| Westbrook 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 475 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sun., 8/28 | V Field Hockey | TBA | Away - Enfield HS | 11:15 a.m. | ||
| Tue., 8/30 | V Boys Soccer | St. Bernard (Scrim.) | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 4:00 p.m. | ||
| Tue., 8/30 | V Field Hockey | Guilford (Scrim.) | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | ||
| Thu., 9/1 | V Football | Lyman Hall (Scrim.) | Away - Lyman Hall HS-Fitzgerald Field [Directions] | 5:30 p.m. | ||
| Thu., 9/1 | V Boys Soccer | Windsor Locks (Scrim.) | Away - Windsor Locks HS-Soccer Field 1 Upper [Directions] | 4:30 p.m. | ||
| Thu., 9/1 | V Field Hockey | Mercy (Scrim.) | Away - Mercy HS-Field Hockey Field [Directions] | 3:45 p.m. | ||
| Fri., 9/2 | V Field Hockey | Fitch (Scrim.) | Away - Groton MS-Groton Middle School-Turf Feld [Directions] | 3:45 p.m. | ||
| Fri., 9/2 | V Girls Soccer | East Granby (Scrim.) | Away - East Granby HS-Lower Soccer Field [Directions] | 4:15 p.m. | ||
| Sat., 9/3 | V Boys Cross Country | Old Lyme, Morgan (Scrim.) | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 9:30 a.m. | ||
| Sat., 9/3 | V Girls Soccer | St. Bernard, Griswold, Haddam-Killingworth, Montville, New London, Plainfield, Waterford | Away - St. Bernard School-Upper Soccer Field | 10:00 a.m. | ||
| Mon., 9/5 | Miscellaneous Events | School Closed- Labor Day | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Thu., 9/8 | V Football | Cromwell/Portland | Away - Pierson Park (Cromwell, CT)-Football Field [Directions] | 6:00 p.m. | L 0-41 | |
| Thu., 9/8 | V Field Hockey | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 4:00 p.m. | L 0-3 | |
| Thu., 9/8 | JV Field Hockey | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 5:15 p.m. | ||
| Fri., 9/9 | V Boys Soccer | Morgan | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 9/9 | V Girls Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 3:45 p.m. | L 0-9 | |
| Sat., 9/10 | V Field Hockey | Killingly | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 11:00 a.m. | W 6-1 | |
| Sat., 9/10 | JV Field Hockey | Killingly | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 12:15 p.m. | ||
| Mon., 9/12 | V Boys Soccer | Cromwell | Away - Cromwell HS-Main field [Directions] | 3:45 p.m. | L 0-3 | |
| Mon., 9/12 | V Girls Soccer | Cromwell | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 9/14 | V Boys Cross Country | Morgan, Old Lyme, Valley Regional | Away - Indian River Complex-XC Course [Directions] | 3:45 p.m. | ||
| Wed., 9/14 | V Field Hockey | Old Saybrook | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 0-1 | |
| Wed., 9/14 | JV Field Hockey | Old Saybrook | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Thu., 9/15 | V Girls Soccer | North Branford/Hale Ray | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | W 3-1 | |
| Fri., 9/16 | V Boys Soccer | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | 3:45 p.m. | W 4-0 | |
| Fri., 9/16 | V Field Hockey | Valley Regional | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | T 0-0 | |
| Fri., 9/16 | JV Field Hockey | Valley Regional | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Sat., 9/17 | V Football | Haddam-Killingworth | Home - Peters Complex-Football Field [Directions] | 1:00 p.m. | W 30-23 | |
| Sat., 9/17 | JV Football | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | Canceled | Cancelled | |
| Mon., 9/19 | V Boys Soccer | East Hampton | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 0-8 | |
| Mon., 9/19 | V Girls Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 6:00 p.m. | L 0-4 | |
| Tue., 9/20 | V Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | T 0-0 | |
| Tue., 9/20 | JV Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 5:15 p.m. | ||
| Wed., 9/21 | V Boys Cross Country | Coginchaug - Going to the Sun Cross Country Meet | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:30 p.m. | ||||||
| Wed., 9/21 | V Boys Soccer | Amistad | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | T 1-1 | |
| Thu., 9/22 | V Field Hockey | Morgan | Away - Indian River Complex-Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 9/22 | JV Field Hockey | Morgan | Away - Indian River Complex-Turf Field [Directions] | 5:15 p.m. | ||
| Thu., 9/22 | V Girls Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | L 1 - 2 | |
| Thu., 9/22 | V | LymeOldLyme | Away - Lyme-Old Lyme HS [Directions] | 3:00 p.m. | ||
| Fri., 9/23 | V Football | Valley Regional/Old Lyme | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 6:30 p.m. | L 0-48 | |
| Fri., 9/23 | V Boys Soccer | Old Saybrook | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 4:00 p.m. | L 0-3 | |
| Sat., 9/24 | JV Football | Valley Regional/Old Lyme | Home - Peters Complex-Football Field [Directions] | 10:30 a.m. | ||
| Mon., 9/26 | V Girls Soccer | Lyman Memorial | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 0-5 | |
| Tue., 9/27 | V Boys Soccer | Hale Ray | Away - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 6:00 p.m. | W 4-1 | Non-league game |
| Wed., 9/28 | V Girls Soccer | Harding | Away - Warren Harding HS-Lewis Field [Directions] | 3:30 p.m. | W 7-0 | |
| Fri., 9/30 | V Football | Capital/Achievement | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | L 28-35 | |
| Fri., 9/30 | V Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 p.m. | T 0-0 | |
| Fri., 9/30 | V Field Hockey | North Branford | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 1-3 | |
| Fri., 9/30 | JV Field Hockey | North Branford | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Fri., 9/30 | V Girls Soccer | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 0-5 | |
| Mon., 10/3 | JV Football | Old Saybrook, Coginchaug/Hale Ray/East Hampton | Away - Peters Complex-Football Field [Directions] | 6:00 p.m. | ||
| Mon., 10/3 | V Boys Soccer | Harding | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 4:30 p.m. | L 2-3 | |
| Mon., 10/3 | V Field Hockey | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:30 p.m. | L 2-3 | |
| Mon., 10/3 | JV Field Hockey | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | ||
