| Westbrook 2017-18 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 580 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | V Baseball | Parish Hill (Scrim.) | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | Cancelled | Cancelled | |
| TBA | V Baseball | Coventry (Scrim.) | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | Cancelled | Cancelled | |
| TBA | JV Baseball | Morgan | Away - Morgan HS [Directions] | 10:30 a.m. | ||
| TBA | JV Baseball | Haddam-Killingworth | Home - Valley Regional HS [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Westbrook | Home - Valley Regional HS [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Cromwell | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | North Branford | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | ValleyReg/Westbrook | Away - Valley Regional HS [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Old Lyme | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Old Saybrook | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Portland | Away - Portland HS [Directions] | 4:00 p.m. | ||
| TBA | JV Baseball | Creed | Away - West Rock Park | TBA | ||
| TBA | JV Baseball | Coginchaug | Home - Valley Regional HS [Directions] | Cancelled | Cancelled | |
| TBA | JV Baseball | Creed | Home - Valley Regional HS [Directions] | TBA | ||
| TBA | JV Baseball | Portland | Away - Portland HS [Directions] | TBA | ||
| TBA | FR Boys Basketball | Coginchaug | Home - Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| TBA | V Boys Outdoor Track | Black & Purple Scrimmage | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | Cancelled | Cancelled | CANCELLED |
| TBA | JV Boys Soccer | Morgan | Away - Morgan HS [Directions] | 10:30 a.m. | ||
| TBA | JV Boys Soccer | Hale Ray | Away - Hale-Ray HS [Directions] | Cancelled | Cancelled | |
| TBA | JV Boys Soccer | Coginchaug | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | ||
| TBA | V Girls Outdoor Track | Purple & Black Scrimmage | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | Cancelled | Cancelled | CANCELLED |
| TBA | V Softball | Hillhouse (Scrim.) | Home - Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | Hale Ray | Away - Hale-Ray HS, Lou Milardo Field [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | Morgan | Home - Westbrook HS Field #5 - Softball [Directions] | TBA | ||
| TBA | Unified Sports Volleyball | Shoreline Conference Unified Volleyball Tournament | Away - Haddam-Killingworth HS | 3:00 p.m. | ||
| TBA | Unified Sports Volleyball | Hale Ray | Away - Hale Ray HS [Directions] | 3:00 p.m. | ||
| Wed., 4/26 | Unified Sports Volleyball | SLC Unified Volleyball Tourney | Away - Sports on 66: East Hampton | 3:30 p.m. | ||
| Wed., 8/23 | V Football | Waterford (Scrim.) | Away [Directions] | 9:00 a.m. | ||
| Sat., 8/26 | V Football | Stonington (Scrim.) | Away [Directions] | 9:00 a.m. | ||
| Sun., 8/27 | V Field Hockey | Mustang Jamboree | Away - Immaculate HS - Danbury | 12:00 p.m. | ||
| Tue., 8/29 | V Girls Soccer | Fitch (Scrim.) | Home - Westbrook MS Field #1 - Soccer [Directions] | 3:45 p.m. | 3 teams Fitch, Griswold, Westbrook | |
| Wed., 8/30 | V Boys Soccer | St. Bernard (Scrim.) | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | ||
| Wed., 8/30 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Thu., 8/31 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Fri., 9/1 | V Football | Daniel Hand (Scrim.) | Away - Surf Club [Directions] | 6:00 p.m. | ||
| Fri., 9/1 | V Field Hockey | Farmington Playday | Away - Farmington HS | 4:00 p.m. | ||
| Fri., 9/1 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Sat., 9/2 | V Boys Soccer | Hale Ray Jamboree | Away - Hale Ray HS - Nevers Field | 10:00 a.m. | ||
| Tue., 9/5 | V Field Hockey | Guilford (Scrim.) | Away - Kavanaugh Turf Field at GHS [Directions] | 3:45 p.m. | ||
| Wed., 9/6 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Thu., 9/7 | V Boys Soccer | Wilcox Tech (Scrim.) | Away - Wilcox Tech School Field [Directions] | 4:00 p.m. | ||
| Thu., 9/7 | V Girls Soccer | East Haven (Scrim.) | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | ||
| Thu., 9/7 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Fri., 9/8 | V Boys Cross Country | Middletown | Away [Directions] | 3:00 p.m. | ||
| Fri., 9/8 | V Football | Stafford/East Windsor/Somers | Away - Stafford High, Lighted field behind school [Directions] | 6:30 p.m. | L 0-36 | |
| Fri., 9/8 | V Field Hockey | Suffield | Away - Ted Beneski Turf Field [Directions] | 4:15 p.m. | T 0-0 | |
| Fri., 9/8 | JV Field Hockey | Suffield | Away - Ted Beneski Turf Field [Directions] | 5:45 p.m. | ||
| Fri., 9/8 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Sat., 9/9 | V Boys Cross Country | Martha's Vineyard Invitational | Away | 10:00 a.m. | ||
| Sat., 9/9 | JV Football | Stafford/East Windsor/Somers | Home - Peters Complex [Directions] | 10:30 a.m. | ||
| Sat., 9/9 | V Boys Soccer | Hale Ray | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:00 p.m. | W 1-0 | Non-Conference |
| Sat., 9/9 | V Girls Soccer | Hale Ray | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 1:00 p.m. | W 8-1 | Non-Conference |
| Mon., 9/11 | V Boys Soccer | East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | L 0-1 | |
| Mon., 9/11 | V Field Hockey | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | 3:45 p.m. | W 1-0 | |
| Mon., 9/11 | JV Field Hockey | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | 5:15 p.m. | ||
| Mon., 9/11 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Tue., 9/12 | JV Boys Soccer | East Hampton | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Girls Soccer | East Hampton | Away - East Hampton HS [Directions] | 6:30 p.m. | L 0-3 | |
| Tue., 9/12 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Wed., 9/13 | JV Girls Soccer | East Hampton | Home - Westbrook MS Field #4 - Softball [Directions] | 3:45 p.m. | ||
| Wed., 9/13 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Thu., 9/14 | V Boys Soccer | Old Lyme | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | W 2-1 | |
| Thu., 9/14 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Fri., 9/15 | V Football | Valley Regional/Old Lyme | Away - VRHS Football Field [Directions] | 6:30 p.m. | L 7-48 | |
| Fri., 9/15 | V Field Hockey | Valley Regional | Away - Valley Regional Hockey Field [Directions] | 3:45 p.m. | T 0-0 | |
| Fri., 9/15 | JV Field Hockey | Valley Regional | Away - Valley Regional Hockey Field [Directions] | 5:15 p.m. | ||
| Fri., 9/15 | V Girls Soccer | Old Lyme | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | L 0-6 | |
| Fri., 9/15 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Sat., 9/16 | V Boys Cross Country | Connecticut Valley Invitational | Away | 10:00 a.m. | Cromwell | |
| Sat., 9/16 | JV Football | Valley Regional/Old Lyme | Home - Peters Complex [Directions] | 10:30 a.m. | ||
| Mon., 9/18 | V Boys Soccer | North Branford | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | W 3-0 | |
| Mon., 9/18 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Tue., 9/19 | JV Boys Soccer | North Branford | Away - North Branford HS [Directions] | Cancelled | Cancelled | |
| Tue., 9/19 | V Girls Soccer | North Branford/Hale Ray | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | L 1-4 | |
| Tue., 9/19 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Wed., 9/20 | V Boys Soccer | Bassick | Away - Luis Munoz Marin School [Directions] | 3:45 p.m. | L 2-3 | Non-Conference |
