford Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | Cancelled | ||
| Sun., 3/14 | V Girls Ice Hockey | Guilford Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | Cancelled | ||
| Mon., 3/15 | V Boys Basketball | North Haven | Home - Cheshire HS-Gym West [Directions] | L 39-43 | ||
| Mon., 3/15 | V Boys Ice Hockey | Branford | Home - Hamden-Lou Astorino Ice Rink [Directions] | W 7-5 | 2:30 PM | |
| Mon., 3/15 | V Girls Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | L 41-64 | 3:45 PM | |
| Tue., 3/16 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion-Red [Directions] | W 4-3 | 7:30 PM | |
| Tue., 3/16 | V Boys Swimming and Diving | Greater New Haven | Home - Cheshire Community Pool [Directions] | Cheshire 92 - GNH 94 (8-2) | ||
| Tue., 3/16 | V Boys Swimming and Diving | Greater New Haven | Away - Walter Gawrych Community Pool [Directions] | 4:00 p.m. | ||
| Tue., 3/16 | V Girls Ice Hockey | Masuk Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | Cancelled | ||
| Wed., 3/17 | V Girls Ice Hockey | Hamden Coop | Home - Hamden-Lou Astorino Ice Rink [Directions] | Cancelled | ||
| Fri., 3/19 | V Girls Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 6:00 p.m. | 4:30 PM | |
| Sat., 3/20 | V Boys Basketball | Daniel Hand | Away - Daniel Hand HS-Polson Gym/DHHS Campus [Directions] | L 54-69 | 10:00 AM | |
| Sat., 3/20 | V Boys Indoor Track | Amity | Away - Floyd Little Athletic Center-Field House [Directions] | 9:00 a.m. | ||
| Sat., 3/20 | V Boys Indoor Track | Amity | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 9:00 a.m. | 7:45 AM | |
| Sat., 3/20 | V Boys Swimming and Diving | SCC Dive Championship | Away - Sheehan HS-Sheehan HS Pool | 10:00 a.m. | ||
| Sat., 3/20 | V Girls Indoor Track | Amity | Away - Floyd Little Athletic Center-Field House [Directions] | 9:00 a.m. | ||
| Sat., 3/20 | V Girls Indoor Track | Amity | Home - New Haven Athletic Center/Hillhouse HS [Directions] | 9:00 a.m. | 7:45 AM | |
| Mon., 3/22 | V Girls Basketball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | L 50-76 | 4:00 PM | |
| Wed., 3/24 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavilion-Red [Directions] | W 4-3 | 7:00 PM | |
| Thu., 3/25 | V Boys Swimming and Diving | TBA | Home - Cheshire Community Pool [Directions] | 6:00 p.m. | ||
| Sat., 3/27 | V Boys Ice Hockey | North Haven | Home - West Haven HS-Bennett Rink [Directions] | 4:00 p.m. | 2:30 PM | |
| Thu., 4/1 | V Softball | Seymour (Scrim.) | Away - Seymour HS-Softball Diamond [Directions] | Cancelled | 2:30 PM | |
| Sat., 4/3 | V Boys Lacrosse | St. Joseph, New Milford (Scrim.) | Away - St. Joseph HS-Upper Turf [Directions] | 10:00 a.m. | 8:30 AM | |
| Mon., 4/5 | V Baseball | Maloney (Scrim.) | Home - Cheshire HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/5 | V Softball | Masuk (Scrim.) | Away - Masuk HS-Masuk High School Softball Field [Directions] | Cancelled | 2:15 PM | |
| Tue., 4/6 | V Baseball | Southington (Scrim.) | Away - Southington HS-Baseball Varsity Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 4/6 | V Boys Tennis | Pomperaug (Scrim.) | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | 3:45 p.m. [Detailed Results] | ||
| Wed., 4/7 | V Softball | Fairfield Ludlowe (Scrim.) | Home - Cheshire HS-Softball Diamond [Directions] | 3:45 p.m. | ||
