| Cheshire 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 228 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Football | Daniel Hand | Away - DHHS Turf Field [Directions] | TBA | ||
| TBA | FR Football | Fairfield Prep | Away - Rafferty Stadium, Fairfield University [Directions] | TBA | ||
| TBA | V Boys Soccer | Glastonbury (Scrim.) | Home - Cheshire High Main Game field [Directions] | TBA | ||
| TBA | JV Field Hockey | Mercy | Home - Cheshire High Field Hockey field [Directions] | TBA | ||
| TBA | JV Field Hockey | Sacred Heart Academy | Home - Cheshire High Field Hockey field [Directions] | TBA | ||
| TBA | FR Field Hockey | Farmington | Away [Directions] | Cancelled | Cancelled | |
| TBA | V Girls Soccer | Woodland (Scrim.) | Home - Cheshire HS soccer field [Directions] | 5:00 p.m. | ||
| TBA | JV Girls Soccer | Daniel Hand | Home - Cheshire HS soccer field [Directions] | TBA | ||
| TBA | FR Girls Soccer | Mercy | Away - Mercy [Directions] | TBA | ||
| Mon., 8/27 | JV Girls Soccer | Southington (Scrim.) | Home - Cheshire [Directions] | Cancelled | Cancelled | |
| Tue., 8/28 | V Girls Soccer | Southington (Scrim.) | Home - Cheshire High Main Game field [Directions] | 9:00 a.m. | ||
| Thu., 8/30 | V Football | Windsor (Scrim.) | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 8/30 | V Boys Soccer | Woodland (Scrim.) | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | ||
| Fri., 8/31 | V Boys Cross Country | Simsbury (Scrim.) | Away - Stratton Brook [Directions] | 3:45 p.m. | ||
| Fri., 8/31 | V Girls Cross Country | Simsbury (Scrim.) | Away - Stratton Brook [Directions] | 3:45 p.m. | ||
| Fri., 8/31 | V Girls Soccer | Watertown (Scrim.) | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | ||
| Sat., 9/1 | V Boys Soccer | Pomperaug (Scrim.) | Away - Sports Complex & Track [Directions] | 6:00 p.m. | ||
| Sat., 9/1 | JV Boys Soccer | Pomperaug (Scrim.) | Away - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Sat., 9/1 | V Field Hockey | Avon Scrimmage | Away - Avon High | 9:00 a.m. | ||
| Wed., 9/5 | FR Football | Shelton (Scrim.) | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Wed., 9/5 | V Field Hockey | Pomperaug (Scrim.) | Away - Sports Complex & Track [Directions] | 4:30 p.m. | ||
| Fri., 9/7 | V Football | Shelton | Away - Xavier High school [Directions] | 7:00 p.m. | L 10-17 | |
| Fri., 9/7 | V Field Hockey | Shelton | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 9/7 | JV Field Hockey | Shelton | Home - Cheshire High Field Hockey field [Directions] | 5:15 p.m. | ||
| Fri., 9/7 | V Girls Soccer | Guilford | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | T 2-2 | |
| Sat., 9/8 | V Boys Cross Country | Windham Invite | Away - Windam High | 9:00 a.m. | ||
| Sat., 9/8 | JV Football | Shelton | Home - Cheshire High Main Game field [Directions] | 10:00 a.m. | ||
| Sat., 9/8 | V Boys Soccer | Bristol Eastern (Scrim.) | Away - Alumni Field-Turf [Directions] | 10:30 a.m. | ||
| Sat., 9/8 | V Girls Cross Country | Windham Invite | Away - Windaham high | 9:00 a.m. | ||
| Sat., 9/8 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 11:00 a.m. | W 2-0 | |
| Sat., 9/8 | JV Girls Soccer | Guilford | Home - Cheshire HS soccer field [Directions] | 10:00 a.m. | ||
| Tue., 9/11 | V Girls Soccer | Daniel Hand | Away - Surf Club [Directions] | 6:00 p.m. | T 1-1 | |
| Thu., 9/13 | V Boys Cross Country | Hamden | Home - Cheshire park [Directions] | 4:00 p.m. | ||