| Wed., 9/20 | V Field Hockey | North Branford | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 9/20 | JV Field Hockey | North Branford | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Wed., 9/20 | V Girls Soccer | Bassick | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | W 7-1 | Non-Conference |
| Wed., 9/20 | JV Girls Soccer | North Branford/Hale Ray | Away - North Branford HS [Directions] | Cancelled | Cancelled | |
| Wed., 9/20 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Thu., 9/21 | V Boys Cross Country | Run to the Sun | Away | 3:00 p.m. | Durham | |
| Thu., 9/21 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Fri., 9/22 | V Football | Haddam-Killingworth | Home - Peters Complex [Directions] | 6:30 p.m. | L 7-21 | |
| Fri., 9/22 | V Boys Soccer | Portland | Away - Portland HS [Directions] | 7:00 p.m. | L 0-3 | |
| Fri., 9/22 | V Field Hockey | Morgan | Away - Indian River Complex [Directions] | 3:45 p.m. | T 0-0 | |
| Fri., 9/22 | JV Field Hockey | Morgan | Away - Indian River Complex [Directions] | 5:15 p.m. | ||
| Fri., 9/22 | V Girls Soccer | Portland | Away - Portland HS [Directions] | 5:00 p.m. | T 0-0 | |
| Fri., 9/22 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Sat., 9/23 | V Boys Cross Country | Ocean State Invitational | Away | 10:00 a.m. | Rhode Island | |
| Sat., 9/23 | JV Football | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 10:30 a.m. | ||
| Sat., 9/23 | JV Boys Soccer | Portland | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | Cancelled | Cancelled | |
| Mon., 9/25 | V Boys Soccer | Valley Regional | Away - VRHS Football Field [Directions] | 3:45 p.m. | L 0-8 | |
| Mon., 9/25 | JV Girls Soccer | Portland | Home - Westbrook HS Field #5 - Softball [Directions] | Cancelled | Cancelled | 8v8 @ WHS SB Field area |
| Mon., 9/25 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Tue., 9/26 | V Boys Cross Country | East Hampton, Hale Ray, Old Lyme, Creed | Away [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Girls Soccer | Valley Regional | Away - VRHS Football Field [Directions] | 3:45 p.m. | L 0-5 | |
| Tue., 9/26 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Wed., 9/27 | V Boys Soccer | Cromwell | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 9/27 | V Field Hockey | Haddam-Killingworth | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | W 1-0 | |
| Wed., 9/27 | JV Field Hockey | Haddam-Killingworth | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Wed., 9/27 | JV Girls Soccer | Hale Ray | Home - Westbrook MS Field #4 - Softball [Directions] | 3:45 p.m. | 8 v 8; Small sided by SB Field | |
| Wed., 9/27 | JV Girls Soccer | Valley Regional | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | Cancelled | Cancelled | |
| Wed., 9/27 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Thu., 9/28 | V Football | North Branford | Away - Colafati Field - NBHS [Directions] | 6:30 p.m. | L 2-41 | |
| Thu., 9/28 | V Girls Soccer | Cromwell | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | L 0-3 | |
| Thu., 9/28 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Fri., 9/29 | V Boys Cross Country | Husky Invitational | Away | 3:30 p.m. | ||
| Fri., 9/29 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Sat., 9/30 | JV Football | North Branford | Home - Peters Complex [Directions] | Cancelled | Cancelled | |
| Sat., 9/30 | V Field Hockey | Somers/Rockville Coop | Away - Somers HS [Directions] | 12:00 p.m. | W 4-0 | |
| Sat., 9/30 | JV Field Hockey | Somers/Rockville Coop | Away - Somers HS [Directions] | 1:30 p.m. | ||
| Mon., 10/2 | V Girls Soccer | Haddam-Killingworth | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | L 0-2 | |
| Mon., 10/2 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Tue., 10/3 | V Boys Soccer | Haddam-Killingworth | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | L 0-8 | |
| Tue., 10/3 | V Field Hockey | Old Saybrook | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | W 4-1 | |
| Tue., 10/3 | JV Field Hockey | Old Saybrook | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Tue., 10/3 | JV Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Wed., 10/4 | V Boys Cross Country | Cougar Invitational | Away - Totocket Park North Branford | 3:30 p.m. | ||
| Wed., 10/4 | JV Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | Cancelled | Cancelled | |
| Wed., 10/4 | V Girls Soccer | Bassick | Away - Went Field [Directions] | 3:45 p.m. | W 4-0 | Non-Conference |
| Wed., 10/4 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Thu., 10/5 | V Field Hockey | Stafford | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 10/5 | JV Field Hockey | Stafford | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Fri., 10/6 | V Football | Nonnewaug | Home - Peters Complex [Directions] | 6:30 p.m. | L 22-30 | |
| Fri., 10/6 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Sat., 10/7 | V Boys Cross Country | Wickham Invitational | Away | TBA | ||
| Sat., 10/7 | JV Football | Nonnewaug | Away - Nonnewaug HS Football Field [Directions] | Cancelled | Cancelled | |
| Sat., 10/7 | V Boys Soccer | Hale Ray | Away - Hale-Ray HS, Nevers Field [Directions] | 7:00 p.m. | W 3-2 | |
| Sat., 10/7 | V Girls Soccer | Hale Ray | Away - Hale-Ray HS, Nevers Field [Directions] | 5:00 p.m. | W 4-0 | Non-Conference |
| Tue., 10/10 | V Boys Soccer | Old Saybrook | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | L 0-4 | |
| Tue., 10/10 | JV Girls Soccer | Old Saybrook | Away - Old Saybrook HS [Directions] | Cancelled | Cancelled | |
| Tue., 10/10 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Wed., 10/11 | V Field Hockey | Valley Regional | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | T 0-0 | |
| Wed., 10/11 | JV Field Hockey | Valley Regional | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Wed., 10/11 | V Girls Soccer | Old Saybrook | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | L 1-6 | |
| Wed., 10/11 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Thu., 10/12 | V Boys Cross Country | Old Lyme | Away [Directions] | 3:45 p.m. | ||
| Thu., 10/12 | V Girls Soccer | Morgan | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | L 8-2 | |
| Thu., 10/12 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Fri., 10/13 | V Boys Soccer | Morgan | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | L 0-4 | |
| Fri., 10/13 | V Field Hockey | North Branford | Away - North Branford HS [Directions] | 6:30 p.m. | L 0-2 | |
| Fri., 10/13 | JV Field Hockey | North Branford | Away - North Branford HS [Directions] | Cancelled | Cancelled | |
| Fri., 10/13 | JV Girls Soccer | Morgan | Away - Morgan HS [Directions] | Cancelled | Cancelled | |
| Fri., 10/13 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Mon., 10/16 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Tue., 10/17 | V Boys Soccer | Coginchaug | Away - CRHS Stadium Field & Track [Directions] | 3:45 p.m. | L 1-4 | |
| Tue., 10/17 | V Field Hockey | Morgan | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | W 2-0 | |
| Tue., 10/17 | JV Field Hockey | Morgan | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Tue., 10/17 | V Girls Soccer | Coginchaug | Away - Field #2 - Middle Field @ CRHS [Directions] | 3:45 p.m. | L 1-2 | |
| Tue., 10/17 | JV Girls Soccer | Coginchaug | Home - Westbrook MS Field #4 - Softball [Directions] | Cancelled | Cancelled | |
| Tue., 10/17 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Wed., 10/18 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Thu., 10/19 | V Boys Soccer | North Branford | Away - Colafati Field - NBHS [Directions] | 6:30 p.m. | L 0-1 | Non-Conference |
| Thu., 10/19 | V Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | L 0-2 | |
| Thu., 10/19 | JV Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:15 p.m. | ||