| Thu., 4/8 | V Softball | Southington (Scrim.) | Away - Southington HS-Softball Varsity Field [Directions] | 3:45 p.m. | 2:30 PM | |
| Sat., 4/10 | V Baseball | Notre Dame-West Haven | Away - Quigley Stadium [Directions] | L 6-4 | 9:30 AM | |
| Sat., 4/10 | V Boys Lacrosse | Southington | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 17-6 | ||
| Sat., 4/10 | V Boys Tennis | Guilford | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Sat., 4/10 | V Girls Lacrosse | Amity | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 16-6 | ||
| Sat., 4/10 | V Softball | Guilford | Away - Guilford HS-Varsity softball field [Directions] | W 9-0 | 9:00 AM | |
| Sat., 4/10 | V Girls Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | L 0-7 | 9:30 AM | |
| Mon., 4/12 | V Baseball | Sheehan | Away - Sheehan HS-Neubauer Baseball Field @ Sheehan HS [Directions] | L 4-3(8) | 9:30 AM | |
| Mon., 4/12 | V Boys Lacrosse | Daniel Hand | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 13-4 | ||
| Mon., 4/12 | V Boys Tennis | Branford | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Mon., 4/12 | V Boys Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | W 3-2 | ||
| Mon., 4/12 | V Softball | Hamden | Away - Hamden HS-HHS Softball Field [Directions] | W 17-1 | 2:15 PM | |
| Mon., 4/12 | V Girls Tennis | Lauralton Hall | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | L 1-6 | ||
| Wed., 4/14 | V Baseball | Hamden | Away - Hamden HS-HHS Baseball Field [Directions] | L 4-0 | 2:30 PM | |
| Wed., 4/14 | V Boys Golf | Hamden | Away - Laurel View Golf Course [Directions] | Cheshire 168 Hamden 192 | 1:00 PM | |
| Wed., 4/14 | V Boys Tennis | Shelton | Away - Shelton HS-High School - Tennis Courts [Directions] | W 6-1 [Detailed Results] | 8:30 AM | |
| Wed., 4/14 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | L 0-3 | 2:30 PM | |
| Wed., 4/14 | V Softball | Daniel Hand | Away - Daniel Hand HS-Green Hill Softball Turf Field [Directions] | W 16-1 | 2:15 PM | |
| Wed., 4/14 | V Girls Tennis | Mercy | Away - Wesleyan University-Tennis Courts [Directions] | W 6-1 | 2:30 PM | |
| Fri., 4/16 | V Girls Lacrosse | Lauralton Hall | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 13-4 | ||
| Sat., 4/17 | V Baseball | Amity | Home - Cheshire HS-Baseball Diamond [Directions] | L 9-0 | ||
| Sat., 4/17 | V Boys Lacrosse | Sheehan | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 15-2 | ||
| Sat., 4/17 | V Boys Tennis | North Haven | Away - North Haven Athletic Complex-Tennis Courts [Directions] | W 7-0 [Detailed Results] | 11:00 AM | |
| Sat., 4/17 | V Girls Lacrosse | North Branford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 16-4 | ||
| Sat., 4/17 | V Softball | Amity | Home - Cheshire HS-Softball Diamond [Directions] | W 4-0 | ||
| Mon., 4/19 | V Baseball | North Haven | Away - North Haven Athletic Complex-Robert E. DeMayo Field [Directions] | L 12-11 | 2:30 PM | |
| Mon., 4/19 | V Boys Tennis | Fairfield Prep | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | W 4-3 [Detailed Results] | ||
| Mon., 4/19 | V Softball | Sheehan | Home - Cheshire HS-Softball Diamond [Directions] | W 13-0 | ||
| Mon., 4/19 | V Girls Tennis | Daniel Hand | Away - Polson MS, Madison-Polson Tennis Courts/DHHS Campus [Directions] | L 2-5 | 2:30 PM | |
| Tue., 4/20 | V Boys Golf | Guilford | Home - Farms Country club [Directions] | Cheshire 169 Guilford 182 | 1:00 PM | |