| Thu., 9/13 | FR Football | Newtown | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 9/13 | JV Boys Soccer | Daniel Hand | Home - Cheshire HS soccer field [Directions] | 3:45 p.m. | T 0-0 | |
| Thu., 9/13 | V Girls Cross Country | Hamden | Home - Cheshire park [Directions] | 4:00 p.m. | ||
| Thu., 9/13 | V Girls Soccer | Hamden | Away - HHS Turf Field #2 [Directions] | 5:00 p.m. | T 1-1 | |
| Thu., 9/13 | JV Girls Soccer | Hamden | Away - HHS Turf Field #2 [Directions] | 6:30 p.m. | ||
| Thu., 9/13 | FR Girls Soccer | Amity | Away - Center Field - Woodbridge [Directions] | 3:45 p.m. | ||
| Thu., 9/13 | V Girls Swimming and Diving | Sheehan | Home - Cheshire Community pool [Directions] | 7:00 p.m. | Cheshire-106, Sheehan-49 | |
| Thu., 9/13 | V Girls Swimming and Diving | Mercy | Home - Cheshire Community pool [Directions] | 7:00 p.m. | Cheshire-107, Mercy-73 | |
| Fri., 9/14 | V Football | Newtown | Away - Blue and Gold Stadium [Directions] | 7:00 p.m. | L 7-47 | |
| Fri., 9/14 | V Boys Soccer | Lyman Hall | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 1-0 | |
| Fri., 9/14 | JV Boys Soccer | East Haven | Away - East Haven HS [Directions] | Cancelled | Cancelled | |
| Fri., 9/14 | FR Boys Soccer | Guilford | Away - Long Hill Park - Guilford [Directions] | 4:00 p.m. | W 4-1 | |
| Fri., 9/14 | V Field Hockey | Simsbury | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 6-0 | |
| Fri., 9/14 | JV Field Hockey | Simsbury | Home - Cheshire High Field Hockey field [Directions] | 5:30 p.m. | ||
| Fri., 9/14 | FR Field Hockey | Amity | Away - Amity HS [Directions] | 4:00 p.m. | ||
| Sat., 9/15 | JV Football | Newtown | Home - Cheshire High Main Game field [Directions] | 10:00 a.m. | ||
| Mon., 9/17 | V Boys Cross Country | Lyman Hall, Jonathan Law, Foran | Away - Eisenhower Park [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | JV Boys Soccer | Lyman Hall | Home - Cheshire HS soccer field [Directions] | 3:45 p.m. | W 6-0 | |
| Mon., 9/17 | FR Boys Soccer | Daniel Hand | Away - Janssen Field/DHHS Campus [Directions] | 3:45 p.m. | W 2-1 | |
| Mon., 9/17 | V Girls Cross Country | Lyman Hall, Jonathan Law, Foran | Away - Eisenhower Park [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | V Girls Swimming and Diving | Hamden | Home - Cheshire Community pool [Directions] | 7:00 p.m. | Cheshire-96, Hamden-80 | |
| Tue., 9/18 | V Boys Soccer | East Haven | Away - East Haven HS [Directions] | 6:30 p.m. | W 8-0 | |
| Tue., 9/18 | V Field Hockey | Mercy | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | W 5-0 | |
| Thu., 9/20 | FR Football | Sheehan | Away - Sheehan HS Riccitelli Field [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | V Boys Soccer | Branford | Away - Branford HS-Turf Field [Directions] | 6:30 p.m. | T 0-0 | |
| Thu., 9/20 | V Field Hockey | Lauralton Hall | Away - Lauralton Hall Field [Directions] | 3:45 p.m. | W 3-0 | |
| Thu., 9/20 | JV Field Hockey | Lauralton Hall | Away - Lauralton Hall Field [Directions] | 5:15 p.m. | ||
| Thu., 9/20 | V Girls Soccer | North Haven | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 9/20 | FR Girls Soccer | Guilford | Home - Cheshire HS soccer field [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | V Girls Swimming and Diving | Lyman Hall | Home - Cheshire Community pool [Directions] | 7:00 p.m. | Cheshire-95, Lyman Hall-82 | |
| Fri., 9/21 | V Football | North Haven | Away - Vanacore Field [Directions] | 7:00 p.m. | L 21-34 | |
| Fri., 9/21 | JV Boys Soccer | Branford | Away - 'Flax Mill Field [Directions] | 3:45 p.m. | W 2-0 | |