| Thu., 10/19 | V Girls Soccer | Amistad | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | W 7-0 | Non-Conference |
| Thu., 10/19 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Thu., 10/19 | Unified Sports Soccer | Coginchaug | Away - Coginchaug HS [Directions] | 11:00 a.m. | ||
| Fri., 10/20 | V Boys Cross Country | Shoreline Championship | Away | 2:30 p.m. | Lyme Old Lyme | |
| Fri., 10/20 | V Football | Ellington | Home - Peters Complex [Directions] | 6:30 p.m. | L 7-33 | |
| Fri., 10/20 | JV Boys Soccer | North Branford | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | Cancelled | Cancelled | Non-Conference |
| Fri., 10/20 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Sat., 10/21 | JV Football | Ellington | Away - Ellington HS [Directions] | Cancelled | Cancelled | |
| Sat., 10/21 | V Field Hockey | Killingly | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 11:00 a.m. | W 2-0 | |
| Sat., 10/21 | JV Field Hockey | Killingly | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 12:30 p.m. | ||
| Mon., 10/23 | V Boys Soccer | Amistad | Away - AF Amistad HS [Directions] | 4:00 p.m. | W 2-0 | Non-Conference |
| Mon., 10/23 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Mon., 10/23 | Unified Sports Soccer | Old Saybrook | Away - Old Saybrook HS [Directions] | 3:00 p.m. | ||
| Tue., 10/24 | V Boys Cross Country | Fresh/Soph | Home - Old Saybrook HS [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Tue., 10/24 | Unified Sports Soccer | Morgan | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | Cancelled | Cancelled | |
| Wed., 10/25 | V Boys Soccer | Whitney Tech | Away - Whitney Tech School Field [Directions] | 3:30 p.m. | L 2-4 | Non-Conference |
| Wed., 10/25 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Thu., 10/26 | V Field Hockey | Canton | Away - Canton H.S. Turf [Directions] | 3:45 p.m. | W 1-0(OT) | |
| Thu., 10/26 | JV Field Hockey | Canton | Away - Canton H.S. Turf [Directions] | 5:15 p.m. | ||
| Thu., 10/26 | V Girls Soccer | Amistad | Away - AF Amistad HS [Directions] | 3:00 p.m. | W 5-0 | Non-Conference |
| Thu., 10/26 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Fri., 10/27 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Sat., 10/28 | V Boys Cross Country | CIAC Class SS Championship | Away - Wickham Park - East Hartford [Directions] | 3:45 p.m. | ||
| Sat., 10/28 | V Football | Lewis Mills | Home - Peters Complex [Directions] | 1:30 p.m. | L 0-29 | Homecoming |
| Sat., 10/28 | JV Boys Soccer | Old Saybrook | Away - OSHS - Grass Field [Directions] | 10:00 a.m. | vs OSHS Frosh | |
| Sat., 10/28 | V Field Hockey | Granby Memorial | Away - Granby Memorial HS [Directions] | 3:30 p.m. | T 0-0 | |
| Sat., 10/28 | JV Field Hockey | Granby Memorial | Away - Granby Memorial HS [Directions] | 5:00 p.m. | ||
| Mon., 10/30 | V Boys Cross Country | Freshman @ John Winthrop | Away | 3:30 p.m. | ||
| Mon., 10/30 | JV Football | Lewis Mills | Home - Peters Complex [Directions] | Cancelled | Cancelled | |
| Tue., 10/31 | V Field Hockey | Valley Regional | Away - Valley Regional Hockey Field [Directions] | 3:30 p.m. | OT-L 1-2 | #2 VR vs #3 Westbrook SLC FH Semi-Finals |
| Tue., 10/31 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Wed., 11/1 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Wed., 11/1 | Unified Sports Soccer | SLC Unified Soccer Tournament | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:15 p.m. | ||
| Thu., 11/2 | V Field Hockey | SLC FH Championship | Away - Indian River Complex - Clinton | 7:00 p.m. | ||
| Thu., 11/2 | Miscellaneous Events | SLC Student-Athlete Leadership Conference | Away - Old Lyme HS | 9:00 a.m. | 9am - 12p | |
| Thu., 11/2 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Fri., 11/3 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | ||
| Fri., 11/3 | V Football | Cromwell/Portland | Home - Peters Complex [Directions] | 6:30 p.m. | L 8-33 | |
| Fri., 11/3 | JV Boys Soccer | Hale Ray (Scrim.) | Away - Hale-Ray HS [Directions] | 3:30 p.m. | ||
| Fri., 11/3 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Sat., 11/4 | JV Football | Cromwell/Portland | Away - Pierson Park, Cromwell [Directions] | Cancelled | Cancelled | |
| Mon., 11/6 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Tue., 11/7 | V Field Hockey | Waterford | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 2:00 p.m. | W 1-0 | |
| Tue., 11/7 | V Girls Soccer | East Granby | Away - East Granby HS [Directions] | 2:00 p.m. | L 2-3 (3-2 PKs) | CIAC Class S 1st Round |
| Tue., 11/7 | School Holidays and Closings | No School: PD Day | ||||
| Wed., 11/8 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Thu., 11/9 | V Field Hockey | North Branford | Away - Colafati Field - NBHS [Directions] | 2:00 p.m. | L 0-6 | CIAC Class S Quarterfinals |
| Thu., 11/9 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Fri., 11/10 | V Football | Coginchaug/Hale Ray/East Hampton | Away - CRHS Stadium Field & Track [Directions] | 7:00 p.m. | L 21-42 | |
| Fri., 11/10 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Sat., 11/11 | V Boys Cross Country | New England Championship | Away - Troy Howard MS (Belfast, ME) [Directions] | TBA | ||
| Sat., 11/11 | JV Football | Coginchaug/Hale Ray/East Hampton | Home - Peters Complex [Directions] | Cancelled | Cancelled | |
| Sat., 11/11 | V Field Hockey | Memorial Serivice - P. Kamercia | Away - Haddam-Killingworth HS | 1:00 p.m. | ||
| Mon., 11/13 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Tue., 11/14 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Wed., 11/15 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Thu., 11/16 | Miscellaneous Events | CIAC Sportsmanship Workshop | Away - Aqua Turf - Plantsville | 8:00 a.m. | ||
| Thu., 11/16 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Fri., 11/17 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Sat., 11/18 | JV Football | Old Saybrook | Home - Peters Complex [Directions] | Cancelled | Cancelled | |
| Mon., 11/20 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 2:30 p.m. | OSW FB, XC, Cheer - leaves 2;30 pm Prompt | |
| Wed., 11/22 | Miscellaneous Events | OSHS Shuttle | Away - Old Saybrook HS | 12:15 p.m. | OSW FB,Cheer - leaves 12:20 pm | |
| Thu., 11/23 | V Football | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | 10:30 a.m. | L 0-35 | |
| Mon., 11/27 | Miscellaneous Events | Winter Sports Parent & Student Athlete Meeting | Home - Westbrook HS Auditorium [Directions] | 7:00 p.m. | ||
| Tue., 11/28 | V Football | CIAC Quarterfinals | Home - Peters Complex [Directions] | Cancelled | Cancelled | |
| Sat., 12/2 | V Girls Basketball | Bulldog Bash | Away - Lyman Memorial HS | 2:00 p.m. | ||
| Sat., 12/2 | V Girls Ice Hockey | Guilford Jamboree | Away - East Haven | 5:00 p.m. | ||
| Sun., 12/3 | V Football | CIAC Semifinals | Home - Peters Complex [Directions] | Cancelled | Cancelled | |
| Tue., 12/5 | V Girls Basketball | Platt (Scrim.) | Away - Platt high school [Directions] | 5:00 p.m. | ||
| Fri., 12/8 | V Boys Basketball | Platt (Scrim.) | Home - Platt HS - Meriden [Directions] | 5:00 p.m. | ||
| Sat., 12/9 | V Football | CIAC Finals | Away - TBA | Cancelled | Cancelled | |
| Tue., 12/12 | V Boys Basketball | Sheehan (Scrim.) | Home - Westbrook HS [Directions] | 3:30 p.m. | ||
| Tue., 12/12 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | 6:00 p.m. | L 31-40 | |
| Wed., 12/13 | FR Boys Basketball | Montville (Scrim.) | Away - Montville HS [Directions] | 6:30 p.m. | ||
| Wed., 12/13 | V Boys Indoor Track | SLC Developmental Meet | Away - Floyd Little AC - Hillhouse | 5:00 p.m. | share bus with girls | |
