| Westbrook 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 481 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 8/28 | V Football | Bristol Eastern, New Britain, Newington (Scrim.) | Away - Bristol Eastern HS-Alumni Field-Turf [Directions] | 9:00 a.m. | ||
| Mon., 8/30 | Miscellaneous Events | First Day of School | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Wed., 9/1 | V Football | St. Paul Catholic (Scrim.) | Away - St. Paul Catholic HS-McPhee Field / Stadium Field [Directions] | Canceled | Cancelled | |
| Thu., 9/2 | V Football | East Haven (Scrim.) | Away - East Haven HS-EHHS Turf Field & Track [Directions] | 3:30 p.m. | ||
| Thu., 9/2 | V Field Hockey | Lyman Hall (Scrim.) | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | ||
| Fri., 9/3 | V Field Hockey | North Haven (Scrim.) | Away - North Haven MS-East Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 9/3 | V Girls Soccer | East Granby (Scrim.) | Away - East Granby HS-Lower Soccer Field [Directions] | 4:00 p.m. | L 0-1 | |
| Sat., 9/4 | V Boys Cross Country | Old Lyme (Scrim.) | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 9:30 a.m. | ||
| Mon., 9/6 | Miscellaneous Events | Holiday - Labor Day | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Tue., 9/7 | V Boys Soccer | East Haven (Scrim.) | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | ||
| Tue., 9/7 | V Field Hockey | Waterford (Scrim.) | Away - Waterford HS - official -Alumni Turf Field/Track [Directions] | 3:30 p.m. | ||
| Fri., 9/10 | V Football | Cromwell/Portland | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | L 8-36 | |
| Fri., 9/10 | V Boys Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:45 p.m. | L 0-1 | |
| Fri., 9/10 | JV Boys Soccer | Coginchaug | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | Postponed | ||
| Fri., 9/10 | V Girls Soccer | Coginchaug | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 0-6 | |
| Sat., 9/11 | JV Football | Cromwell/Portland | Away - Pierson Park, Cromwell [Directions] | Canceled | Cancelled | |
| Sat., 9/11 | V Boys Soccer | Amistad | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 11:00 a.m. | W 3-0 | |
| Sat., 9/11 | V Field Hockey | Norwich Free Academy | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 11:00 a.m. | W 5-0 | |
| Mon., 9/13 | V Boys Soccer | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:45 p.m. | L 0-8 | |
| Mon., 9/13 | V Field Hockey | North Branford | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 9/14 | V Boys Cross Country | Morgan, Old Lyme, Valley Regional | Away - Indian River Complex-XC Course [Directions] | 3:45 p.m. | ||
| Tue., 9/14 | JV Boys Soccer | Valley Regional | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | ||
| Tue., 9/14 | V Girls Soccer | Valley Regional | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 0-3 | |
| Wed., 9/15 | JV Girls Soccer | Valley Regional | Away - Valley Regional HS-JV Girls Soccer Field [Directions] | 3:45 p.m. | T 1-1 | |
| Thu., 9/16 | V Field Hockey | Somers/Rockville Coop | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:30 p.m. | L 1-2 | |
| Thu., 9/16 | V Girls Soccer | Hale Ray | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | W 3-1 | (non-conference) counting game is 10/18 at Hale-Ray |
| Fri., 9/17 | V Football | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | 6:30 p.m. | W 36-22 | |
| Fri., 9/17 | V Boys Soccer | Hale Ray | Away - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 6:00 p.m. | L 0-1 | |
| Sat., 9/18 | V Boys Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 8:30 a.m. | ||
| Sat., 9/18 | JV Football | Haddam-Killingworth | Home - Peters Complex-Football Field [Directions] | 10:30 a.m. | ||
| Sat., 9/18 | V Girls Soccer | Amistad | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 1:00 p.m. | W Forfeit | |
| Mon., 9/20 | V Boys Soccer | Cromwell | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 0-1 | |
| Mon., 9/20 | V Field Hockey | Valley Regional | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | L 0-9 | |