| Fri., 9/21 | JV Girls Soccer | North Haven | Home - Bartlem park [Directions] | 3:45 p.m. | ||
| Sat., 9/22 | V Boys Cross Country | Winding Trails Invite | Away - Winding Trails, Farmington | 9:00 a.m. | ||
| Sat., 9/22 | JV Football | North Haven | Home - Cheshire High Main Game field [Directions] | 10:00 a.m. | ||
| Sat., 9/22 | V Boys Soccer | Guilford | Away - Bittner Park - Guilford [Directions] | 3:00 p.m. | W 1-0 | |
| Sat., 9/22 | JV Boys Soccer | Guilford | Away - Bittner Park - Guilford [Directions] | 1:00 p.m. | W 1-0 | |
| Sat., 9/22 | V Girls Cross Country | Winding Trails Invite | Away - Winding Trails, Farmington | 9:00 a.m. | ||
| Mon., 9/24 | JV Boys Soccer | Hamden | Home - Cheshire HS soccer field [Directions] | 3:45 p.m. | W 2-1 | |
| Mon., 9/24 | FR Field Hockey | Daniel Hand | Home - Cheshire High Field Hockey field [Directions] | 4:00 p.m. | ||
| Mon., 9/24 | V Girls Soccer | Amity | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | L 2-3 | |
| Mon., 9/24 | V Girls Swimming and Diving | Foran | Away - Foran HS [Directions] | 4:00 p.m. | Cheshire-98, Foran-78 | |
| Wed., 9/26 | V Boys Cross Country | Sheehan, Career Magnet, North Haven | Away - Sheehan HS [Directions] | 4:00 p.m. | ||
| Wed., 9/26 | V Girls Cross Country | Sheehan, Career Magnet, North Haven | Away - Sheehan HS [Directions] | 4:00 p.m. | ||
| Wed., 9/26 | V Field Hockey | Sacred Heart Academy | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | W 6-0 | |
| Wed., 9/26 | V Girls Soccer | Mercy | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | L 0-2 | |
| Thu., 9/27 | V Boys Soccer | Shelton | Away - Shelton HS Finn Stadium [Directions] | 7:00 p.m. | W 1-0 | |
| Thu., 9/27 | JV Boys Soccer | Shelton | Away - Shelton HS Finn Stadium [Directions] | 5:30 p.m. | L 0-1 | |
| Thu., 9/27 | JV Girls Soccer | Mercy | Home - Bartlem -field 2 [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | FR Girls Soccer | Daniel Hand | Away - Janssen Field/DHHS Campus [Directions] | 4:00 p.m. | ||
| Fri., 9/28 | V Boys Cross Country | Nonnewaug Invite | Away - Nonnewaug High school | 4:00 p.m. | ||
| Fri., 9/28 | V Football | Jonathan Law | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | L 30-33 (OT) | |
| Fri., 9/28 | FR Boys Soccer | Shelton | Home - Cheshire HS soccer field [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 9/28 | V Girls Cross Country | Nonnewaug Invite | Away - Nonnewaug HS | 4:00 p.m. | ||
| Fri., 9/28 | V Girls Swimming and Diving | Branford | Home - Cheshire Community pool [Directions] | 7:00 p.m. | Cheshire-95, Branford-73 | |
| Sat., 9/29 | JV Football | Jonathan Law | Away - Lawmen Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/29 | FR Boys Soccer | Xavier | Away - Larry McHugh Field (Xavier H.S.) [Directions] | 12:30 p.m. | T 1-1 | |
| Sat., 9/29 | V Girls Soccer | Sheehan | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 1-0 | |
| Sat., 9/29 | JV Girls Soccer | Sheehan | Home - Cheshire HS soccer field [Directions] | 4:00 p.m. | ||
| Mon., 10/1 | V Boys Soccer | University/Prince Tech | Home - Cheshire High Main Game field [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 10/1 | JV Boys Soccer | University/Prince Tech | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | W 8-0 | |
| Mon., 10/1 | V Field Hockey | Daniel Hand | Away - DHHS Turf Field [Directions] | 7:00 p.m. | W 2-1 | |
| Mon., 10/1 | JV Field Hockey | Daniel Hand | Away - DHHS Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 10/1 | V Girls Soccer | Guilford | Away - Bittner Park - Guilford [Directions] | 6:00 p.m. | W 2-1 | |