| Wed., 12/13 | V Girls Ice Hockey | East Catholic Coop | Home - Northford Ice Pavilion [Directions] | 4:00 p.m. | W 2-1 (OT) | |
| Wed., 12/13 | V Girls Indoor Track | SLC League Developmental Meet | Away - Floyd Little AC - Hillhouse | 5:00 p.m. | share bus with boys | |
| Wed., 12/13 | Unified Sports Bowling | SLC Unified Bowling Tournament | Away - Callahan's Bowl-a-Rama (Newington) | 3:15 p.m. | 3:15 pm - 5:15 pm | |
| Fri., 12/15 | Unified Sports Basketball | Unified Sports Youth Leadership Summit | Away - The Aetna Hartford CT | 8:00 a.m. | Aetna, 151 Farmington Ave., Hartford CT 06156. | |
| Sat., 12/16 | V Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 7:00 p.m. | L 39-59 | |
| Sat., 12/16 | JV Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 5:30 p.m. | ||
| Sat., 12/16 | FR Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 10:00 a.m. | ||
| Sat., 12/16 | V Girls Basketball | Cromwell | Home - Westbrook HS Gym [Directions] | 2:00 p.m. | L 15-66 | |
| Sat., 12/16 | V Girls Ice Hockey | West Haven/SHA | Home - Northford Ice Pavilion [Directions] | 8:15 p.m. | L 1-0 | |
| Mon., 12/18 | V Girls Basketball | Oxford | Away - OHS-Main Gym [Directions] | 6:30 p.m. | L Forfeit | |
| Wed., 12/20 | FR Boys Basketball | East Hampton | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | ||
| Wed., 12/20 | V Girls Ice Hockey | Masuk Coop | Home - Northford Ice Pavilion [Directions] | 4:00 p.m. | W 9-0 | |
| Thu., 12/21 | V Boys Basketball | North Branford | Away - North Branford HS [Directions] | 7:00 p.m. | L 32-69 | |
| Thu., 12/21 | JV Boys Basketball | North Branford | Away - North Branford HS [Directions] | 5:30 p.m. | ||
| Thu., 12/21 | V Boys Indoor Track | Old Saybrook Qualifier Meet | Away - Floyd Little AC - Hillhouse | 5:00 p.m. | share bus with girls | |
| Thu., 12/21 | V Girls Indoor Track | Old Saybrook Qualifier Meet | Away - Floyd Little AC - Hillhouse | 5:00 p.m. | share bus with boys | |
| Wed., 12/27 | V Girls Gymnastics | Stonington, Valley Regional, Mercy | Away - Flip Flop [Directions] | 10:00 a.m. | 96.15 | |
| Wed., 12/27 | V Girls Ice Hockey | Guilford Coop | Away - East Haven Ice Rink [Directions] | 7:30 p.m. | W 2-1 | |
| Thu., 12/28 | V Boys Basketball | Old Lyme | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | L 43-57 | |
| Thu., 12/28 | JV Boys Basketball | Old Lyme | Home - Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/28 | FR Boys Basketball | Morgan | Away - Morgan HS [Directions] | 9:00 a.m. | ||
| Thu., 12/28 | V Boys Indoor Track | H-K Invitational | Away - Floyd Little AC - Hillhouse | 11:30 a.m. | share bus with girls | |
| Thu., 12/28 | V Girls Indoor Track | H-K Invitational | Away - Floyd Little AC - Hillhouse | 11:30 a.m. | share bus with boys | |
| Fri., 12/29 | V Girls Gymnastics | Mercy, Valley Regional | Away - Flip Flop [Directions] | 10:00 a.m. | 92.50 | |
| Sat., 12/30 | FR Boys Basketball | Valley Regional | Home - Westbrook HS Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/30 | V Girls Ice Hockey | Alumni Game | Home - Northford Ice Pavilion [Directions] | 3:15 p.m. | ||
| Tue., 1/2 | V Boys Basketball | Coginchaug | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | L 37-54 | |
| Tue., 1/2 | JV Boys Basketball | Coginchaug | Home - Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | V Boys Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | 7:00 p.m. | L 39-55 | |
| Wed., 1/3 | JV Boys Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | V Boys Indoor Track | SLC League Meet #1 | Away - Floyd Little AC - Hillhouse | 5:00 p.m. | share bus with girls | |
| Wed., 1/3 | V Girls Ice Hockey | Lauralton Hall | Home - Northford Ice Pavilion [Directions] | 3:50 p.m. | W 11-0 | |
| Wed., 1/3 | V Girls Indoor Track | SLC League Meet #1 | Away | 5:00 p.m. | share bus with boys | |
| Sat., 1/6 | FR Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 9:00 a.m. | ||
| Sat., 1/6 | V Girls Basketball | Wheeler | Home - Westbrook HS Gym [Directions] | 6:00 p.m. | W 45-10 | |
| Sat., 1/6 | V Girls Gymnastics | Mercy, Hamden, Foran, Valley Regional | Away - Flip Flop Gymnastics, Deep River [Directions] | 3:00 p.m. | 120.05 | |
| Sat., 1/6 | V Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | 3:15 p.m. | L 1-2 | |
| Tue., 1/9 | V Boys Basketball | Portland | Away - Portland HS [Directions] | 7:00 p.m. | L 49-80 | |
| Tue., 1/9 | JV Boys Basketball | Portland | Away - Portland HS [Directions] | 5:30 p.m. | ||
| Tue., 1/9 | FR Boys Basketball | Portland | Away - Portland HS [Directions] | 4:00 p.m. | ||
| Tue., 1/9 | V Girls Basketball | Portland | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | W 44-39 | |
| Wed., 1/10 | V Boys Basketball | Wilcox Tech | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | L 37-53 | |
| Wed., 1/10 | JV Boys Basketball | Wilcox Tech | Home - Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/11 | V Girls Gymnastics | Valley Regional | Away - Flip Flop Gym [Directions] | 7:15 p.m. | 122.75 | |
| Fri., 1/12 | V Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 7:00 p.m. | L 35-51 | |
| Fri., 1/12 | JV Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 5:30 p.m. | ||
| Fri., 1/12 | V Girls Basketball | East Hampton | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | L 51-55 | |
| Fri., 1/12 | V Girls Ice Hockey | Suffield Coop | Away - Northford Ice Pavilion [Directions] | 8:15 p.m. | L 3-4 | |
| Sat., 1/13 | FR Boys Basketball | Old Saybrook | Home - Westbrook HS Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/13 | V Girls Ice Hockey | Lauralton Hall | Away - Wonderland of Ice [Directions] | 1:15 p.m. | W 5-0 | |
| Mon., 1/15 | V Boys Basketball | Creed | Home - Westbrook HS Gym [Directions] | 2:30 p.m. | L 30-55 | |
| Mon., 1/15 | V Girls Basketball | Creed | Home - Westbrook HS Gym [Directions] | 1:00 p.m. | W 43-25 | |
| Mon., 1/15 | School Holidays and Closings | School Closed - MLK Day | ||||
| Tue., 1/16 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Northford Ice Pavilion [Directions] | 4:00 p.m. | W 1-0 | |
| Wed., 1/17 | V Girls Basketball | Old Saybrook | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | W 41-38 | |
| Wed., 1/17 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners Ice Rink [Directions] | 4:00 p.m. | W 4-1 | |
| Thu., 1/18 | V Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 7:00 p.m. | L 48-54(OT) | |
| Thu., 1/18 | JV Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Hale Ray | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | W 52-37 | |
| Sat., 1/20 | V Boys Basketball | North Branford | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | L 44-51 | Non-conference |
| Sat., 1/20 | JV Boys Basketball | North Branford | Home - Westbrook HS Gym [Directions] | 5:30 p.m. | Non-confernece game | |
| Sat., 1/20 | FR Boys Basketball | Creed | Away - Fair Haven School | 12:00 p.m. | ||
| Sat., 1/20 | V Boys Indoor Track | SLC Coaches Invitational | Away - Floyd Little AC - Hillhouse | 10:00 a.m. | share bus with girls | |
| Sat., 1/20 | V Girls Ice Hockey | Avon | Home - Northford Ice Pavilion [Directions] | 3:15 p.m. | W 3-2 | |
| Sat., 1/20 | V Girls Indoor Track | SLC Coaches Invitational | Away - Floyd Little AC - Hillhouse | 10:00 a.m. | share bus with boys | |
| Mon., 1/22 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | 5:00 p.m. | L 3-1 | |
| Mon., 1/22 | Miscellaneous Events | Mid Term Exams | Home - Westbrook HS [Directions] | 8:00 a.m.-12:30pm | ||
| Tue., 1/23 | Miscellaneous Events | Mid Term Exams | Home - Westbrook HS [Directions] | 8:00 a.m.-12:30 p.m. | ||