| Tue., 9/21 | JV Boys Soccer | Cromwell | Away - Cromwell HS-soccer field 1 [Directions] | 3:45 p.m. | ||
| Tue., 9/21 | V Girls Soccer | Cromwell | Away - Cromwell HS-Main field [Directions] | 3:45 p.m. | L 0-1 | |
| Wed., 9/22 | V Boys Cross Country | Coginchaug - Going to the Sun Cross Country Meet | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:15 p.m. | ||||||
| Wed., 9/22 | JV Girls Soccer | Cromwell | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 2-3 | |
| Thu., 9/23 | V Boys Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 3:45 p.m. | L 1-4 | |
| Thu., 9/23 | V Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | W 2-1 | |
| Thu., 9/23 | V | LymeOldLyme | Away - Lyme-Old Lyme HS [Directions] | 3:00 p.m. | ||
| Sat., 9/25 | V Football | CREC Coop | Home - Peters Complex-Football Field [Directions] | 1:00 p.m. | W 54-6 | Game will be continued from the point of interruption |
| Sat., 9/25 | JV Football | CREC Coop | Away - Civic Leadership HS-Civic Leadership Turf Field [Directions] | Canceled | Cancelled | |
| Sat., 9/25 | V Field Hockey | Fitch | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 11:00 a.m. | L 1-2 | |
| Sat., 9/25 | V Girls Soccer | Morgan | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 11:00 a.m. | L 0-4 | |
| Mon., 9/27 | V Boys Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 9/27 | V Field Hockey | Morgan | Away - Indian River Complex-Turf Field [Directions] | 6:00 p.m. | L 0-2 | |
| Tue., 9/28 | V Boys Cross Country | LEAGUE MEET #1 Small Schools | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:30 p.m. | ||
| Tue., 9/28 | V Boys Cross Country | LEAGUE MEET #1 Small Schools | Away - Old Saybrook HS-Old Saybrook Campus | 3:30 p.m. | ||
| Tue., 9/28 | JV Boys Soccer | East Hampton | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:30 p.m. | ||
| Tue., 9/28 | V Girls Cross Country | LEAGUE MEET #1 Small Schools | Away - Old Saybrook HS-Old Saybrook Campus | 3:30 p.m. | ||
| Tue., 9/28 | V Girls Soccer | East Hampton | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 4:30 p.m. | L 1-3 | |
| Wed., 9/29 | V Boys Soccer | Harding | Away - Warren Harding HS-Lewis Field [Directions] | 4:30 p.m. | W 5-0 | |
| Thu., 9/30 | V Field Hockey | Old Saybrook | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 9/30 | V Girls Soccer | Portland | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 0-6 | |
| Fri., 10/1 | V Football | Valley Regional/Old Lyme | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | W 20-15 | |
| Fri., 10/1 | V Boys Soccer | Portland | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 1-3 | |
| Fri., 10/1 | JV Girls Soccer | Portland | Away - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | W 2-1 | |
| Sat., 10/2 | JV Football | Valley Regional/Old Lyme | Away - Valley Regional HS-Practice Football Field [Directions] | 10:00 a.m. | ||
| Sat., 10/2 | JV Girls Soccer | Morgan | Away - Morgan School-Soccer/Lax Field [Directions] | 10:30 a.m. | L 3-2 | |
| Mon., 10/4 | V Field Hockey | North Branford | Away - North Branford HS-NBHS Back Field [Directions] | 6:00 p.m. | L 0-4 | |
| Tue., 10/5 | V Boys Cross Country | North Branford, Haddam-Killingworth, Old Lyme, Morgan, Valley Regional | Away - Totoket Valley Park - North Branford-Totoket Park - North Branford | 3:30 p.m. | ||
| Tue., 10/5 | V Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | 3:45 p.m. | L 0-3 | |
| Tue., 10/5 | V | Shoreline Conference Unified Soccer Tournament | Away - Cromwell HS-Soccer field 2 | 3:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Westbrook HS | ||||||
| Wed., 10/6 | JV Boys Soccer | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 5:00 p.m. | ||
| Wed., 10/6 | V Girls Soccer | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 5:00 p.m. | L 1-5 | |
| Thu., 10/7 | V Field Hockey | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 3:45 p.m. | L 0-4 | |
| Thu., 10/7 | V Girls Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:45 p.m. | L 1-4 | |
| Thu., 10/7 | Miscellaneous Events | Early Dismissal - PD | Home - Westbrook HS [Directions] | 12:15 p.m. | ||