| Tue., 10/2 | FR Field Hockey | Amity | Home - Cheshire High Field Hockey field [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | JV Girls Soccer | Guilford | Away - Bittner Park - Guilford [Directions] | 3:45 p.m. | ||
| Tue., 10/2 | V Girls Swimming and Diving | North Haven | Away - Gawrych Town Pool [Directions] | 4:00 p.m. | Cheshire-100, North Haven-81 | |
| Wed., 10/3 | V Boys Soccer | Hamden | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | W 2-0 | |
| Wed., 10/3 | FR Field Hockey | Wethersfield | Home - Cheshire HS Field Hockey Field [Directions] | 4:00 p.m. | ||
| Wed., 10/3 | V Girls Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/5 | V Boys Soccer | Daniel Hand | Away - Surf Club [Directions] | 6:00 p.m. | T 1-1 | |
| Fri., 10/5 | JV Boys Soccer | Daniel Hand | Away - Surf Club [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 10/5 | V Field Hockey | Norwalk | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | W 2-0 | |
| Fri., 10/5 | JV Field Hockey | Norwalk | Home - Cheshire High Field Hockey field [Directions] | 5:15 p.m. | ||
| Fri., 10/5 | V Girls Swimming and Diving | Shelton | Home - Cheshire Community pool [Directions] | 7:00 p.m. | Cheshire-104, Shelton-71 | |
| Sat., 10/6 | V Boys Cross Country | Wickham Invite | Away - Wickham Park | 9:00 a.m. | ||
| Sat., 10/6 | FR Boys Soccer | Guilford | Home - Bartlem park [Directions] | 10:00 a.m. | W 2-1 | |
| Sat., 10/6 | V Girls Cross Country | Wickham Invite | Away - Wickham Park | 9:00 a.m. | ||
| Mon., 10/8 | JV Boys Soccer | Hamden | Home - Cheshire High Main Game field [Directions] | 12:30 p.m. | W 1-0 | |
| Tue., 10/9 | V Boys Soccer | Lyman Hall | Away - Lyman Hall Fitzgerald Field [Directions] | 3:45 p.m. | W 5-0 | |
| Tue., 10/9 | V Field Hockey | Sheehan | Away - Sheehan HS Riccitelli Field [Directions] | 5:00 p.m. | W 5-0 | |
| Tue., 10/9 | JV Field Hockey | Sheehan | Away - Sheehan HS Riccitelli Field [Directions] | 3:45 p.m. | ||
| Tue., 10/9 | V Girls Soccer | Hamden | Home - Cheshire High Main Game field [Directions] | 6:30 p.m. | W 2-1 | |
| Tue., 10/9 | FR Girls Soccer | Daniel Hand | Home - Bartlem park [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | V Boys Cross Country | Amity, Shelton | Away - Fitzgerald Trail - Woodbridge [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | JV Boys Soccer | Lyman Hall | Away - Lyman Hall Field #1 [Directions] | 3:45 p.m. | W 5-0 | |
| Wed., 10/10 | V Girls Cross Country | Amity, Shelton | Away - Fitzgerald Trail - Woodbridge [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | V Field Hockey | Lyman Hall | Away - Lyman Hall Fitzgerald Field [Directions] | 3:45 p.m. | W 6-0 | |
| Wed., 10/10 | JV Field Hockey | Lyman Hall | Away - Lyman Hall Fitzgerald Field [Directions] | 5:15 p.m. | ||
| Wed., 10/10 | JV Girls Soccer | Hamden | Home - Bartlem -field 2 [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | V Football | Fairfield Prep | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | L 14-28 | |
| Fri., 10/12 | JV Boys Soccer | Guilford | Home - Bartlem park [Directions] | 3:45 p.m. | L 0-2 | |
| Fri., 10/12 | JV Girls Soccer | Amity | Home - Cheshire HS soccer field [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | V Girls Swimming and Diving | Daniel Hand | Home - Cheshire Community pool [Directions] | 7:00 p.m. | Cheshire-94, Daniel Hand-84 | |