| Wed., 1/24 | V Girls Ice Hockey | Northwest Catholic | Away - Champions Skating Center, Cromwell [Directions] | 4:10 p.m. | W 3-2 (OT) | |
| Wed., 1/24 | Miscellaneous Events | Mid Term Exams | Home - Westbrook HS [Directions] | 8:00 a.m.-12:30 p.m. | ||
| Thu., 1/25 | V Boys Basketball | Valley Regional | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | L 42-74 | |
| Thu., 1/25 | JV Boys Basketball | Valley Regional | Home - Westbrook HS Gym [Directions] | Cancelled | Cancelled | |
| Thu., 1/25 | V Girls Basketball | Morgan | Away - Morgan HS [Directions] | 5:30 p.m. | L 49-54 | |
| Thu., 1/25 | V Girls Gymnastics | Mercy, Daniel Hand, Valley Regional | Away - Hand [Directions] | 6:00 p.m. | 122.20 | |
| Thu., 1/25 | Miscellaneous Events | Mid Term Exams | Home - Westbrook HS [Directions] | 8:00 a.m.-12:30 p.m. | ||
| Fri., 1/26 | V Boys Basketball | Morgan | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | W 74-71 OT | |
| Fri., 1/26 | JV Boys Basketball | Morgan | Home - Westbrook HS Gym [Directions] | Cancelled | Cancelled | |
| Fri., 1/26 | V Boys Indoor Track | SLC League Meet #2 | Away - Floyd Little AC - Hillhouse | 4:30 p.m. | share bus with girls | |
| Fri., 1/26 | V Girls Ice Hockey | Masuk Coop | Away - The Rinks at Shelton [Directions] | 4:00 p.m. | W 6-1 | |
| Fri., 1/26 | V Girls Indoor Track | SLC League Meet #2 | Away - Floyd Little AC - Hillhouse | 4:30 p.m. | share bus with boys | |
| Sat., 1/27 | FR Boys Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | 9:00 a.m. | ||
| Sat., 1/27 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | 6:00 p.m. | L 17-67 | |
| Sat., 1/27 | V Girls Ice Hockey | Northwest Catholic | Home - Northford Ice Pavilion [Directions] | 3:15 p.m. | L 4-0 | |
| Mon., 1/29 | V Girls Basketball | Haddam-Killingworth | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | L 45-49 | |
| Tue., 1/30 | V Girls Ice Hockey | West Haven/SHA | Away - Bennett Rink [Directions] | 5:15 p.m. | L 2-0 | |
| Wed., 1/31 | V Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 7:00 p.m. | W 76-72 | |
| Wed., 1/31 | JV Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Thu., 2/1 | V Girls Basketball | Creed | Away - Truman School | 6:30 p.m. | W 39-28 | |
| Fri., 2/2 | V Boys Basketball | Creed | Away - Fair Haven School | 7:30 p.m. | L 39-36 | |
| Fri., 2/2 | JV Boys Basketball | Creed | Away - Fair Haven School | 6:00 p.m. | ||
| Fri., 2/2 | V Girls Gymnastics | Mercy, Valley Regional | Away - Flip Flop [Directions] | 6:30 p.m. | 119.15 | |
| Sat., 2/3 | FR Boys Basketball | Morgan | Home - Westbrook HS Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/3 | V Boys Indoor Track | SLC Conference Championship | Away - Floyd Little AC - Hillhouse | 10:00 a.m. | share bus with girls | |
| Sat., 2/3 | V Girls Basketball | North Branford | Home - Westbrook HS Gym [Directions] | 4:00 p.m. | W 44-43 | |
| Sat., 2/3 | V Girls Ice Hockey | Hamden Coop | Home - Northford Ice Pavilion [Directions] | 8:15 p.m. | T 1-1 (OT) | |
| Sat., 2/3 | V Girls Indoor Track | SLC Conference Championship | Away - Floyd Little AC - Hillhouse | 10:00 a.m. | share bus with boys | |
| Mon., 2/5 | V Girls Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 7:00 p.m. | L 34-39 | |
| Tue., 2/6 | V Boys Basketball | Hale Ray | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | W 63-44 | |
| Tue., 2/6 | JV Boys Basketball | Hale Ray | Home - Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Portland | Away - Portland HS [Directions] | 5:30 p.m. | L 37-50 | |
| Thu., 2/8 | FR Boys Basketball | Creed | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | ||
| Thu., 2/8 | V Girls Gymnastics | Valley Regional | Away - Flip Flop Gym [Directions] | 7:15 p.m. | 124.9 | |
| Fri., 2/9 | V Boys Basketball | Portland | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | W 69-56 | |
| Fri., 2/9 | JV Boys Basketball | Portland | Home - Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | V Girls Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | L 15-41 | |
| Sat., 2/10 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | ||
| Sat., 2/10 | V Competitive Cheerleading | Shoreline Conference Championship | Home - Westbrook HS ? MS Gyms [Directions] | 4:30 p.m. | ||
| Sat., 2/10 | V Girls Ice Hockey | Guilford Coop | Home - Northford Ice Pavilion [Directions] | 3:15 p.m. | L 2-1 | |
| Sat., 2/10 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | share bus with boys | |
| Sun., 2/11 | V Girls Basketball | Valley Regional | Away - Valley Regional HS [Directions] | 3:00 p.m. | L 35-59 | |
| Mon., 2/12 | V Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | 7:00 p.m. | L 43-56 | |
| Tue., 2/13 | V Boys Basketball | East Hampton | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | L 52-79 | |
| Tue., 2/13 | JV Boys Basketball | East Hampton | Home - Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/13 | V Girls Gymnastics | Mercy, Daniel Hand, Valley Regional | Away - Hand [Directions] | 6:00 p.m. | 116.90 | |
| Tue., 2/13 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Northford Ice Pavilion [Directions] | 4:00 p.m. | L 5-3 | |
| Wed., 2/14 | V Girls Basketball | Old Lyme | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | L 24-55 | |
| Fri., 2/16 | V Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 7:00 p.m. | L 33-58 | |
| Fri., 2/16 | JV Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Fri., 2/16 | V Girls Ice Hockey | Simsbury | Away - Simsbury Farms CC [Directions] | 4:15 p.m. | L 2-1 (OT) | |
| Sat., 2/17 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Mon., 2/19 | V Boys Basketball | Old Saybrook | Home - Westbrook HS Gym [Directions] | 7:00 p.m. | L 27-53 | |
| Mon., 2/19 | JV Boys Basketball | Old Saybrook | Home - Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/19 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - The Rinks at Shelton [Directions] | 5:00 p.m. | L 3-2 | |
| Mon., 2/26 | Unified Sports Basketball | Old Saybrook | Home - Westbrook HS Gym [Directions] | 3:00 p.m. | ||
| Tue., 2/27 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - The Rinks at Shelton [Directions] | 4:00 p.m. | ||
| Wed., 2/28 | Unified Sports Basketball | SLC Unified Basketball Tournament | Home - Westbrook HS Gym [Directions] | 3:00 p.m. | WHS & WMS Gymnasiums | |
| Thu., 3/1 | Miscellaneous Events | CIAC MS Unified Basketball Tournament | Home - Westbrook HS / MS Gyms [Directions] | 3:00 p.m.-5:30pm | ||
| Thu., 3/1 | Unified Sports Basketball | CIAC MS Unified Basketball Tournament | Home - Westbrook HS Gym [Directions] | 3:00 p.m.-5:00pm | WHS Host/Workers, Class Project; WHS & WMS Gyms in use | |
| Fri., 3/2 | Miscellaneous Events | When Students Lead, Culture Follows | Away - Maloney HS - Meriden | 9:00 a.m.-12:30pm | ||
| Sat., 3/3 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sat., 3/3 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sun., 3/4 | V Competitive Cheerleading | CIAC Class S Cheerleading Championship | Away - Floyd Little AC - Hillhouse HS | 2:30 p.m. | ppd fro 3/2. Register at 8:15 am | |
| Mon., 3/5 | Miscellaneous Events | WHS Student-Athlete Mental Toughness Training | Home - WHS Room 213 [Directions] | 3:00 p.m.-4:30 p.m. | ||
| Tue., 3/6 | Miscellaneous Events | WHS Student-Athlete Mental Toughness Training | Home - WHS Room 213 [Directions] | 3:00 p.m.-4:30 p.m. | ||
| Tue., 3/6 | Unified Sports Basketball | Guilford | Away - Guilford HS [Directions] | 3:00 p.m. | ||
| Fri., 3/9 | Miscellaneous Events | WPS Coaches First Aid & CPR Recertification | Home - WHS LMC [Directions] | 3:00 p.m.-6:00 p.m. | rescheduled from 3/7 | |
| Thu., 3/15 | Miscellaneous Events | WMS Geography Fair | Home - Westbrook MS Gym [Directions] | 12:45 p.m.-8:00pm | ||