| Mon., 10/3 | V Girls Soccer | Amistad | Away - Amistad HS-Stadium [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 10/4 | V Boys Cross Country | Haddam-Killingworth, Old Lyme, Morgan, North Branford, Valley Regional | Away - Haddam Killingworth HS (HK)-HKHS Cross Country Course | 3:30 p.m. | ||
| Tue., 10/4 | V Field Hockey | Somers/Rockville Coop | Away - Somers HS-Somers High School Turf Field [Directions] | 6:30 p.m. | W 4-1 | |
| Wed., 10/5 | V Girls Soccer | North Branford/Hale Ray | Away - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | T 2-2 | |
| Thu., 10/6 | V Boys Soccer | Portland | Away - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | L 0-4 | |
| Thu., 10/6 | V Field Hockey | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 4:30 p.m. | L 0-1 | |
| Thu., 10/6 | V Girls Soccer | Portland | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 1-3 | |
| Thu., 10/6 | Miscellaneous Events | Early Dismissal for Students | Home - Westbrook HS [Directions] | 12:15 p.m. | 1/2 Day Professional Development for Teachers | |
| Fri., 10/7 | V Football | Rockville | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | L 14-54 | |
| Fri., 10/7 | Miscellaneous Events | No School for Students- Professional Development | Home - Westbrook HS [Directions] | 7:50 a.m. | Professional Development for Teachers | |
| Mon., 10/10 | Miscellaneous Events | School Closed- Columbus Day | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Tue., 10/11 | JV Football | Old Saybrook, CREC Coop | Away - Old Saybrook HS-Westbrook High School [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Boys Soccer | Hale Ray | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 4:45 p.m. | W 3-0 | League Game |
| Tue., 10/11 | V Field Hockey | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 10/11 | JV Field Hockey | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Wed., 10/12 | V Girls Soccer | Amistad | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | W 6-0 | |
| Thu., 10/13 | V Boys Soccer | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:30 p.m. | L 0-3 | |
| Thu., 10/13 | V Field Hockey | Morgan | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:30 p.m. | W 2-1 | |
| Thu., 10/13 | JV Field Hockey | Morgan | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:45 p.m. | ||
| Thu., 10/13 | Miscellaneous Events | Unified Sports Trip to Mystic Aquarium | Home - Mystic Aquarium [Directions] | 2:30 p.m. | ||
| Thu., 10/13 | V | LymeOldLyme | Home - Mystic Aquarium [Directions] | 2:30 p.m. | ||
| Fri., 10/14 | V Girls Soccer | Harding | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 4:30 p.m. | W 6-0 | |
| Sat., 10/15 | JV Football | North Branford, Old Saybrook | Away - North Branford HS-NBHS Colafati Field [Directions] | 10:00 a.m. | ||
| Sat., 10/15 | V Field Hockey | Killingly | Away - Killingly HS-Morgan Field [Directions] | 12:00 p.m. | W 2-1 | |
| Sat., 10/15 | JV Field Hockey | Killingly | Away - Killingly HS-Morgan Field [Directions] | 1:30 p.m. | ||
| Mon., 10/17 | V Boys Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | 3:45 p.m. | L 0-3 | |
| Wed., 10/19 | V Field Hockey | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 4:30 p.m. | L 0-2 | |
| Wed., 10/19 | JV Field Hockey | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 5:45 p.m. | ||
| Wed., 10/19 | V Girls Soccer | Old Lyme | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 0-5 | |
| Wed., 10/19 | V | ValleyReg | Home - Westbrook HS-Westbrook HS Gym [Directions] | 3:00 p.m. | ||
| Thu., 10/20 | V Boys Cross Country | Shoreline Cross Country Championship | Away - Hammonasset Park | 1:30 p.m. | ||
| Thu., 10/20 | V Boys Soccer | Coginchaug | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | W 2-1 | |
| Fri., 10/21 | V Field Hockey | Newington | Away - Newington HS-Clem Lemire Turf Field (150 New Britain Ave) [Directions] | 4:00 p.m. | W 1-0 | |
| Sat., 10/22 | V Football | Coginchaug/Hale Ray/East Hampton | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 1:00 p.m. | W 58-39 | |
| Mon., 10/24 | JV Football | Cromwell/Portland, Old Saybrook | Away - Pierson Park (Cromwell, CT)-Football Field [Directions] | Canceled | Cancelled | |
| Mon., 10/24 | V Boys Soccer | Harding | Away - Warren Harding HS-Lewis Field [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 10/25 | V Boys Cross Country | Guilford | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 4:00 p.m. | ||
| Tue., 10/25 | V Boys Cross Country | Daniel Hand | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 4:15 p.m. | ||
| Tue., 10/25 | V Girls Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:45 p.m. | L 5-0 | |
| Wed., 10/26 | V Boys Cross Country | Middle School Invitational | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:45 p.m. | ||
| Wed., 10/26 | V Field Hockey | Waterford | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/26 | JV Field Hockey | Waterford | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Thu., 10/27 | FR Field Hockey | Guilford | Away - Guilford HS-Maturo Field [Directions] | 3:45 p.m. | ||
| Thu., 10/27 | V Girls Soccer | Valley Regional | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 0-4 | |
| Thu., 10/27 | Miscellaneous Events | Early Dismissal- Conferences | Home - Westbrook HS [Directions] | 12:15 p.m. | ||
| Sat., 10/29 | V Boys Cross Country | CIAC Class S Championship | Away - Wickham Park | 11:55 a.m. | ||
| Tue., 11/1 | V Field Hockey | North Branford | Away - Indian River Complex-Turf Field [Directions] | 7:00 p.m. | ||
| Wed., 11/2 | V Boys Soccer | Amistad | Away - Amistad HS-Stadium [Directions] | 4:00 p.m. | W 4-1 | |
| Thu., 11/3 | Miscellaneous Events | Unified Sports Fall Festival | Home - DAISY INGRAHAM SCHOOL-Outside [Directions] | 3:00 p.m. | ||
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | V Football | Granby/Canton | Away - Granby Memorial HS-Stadium Field [Directions] | 6:30 p.m. | L 22-38 | |
| Mon., 11/7 | JV Football | Coventry/Windham Tech/Bolton/Lyman, Old Saybrook | Away - Coventry HS-Football Field [Directions] | 5:00 p.m. | ||
| Mon., 11/7 | V Boys Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | L 0-3 | |
| Mon., 11/7 | V Field Hockey | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 2:00 p.m. | ||
| Tue., 11/8 | V Field Hockey | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 2:00 p.m. | ||