| Sat., 10/13 | JV Football | Fairfield Prep | Away - Barlow Field, Fairfield University [Directions] | 10:00 a.m. | ||
| Sat., 10/13 | V Boys Soccer | East Haven | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 4-0 | |
| Sat., 10/13 | FR Boys Soccer | Daniel Hand | Home - Cheshire HS soccer field [Directions] | 3:30 p.m. | W 3-0 | |
| Sat., 10/13 | V Girls Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | 7:00 p.m. | L 3-0 | |
| Sun., 10/14 | V Field Hockey | Amity | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 3-0 | |
| Sun., 10/14 | JV Field Hockey | Amity | Home - Cheshire High Main Game field [Directions] | 5:30 p.m. | ||
| Mon., 10/15 | V Boys Soccer | Branford | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 5-0 | |
| Mon., 10/15 | FR Boys Soccer | Amity | Home - Cheshire HS soccer field [Directions] | 3:45 p.m. | W 5-1 | |
| Mon., 10/15 | V Field Hockey | North Haven | Home - Cheshire High Main Game field [Directions] | 3:45 p.m. | W 7-0 | |
| Mon., 10/15 | JV Field Hockey | North Haven | Home - Cheshire High Field Hockey field [Directions] | 5:15 p.m. | ||
| Mon., 10/15 | FR Field Hockey | Guilford | Away - Maturo Field at GHS [Directions] | 4:00 p.m. | ||
| Mon., 10/15 | V Girls Soccer | North Haven | Away - North Haven MS Turf Field [Directions] | 7:00 p.m. | W 9-0 | |
| Mon., 10/15 | FR Girls Soccer | Guilford | Away - Cox School Field - Guilford [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | JV Boys Soccer | Branford | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/16 | JV Girls Soccer | North Haven | Away - North Haven MS Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 10/16 | V Girls Swimming and Diving | Lauralton Hall | Away - Foran HS Pool [Directions] | 6:00 p.m. | Cheshire-98, Lauralton-Hall-83 | |
| Wed., 10/17 | V Boys Soccer | Guilford | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | L 0-2 | |
| Wed., 10/17 | FR Boys Soccer | Notre Dame-West Haven | Home - Cheshire HS soccer field [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/17 | V Field Hockey | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 1-0 | |
| Wed., 10/17 | JV Field Hockey | Daniel Hand | Home - Cheshire High Field Hockey field [Directions] | 5:15 p.m. | ||
| Wed., 10/17 | FR Field Hockey | Wethersfield | Away - Esposito Field at WHS [Directions] | 4:00 p.m. | ||
| Wed., 10/17 | V Girls Soccer | Amity | Away - Amity HS - Field # 3 [Directions] | 3:45 p.m. | L 2-1 | |
| Thu., 10/18 | FR Football | West Haven | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 10/18 | FR Field Hockey | Daniel Hand | Away - Polson Front Field/DHHS Campus [Directions] | 4:00 p.m. | ||
| Thu., 10/18 | JV Girls Soccer | Amity | Away - Amity HS - Field # 2 [Directions] | 3:45 p.m. | ||
| Thu., 10/18 | FR Girls Soccer | Amity | Home - CHS [Directions] | 3:45 p.m. | ||
| Fri., 10/19 | V Boys Cross Country | SCC Championship | Away - East Shore Park, New Haven | 1:00 p.m. | ||
| Fri., 10/19 | V Football | West Haven | Away - Ken Strong Stadium [Directions] | 7:00 p.m. | W 21-14 | |
| Fri., 10/19 | V Boys Soccer | Hamden | Away - HHS Turf Field #1 [Directions] | 7:00 p.m. | W 3-0 | |
| Fri., 10/19 | JV Boys Soccer | Hamden | Away - HHS Turf Field #1 [Directions] | 5:30 p.m. | T 0-0 | |
| Fri., 10/19 | V Girls Cross Country | SCC Championship | Away - East Shore Park, New Haven | 1:00 p.m. | ||
| Fri., 10/19 | V Field Hockey | Guilford | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 1-0 | |