| Sat., 3/17 | Miscellaneous Events | B&G Tennis Practice | Away - Madison Racquet Club - New Road | 6:30 p.m. | ||
| Sun., 3/18 | Miscellaneous Events | B&G Tennis Practice | Away - Madison Racquet Club - New Road | 7:30 p.m. | ||
| Mon., 3/19 | Miscellaneous Events | B&G Tennis Practice | Away - Madison Racquet Club - New Road | 8:00 p.m. | ||
| Mon., 3/19 | Unified Sports Basketball | Daniel Hand / Coginchaug | Away - Polson MS Gym | 3:00 p.m. | ||
| Tue., 3/20 | Miscellaneous Events | B&G Tennis Practice | Away - Madison Racquet Club - New Road | 8:00 p.m. | ||
| Sat., 3/24 | V Girls Tennis | Guilford (Scrim.) | Away - Tennis Courts at GHS [Directions] | 11:30 a.m. | ||
| Mon., 3/26 | V Boys Tennis | Sheehan (Scrim.) | Away - Sheehan HS Tennis Courts [Directions] | 3:45 p.m. | ||
| Mon., 3/26 | V Girls Tennis | Daniel Hand (Scrim.) | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:30 p.m. | ||
| Tue., 3/27 | V Baseball | Maloney (Scrim.) | Away - Legion Park [Directions] | 3:30 p.m. | ||
| Tue., 3/27 | V Baseball | HMTCA/SMSA (Scrim.) | Away - Hyland Park [Directions] | 4:00 p.m. | no metal cleats | |
| Tue., 3/27 | V Girls Tennis | Waterford / Bridgeport Central | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 3/28 | V Softball | Career Magnet (Scrim.) | Home - Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | ||
| Thu., 3/29 | V Baseball | Portland (Scrim.) | Away - Portland HS [Directions] | 3:45 p.m. | ||
| Thu., 3/29 | V Softball | Montville (Scrim.) | Away - Montville H.S. [Directions] | 4:00 p.m. | ||
| Sat., 3/31 | V Baseball | New London | Away - Sal Amanti Field [Directions] | 11:00 a.m. | W 16-9 | |
| Sat., 3/31 | V Baseball | Griswold | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 1:00 p.m. | W 9-8 | |
| Thu., 4/5 | V Baseball | Cromwell | Away - Fran Monnes Baseball Field @ Cromwell HS [Directions] | 3:45 p.m. | L 3-8 | |
| Thu., 4/5 | V Boys Outdoor Track | SLC Tr-Meet | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | Morgan, Old Saybrook | |
| Thu., 4/5 | V Boys Tennis | Ledyard | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 4/5 | V Girls Outdoor Track | SLC Tr-Meet | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | Morgan, Old Saybrook | |
| Thu., 4/5 | V Softball | Old Lyme | Home - Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L 1-13 (5) | |
| Thu., 4/5 | V Girls Tennis | Portland | Away - Portland HS [Directions] | 3:45 p.m. | W 7-0 | |
| Sat., 4/7 | V Baseball | Hale Ray | Away - Legion Field, Neptune Ave, Moodus [Directions] | 12:00 p.m. | W 8-1 | |
| Sat., 4/7 | JV Baseball | Old Lyme | Away - Old Lyme HS [Directions] | 11:00 a.m. | ||
| Sat., 4/7 | JV Baseball | Hale Ray | Away - Legion Field, Neptune Ave, Moodus [Directions] | 2:30 p.m. | W 11-1 | |
| Sat., 4/7 | V Boys Outdoor Track | Bellringer Invitational | Away - East Hampton HS | 9:30 a.m. | ||
| Sat., 4/7 | V Boys Tennis | Coginchaug | Home - Westbrook HS/MS Tennis Courts [Directions] | 9:00 a.m. | W 7-0 | |
| Sat., 4/7 | V Girls Outdoor Track | Hammonassett Freshmen Invitational | Away - Daniel Hand HS - Madison | 9:00 a.m. | ||
| Sat., 4/7 | V Girls Outdoor Track | Bellringer Invitational | Away - East Hampton HS | 9:30 a.m. | ||
| Sat., 4/7 | V Softball | East Hampton | Home - Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | W 12-6 | |
| Sat., 4/7 | JV Softball | North Branford | Away - North Branford HS [Directions] | Cancelled | Cancelled | |
| Sat., 4/7 | V Girls Tennis | Coginchaug | Away - Tennis Courts @ CRHS [Directions] | 10:00 a.m. | W 4-3 | |
| Mon., 4/9 | V Baseball | North Branford | Away - North Branford HS [Directions] | 3:45 p.m. | L 0-1 | |
| Mon., 4/9 | V Baseball | Old Saybrook | Home - Valley Regional HS [Directions] | 3:45 p.m. | L 5-8 | |
| Mon., 4/9 | V Boys Tennis | Old Saybrook | Away - Old Saybrook HS [Directions] | 3:45 p.m. | L 1-6 | |
| Mon., 4/9 | V Girls Tennis | Old Saybrook | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 4/10 | V Boys Outdoor Track | SLC Quad Meet | Away - East Hampton | 3:45 p.m. | H-K, Hale Ray, East Hampton | |
| Tue., 4/10 | V Girls Outdoor Track | SLC Quad Meet | Away - East Hampton | 3:45 p.m. | H-K, Hale Ray, East Hampton | |
| Tue., 4/10 | V Softball | Portland | Away - Nolan Field [Directions] | 3:45 p.m. | W 15-7 | |
| Wed., 4/11 | V Baseball | Coginchaug | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | W 2-1 | |
| Wed., 4/11 | V Baseball | Cromwell | Away - Fran Monnes Baseball Field @ Cromwell HS [Directions] | 4:00 p.m. | L 1-5 | |
| Wed., 4/11 | JV Baseball | Old Saybrook | Home - Valley Regional HS [Directions] | 3:45 p.m. | L 4-6 | |
| Wed., 4/11 | V Boys Tennis | East Hampton | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Wed., 4/11 | V Softball | North Branford | Home - Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L 0-17 | |
| Wed., 4/11 | V Girls Tennis | East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/12 | JV Baseball | Coginchaug | Away - Field #1 - Brookside Field @ CRHS [Directions] | 3:45 p.m. | ||
| Thu., 4/12 | JV Baseball | Cromwell | Home - Valley Regional HS [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 4/12 | V Softball | Valley Regional | Away - Valley Regional HS [Directions] | 3:45 p.m. | L 0-15 | |
| Fri., 4/13 | V Baseball | Old Saybrook | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | L 3-14 | |
| Fri., 4/13 | V Boys Tennis | Haddam-Killingworth | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 4/13 | V Girls Tennis | Haddam-Killingworth | Home - Westbrook HS [Directions] | 3:45 p.m. | W 4-3 | |
| Sat., 4/14 | V Baseball | Ledyard | Away - Matt Buriak Field [Directions] | 11:00 a.m. | W 4-3 (8) | |
| Sat., 4/14 | JV Baseball | Ledyard | Away - Lower Baseball Field [Directions] | 11:00 a.m. | L 2-8 | w/ var |
| Sat., 4/14 | JV Baseball | Old Saybrook | Away - Old Saybrook HS [Directions] | 11:00 a.m. | ||
| Tue., 4/17 | V Baseball | Portland | Away - Portland HS [Directions] | 3:45 p.m. | W 6-5 | |
| Tue., 4/17 | V Baseball | Morgan | Away - Morgan HS [Directions] | 3:45 p.m. | W 12-7 | |
| Tue., 4/17 | JV Baseball | Morgan | Home - Valley Regional HS [Directions] | 3:45 p.m. | W 15-5 | |
| Tue., 4/17 | V Boys Tennis | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 4/17 | V Softball | Cromwell | Home - Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L 0-15 | |
| Tue., 4/17 | V Girls Tennis | Old Lyme | Home - Westbrook HS/MS Tennis Courts [Directions] | 11:00 a.m. | W 7-0 | |
| Wed., 4/18 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | L 2-4 | |
| Wed., 4/18 | V Baseball | East Hampton | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | W 6-5 | |
| Wed., 4/18 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | L 1-15 | |
| Wed., 4/18 | V Girls Tennis | North Branford | Home - Westbrook HS/MS Tennis Courts [Directions] | 11:00 a.m. | W 5-2 | |
| Fri., 4/20 | V Baseball | Creed | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:00 p.m. | W 15-5 | |
| Fri., 4/20 | V Baseball | Old Lyme | Home - Valley Regional HS [Directions] | 3:45 p.m. | W 3-2 | |
| Fri., 4/20 | JV Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | L 1-11 | |
| Fri., 4/20 | V Boys Tennis | Cromwell | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Fri., 4/20 | V Softball | Hale Ray | Away - Hale-Ray HS, Lou Milardo Field [Directions] | 2:00 p.m. | L 1-18 | |
| Fri., 4/20 | V Girls Tennis | Cromwell | Away - Cromwell HS [Directions] | 3:45 p.m. | W 4-3 | |
| Sat., 4/21 | JV Baseball | Old Lyme | Away - Old Lyme HS [Directions] | 11:00 a.m. | L 10-12 | |