| Tue., 4/20 | V Boys Lacrosse | Shelton | Away - Shelton HS-Finn Stadium [Directions] | W 9-7 | 4:00 PM | |
| Tue., 4/20 | V Boys Volleyball | Masuk | Home - Cheshire HS-Gym West [Directions] | L 2-3 | ||
| Tue., 4/20 | V Girls Golf | Lauralton Hall | Home - Southington Country Club [Directions] | CHS 185 Lauralton Hall 213 | ||
| Tue., 4/20 | V Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | L 10-17 | 2:15 PM | |
| Tue., 4/20 | V Softball | East Haven | Home - Cheshire HS-Softball Diamond [Directions] | W 7-0 | ||
| Tue., 4/20 | V Girls Tennis | Guilford | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | L 2-5 | ||
| Wed., 4/21 | V Boys Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | W 3-0 | 2:30 PM | |
| Thu., 4/22 | V Boys Golf | Jonathan Law | Away - Orange Hills Country Club [Directions] | Cheshire 172 Law 208 | 1:30 PM | |
| Thu., 4/22 | V Boys Outdoor Track | Guilford | Home - Cheshire High Main Game field [Directions] | Cheshire 99 Guilford 28 [Detailed Results] | ||
| Thu., 4/22 | V Boys Volleyball | Pomperaug | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Thu., 4/22 | V Girls Outdoor Track | Guilford | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Fri., 4/23 | V Baseball | Lyman Hall | Home - Cheshire HS-Baseball Diamond [Directions] | W 11-10(8) | ||
| Fri., 4/23 | V Girls Lacrosse | Daniel Hand | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 17-10 | ||
| Fri., 4/23 | V Girls Tennis | Sacred Heart Academy | Away - Hamden MS-Tennis Courts [Directions] | W 4-3 | 2:30 PM | |
| Sat., 4/24 | V Baseball | Daniel Hand | Home - Cheshire HS-Baseball Diamond [Directions] | L 12-3 | ||
| Sat., 4/24 | V Boys Tennis | Xavier | Away - Wesleyan University-Tennis Courts [Directions] | W 4-3 [Detailed Results] | 10:30 AM | |
| Mon., 4/26 | V Baseball | Guilford | Home - Cheshire HS-Baseball Diamond [Directions] | W 10-9 | ||
| Mon., 4/26 | V Boys Tennis | Daniel Hand | Away - Polson MS, Madison-Polson Tennis Courts/DHHS Campus [Directions] | L 3-4 [Detailed Results] | 2:30 PM | |
| Mon., 4/26 | V Boys Volleyball | Kolbe Cathedral | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Mon., 4/26 | V Girls Golf | Mercy | Away - Lyman Orchards [Directions] | CHS 195 Mercy 259 | 2:15 PM | |
| Mon., 4/26 | V Girls Lacrosse | Trumbull | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 20-4 | ||
| Mon., 4/26 | V Softball | West Haven | Home - Cheshire HS-Softball Diamond [Directions] | W 7-4 | ||
| Mon., 4/26 | V Girls Tennis | North Haven | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | L 3-4 | ||
| Tue., 4/27 | V Boys Golf | Jonathan Law | Home - Farms Country club [Directions] | Cheshire 167 Law 205 | 1:00 PM | |
| Tue., 4/27 | V Boys Lacrosse | Staples | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | L 9-12 | ||
| Tue., 4/27 | V Boys Outdoor Track | Hillhouse | Away - Bowen Field-Football Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 4/27 | V Girls Lacrosse | Mercy | Away - Mercy HS-Lacrosse Field [Directions] | W 20-8 | 2:15 PM | |
| Tue., 4/27 | V Girls Outdoor Track | Hillhouse | Away - Bowen Field-Football Field [Directions] | Postponed | 2:30 PM | |
| Wed., 4/28 | V Baseball | Fairfield Prep | Home - Cheshire HS-Baseball Diamond [Directions] | L 13-3 | ||