| Tue., 11/8 | Miscellaneous Events | No School for Students- Professional Development | Home - Westbrook HS [Directions] | 7:50 a.m. | Professional Development for Teachers | |
| Thu., 11/10 | V Football | Ellington | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | L 28-48 | |
| Mon., 11/14 | JV Football | Old Saybrook, Windsor Locks/Suffield/East Granby | Away - Old Saybrook HS-Old Saybrook Campus [Directions] | 4:30 p.m. | ||
| Fri., 11/18 | V Football | North Branford | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | L 14-55 | |
| Fri., 11/18 | JV Football | Old Saybrook, Valley Regional/Old Lyme | Away - Old Saybrook HS-Old Saybrook Campus [Directions] | Canceled | Cancelled | |
| Wed., 11/23 | V Football | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | W 32-14 | |
| Wed., 11/23 | Miscellaneous Events | School Closed- Thanksgiving Break | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Thu., 11/24 | Miscellaneous Events | School Closed- Thanksgiving | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Fri., 11/25 | Miscellaneous Events | School Closed- Thanksgiving Break | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Sat., 12/3 | V Boys Ice Hockey | Northeastern Shamrocks (Scrim.) | Away - Bolton Ice Palace-Ice Rink [Directions] | 6:00 p.m. | ||
| Sat., 12/3 | V Girls Basketball | Granby Memorial (Scrim.) | Away - Granby Memorial HS-K.L. King Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 12/3 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate (Scrim.) | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:15 p.m. | ||
| Tue., 12/6 | V Boys Basketball | TBA | Home - Westbrook HS-Westbrook HS Gym [Directions] | 3:30 p.m. | ||
| Tue., 12/6 | V Girls Basketball | Guilford (Scrim.) | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:30 p.m. | ||
| Wed., 12/7 | V Boys Ice Hockey | Masuk (Scrim.) | Home - Cromwell-Upper Rink [Directions] | 4:20 p.m. | ||
| Wed., 12/7 | V Boys Indoor Track | Shoreline Conference Indoor Track Developmental | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 12/13 | ||||||
| Wed., 12/7 | V Girls Indoor Track | Shoreline Conference Indoor Track Developmental | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 12/13 | ||||||
| Thu., 12/8 | V Boys Basketball | Sheehan (Scrim.) | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 12/8 | V Girls Basketball | Amistad (Scrim.) | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:45 p.m. | ||
| Fri., 12/9 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Northford-Red [Directions] | 3:45 p.m. | W 54 | |
| Sat., 12/10 | V Boys Ice Hockey | Rocky Hill Coop (Scrim.) | Home - Cromwell-Upper Rink [Directions] | 7:30 p.m. | ||
| Mon., 12/12 | V Boys Basketball | Putnam (Scrim.) | Away - Putnam HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 12/14 | V Boys Ice Hockey | Cheshire | Away - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | L 3-4 | |
| Wed., 12/14 | V Girls Ice Hockey | Hamden Coop | Home - Northford-Red [Directions] | 3:45 p.m. | W 43 | |
| Thu., 12/15 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | L 62-74 | |
| Thu., 12/15 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Thu., 12/15 | V | Basketball | Away - Valley Regional HS-Valley Regional High School Gym | 3:30 p.m. | ||
| Fri., 12/16 | V Girls Basketball | Coginchaug | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:00 p.m. | L 22-57 | |
| Sat., 12/17 | FR Boys Basketball | Valley Regional | Home - Westbrook HS-Westbrook HS Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/17 | V Boys Ice Hockey | Northeastern Shamrocks | Away - Bolton Ice Palace-Ice Rink [Directions] | 6:00 p.m. | L 2-5 | |
| Sat., 12/17 | V Girls Ice Hockey | West Haven/SHA | Home - Northford-Red [Directions] | 7:45 p.m. | L 4-10 | |
| Mon., 12/19 | V Girls Ice Hockey | Guilford Coop | Away - East Haven HS-Veterans Rink [Directions] | 8:00 p.m. | W 4-3 | |
| Tue., 12/20 | V Boys Basketball | Old Saybrook | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | L 34-63 | |
| Tue., 12/20 | JV Boys Basketball | Old Saybrook | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/20 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 24-46 | |
| Tue., 12/20 | JV Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 12/21 | V Boys Ice Hockey | E.O. Smith-Tolland | Away - UConn Storrs-Freitas Ice Forum [Directions] | 7:30 p.m. | L 3-4 | |
| Wed., 12/21 | V Girls Ice Hockey | Masuk Coop | Home - Northford-Red [Directions] | 4:00 p.m. | W 7-4 | |
| Thu., 12/22 | V Boys Basketball | Old Lyme | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:00 p.m. | L 49-53 | |
| Thu., 12/22 | JV Boys Basketball | Old Lyme | Home - Westbrook HS-Westbrook HS Gym [Directions] | 4:30 p.m. | ||
| Thu., 12/22 | V Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | W 47-37 | |
| Thu., 12/22 | V Girls Gymnastics | Valley Regional | Away - Flip Flop Gymnastics [Directions] | 4:30 p.m. | 130.25 | |
| Mon., 12/26 | Miscellaneous Events | School Closed- Holiday Recess | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Tue., 12/27 | V Boys Basketball | Whitney Tech | Away - Eli Whitney RVTS-GYM [Directions] | 2:00 p.m. | L 43-69 | |
| Tue., 12/27 | V Girls Basketball | Lyman Memorial | Away - Lyman Memorial HS-Gym [Directions] | 6:00 p.m. | L 21-55 | |
| Tue., 12/27 | JV Girls Basketball | Lyman Memorial | Away - Lyman Memorial HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 12/27 | Miscellaneous Events | School Closed- Holiday Recess | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Wed., 12/28 | V Boys Basketball | Wright Tech | Home - Eli Whitney RVTS-GYM [Directions] | 12:00 p.m. | W 42-39 | |
| Wed., 12/28 | V Boys Ice Hockey | Hall | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 11:00 a.m. | L 3-6 | |
| Wed., 12/28 | Miscellaneous Events | School Closed- Holiday Recess | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Thu., 12/29 | V Girls Gymnastics | Mercy, Stonington, Valley Regional | Away - Flip Flop Gymnastics [Directions] | 10:00 a.m. | 127.1 | |
| Thu., 12/29 | Miscellaneous Events | School Closed- Holiday Recess | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Fri., 12/30 | V Boys Basketball | Lyman Memorial | Away - Lyman Memorial HS-Gym [Directions] | 6:15 p.m. | L 44-62 | |
| Fri., 12/30 | JV Boys Basketball | Lyman Memorial | Away - Lyman Memorial HS-Gym [Directions] | 4:45 p.m. | ||