| Sat., 4/21 | JV Softball | Hale Ray | Home - Westbrook HS Field #5 - Softball [Directions] | 10:30 a.m. | ||
| Mon., 4/23 | V Baseball | North Branford | Home - Valley Regional HS [Directions] | 3:45 p.m. | W 11-10 (8) | |
| Mon., 4/23 | V Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | 3:45 p.m. | L 2-3 | |
| Mon., 4/23 | V Boys Tennis | Valley Regional | Away - Valley Regional HS [Directions] | 3:45 p.m. | L 3-4 | |
| Mon., 4/23 | V Softball | Old Saybrook | Home - Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L 6-13 | |
| Mon., 4/23 | V Girls Tennis | Valley Regional | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Mon., 4/23 | Miscellaneous Events | CIAC Unified Sports Michael's Cup | Away - Aqua Turf - Southignton | 5:30 p.m. | ||
| Tue., 4/24 | JV Baseball | North Branford | Away - North Branford HS [Directions] | 3:45 p.m. | W 14-2 | |
| Tue., 4/24 | JV Baseball | Hale Ray | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | ||
| Tue., 4/24 | V Boys Outdoor Track | SLC Tri-Meet | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | North Branford, Cromwell | |
| Tue., 4/24 | V Girls Outdoor Track | SLC Tri-Meet | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | North Branford, Cromwell | |
| Thu., 4/26 | V Baseball | Westbrook | Away - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | L 8-9 | |
| Thu., 4/26 | V Baseball | ValleyReg/Westbrook | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | W 9-8 | |
| Thu., 4/26 | V Softball | Morgan | Home - Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L 12-23 | |
| Sat., 4/28 | V Baseball | New London | Home - Valley Regional HS [Directions] | 1:00 p.m. | W 9-8 | |
| Sat., 4/28 | JV Baseball | New London | Home - Valley Regional HS [Directions] | 3:00 p.m. | L 8-9 | |
| Sat., 4/28 | V Boys Outdoor Track | Stafford Invitational | Away - Stafford HS | 11:00 a.m. | share bus with girls | |
| Sat., 4/28 | V Boys Tennis | Granby Memorial | Away - Granby Memorial HS [Directions] | 11:30 a.m. | L 2-5 | |
| Sat., 4/28 | V Girls Outdoor Track | Stafford Invitational | Away - Stafford HS | 11:00 a.m. | share bus with boys | |
| Mon., 4/30 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | L 2-4 | |
| Mon., 4/30 | V Baseball | Creed | Away - West Rock Park | 4:00 p.m. | W 17-4 | |
| Mon., 4/30 | V Boys Tennis | Coginchaug | Away - Tennis Courts @ CRHS [Directions] | 3:45 p.m. | W 4-3 | |
| Mon., 4/30 | V Softball | Hale Ray | Home - Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L 1-20 | |
| Mon., 4/30 | V Girls Tennis | Coginchaug | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 5/1 | V Baseball | Morgan | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | L 8-10 (9) | |
| Tue., 5/1 | V Baseball | East Hampton | Away - Valley Regional HS [Directions] | 4:00 p.m. | W 8-0 | |
| Tue., 5/1 | V Boys Outdoor Track | SLC Tri-Meet | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | Creed, Valley Regional | |
| Tue., 5/1 | V Boys Tennis | Morgan | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 5/1 | V Girls Outdoor Track | SLC Tri-Meet | Home - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | Creed, Valley Regional | |
| Tue., 5/1 | V Softball | Coginchaug | Away - Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 3:45 p.m. | L 2-18 | |
| Tue., 5/1 | JV Softball | Coginchaug | Away - Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 5:15 p.m. | ||
| Tue., 5/1 | V Girls Tennis | Morgan | Away - Morgan HS [Directions] | 3:45 p.m. | W 6-1 | |
| Wed., 5/2 | V Baseball | Haddam-Killingworth | Home - Valley Regional HS [Directions] | 4:00 p.m. | L 8-3 | |
| Wed., 5/2 | V Baseball | Creed | Away - West Rock Park | 4:00 p.m. | W 13-3 (5) | |
| Wed., 5/2 | V Boys Tennis | Stonington | Home - Westbrook HS/MS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Wed., 5/2 | V Softball | Portland | Home - Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | W 10-8 | |
| Thu., 5/3 | JV Baseball | Creed | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | ||
| Thu., 5/3 | JV Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 4:00 p.m. | W 9-8 | |
| Thu., 5/3 | V Girls Tennis | Portland | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 5/4 | V Baseball | Hale Ray | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | W 13-0 (5) | |
| Fri., 5/4 | V Boys Tennis | Old Saybrook | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Fri., 5/4 | V Softball | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | L 3-19 | |
| Fri., 5/4 | V Girls Tennis | Old Saybrook | Away [Directions] | 3:45 p.m. | L 2-5 | |
| Sat., 5/5 | V Baseball | Morgan | Home - Valley Regional HS [Directions] | 10:30 a.m. | W 3-2 | |
| Sat., 5/5 | JV Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | 10:30 a.m. | ||
| Sat., 5/5 | JV Baseball | Morgan | Home - Valley Regional HS [Directions] | 1:00 p.m. | W 12-8 | |
| Sat., 5/5 | V Boys Outdoor Track | Coginchaug Invitational | Away - Coginchaug HS | 10:00 a.m. | share bus with girls | |
| Sat., 5/5 | V Boys Tennis | Granby Memorial | Home - Westbrook HS/MS Tennis Courts [Directions] | 11:30 a.m. | L 1-6 | |
| Sat., 5/5 | V Girls Outdoor Track | Coginchaug Invitational | Away - Coginchaug HS | 10:00 a.m. | share large bus with boys | |
| Sat., 5/5 | JV Softball | Old Saybrook | Away - Old Saybrook HS [Directions] | 9:00 a.m. | ||
| Mon., 5/7 | V Baseball | Portland | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | L 2-3 | |
| Mon., 5/7 | V Baseball | Cromwell | Home - Valley Regional HS [Directions] | 4:00 p.m. | L 2-14 | |
| Mon., 5/7 | V Boys Tennis | East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | W 5-2 | |
| Mon., 5/7 | V Softball | Old Saybrook | Away - Old Saybrook HS [Directions] | 4:30 p.m. | L 4-16 | |
| Mon., 5/7 | V Girls Tennis | East Hampton | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 5/8 | JV Baseball | Cromwell | Away - Fran Monnes Baseball Field @ Cromwell HS [Directions] | 4:00 p.m. | L 2-3 | |
| Tue., 5/8 | V Boys Outdoor Track | SLC Tri-Meet | Away - North Branford HS | 3:45 p.m. | share bus with girls | |
| Tue., 5/8 | V Girls Outdoor Track | SLC Tri-Meet | Away - North Branford HS | 3:45 p.m. | share large bus with boys | |
| Tue., 5/8 | JV Softball | Old Saybrook | Home - Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | ||
| Wed., 5/9 | V Baseball | East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | L 3-4 | |
| Wed., 5/9 | V Baseball | North Branford | Away - North Branford HS [Directions] | 4:00 p.m. | W 5-4 | |
| Wed., 5/9 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/9 | V Softball | East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | L 2-17 | |
| Wed., 5/9 | V Girls Tennis | Haddam-Killingworth | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Thu., 5/10 | JV Baseball | North Branford | Home - Valley Regional HS [Directions] | 3:45 p.m. | W 12-11 | |
| Thu., 5/10 | V Softball | Acad. of the Holy Family | Away - Franklin Field [Directions] | 3:45 p.m. | W 16-0 | |
| Fri., 5/11 | V Baseball | Coginchaug | Home - Valley Regional HS [Directions] | 3:45 p.m. | W 3-2 | |
| Fri., 5/11 | V Baseball | Old Lyme | Home - Dodd Stadium - Norwich [Directions] | 7:00 p.m. | L 17-4 (8) | |
| Fri., 5/11 | V Boys Tennis | Old Lyme | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 5/11 | V Girls Tennis | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | L 3-4 | |
| Sat., 5/12 | JV Baseball | Coginchaug | Away - Field #1 - Brookside Field @ CRHS [Directions] | Cancelled | Cancelled | |
| Sat., 5/12 | V Boys Outdoor Track | Old Saybrook Invitational | Away - Old Saybrook HS | 8:30 a.m. | share bus with girls | |