| Wed., 4/28 | V Boys Golf | Fairfield Prep | Away - Brooklawn Country Club [Directions] | Cheshire 173 Fairfield Prep 157 | 1:30 PM | |
| Wed., 4/28 | V Boys Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | W 3-0 | 2:30 PM | |
| Wed., 4/28 | V Girls Golf | Amity | Home - Southington Country Club [Directions] | CHS 189 Amity 197 | ||
| Wed., 4/28 | V Softball | Lyman Hall | Away - Lyman Hall HS-Varsity Softball Field [Directions] | W 11-2 | 2:15 PM | |
| Thu., 4/29 | V Boys Golf | Xavier | Home - Farms Country club [Directions] | Cheshire 174 Xavier 183 | 1:00 PM | |
| Thu., 4/29 | V Boys Lacrosse | Notre Dame-West Haven | Away - Notre Dame HS-Veteran's Stadium [Directions] | W 18-7 | 4:00 PM | |
| Thu., 4/29 | V Girls Lacrosse | North Haven | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 21-2 | ||
| Fri., 4/30 | V Baseball | Sheehan | Home - Cheshire HS-Baseball Diamond [Directions] | L 6-3 | ||
| Fri., 4/30 | V Boys Volleyball | Norwich Free Academy | Away - Norwich Free Academy-Alumni Gym [Directions] | W 3-0 | 2:30 PM | |
| Fri., 4/30 | V Softball | Hamden | Home - Cheshire HS-Softball Diamond [Directions] | W 16-4 | ||
| Fri., 4/30 | V Girls Tennis | Amity | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | L 0-7 | ||
| Sat., 5/1 | V Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | L 5-15 | 4:00 PM | |
| Sat., 5/1 | V Boys Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | W 4-3 [Detailed Results] | 10:30 AM | |
| Sat., 5/1 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | L 5-15 | 10:45 AM | |
| Sat., 5/1 | V Girls Tennis | Foran | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | W 6-1 | ||
| Mon., 5/3 | V Baseball | Hamden | Home - Cheshire HS-Baseball Diamond [Directions] | L 6-2 | ||
| Mon., 5/3 | V Boys Golf | Guilford | Away - Madison Country Club [Directions] | Cheshire 171 Guilford 173 | 1:00 PM | |
| Mon., 5/3 | V Boys Tennis | Branford | Away - Branford HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | 2:30 PM | |
| Mon., 5/3 | V Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | W 3-0 | 2:30 PM | |
| Mon., 5/3 | V Softball | Sheehan | Away - Sheehan HS-Sheehan HS Softball Field [Directions] | W 7-2 | 2:15 PM | |
| Mon., 5/3 | Miscellaneous Events | cheer tryout | Home - Cheshire HS-Gym West [Directions] | 6:15 p.m. | ||
| Tue., 5/4 | V Boys Golf | Hamden | Home - Farms Country club [Directions] | Cheshire 167 Hamden 206 | 1:00 PM | |
| Tue., 5/4 | V Boys Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | W 20-7 | 4:30 PM | |
| Tue., 5/4 | V Boys Tennis | Shelton | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Tue., 5/4 | V Girls Golf | Mercy | Home - Southington Country Club [Directions] | 3:00 p.m. | ||
| Tue., 5/4 | V Girls Lacrosse | Branford | Away - Branford HS-Athletic Turf Field [Directions] | W 17-3 | 4:00 PM | |
| Wed., 5/5 | V Boys Golf | Daniel Hand | Away - Madison Country Club [Directions] | Cheshire 168 Hand 145 | 1:00 PM | |
| Wed., 5/5 | V Boys Volleyball | Newtown | Away - Newtown HS-Newtown High School Gym [Directions] | W 3-0 | 2:30 PM | |
| Wed., 5/5 | V Girls Golf | Daniel Hand | Away - Madison Country Club [Directions] | CHS 179 Hand 226 | 1:45 PM | |
| Wed., 5/5 | Miscellaneous Events | cheer tryout | Home - Cheshire HS-Gym West [Directions] | 6:15 p.m. | ||
| Thu., 5/6 | V Baseball | Daniel Hand | Away - Daniel Hand HS-Polson Baseball Field /DHHS Campus [Directions] | L 7-6 | 2:30 PM | |