| Fri., 10/19 | JV Field Hockey | Guilford | Home - Cheshire High Field Hockey field [Directions] | 4:00 p.m. | ||
| Fri., 10/19 | V Girls Swimming and Diving | Amity | Away - Orange Community Center Pool [Directions] | 6:30 p.m. | Cheshire-98, Amity-80 | |
| Sat., 10/20 | JV Football | West Haven | Home - Cheshire High Main Game field [Directions] | 10:00 a.m. | ||
| Sat., 10/20 | FR Boys Soccer | Notre Dame-West Haven | Away - Notre Dame HS [Directions] | 10:30 a.m. | W 4-3 | |
| Sat., 10/20 | V Field Hockey | Hamden | Away - HHS Turf Field #2 [Directions] | 12:00 p.m. | W 5-0 | |
| Sat., 10/20 | JV Field Hockey | Hamden | Away - HHS Turf Field #2 [Directions] | 1:30 p.m. | ||
| Sat., 10/20 | V Girls Soccer | Mercy | Away - Mercy [Directions] | 3:00 p.m. | T 1-1 | |
| Sat., 10/20 | JV Girls Soccer | Mercy | Away - Mercy [Directions] | 10:30 a.m. | ||
| Mon., 10/22 | V Boys Soccer | Shelton | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | T 1-1 | |
| Mon., 10/22 | JV Boys Soccer | Shelton | Home - Cheshire HS soccer field [Directions] | 4:00 p.m. | W 2-0 | |
| Mon., 10/22 | V Field Hockey | Branford | Away - Branford HS-Turf Field [Directions] | 7:00 p.m. | W 2-0 | |
| Mon., 10/22 | JV Field Hockey | Branford | Away - Branford HS-Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 10/22 | V Girls Soccer | Sheehan | Away - Sheehan HS Riccitelli Field [Directions] | 6:15 p.m. | W 5-1 | |
| Mon., 10/22 | JV Girls Soccer | Sheehan | Away - Sheehan HS Riccitelli Field [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | FR Girls Soccer | Mercy | Home - Bartlem -field 2 [Directions] | 4:00 p.m. | ||
| Tue., 10/23 | FR Boys Soccer | Shelton | Away - Shelton HS Finn Stadium [Directions] | 6:00 p.m. | T 0-0 | |
| Tue., 10/23 | JV Girls Soccer | Daniel Hand | Away - Janssen Field/DHHS Campus [Directions] | 4:00 p.m. | ||
| Wed., 10/24 | FR Field Hockey | Guilford | Home - Cheshire High Field Hockey field [Directions] | 4:00 p.m. | ||
| Wed., 10/24 | V Girls Soccer | Old Lyme | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | L 3-1 | |
| Thu., 10/25 | FR Football | Notre Dame-West Haven | Away - Veteran's Stadium [Directions] | 4:00 p.m. | ||
| Thu., 10/25 | V Boys Soccer | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | L 0-2 | |
| Thu., 10/25 | FR Boys Soccer | Amity | Away - Pease Rd. - Woodbridge [Directions] | 4:00 p.m. | W 4-0 | |
| Fri., 10/26 | V Football | Notre Dame-West Haven | Home - Cheshire High Main Game field [Directions] | 7:00 p.m. | W 21-14 | |
| Fri., 10/26 | V Field Hockey | Lauralton Hall | Home - Cheshire High Main Game field [Directions] | 3:30 p.m. | W 6-0 | |
| Fri., 10/26 | V Girls Soccer | Shelton | Away [Directions] | 7:00 p.m. | L 3-2 | |
| Sat., 10/27 | V Boys Cross Country | CIAC Class L Championship | Away - Wickham Park - East Hartford [Directions] | 9:15 a.m. | ||
| Sat., 10/27 | JV Football | Notre Dame-West Haven | Away - Veteran's Stadium [Directions] | TBA | ||
| Sat., 10/27 | V Girls Cross Country | CIAC Class L Championship | Away - Wickham Park - East Hartford [Directions] | 9:45 a.m. | ||
| Sat., 10/27 | V Girls Swimming and Diving | SCC Diving championship | Away - Sheehan HS | 10:00 a.m. | Cheshire - 1st, 12th, 25th | |
| Sun., 10/28 | V Boys Soccer | Branford | Away - Branford HS-Turf Field [Directions] | 6:30 p.m. | L 1-0 | |
| Tue., 10/30 | V Field Hockey | Branford | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 5-0 | |
| Tue., 10/30 | V Girls Swimming and Diving | SCC Qualifying | Home - Cheshire Community pool [Directions] | 4:00 p.m. | ||