| Fri., 10/8 | V Boys Soccer | Old Saybrook | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 10/8 | JV Girls Soccer | Old Saybrook | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L 1-5 | |
| Sat., 10/9 | JV Boys Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | ||
| Sat., 10/9 | V Field Hockey | Suffield | Away - Suffield HS-Ted Beneski Turf Field [Directions] | 1:30 p.m. | L 0-1 | |
| Mon., 10/11 | V Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | 10:00 a.m. | L 0-5 | |
| Mon., 10/11 | Miscellaneous Events | Holiday - Columbus Day | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Tue., 10/12 | V Boys Soccer | Old Lyme | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 2-3 | |
| Tue., 10/12 | V Field Hockey | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | W 1-0 | |
| Tue., 10/12 | JV Girls Soccer | Old Lyme | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L 0-2 | |
| Wed., 10/13 | JV Boys Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:45 p.m. | ||
| Wed., 10/13 | V Girls Soccer | Harding | Away - Warren Harding HS-Lewis Field [Directions] | 3:45 p.m. | W 8-0 | |
| Thu., 10/14 | V Boys Cross Country | SLC Mega Meet | Away - East Hampton HS-Cross Country Course | 2:30 p.m. | ||
| Thu., 10/14 | V Boys Cross Country | SLC Mega Meet | Away - East Hampton HS-Cross Country Course | 2:30 p.m. | ||
| Thu., 10/14 | V Girls Cross Country | Shoreline Conference Mega Meet | Away - East Hampton HS-Cross Country Course | 3:30 p.m. | ||
| Thu., 10/14 | V Field Hockey | Morgan | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 10/15 | V Boys Soccer | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | W 9-0 | |
| Fri., 10/15 | V Girls Soccer | North Branford/Hale Ray | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | W 4-0 | |
| Sat., 10/16 | V Football | SMSA Coop | Away - Hartford Public HS-Turf field [Directions] | 12:00 p.m. | W 44-42 | |
| Sat., 10/16 | V Field Hockey | Waterford | Away - Waterford HS - official -Alumni Turf Field/Track [Directions] | 10:00 a.m. | L 2-7 | |
| Mon., 10/18 | JV Football | SMSA Coop | Home - Peters Complex-Football Field [Directions] | Canceled | Cancelled | |
| Mon., 10/18 | V Field Hockey | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | L 0-2 | |
| Mon., 10/18 | V Girls Soccer | Hale Ray | Away - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 4:00 p.m. | L 2-4 | |
| Tue., 10/19 | V Boys Soccer | Hale Ray | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | T 2-2 | |
| Wed., 10/20 | V Girls Soccer | Amistad | Away - Amistad HS-Stadium [Directions] | 3:30 p.m. | W Forfeit | |
| Wed., 10/20 | V Girls Soccer | Harding | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | W 9-0 | |
| Thu., 10/21 | V Boys Soccer | Amistad | Away - Amistad HS-Stadium [Directions] | 3:45 p.m. | T 1-1 | |
| Fri., 10/22 | V Boys Cross Country | TBA, TBA, TBA, Hale Ray, Valley Regional | Away - TBA-connell memorial rink | 2:30 p.m. | ||
| Fri., 10/22 | V Football | Coginchaug/Hale Ray/East Hampton | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | W 50-20 | |
| Fri., 10/22 | JV Boys Soccer | Old Lyme | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | ||
| Fri., 10/22 | V Girls Cross Country | Shoreline Cross Country Championship | Away - TBA-Grandville HS | 2:30 p.m. | ||
| Sat., 10/23 | V Boys Cross Country | Shoreline Cross Country Championship | Away - East Hampton HS-Cross Country Course | 10:45 a.m. | ||
| Sat., 10/23 | V Boys Cross Country | Shoreline Cross Country Championship | Away - East Hampton HS-Cross Country Course | 10:45 a.m. | ||
| Sat., 10/23 | JV Football | Coginchaug/Hale Ray/East Hampton | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 11:00 a.m. | ||
| Sat., 10/23 | V Girls Cross Country | Shoreline Cross Country Championship | Away - East Hampton HS-Cross Country Course | 10:00 a.m. | ||
| Mon., 10/25 | JV Boys Soccer | Morgan | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | ||
| Tue., 10/26 | V Boys Cross Country | Frosh/Soph Invitational | Away - Old Saybrook HS-Old Saybrook Campus | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 10/27 | ||||||