| Thu., 5/6 | V Boys Golf | Notre Dame-West Haven | Away - Race Brook C.C. [Directions] | Cheshire 164 Notre Dame 150 | 1:30 PM | |
| Thu., 5/6 | V Girls Golf | St. Paul Catholic | Home - Southington Country Club [Directions] | CHS 190 St. Paul 201 | ||
| Thu., 5/6 | V Girls Lacrosse | Glastonbury | Away - Glastonbury HS-Field 12 [Directions] | W 14-9 | 2:15 PM | |
| Thu., 5/6 | V Girls Tennis | Foran | Away - Foran HS -Foran Tennis Courts [Directions] | W 4-3 | 2:30 PM | |
| Thu., 5/6 | Miscellaneous Events | Dodd track meet | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | ||
| Fri., 5/7 | V | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | W 11-8 | 3:00 PM | |
| Fri., 5/7 | V Baseball | Guilford | Away - Guilford HS-Baseball Diamond [Directions] | L 6-1 | 2:15 PM | |
| Fri., 5/7 | V Boys Outdoor Track | Amity | Home - Cheshire High Main Game field [Directions] | Cheshire 74 Amity 76 | ||
| Fri., 5/7 | V Boys Tennis | North Haven | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Fri., 5/7 | V Boys Volleyball | Xavier | Away - Xavier HS-Gym [Directions] | W 3-1 | 2:30 PM | |
| Fri., 5/7 | V Girls Outdoor Track | Amity | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Fri., 5/7 | V Softball | North Haven | Home - Cheshire HS-Softball Diamond [Directions] | W 12-0 | ||
| Fri., 5/7 | V Softball | North Haven | Home - Cheshire HS-Softball Diamond [Directions] | W 8-4 | ||
| Fri., 5/7 | V Girls Tennis | Lauralton Hall | Away - Eisenhower Park [Directions] | L 2-5 | 2:30 PM | |
| Fri., 5/7 | Miscellaneous Events | cheer tryout | Home - Cheshire HS-Gym West [Directions] | 6:15 p.m. | ||
| Sat., 5/8 | V Boys Lacrosse | Xavier | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 17-4 | ||
| Sat., 5/8 | V Boys Tennis | Southington | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Sat., 5/8 | V Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | L 4-13 | 7:45 AM | |
| Sat., 5/8 | V Girls Tennis | Mercy | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | W 7-0 | ||
| Mon., 5/10 | V Baseball | Amity | Away - Old Tavern Road Complex-Brinley Field [Directions] | L 12-0 | 5:00 PM | |
| Mon., 5/10 | V Boys Golf | Shelton | Away - Brownson Country Club [Directions] | Cheshire 160 Shelton 157 | 1:30 PM | |
| Mon., 5/10 | V Boys Lacrosse | North Haven | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 19-2 | ||
| Mon., 5/10 | V Boys Outdoor Track | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 3:45 p.m. | 2:30 PM | |
| Mon., 5/10 | V Boys Tennis | Fairfield Prep | Away - Fairfield University-Walsh Athletic Center - Tennis Courts [Directions] | W 4-3 [Detailed Results] | 2:30 PM | |
| Mon., 5/10 | V Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | W 3-1 | 2:30 PM | |
| Mon., 5/10 | V Girls Golf | Lauralton Hall | Home - Southington Country Club [Directions] | CHS 208 Lauralton Hall 206 | ||
| Mon., 5/10 | V Girls Outdoor Track | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 3:45 p.m. | 2:30 PM | |
| Mon., 5/10 | V Girls Tennis | Daniel Hand | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | L 1-6 | ||
| Tue., 5/11 | V Girls Golf | Amity | Away - Race Brook C.C. [Directions] | CHS 185 Amity 193 | 2:15 PM | |
| Tue., 5/11 | V Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | W 10-6 | 3:30 PM | |