| Fri., 12/30 | V Boys Ice Hockey | Rocky Hill Coop | Home - Cromwell-Upper Rink [Directions] | 4:20 p.m. | L 2-3 | |
| Fri., 12/30 | V Girls Basketball | Norwich Tech | Away - Norwich Technical HS-NTHS Gymnasium [Directions] | 1:00 p.m. | W 38-21 | |
| Fri., 12/30 | Miscellaneous Events | School Closed- Holiday Recess | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Mon., 1/2 | Miscellaneous Events | School Closed- Holiday Recess | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Tue., 1/3 | V Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 49-77 | |
| Tue., 1/3 | JV Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | V Girls Basketball | Portland | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:30 p.m. | W 52-31 | |
| Tue., 1/3 | JV Girls Basketball | Portland | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/4 | V Boys Ice Hockey | Newington Coop | Away - Newington-Blue Rink [Directions] | 4:00 p.m. | L 2-11 | |
| Thu., 1/5 | V Boys Indoor Track | Shoreline League Meet 1 | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Thu., 1/5 | V Girls Basketball | Wheeler | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:30 p.m. | W 32-24 | |
| Thu., 1/5 | V Girls Indoor Track | Shoreline League Meet 1 | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Fri., 1/6 | V Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | L 45-57 | |
| Fri., 1/6 | JV Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Home - Cromwell-Upper Rink [Directions] | 8:00 p.m. | L 2-4 | |
| Fri., 1/6 | V Girls Basketball | Hale Ray | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:00 p.m. | W 37-27 | |
| Fri., 1/6 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Northford-Red [Directions] | 3:45 p.m. | W 9-5 | |
| Sat., 1/7 | FR Boys Basketball | Morgan | Home - Westbrook HS-Westbrook HS Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/7 | V Girls Ice Hockey | Hall/Conard | Home - Northford-Red [Directions] | 7:00 p.m. | L 2-8 | |
| Mon., 1/9 | V Boys Basketball | North Branford | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | L 31-50 | |
| Mon., 1/9 | JV Boys Basketball | North Branford | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Mon., 1/9 | JV Boys Ice Hockey | Northeastern Shamrocks (Scrim.) | Home - Cromwell-Upper Rink [Directions] | 4:00 p.m. | ||
| Tue., 1/10 | V Girls Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 7:00 p.m. | L 62-15 | |
| Tue., 1/10 | JV Girls Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/11 | V Boys Basketball | Wheeler | Away - Wheeler HS-Gym [Directions] | 7:00 p.m. | L 59-46 | |
| Wed., 1/11 | JV Boys Basketball | Wheeler | Away - Wheeler HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/11 | V Boys Ice Hockey | Conard | Home - Cromwell-Upper Rink [Directions] | 4:20 p.m. | L 0-4 | |
| Wed., 1/11 | V Girls Gymnastics | Jonathan Law, Mercy, Valley Regional | Away - Jonathan Law HS-North Gymnasium [Directions] | 6:00 p.m. | 101.9 | |
| Fri., 1/13 | V Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 7:00 p.m. | L 51-68 | |
| Fri., 1/13 | JV Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:30 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:30 p.m. | L 32-62 | |
| Sat., 1/14 | FR Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/14 | V Boys Ice Hockey | New Milford | Home - Cromwell-Upper Rink [Directions] | 5:20 p.m. | L 0-3 | |
| Sat., 1/14 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Cromwell-Lower Rink [Directions] | 7:30 p.m. | L 1-7 | |
| Mon., 1/16 | Miscellaneous Events | School Closed- MLK, Jr. Day | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Tue., 1/17 | V Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:30 p.m. | L 29-77 | |
| Tue., 1/17 | JV Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Cromwell | Home - Westbrook HS-Westbrook HS Gym [Directions] | 4:30 p.m. | L 28-61 | |
| Thu., 1/19 | V Girls Ice Hockey | Guilford Coop | Home - Northford-Red [Directions] | 8:30 p.m. | W 2-1 | |
| Fri., 1/20 | V Boys Basketball | Valley Regional | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | L 50-49 | |
| Fri., 1/20 | JV Boys Basketball | Valley Regional | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | V Boys Ice Hockey | Newington Coop | Home - Cromwell-Upper Rink [Directions] | 8:00 p.m. | L 1-5 | |
| Fri., 1/20 | V Girls Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 6:00 p.m. | L 24-69 | |
| Fri., 1/20 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 9-6 | |
| Sat., 1/21 | FR Boys Basketball | Old Saybrook | Home - Westbrook HS-Westbrook HS Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/21 | JV Boys Ice Hockey | Newington Coop | Away - Newington-Blue Rink [Directions] | 8:45 p.m. | ||
| Sat., 1/21 | V Girls Gymnastics | Valley Regional, Hamden, Mercy | Away - Flip Flop Gymnastics [Directions] | 2:15 p.m. | 135.25 | |
| Sat., 1/21 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 1:00 p.m. | W 5-4 OT | |
| Mon., 1/23 | V Boys Indoor Track | Shoreline Coaches Invite | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Mon., 1/23 | V Girls Indoor Track | Shoreline Coaches Invite | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Tue., 1/24 | V Boys Basketball | Morgan | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | L 52-38 | |
| Tue., 1/24 | JV Boys Basketball | Morgan | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | 7:00 p.m. | L 33-25 | |
| Tue., 1/24 | JV Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | 6:00 p.m. | ||
| Tue., 1/24 | V Girls Gymnastics | Daniel Hand, Mercy, Valley Regional | Away - Polson MS, Small Gym-Polson Middle School/DHHS Campus [Directions] | 7:00 p.m. | 127.40 | |
| Thu., 1/26 | V | DanielHand | Home - Westbrook HS-Westbrook HS Gym [Directions] | 3:00 p.m. | ||
| Thu., 1/26 | V | LymeOldLyme | Home - Westbrook HS-Westbrook HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/27 | V Boys Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 7:00 p.m. | L 60-45 | |
| Fri., 1/27 | JV Boys Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Away - Enfield Twin Rinks-Rink 2 [Directions] | 7:45 p.m. | L 2-3 | |
| Fri., 1/27 | V Girls Basketball | East Hampton | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:30 p.m. | L 64-16 | |