| Thu., 11/1 | FR Football | Daniel Hand | Away - DHHS Turf Field [Directions] | 7:00 p.m. | ||
| Thu., 11/1 | V Girls Swimming and Diving | SCC Championship | Away - SCSU pool | 6:00 p.m. | Cheshire - SCC Champion | |
| Fri., 11/2 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | ||
| Fri., 11/2 | V Football | Daniel Hand | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | L 14-49 | |
| Fri., 11/2 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | ||
| Sat., 11/3 | V Field Hockey | Guilford | Away - Kavanaugh Turf Field at GHS [Directions] | 3:00 p.m. | ||
| Mon., 11/5 | V Field Hockey | CIAC Tourney Qualifying Round | Away - Site TBA | TBA | ||
| Mon., 11/5 | V Girls Soccer | Trumbull | Away - New Turf Field [Directions] | 2:00 p.m. | ||
| Tue., 11/6 | V Boys Soccer | E.O. Smith | Home - Cheshire High Main Game field [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 11/7 | V Field Hockey | Fairfield Warde | Home - Cheshire High Main Game field [Directions] | 3:00 p.m. | ||
| Wed., 11/7 | V Girls Soccer | CIAC Tourney 2nd Round | Away - Higher Seed | TBA | ||
| Thu., 11/8 | FR Football | Harding | Away [Directions] | 6:00 p.m. | ||
| Thu., 11/8 | V Boys Soccer | Staples | Home - Cheshire High Main Game field [Directions] | 5:00 p.m. | ||
| Thu., 11/8 | V Girls Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Fri., 11/9 | V Football | Harding | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 40-0 | |
| Fri., 11/9 | V Field Hockey | CIAC Tourney Quarterfinals (Possible Date) | Away - Higher Seed | TBA | ||
| Fri., 11/9 | V Girls Soccer | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Sat., 11/10 | V Boys Cross Country | New England Championship | Away - Derryfield Park (Manchester, NH) [Directions] | TBA | ||
| Sat., 11/10 | JV Football | Harding | Away - Harding HS-John L. Lewis Memorial Field [Directions] | 10:00 a.m. | ||
| Sat., 11/10 | V Boys Soccer | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Sat., 11/10 | V Girls Cross Country | New England Championship | Away - Derryfield Park (Manchester, NH) [Directions] | TBA | ||
| Sat., 11/10 | V Field Hockey | CIAC Tourney Quarterfinals (Possible Date) | Away - Higher Seed | TBA | ||
| Sat., 11/10 | V Girls Swimming and Diving | CIAC Class L Qualifying | Away - Cornerstone Pool [Directions] | 3:15 p.m. | ||
| Mon., 11/12 | V Girls Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Tue., 11/13 | V Boys Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Tue., 11/13 | V Field Hockey | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Tue., 11/13 | V Girls Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Tue., 11/13 | V Girls Swimming and Diving | CIAC Class L Finals | Away - SCSU [Directions] | 6:00 p.m. | ||
| Wed., 11/14 | V Boys Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Wed., 11/14 | V Field Hockey | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Thu., 11/15 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Sat., 11/17 | V Boys Soccer | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Sat., 11/17 | V Field Hockey | CIAC Tourney Final | Away - Wethersfield [Directions] | TBA | ||
| Sat., 11/17 | V Girls Soccer | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Sat., 11/17 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Mon., 11/19 | FR Football | Southington | Home - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Wed., 11/21 | V Football | Southington | Away - Turf Field SHS [Directions] | 6:00 p.m. | L 13-23 | |