| Tue., 5/11 | V Softball | East Haven | Away - East Haven HS-Softball Diamond [Directions] | W 3-0 | 2:30 PM | |
| Tue., 5/11 | Miscellaneous Events | Dodd track meet | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | ||
| Wed., 5/12 | V Baseball | North Haven | Home - Cheshire HS-Baseball Diamond [Directions] | W 11-4 | ||
| Wed., 5/12 | V Boys Outdoor Track | Shelton | Home - Cheshire High Main Game field [Directions] | Cheshire 65 Shelton 85 | ||
| Wed., 5/12 | V Boys Tennis | Xavier | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | W 5-2 [Detailed Results] | ||
| Wed., 5/12 | V Boys Volleyball | Norwich Free Academy | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Wed., 5/12 | V Girls Golf | Newington, Berlin | Away - Indian Hill Country Club [Directions] | CHS 190 Newington 232 Berlin 202 | 1:30 PM | |
| Wed., 5/12 | V Girls Outdoor Track | Shelton | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Wed., 5/12 | V Softball | Lyman Hall | Home - Cheshire HS-Softball Diamond [Directions] | W 5-3 | ||
| Wed., 5/12 | V Girls Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | L 1-6 | 2:30 PM | |
| Thu., 5/13 | V | Shelton | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 21-6 | ||
| Thu., 5/13 | V Girls Golf | Lauralton Hall | Away - Oronoque Country Club [Directions] | CHS 184 Lauralton Hall 212 | 1:45 PM | |
| Fri., 5/14 | V Baseball | Lyman Hall | Away - Pat Wall Field-Baseball Field [Directions] | W 9-6 | 2:30 PM | |
| Fri., 5/14 | V Boys Tennis | Notre Dame-West Haven | Away - U New Haven-UNH Tennis Courts [Directions] | W 6-1 [Detailed Results] | 2:30 PM | |
| Fri., 5/14 | V Boys Volleyball | Shelton | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Fri., 5/14 | V Girls Lacrosse | Guilford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | L 3-17 | ||
| Fri., 5/14 | V Softball | Amity | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | L 4-3 | 2:30 PM | |
| Fri., 5/14 | V Girls Tennis | Sacred Heart Academy | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | W 4-3 | ||
| Sat., 5/15 | V Boys Lacrosse | Simsbury | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 18-4 | ||
| Sat., 5/15 | V Softball | West Haven | Away - West Haven HS-Frank Biondi Field [Directions] | W 7-3 | 5:00 PM | |
| Mon., 5/17 | V | NotreDame | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 16-9 | ||
| Mon., 5/17 | V Baseball | Fairfield Prep | Away - Fairfield University-Alumni Diamond [Directions] | W 7-0 | 2:15 PM | |
| Mon., 5/17 | V Boys Golf | Southington, Conard | Away - Southington HS-Hawk's Landing Country Club [Directions] | Cheshire 154 Southington 158 | ||
| Mon., 5/17 | V Boys Outdoor Track | SCC East Sectional Track & Field Qualifier | Away - Bowen Field-Track | 2:30 p.m. | 12:30 PM, Return 6:00 PM | |
| Pending change awaiting acceptance by one or more parties involved: Date to 5/19 | ||||||
| Mon., 5/17 | V Boys Volleyball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | W 3-1 | ||
| Mon., 5/17 | V Girls Golf | Amity | Home - Southington Country Club [Directions] | CHS 187 Amity 196 | ||
| Mon., 5/17 | V Girls Outdoor Track | SCC East Sectional Track & Field Qualifier | Away - Bowen Field-Track | 2:30 p.m. | 12:30 PM, Return 6:00 PM | |
| Pending change awaiting acceptance by one or more parties involved: Date to 5/19 | ||||||
| Mon., 5/17 | V Girls Tennis | North Haven | Away - North Haven Athletic Complex-Tennis Courts [Directions] | L 2-5 | 2:30 PM | |