| Fri., 1/27 | JV Girls Basketball | East Hampton | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/28 | FR Boys Basketball | North Branford | Home - Westbrook HS-Westbrook HS Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/28 | V Girls Ice Hockey | Suffield Coop | Home - Northford-Red [Directions] | 2:30 p.m. | L 5-4 | |
| Sun., 1/29 | V Boys Ice Hockey | New Milford (Scrim.) | Away - Canterbury School-O'Neill Arena [Directions] | 10:00 a.m. | L 2-5 | |
| Mon., 1/30 | V Boys Ice Hockey | Rocky Hill Coop | Away - Cromwell-Upper Rink [Directions] | 7:45 p.m. | W 5-2 | |
| Tue., 1/31 | V Boys Basketball | Coginchaug | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | L 53-51 | |
| Tue., 1/31 | JV Boys Basketball | Coginchaug | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | JV Boys Ice Hockey | Northeastern Shamrocks | Away - Bolton Ice Palace-Ice Rink [Directions] | 3:00 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 6:00 p.m. | L 21-60 | |
| Wed., 2/1 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | W 6-3 | |
| Wed., 2/1 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 6:30 p.m. | L 6-0 | |
| Thu., 2/2 | JV Boys Ice Hockey | West Haven Coop | Home - Cromwell-Upper Rink [Directions] | 4:00 p.m. | ||
| Fri., 2/3 | V Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 29-53 | |
| Fri., 2/3 | JV Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/3 | V Boys Indoor Track | Shoreline Conference Indoor Track Championship | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Fri., 2/3 | V Girls Basketball | Old Saybrook | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | L 34-46 | |
| Fri., 2/3 | V Girls Ice Hockey | Woodstock Academy Coop | Away - Pomfret School-Jahn Rink [Directions] | 7:00 p.m. | W 4-2 | |
| Fri., 2/3 | V Girls Indoor Track | Shoreline Conference Indoor Track Championship | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Fri., 2/3 | V | DanielHand | Away - Polson MS, Madison [Directions] | 3:00 p.m. | ||
| Sat., 2/4 | FR Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 10:00 a.m. | ||
| Sat., 2/4 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 6:15 p.m. | W 8-3 | |
| Sat., 2/4 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | W 4-3 | |
| Mon., 2/6 | V Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 7:00 p.m. | L 46-33 | |
| Mon., 2/6 | JV Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/6 | V Girls Basketball | Old Lyme | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:00 p.m. | W 39-21 | |
| Tue., 2/7 | JV Boys Ice Hockey | Newington Coop | Home - Cromwell-Upper Rink [Directions] | 4:20 p.m. | ||
| Wed., 2/8 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Cromwell-Upper Rink [Directions] | 4:20 p.m. | W 4-3 (OT) | |
| Wed., 2/8 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | L 5-0 | |
| Thu., 2/9 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Thu., 2/9 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/10 | V Boys Basketball | Portland | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | L 52-84 | |
| Fri., 2/10 | JV Boys Basketball | Portland | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/10 | JV Boys Ice Hockey | E.O. Smith-Tolland | Away - UConn Storrs-Freitas Ice Forum [Directions] | 4:15 p.m. | ||
| Fri., 2/10 | V Girls Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 51-26 | |
| Fri., 2/10 | JV Girls Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 6:00 p.m. | ||
| Mon., 2/13 | V Girls Basketball | Whitney Tech | Home - Westbrook HS-Westbrook HS Gym [Directions] | 4:30 p.m. | W 46-7 | |
| Mon., 2/13 | V Girls Gymnastics | Shoreline Conference Championship | Away - ABC Gymnastics | 6:30 p.m. | 87.35 | |
| Tue., 2/14 | V Girls Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 32-29 | |
| Tue., 2/14 | V Girls Gymnastics | Daniel Hand, Mercy, Valley Regional | Away - Polson MS, Small Gym-Polson Middle School/DHHS Campus [Directions] | 6:00 p.m. | 91.35 | |
| Wed., 2/15 | V Boys Basketball | Hale Ray | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 52-40 | |
| Wed., 2/15 | JV Boys Basketball | Hale Ray | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/15 | V Boys Ice Hockey | Northeastern Shamrocks | Home - Cromwell-Upper Rink [Directions] | 4:20 p.m. | W 3-0 | |
| Wed., 2/15 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | W 7-4 | |
| Sat., 2/18 | FR Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 2/18 | V Boys Ice Hockey | E.O. Smith-Tolland | Home - Cromwell-Upper Rink [Directions] | 7:30 p.m. | L 3-5 | |
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Northford-Red [Directions] | 2:30 p.m. | L 7-4 | |
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/20 | V Boys Ice Hockey | Staples | Home - Cromwell-Upper Rink [Directions] | 5:00 p.m. | W 4-2 | |
| Mon., 2/20 | V Girls Gymnastics | Valley Regional, Mercy | Away - Flip Flop Gymnastics [Directions] | 10:00 a.m. | 104.35 | |
| Mon., 2/20 | Miscellaneous Events | School Closed- February Break | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Tue., 2/21 | Miscellaneous Events | School Closed- February Break | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Wed., 2/22 | V Boys Ice Hockey | Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 7:20 p.m. | L 3-0 | |
| Wed., 2/22 | V Girls Ice Hockey | Hamden Coop | Home - Northford-Red [Directions] | 3:30 p.m. | ||
| Thu., 2/23 | V Girls Basketball | Plainfield (Scrim.) | Home - Westbrook HS-Westbrook HS Gym [Directions] | 4:30 p.m. | ||
| Sat., 2/25 | V Boys Ice Hockey | Hall | Home - Cromwell-Upper Rink [Directions] | 6:40 p.m. | L 2-1 | |
| Sat., 2/25 | V Girls Gymnastics | CIAC Divisional Championships | Away - Jonathan Law | TBA | ||
| Mon., 2/27 | V Girls Ice Hockey | Suffield Coop | Home - Northford-White [Directions] | 3:30 p.m. | L 6-7 | |
| Wed., 3/1 | V Girls Basketball | St. Bernard | Away - St. Bernard School-Powers Gym [Directions] | 5:30 p.m. | ||
| Fri., 3/3 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 3:30 p.m. | ||
| Sat., 3/4 | V Girls Gymnastics | CIAC State Open | Away - New Milford | 4:00 p.m. | ||
| Mon., 3/6 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:00 p.m. | ||
| Thu., 3/9 | Miscellaneous Events | Early Dismissal for Students | Home - Westbrook HS [Directions] | 12:15 p.m. | 1/2 Day Professional Development for Teachers | |