| Tue., 10/26 | V Boys Cross Country | Frosh/Soph Invitational | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 10/27 | ||||||
| Tue., 10/26 | V Girls Cross Country | Frosh/Soph Invitational | Away - Old Saybrook HS-Old Saybrook Campus | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 10/27 | ||||||
| Thu., 10/28 | V Boys Soccer | Harding | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 4:15 p.m. | W 4-0 | |
| Thu., 10/28 | V Field Hockey | Canton | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 0-3 | |
| Thu., 10/28 | Miscellaneous Events | Early Dismissal - Parent Conferences | Home - Westbrook HS [Directions] | 12:15 p.m. | ||
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class S Championship | Away - Wickham Park | 2:05 p.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class S Championship | Away - Wickham Park | 2:35 p.m. | ||
| Tue., 11/2 | Miscellaneous Events | No School - PD | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | Coventry/Windham Tech/Bolton/Lyman | Away - Coventry HS-Football Field [Directions] | 6:30 p.m. | W 41-21 | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | JV Football | Coventry/Windham Tech/Bolton/Lyman | Home - Peters Complex-Football Field [Directions] | 10:30 a.m. | ||
| Fri., 11/12 | V Football | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 6:30 p.m. | W 46-6 | |
| Sat., 11/13 | JV Football | North Branford | Home - Peters Complex-Football Field [Directions] | Canceled | Cancelled | |
| Fri., 11/19 | V Football | Ellington | Away - Ellington HS-Main Field [Directions] | 6:30 p.m. | L 26-28 | |
| Sat., 11/20 | JV Football | Valley Regional/Old Lyme | Home - Peters Complex-Football Field [Directions] | Canceled | Cancelled | |
| Wed., 11/24 | V Football | Old Saybrook | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | W 46-8 | Senior Night |
| Wed., 11/24 | Miscellaneous Events | Early Dismissal | Home - Westbrook HS [Directions] | 12:15 p.m. | ||
| Thu., 11/25 | Miscellaneous Events | Holiday - Thanksgiving | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Fri., 11/26 | Miscellaneous Events | Holiday - Thanksgiving | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Tue., 11/30 | V Football | Bloomfield | Away - Bloomfield HS-Phil Rubin Stadium- Turf Field & Track [Directions] | 6:30 p.m. | ||
| Sat., 12/4 | V Boys Ice Hockey | Masuk (Scrim.) | Home - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 8:00 p.m. | ||
| Sat., 12/4 | V Girls Basketball | Griswold (Scrim.) | Away - Griswold HS-GHS Gym [Directions] | 10:00 a.m. | ||
| Tue., 12/7 | V Boys Basketball | Montville (Scrim.) | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/7 | V Girls Basketball | North Haven (Scrim.) | Home - Westbrook HS-Westbrook HS Gym [Directions] | 3:15 p.m. | ||
| Wed., 12/8 | V Boys Ice Hockey | Hall (Scrim.) | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 7:20 p.m. | ||
| Wed., 12/8 | V Boys Indoor Track | Shoreline Developmental Track Meet | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Wed., 12/8 | V Girls Ice Hockey | West Haven/SHA | Home - Northford Ice Pavilion-White [Directions] | 8:30 p.m. | L 2-3 | |
| Wed., 12/8 | V Girls Indoor Track | Shoreline Developmental Track Meet | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Fri., 12/10 | V Boys Basketball | Sheehan (Scrim.) | Away - Sheehan HS-Sheehan HS Gymnasium [Directions] | 6:00 p.m. | ||
| Sat., 12/11 | V Boys Ice Hockey | E.O. Smith-Tolland (Scrim.) | Away - UConn Storrs-Freitas Ice Forum [Directions] | 3:30 p.m. | ||
| Sat., 12/11 | V Girls Basketball | East Haven (Scrim.) | Home - Westbrook HS-Westbrook HS Gym [Directions] | 11:00 a.m. | ||
| Mon., 12/13 | V Boys Basketball | TBA | Home - Westbrook HS-Westbrook HS Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/15 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:50 p.m. | L 0-6 | |
| Thu., 12/16 | V Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 58-65 | |
| Thu., 12/16 | JV Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/16 | V Girls Basketball | Portland | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 48-36 | |