| Tue., 5/18 | V Boys Golf | Notre Dame-West Haven | Home - Farms Country club [Directions] | Cheshire 173 Notre Dame 167 | 1:00 PM | |
| Tue., 5/18 | V Boys Tennis | Daniel Hand | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | L 1-6 [Detailed Results] | ||
| Tue., 5/18 | V Boys Volleyball | Xavier | Home - Cheshire HS-Gym West [Directions] | W 3-0 | ||
| Tue., 5/18 | V Girls Lacrosse | Branford | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | W 18-3 | ||
| Tue., 5/18 | V Softball | Daniel Hand | Home - Cheshire HS-Softball Diamond [Directions] | W 14-2 | ||
| Wed., 5/19 | V Baseball | Notre Dame-West Haven | Home - Cheshire HS-Baseball Diamond [Directions] | W 5-4 | ||
| Wed., 5/19 | V Boys Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | W 13-8 | 2:30 PM | |
| Wed., 5/19 | V Boys Tennis | Notre Dame-West Haven | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | W 4-3 [Detailed Results] | ||
| Wed., 5/19 | V Girls Golf | Daniel Hand | Away - Madison Country Club [Directions] | CHS 171 Hand 225 | 1:00 PM | |
| Wed., 5/19 | V Softball | Guilford | Home - Cheshire HS-Softball Diamond [Directions] | W 12-0 | ||
| Wed., 5/19 | Miscellaneous Events | Dodd Track meet | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Thu., 5/20 | V Boys Golf | Shelton | Home - Farms Country club [Directions] | Cheshire 181 Shelton 168 | 1:00 PM | |
| Thu., 5/20 | V Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 10-9 | 3:00 PM | |
| Thu., 5/20 | V Boys Outdoor Track | Amity, Lyman Hall, Sheehan, Shelton | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | ||
| Thu., 5/20 | V Girls Outdoor Track | Amity, Lyman Hall, Sheehan, Shelton | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | ||
| Thu., 5/20 | V Softball | Southington | Away - Southington HS-Softball Varsity Field [Directions] | L 3-2 | 2:30 PM | |
| Fri., 5/21 | V Boys Outdoor Track | Lyman Hall | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Fri., 5/21 | V Girls Outdoor Track | Lyman Hall | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Mon., 5/24 | V Softball | TBA | Home - Cheshire HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/24 | V Girls Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | 3:45 p.m. | 1:45 PM | |
| Mon., 5/24 | Miscellaneous Events | Dodd track meet | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | ||
| Tue., 5/25 | V Boys Outdoor Track | SCC Chamionship meet | Away - Bowen Field-Track | 1:00 p.m. | 11:30 AM | |
| Tue., 5/25 | V Boys Tennis | Amity | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | W 4-3 [Detailed Results] | ||
| Tue., 5/25 | V Girls Golf | Mercy | Away - Lyman Orchards [Directions] | CHS 168 Mercy 234 | 1:30 PM | |
| Tue., 5/25 | V Girls Outdoor Track | SCC Championship Meet | Away - Hillhouse HS-Bowen Field | 1:30 p.m. | 11:30 AM | |
| Tue., 5/25 | V Softball | Shelton | Home - Cheshire HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/26 | V Boys Golf | Sheehan | Home - Farms Country club [Directions] | Cheshire 167 Sheehan 189 | ||
| Wed., 5/26 | V Boys Tennis | Daniel Hand | Away - Polson MS, Madison-Polson Tennis Courts/DHHS Campus [Directions] | L 2-5 [Detailed Results] | 2:00 PM | |
| Wed., 5/26 | V Boys Volleyball | Daniel Hand | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Wed., 5/26 | V Girls Golf | Daniel Hand | Home - Southington Country Club [Directions] | CHS 172 Hand 237 | ||