| Fri., 3/10 | Miscellaneous Events | No School for Students- Professional Development | Home - Westbrook HS [Directions] | 7:50 a.m. | Professional Development for Teachers | |
| Thu., 3/16 | Miscellaneous Events | Early Dismissal- Conferences | Home - Westbrook HS [Directions] | 12:15 p.m. | ||
| Wed., 3/22 | V Baseball | Old Saybrook (Scrim.) | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | ||
| Wed., 3/22 | V Boys Tennis | Sheehan (Scrim.) | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 3/22 | V Girls Tennis | Sheehan (Scrim.) | Away - Sheehan HS-Sheehan HS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 3/24 | V Baseball | East Haven (Scrim.) | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Sat., 3/25 | V Baseball | Manchester (Scrim.) | Away - Mt. Nebo Park-Baseball Diamond [Directions] | 12:00 p.m. | Cancelled | |
| Sat., 3/25 | V Girls Tennis | Guilford (Scrim.) | Away - Guilford HS-GHS Tennis Courts [Directions] | 12:00 p.m. | ||
| Mon., 3/27 | V Baseball | Wilbur Cross (Scrim.) | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | ||
| Mon., 3/27 | V Baseball | East Lyme (Scrim.) | Away - East Lyme HS-Bride Brook Park Baseball Diamond (ELPR) [Directions] | 4:00 p.m. | ||
| Mon., 3/27 | V Boys Tennis | TBA | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 3/28 | V Baseball | Bristol Central (Scrim.) | Away - Page Park-Baseball Diamond [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 3/29 | V Boys Tennis | Waterford (Scrim.) | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 3/29 | V Girls Tennis | Waterford (Scrim.) | Away - Waterford HS-Tennis Courts - WHS [Directions] | 4:00 p.m. | ||
| Mon., 4/3 | V Baseball | East Hampton | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | W 10-0 | |
| Mon., 4/3 | V Baseball | Old Saybrook | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 4-14 | |
| Mon., 4/3 | V Boys Tennis | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Mon., 4/3 | V Softball | Whitney Tech | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 3:45 p.m. | W 27-9 | |
| Mon., 4/3 | V Girls Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/4 | JV Baseball | East Hampton | Away - East Hamprton HS [Directions] | 5:00 p.m. | W 9-3 | |
| Tue., 4/4 | V Girls Tennis | Cromwell | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Wed., 4/5 | V Baseball | Morgan | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | W 10-9 | |
| Wed., 4/5 | V Baseball | Old Lyme | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 5-19 | |
| Wed., 4/5 | V Boys Tennis | East Hampton | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/5 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 4:00 p.m. | L 20-0 | |
| Wed., 4/5 | V Girls Tennis | East Hampton | Away - East Hampton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/6 | V Baseball | Cromwell | Away - Cromwell HS-Fran Monnes Baseball Field [Directions] | 4:00 p.m. | L 6-7 | |
| Thu., 4/6 | V Baseball | Hale Ray | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 2-5 | |
| Thu., 4/6 | JV Baseball | Morgan | Away - Morgan School-Baseball Field [Directions] | 3:45 p.m. | Cancelled | |
| Thu., 4/6 | V Boys Tennis | Cromwell | Away - Watrous park [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Thu., 4/6 | V Softball | Hale Ray | Away - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 4:00 p.m. | L 25-1 | |
| Fri., 4/7 | Miscellaneous Events | School Closed- April Break | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Sat., 4/8 | JV Baseball | Cromwell | Home - Valley Regional HS-Baseball Diamond [Directions] | 10:00 a.m. | W 15-0 | |
| Mon., 4/10 | V Baseball | Portland | Away - Portland HS-Portland HS [Directions] | 11:00 a.m. | W 12-11 | |
| Mon., 4/10 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | L 2-3 | |
| Mon., 4/10 | V Girls Tennis | North Branford | Away - North Branford HS-NBHS Tennis Courts [Directions] | 10:00 a.m. | W 7-0 [Detailed Results] | |
| Mon., 4/10 | Miscellaneous Events | School Closed- April Break | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Tue., 4/11 | JV Baseball | Haddam-Killingworth | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | W 10-6 | |
| Tue., 4/11 | Miscellaneous Events | School Closed- April Break | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Wed., 4/12 | V Baseball | North Branford | Home - Valley Regional HS-Baseball Diamond [Directions] | 12:00 p.m. | L 4-5 | |
| Wed., 4/12 | V Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 4:00 p.m. | L 0-11 | |
| Wed., 4/12 | V Boys Tennis | Old Saybrook | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/12 | V Softball | Coginchaug | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:00 p.m. | L 25-2 | |
| Wed., 4/12 | V Girls Tennis | Old Saybrook | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 2:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/12 | Miscellaneous Events | School Closed- April Break | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Thu., 4/13 | JV Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 4:00 p.m. | L 5-3 | |
| Thu., 4/13 | Miscellaneous Events | School Closed- April Break | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Fri., 4/14 | V Baseball | Hale Ray | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | W 6-1 | |
| Fri., 4/14 | V Baseball | East Hampton | Away - East Hamprton HS [Directions] | 4:00 p.m. | L 4-14 | |
| Fri., 4/14 | V Boys Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 2:00 p.m. | L 0-7 | |
| Fri., 4/14 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Varsity Softball Field [Directions] | 2:30 p.m. | L 15-0 | |
| Fri., 4/14 | V Girls Tennis | Old Lyme | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 10:00 a.m. | L 0-7 [Detailed Results] | |
| Fri., 4/14 | Miscellaneous Events | School Closed- April Break | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Sat., 4/15 | V Baseball | Waterford | Home - Valley Regional HS-Baseball Diamond [Directions] | 11:00 a.m. | L 1-4 | |
| Sat., 4/15 | JV Baseball | Waterford | Home - Valley Regional HS-Baseball Diamond [Directions] | 1:00 p.m. | W 7-5 | |
| Mon., 4/17 | JV Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | L 12-11 | |
| Tue., 4/18 | V Baseball | ValleyReg/Westbrook | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 0-23 | |