| Fri., 12/17 | V Girls Ice Hockey | Guilford Coop | Home - Northford Ice Pavilion-White [Directions] | 8:30 p.m. | L 3-6 | |
| Sat., 12/18 | FR Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | Postponed | ||
| Mon., 12/20 | V Girls Basketball | Whitney Tech | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:00 p.m. | W 47-8 | |
| Thu., 12/23 | V Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | L 41-67 | |
| Thu., 12/23 | JV Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/23 | Miscellaneous Events | Early Dismissal | Home - Westbrook HS [Directions] | 12:15 p.m. | ||
| Fri., 12/24 | Miscellaneous Events | Holiday Break - No School | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Mon., 12/27 | V Boys Ice Hockey | Rocky Hill Coop | Home - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 7:00 p.m. | L 0-9 | |
| Mon., 12/27 | Miscellaneous Events | Holiday Break - No School | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Tue., 12/28 | V Boys Basketball | Old Lyme | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 57-49 | |
| Tue., 12/28 | JV Boys Basketball | Old Lyme | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/28 | V Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 6:00 p.m. | W 39-31 | |
| Tue., 12/28 | Miscellaneous Events | Holiday Break - No School | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Wed., 12/29 | V Boys Ice Hockey | Newington Coop | Away - Newington Ice Arena-Blue Rink [Directions] | 8:00 p.m. | L 0-5 | |
| Wed., 12/29 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 5:00 p.m. | L 0-2 | |
| Wed., 12/29 | Miscellaneous Events | Holiday Break - No School | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Thu., 12/30 | V Boys Basketball | Lyman Memorial | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 59-37 | |
| Thu., 12/30 | V Girls Basketball | Lyman Memorial | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:00 p.m. | L 36-44 | |
| Thu., 12/30 | V Girls Gymnastics | Valley Regional, Mercy, TBA, Stonington | Away - Flip Flop Gymnastics [Directions] | 10:00 a.m. | 90.45 | |
| Thu., 12/30 | Miscellaneous Events | Holiday Break - No School | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Fri., 12/31 | Miscellaneous Events | Holiday Break - No School | Home - Westbrook HS [Directions] | 7:50 a.m. | ||
| Mon., 1/3 | V Boys Ice Hockey | Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 7:20 p.m. | L 0-3 | |
| Tue., 1/4 | V Boys Basketball | Old Saybrook | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:00 p.m. | L 28-44 | |
| Tue., 1/4 | JV Boys Basketball | Old Saybrook | Home - Westbrook HS-Westbrook HS Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/4 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:00 p.m. | W 40-34 | |
| Wed., 1/5 | V Boys Indoor Track | Shoreline League Meet #1 | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Wed., 1/5 | V Girls Indoor Track | Shoreline League Meet #1 | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Sat., 1/8 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 3:30 p.m. | W 60-53 | |
| Sat., 1/8 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 2:00 p.m. | ||
| Sat., 1/8 | FR Boys Basketball | Valley Regional | Home - Westbrook HS-Westbrook HS Gym [Directions] | 10:30 a.m. | ||
| Sat., 1/8 | V Girls Basketball | Coginchaug | Home - Westbrook HS-Westbrook HS Gym [Directions] | 3:00 p.m. | L 28-54 | |
| Sat., 1/8 | V Girls Gymnastics | Foran, Mercy | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 10:00 a.m. | 127.50 | |
| Sat., 1/8 | V Girls Ice Hockey | Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 1:30 p.m. | L 2-5 | |
| Mon., 1/10 | V Boys Indoor Track | HK Invite | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:45 p.m. | ||||||
| Mon., 1/10 | V Girls Indoor Track | HK Invite | Away - Floyd Little Athletic Center-Field House | 4:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Hillhouse HS-Field House | ||||||
| Tue., 1/11 | V Boys Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 7:00 p.m. | L 25-49 | |