| Thu., 5/27 | V Baseball | Ansonia (Scrim.) | Home - Cheshire HS-Baseball Diamond [Directions] | W 6-1 | ||
| Thu., 5/27 | V Girls Golf | St. Paul Catholic | Away - Westwoods Golf Course [Directions] | CHS 148 St. Paul 164 | 1:45 PM | |
| Thu., 5/27 | V Softball | Amity | Home - West Haven HS-Frank Biondi Field [Directions] | 7:00 p.m. | 4:30 PM | |
| Fri., 5/28 | V Boys Tennis | Xavier | Home - Cheshire HS-Park and Rec Tennis Courts [Directions] | L 3-4 | ||
| Fri., 5/28 | V Boys Volleyball | Amity | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Tue., 6/1 | V Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | L 10-3 | 1:30 PM | |
| Tue., 6/1 | V Boys Outdoor Track | CIAC Class L Boys Outdoor Track Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/1 | V Girls Golf | Newington, St. Paul Catholic | Home - Southington Country Club [Directions] | CHS 170 Newington 206 St. Paul 187 | ||
| Tue., 6/1 | V Girls Outdoor Track | CIAC Class L Girls Outdoor Track Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Wed., 6/2 | V Softball | TBA | Home - Cheshire HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 6/2 | Miscellaneous Events | SCC Girls Golf tournament | Home - TBA [Directions] | 8:00 a.m. | ||
| Sat., 6/5 | V Boys Lacrosse | Wilton | Home - Cheshire HS-Cheshire High School Main Game field [Directions] | 5:00 p.m. | ||
| Sat., 6/5 | V Boys Volleyball | Simsbury | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Mon., 6/7 | V Boys Golf | CIAC Boys Div. I Golf Championship | Away - Tallwood CC | 8:00 a.m. | ||
| Mon., 6/7 | V Boys Volleyball | Newington | Away - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 6/7 | Miscellaneous Events | Senior Walk concert | Home - Cheshire HS [Directions] | 3:00 p.m. | ||
| Wed., 6/9 | V Boys Outdoor Track | CIAC Open Boys Outdoor Track Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Wed., 6/9 | V Girls Golf | CIAC Girls Div. I Golf Championship | Away - Grassy Hill | 8:30 a.m. | ||
| Wed., 6/9 | V Girls Outdoor Track | CIAC Open Girls Outdoor Track Championship | Away - Willow Brook Park | 1:30 p.m. | 11:30 AM | |
| Thu., 6/10 | Miscellaneous Events | Band concert | Home - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | ||
| Sat., 6/12 | V Boys Golf | CIAC State Open Golf Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/12 | V Girls Golf | CIAC State Open Golf Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/14 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Manchester | 3:30 p.m. | ||
| Mon., 6/14 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Manchester | 3:30 p.m. | ||
| Tue., 6/15 | V Boys Outdoor Track | CIAC Boys Decathlon Championship Day 1 | Away - Manchester | 10:00 a.m. | ||
| Tue., 6/15 | V Girls Outdoor Track | CIAC Girls Heptathlon Championship Day 1 | Away - Manchester | 10:30 a.m. | ||
| Tue., 6/15 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Manchester | 3:30 p.m. | ||
| Wed., 6/16 | V Boys Outdoor Track | CIAC Boys Decathlon Championship Day 2 | Away - Manchester | 10:00 a.m. | ||
| Wed., 6/16 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Manchester | 3:30 p.m. | ||
| Wed., 6/16 | V Girls Outdoor Track | CIAC Girls Heptathlon Championship Day 2 | Away - Manchester | 10:00 a.m. | ||