| Tue., 4/18 | V Baseball | Westbrook | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | W 23-0 | |
| Tue., 4/18 | V Boys Tennis | Coginchaug | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Tue., 4/18 | V Softball | Valley Regional | Away - Valley Regional HS-Joseph Camarota Memorial Field [Directions] | 3:45 p.m. | L 21-0 | |
| Tue., 4/18 | V Girls Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Wed., 4/19 | V Boys Outdoor Track | Coginchaug, North Branford | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:15 p.m. | ||
| Wed., 4/19 | V Boys Tennis | New London | Away - New London HS-NLHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Wed., 4/19 | V Girls Outdoor Track | Coginchaug, North Branford | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:15 p.m. | ||
| Thu., 4/20 | V Baseball | Morgan | Away - Indian River Complex-Baseball Field [Directions] | 4:00 p.m. | L 7-8 | |
| Thu., 4/20 | V Baseball | Old Saybrook | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 11-1 | |
| Thu., 4/20 | V Softball | Morgan | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:00 p.m. | L 22-4 | |
| Fri., 4/21 | V Boys Tennis | Suffield | Away - Suffield HS-Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Fri., 4/21 | V Softball | East Hampton | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:00 p.m. | L 24-4 | |
| Fri., 4/21 | V Girls Tennis | Portland | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Sat., 4/22 | V Baseball | E.O. Smith | Away - Farrell Field Park-Baseball Diamond - Varsity [Directions] | 11:00 a.m. | W 9-1 | |
| Sat., 4/22 | V Baseball | Griswold | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 12:00 p.m. | L 8-11 | |
| Sun., 4/23 | JV Baseball | E.O. Smith | Away - E.O. Smith HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Mon., 4/24 | V Baseball | Cromwell | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 8-11 | |
| Mon., 4/24 | V Baseball | Portland | Away - Portland HS-Portland HS [Directions] | 4:00 p.m. | W 14-1 | |
| Mon., 4/24 | V Boys Tennis | Morgan | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Mon., 4/24 | V Softball | Cromwell | Away - Cromwell HS-Softball Diamond [Directions] | 4:00 p.m. | L 14-0 | |
| Mon., 4/24 | V Girls Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/25 | JV Baseball | Portland | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 8-3 | |
| Wed., 4/26 | V Baseball | Coginchaug | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | W 12-2 | |
| Wed., 4/26 | V Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 4:00 p.m. | L 2-5 | |
| Wed., 4/26 | V Boys Outdoor Track | Morgan, Old Saybrook | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | ||
| Wed., 4/26 | V Boys Tennis | Valley Regional | Away - Valley Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Wed., 4/26 | V Girls Outdoor Track | Morgan, Old Saybrook | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | ||
| Wed., 4/26 | V Softball | North Branford | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L 18-1 | |
| Wed., 4/26 | V Girls Tennis | Valley Regional | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Thu., 4/27 | V Baseball | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 0-15 | |
| Thu., 4/27 | V Softball | Portland | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | W Forfeit | |
| Fri., 4/28 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Gloria Maddocks Field [Directions] | 4:00 p.m. | L 1-5 | |
| Fri., 4/28 | V Boys Tennis | Montville | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Fri., 4/28 | V Girls Tennis | Portland | Away - Portland HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | Non-conference Match |
| Sat., 4/29 | JV Baseball | Coginchaug | Home - Valley Regional HS-Baseball Diamond [Directions] | 10:00 a.m. | ||
| Sat., 4/29 | JV Baseball | Old Lyme | Home - Valley Regional HS-Baseball Diamond [Directions] | 10:00 a.m. | Cancelled | |
| Sat., 4/29 | V Boys Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 11:00 a.m. | ||
| Sat., 4/29 | V Girls Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 11:00 a.m. | ||
| Mon., 5/1 | V Baseball | Old Saybrook | Away - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | L 3-6 | |
| Mon., 5/1 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Mon., 5/1 | V Softball | Putnam | Away - St. Marie Greenhalgh Sports Complex-Softball Field [Directions] | 5:00 p.m. | W 29-19 | |
| Mon., 5/1 | V Girls Tennis | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/2 | V Boys Outdoor Track | Old Lyme, Haddam-Killingworth | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:30 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | Old Lyme, Haddam-Killingworth | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:30 p.m. | ||
| Wed., 5/3 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Gloria Maddocks Field [Directions] | 4:00 p.m. | L 9-11 | |
| Wed., 5/3 | V Baseball | Morgan | Away - Indian River Complex-Baseball Field [Directions] | 4:30 p.m. | W 11-0 | |
| Wed., 5/3 | V Boys Tennis | Old Saybrook | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/3 | V Softball | Old Lyme | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L 15-1 | |
| Wed., 5/3 | V Girls Tennis | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/4 | JV Baseball | Morgan | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | W 13-1 | |
| Thu., 5/4 | V Boys Tennis | Suffield | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 5/5 | V Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | W 4-0 | |
| Fri., 5/5 | V Baseball | Cromwell | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 10-2 | |
| Fri., 5/5 | V Boys Tennis | Ledyard | Away - Ledyard HS-Tennis Courts [Directions] | 4:15 p.m. | W 5-2 | |
| Fri., 5/5 | V Softball | Hale Ray | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L 16-2 | |
| Sat., 5/6 | V Baseball | East Hampton | Away - East Hampton HS-Baseball Field [Directions] | 3:00 p.m. | W 11-1 | |
| Sat., 5/6 | JV Baseball | Old Lyme, Hale Ray, Old Saybrook | Away - Lyme-Old Lyme HS-Gloria Maddocks Field [Directions] | 10:00 a.m. | ||
| Sat., 5/6 | JV Baseball | East Hampton | Away - East Hampton HS-Baseball Field [Directions] | 5:00 p.m. | W 10-2 | |