| Sat., 5/12 | V Girls Outdoor Track | Old Saybrook Invitational | Away - Old Saybrook HS | 8:30 a.m. | share large bus with boys | |
| Mon., 5/14 | V Baseball | Old Saybrook | Away - Old Saybrook HS [Directions] | 3:45 p.m. | L 1-10 | |
| Mon., 5/14 | V Baseball | Portland | Home - Valley Regional HS [Directions] | 4:00 p.m. | L 4-14 | Senior Night |
| Mon., 5/14 | V Softball | Acad. of the Holy Family | Home - Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | W 18-6 | |
| Mon., 5/14 | V Girls Tennis | North Branford | Away [Directions] | 3:45 p.m. | W 4-3 | |
| Tue., 5/15 | V Baseball | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | L 3-6 | M&J |
| Wed., 5/16 | V Baseball | Coginchaug | Away - Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 3:45 p.m. | L 2-5 | |
| Wed., 5/16 | V Boys Outdoor Track | SLC Quad Meet | Away - Portland HS | 3:45 p.m. | Old Lyme, Hale Ray, Portland - share bus with girls | |
| Wed., 5/16 | V Girls Outdoor Track | SLC Quad Meet | Away - Portland HS | 3:45 p.m. | Old Lyme, Hale Ray, Portland - share large bus with boys | |
| Thu., 5/17 | V Baseball | Stafford | Away - Arute Baseball Fields off of Levinthal Run [Directions] | 4:30 p.m. | W 4-3 | |
| Thu., 5/17 | V Boys Outdoor Track | H-K Freshman Invitational | Away - Haddam-Killingworth HS | 3:45 p.m. | share bus with Old Saybrook (M&J) | |
| Thu., 5/17 | V Boys Tennis | Valley Regional | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Thu., 5/17 | V Girls Outdoor Track | H-K Freshman Invitational | Away - Haddam-Killingworth HS | 3:45 p.m. | share bus with Old Saybrook (M&J | |
| Thu., 5/17 | V Girls Tennis | Valley Regional | Away - Valley Regional HS [Directions] | 3:45 p.m. | W 4-3 | |
| Thu., 5/17 | Unified Sports Track | Coginchaug (Scrim.) | Away - Coginchauf HS [Directions] | 11:15 a.m. | 11:15 am joint track class, lunch 12:20 pm. | |
| Fri., 5/18 | V Softball | Windsor Locks | Away - Windsor Locks HS [Directions] | 4:30 p.m. | L 2-17 | |
| Sat., 5/19 | Miscellaneous Events | WHS Prom | Home - Waters Edge - Westbrook [Directions] | 6:00 p.m. | ||
| Mon., 5/21 | V Boys Tennis | Morgan | Away - Morgan HS [Directions] | 6:30 p.m. | L 2-5 | |
| Mon., 5/21 | V Girls Tennis | Morgan | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/23 | V Baseball | Old Saybrook | Away - Portland HS [Directions] | 4:30 p.m. | W 11-0 | SLC Quarterfinals |
| Wed., 5/23 | V Boys Outdoor Track | SLC Championship | Away - Old Saybrook HS | 1:30 p.m. | share bus with girls | |
| Wed., 5/23 | V Boys Tennis | Cromwell | Away - Cromwell HS [Directions] | 3:30 p.m. | L 2-5 | |
| Wed., 5/23 | V Girls Outdoor Track | SLC Championship | Away - Old Saybrook HS | 1:30 p.m. | share large bus with boys | |
| Wed., 5/23 | V Softball | O'Brien Tech | Away - O'Brien Tech Athletic Complex [Directions] | 4:15 p.m. | W 22-10 | |
| Wed., 5/23 | V Girls Tennis | Cromwell | Home - Westbrook HS/MS Tennis Courts [Directions] | 3:30 p.m. | L 3-4 | |
| Thu., 5/24 | V Baseball | Coginchaug | Away - Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 3:45 p.m. | L 1-4 | Shoreline Conference Semi-Finals |
| Thu., 5/24 | V Boys Tennis | Shoreline Conference Tournanment | Away - Westbrook - dbls, Old Saybrook - 1,2's, Morgan - 3,4, 5's | 9:00 a.m. | share with girls | |
| Thu., 5/24 | V Girls Tennis | Shoreline Conference Championships | Away - Westbrook - dbls; Old Saybrook - 1,2's; Morgan 3,4,5's | 9:00 a.m. | Share bus with boys | |
| Thu., 5/24 | Unified Sports Track | Shoreline Conference Unified Track Tournament | Away - Westbrook HS Field #2 - Track/Soccer | 3:00 p.m. | ||
| Fri., 5/25 | V Boys Tennis | Shoreline Conference Championship | Away - Old Saybrook HS | 12:00 p.m. | ||
| Fri., 5/25 | V Girls Tennis | Shoreline Conference Championships | Home - Westbrook HS/MS Tennis Courts [Directions] | 12:00 p.m. | ||
| Sat., 5/26 | V Boys Tennis | CIAC Tourney Prelim/Early Rounds | Away - Conard HS [Directions] | 8:30 a.m. | ||
| Sat., 5/26 | V Girls Tennis | Valley Regional | Home - Westbrook HS/MS Tennis Courts [Directions] | 12:30 p.m. | W 4-3 | CIAC Class S First Round |
| Tue., 5/29 | V Baseball | Northwest Catholic | Home - Valley Regional HS [Directions] | 3:30 p.m. | L No 2-4 | State Tournament First Round |
| Tue., 5/29 | V Baseball | Cromwell | Away - Fran Monnes Baseball Field @ Cromwell HS [Directions] | 3:30 p.m. | W 6-5 | CIAC Class S 1st Round |
| Tue., 5/29 | V Boys Tennis | CIAC Tourney Round of 16/Quarterfinals | Away - Conard HS [Directions] | 1:00 p.m. | ||
| Tue., 5/29 | V Girls Tennis | Shepaug Valley | Away - Shepaug Valley HS Courts [Directions] | 3:00 p.m. | L 2-5 | |
| Wed., 5/30 | V Baseball | Somers | Home - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:30 p.m. | L 17-9 | CIAC Class S 2nd Round #24 WHS v #25 Somers |
| Wed., 5/30 | V Boys Tennis | CIAC Tourney Semifinals | Away - Yale University [Directions] | 4:00 p.m. | ||
| Wed., 5/30 | V Girls Tennis | CIAC Tourney Semifinals | Away | TBA | ||
| Thu., 5/31 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | share bus with girls | |
| Thu., 5/31 | V Boys Tennis | CIAC Tourney Finals | Away - Yale University [Directions] | 4:00 p.m. | ||
| Thu., 5/31 | V Girls Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | share with boys | |
| Thu., 5/31 | V Girls Tennis | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Thu., 5/31 | Unified Sports Track | Coginchaug (Scrim.) | Away - Coginchaug HS [Directions] | 11:15 a.m. | joint class 11:15 - disc golf, lunch 12:20pm | |
| Sat., 6/2 | V Boys Tennis | State Open Singles Rd. of 16/Doubles Quarterfinals | Away - Amity [Directions] | 12:00 p.m. | ||
| Sun., 6/3 | V Girls Tennis | State Open Qualifying, 1st and 2nd Rounds | Away - Singles @ Conard/Doubles @ Hall | 1:00 p.m. | ||
| Mon., 6/4 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | share bus with girls | |
| Mon., 6/4 | V Boys Tennis | State Open Singles Quarterfinals/Doubles Semifinals | Away - Yale University [Directions] | 4:00 p.m. | ||
| Mon., 6/4 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | share bus with boys | |
| Mon., 6/4 | V Girls Tennis | State Open Round of 16/Quarterfinals | Away - Yale University [Directions] | 12:00 p.m. | ||
| Tue., 6/5 | V Boys Tennis | State Open Singles Semifinals | Away - Yale University [Directions] | 4:00 p.m. | ||
| Tue., 6/5 | V Girls Tennis | State Open Semifinals | Away - Yale University [Directions] | 3:00 p.m. | ||
| Wed., 6/6 | V Boys Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | TBA | ||
| Wed., 6/6 | V Girls Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | TBA | ||
| Sat., 6/9 | V Boys Outdoor Track | New England Championship | Away - Univ. of New Hampshire [Directions] | TBA | ||
| Sat., 6/9 | V Girls Outdoor Track | New England Championship | Away - Univ. of New Hampshire [Directions] | TBA | ||
| Tue., 6/12 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Tue., 6/12 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:30 a.m. | ||
| Wed., 6/13 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Wed., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Fri., 6/15 | Unified Sports Track | Unified Sports Class Field Trip | Away - Rockin' Jump - 709 Foxon Rd., East Haven | 11:30 a.m. | ||
| Wed., 6/20 | Miscellaneous Events | Final Exams | Home - Westbrook HS [Directions] | 8:00 a.m.-12:30 p.m. | ||
| Thu., 6/21 | Miscellaneous Events | Final Exams | Home - Westbrook HS [Directions] | 8:00 a.m.-12:30 p.m. | ||
| Fri., 6/22 | Miscellaneous Events | Final Exams | Home - Westbrook HS [Directions] | 8:00 a.m.-12:30 p.m. | ||
| Mon., 6/25 | Miscellaneous Events | Final Exams | Home - Westbrook HS [Directions] | 8:00 a.m.-12:30 p.m. | ||