| Sat., 5/6 | V Boys Outdoor Track | Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Sat., 5/6 | V Girls Outdoor Track | Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Mon., 5/8 | V Baseball | Haddam-Killingworth | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | W 9-0 | |
| Mon., 5/8 | V Boys Outdoor Track | Cromwell, Hale Ray | Away - Cromwell HS-Don Luke Track [Directions] | 3:30 p.m. | ||
| Mon., 5/8 | V Boys Tennis | Cromwell | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Mon., 5/8 | V Girls Outdoor Track | Cromwell, Hale Ray | Away - Cromwell HS-Don Luke Track [Directions] | 3:30 p.m. | ||
| Mon., 5/8 | V Softball | Portland | Away - Portland HS-PHS Softball Field [Directions] | 4:00 p.m. | W Forfeit | |
| Mon., 5/8 | V Girls Tennis | Cromwell | Away - Watrous park [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Tue., 5/9 | V Baseball | Putnam | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:15 p.m. | L 1-3 | |
| Wed., 5/10 | V Girls Tennis | North Branford | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Wed., 5/10 | V | Shoreline Unified Track Meet | Away - Coginchaug-CRHS Track | 3:00 p.m. | ||
| Thu., 5/11 | V Baseball | Coginchaug | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | L 1-8 | |
| Thu., 5/11 | V Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 4:00 p.m. | W 13-2 | |
| Thu., 5/11 | JV Baseball | North Branford | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 5/12 | JV Baseball | North Branford | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | L 10-9 | |
| Fri., 5/12 | V Boys Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | Non-conference Match |
| Fri., 5/12 | V Softball | Valley Regional | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L 16-2 | Non-conference Game |
| Fri., 5/12 | V Girls Tennis | Morgan | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | Non-conference Match |
| Sat., 5/13 | V Baseball | Weston | Home - Valley Regional HS-Baseball Diamond [Directions] | 12:00 p.m. | L 0-2 | |
| Sat., 5/13 | V Baseball | Portland | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:00 p.m. | L 9-10 | |
| Mon., 5/15 | V Baseball | Bacon Academy | Away - Bacon Academy-Baseball Field [Directions] | 4:00 p.m. | W 16-0 | |
| Mon., 5/15 | JV Baseball | Bacon Academy | Away - Bacon Academy-Baseball Field [Directions] | Canceled | Cancelled | |
| Mon., 5/15 | V Boys Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 3:45 p.m. | W 7-0 | Non-conference Match |
| Mon., 5/15 | V Softball | Stonington | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:15 p.m. | L 26-6 | |
| Mon., 5/15 | V Girls Tennis | Coginchaug | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | Non-conference Match |
| Tue., 5/16 | V Baseball | Bloomfield | Away - Colt Park-Johnny Taylor Field (Baseball #9) [Directions] | 3:45 p.m. | W 18-0 | |
| Tue., 5/16 | JV Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 4:00 p.m. | L 4-2 | |
| Tue., 5/16 | V Boys Outdoor Track | Valley Regional, Portland | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:30 p.m. | ||
| Tue., 5/16 | V Girls Outdoor Track | Valley Regional, Portland | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:30 p.m. | ||
| Tue., 5/16 | V Softball | Coginchaug | Away - Coginchaug Regional HS-Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 4:00 p.m. | L 15-2 | |
| Wed., 5/17 | V Boys Tennis | Portland | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/17 | V Softball | Cromwell | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L 16-0 | Non-conference game |
| Thu., 5/18 | V Baseball | Guilford (Scrim.) | Away - Guilford HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 5/19 | V Baseball | Comp Sci | Away - Stanley Quarter Park-Baseball Diamond [Directions] | 3:30 p.m. | W 10-0 | |
| Fri., 5/19 | V Boys Tennis | Platt Tech | Away - Eisenhower Park-Eisenhower [Directions] | 3:45 p.m. | W 7-0 | |
| Mon., 5/22 | V Baseball | Old Saybrook | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | W 4-0 | |
| Mon., 5/22 | V Softball | Stonington | Away - Stonington HS-Softball Field [Directions] | 2:30 p.m. | L 24-2 | |
| Tue., 5/23 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Gloria Maddocks Field [Directions] | 4:00 p.m. | W 3-2 | |
| Wed., 5/24 | V Girls Outdoor Track | Shoreline Conference Outdoor Championship | Away - East Hampton HS-Track | 2:30 p.m. | ||
| Thu., 5/25 | V | Unified Sports - Outdoor Track | Away - Valley Regional HS-Richard B. Blythe Field | 3:30 p.m. | ||
| Fri., 5/26 | V Baseball | North Branford | Home - Indian River Complex [Directions] | 4:00 p.m. | W 7-4 | |
| Fri., 5/26 | V Boys Tennis | Suffield | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 5/27 | V Girls Tennis | Coginchaug | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 11:00 a.m. | W 6-1 | |
| Mon., 5/29 | Miscellaneous Events | School Closed- Memorial Day | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Tue., 5/30 | V Baseball | Wamogo | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:30 p.m. | W 15-0 | |
| Tue., 5/30 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/30 | V Girls Outdoor Track | CIAC Class S Championships | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/30 | V Girls Tennis | Bolton | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:00 p.m. | W 7-0 | |
| Tue., 5/30 | V | Shoreline Unified Field Day | Away - Lyme-Old Lyme HS | 3:00 p.m. | ||
| Wed., 5/31 | V Baseball | Coginchaug | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Wed., 5/31 | V Girls Tennis | Shepaug Valley | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:00 p.m. | W 4-3 | |
| Sat., 6/3 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic HS-Baseball Diamond [Directions] | 1:00 p.m. | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Tennis | Old Lyme | Away - Wesleyan [Directions] | 10:00 a.m. | L 7-0 | |
| Tue., 6/6 | V Baseball | Coventry | Away - Sage Park Berlin-Zipadelli Field [Directions] | 3:30 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Boys Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Girls Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Girls Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Mon., 6/12 | V Boys Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 2:00 p.m. | ||
| Mon., 6/12 | V Girls Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||