| Tue., 1/11 | JV Boys Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/11 | V Girls Basketball | Valley Regional | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | L 64-38 | |
| Tue., 1/11 | V | LymeOldLyme | Home - Westbrook HS-Westbrook HS Gym [Directions] | 3:00 p.m. | ||
| Wed., 1/12 | V Boys Ice Hockey | Guilford | Away - Blake Field - New Haven-Walker Rink [Directions] | 5:30 p.m. | L 1-10 | |
| Thu., 1/13 | V Boys Indoor Track | Shoreline League Meet #2 | Away - TBA-connell memorial rink | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Hillhouse HS-Field House | ||||||
| Thu., 1/13 | V Girls Gymnastics | Daniel Hand | Away - Polson MS, Small Gym-Polson Middle School/DHHS Campus [Directions] | 3:30 p.m. | ||
| Thu., 1/13 | V Girls Gymnastics | Daniel Hand, Mercy, Morgan, TBA, Valley Regional | Away - Polson MS, Small Gym-Polson Middle School/DHHS Campus | 6:30 p.m. | ||
| Thu., 1/13 | V Girls Indoor Track | Shoreline League Meet #2 | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Fri., 1/14 | V Girls Ice Hockey | Masuk Coop | Home - Northford Ice Pavilion-Red [Directions] | 4:00 p.m. | L 1-5 | |
| Sat., 1/15 | FR Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/15 | V Boys Ice Hockey | Rocky Hill Coop | Away - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 12:00 p.m. | L 1-7 | |
| Sat., 1/15 | V Girls Basketball | Wheeler | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 53-27 | |
| Sat., 1/15 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | W 5-1 | |
| Mon., 1/17 | Miscellaneous Events | Holiday - Martin Luther King Day | Home - Westbrook HS [Directions] | 7:20 a.m. | ||
| Tue., 1/18 | V Boys Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 5:30 p.m. | L 42-68 | |
| Tue., 1/18 | JV Boys Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/18 | V Girls Basketball | East Hampton | Home - Westbrook HS-Westbrook HS Gym [Directions] | 4:00 p.m. | L 20-50 | |
| Tue., 1/18 | JV Girls Basketball | East Hampton | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/19 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 7:30 p.m. | L 1-4 | |
| Wed., 1/19 | V Girls Basketball | Norwich Tech | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 53-25 | |
| Wed., 1/19 | V Girls Ice Hockey | Guilford Coop | Away - Northford Ice Pavilion-Blue [Directions] | 3:15 p.m. | L 3-4 | |
| Fri., 1/21 | V Boys Basketball | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:00 p.m. | W 61-46 | |
| Fri., 1/21 | V Boys Ice Hockey | New Milford | Away - Canterbury School-O'Neill Arena [Directions] | 8:30 p.m. | L 1-5 | |
| Fri., 1/21 | V Girls Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 7:00 p.m. | L 13-33 | |
| Sat., 1/22 | FR Boys Basketball | Portland | Home - Westbrook HS-Westbrook HS Gym [Directions] | 10:30 a.m. | ||
| Sat., 1/22 | V Girls Gymnastics | Valley Regional, Hamden, Mercy, TBA | Away - Flip Flop Gymnastics [Directions] | TBA | 130.85 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Tue., 1/25 | V Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 7:00 p.m. | L 50-70 | |
| Tue., 1/25 | JV Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/25 | V Girls Basketball | Morgan | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | L 39-32 | |
| Tue., 1/25 | JV Girls Basketball | Morgan | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | ||
| Tue., 1/25 | V | Unified Basketball Tournament | Home - Westbrook HS-Westbrook HS Gym [Directions] | 3:00 p.m. | ||
| Wed., 1/26 | V Boys Basketball | Whitney Tech | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | L 52-63 | |
| Wed., 1/26 | JV Boys Basketball | Whitney Tech | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/26 | V Boys Ice Hockey | E.O. Smith-Tolland | Home - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 8:00 p.m. | L 2-6 | |
| Wed., 1/26 | V Girls Ice Hockey | Avon | Away - Newington Ice Arena-Blue Rink [Directions] | 5:10 p.m. | L 0-6 | |
| Fri., 1/28 | V Boys Basketball | North Branford | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 52-43 | |
| Fri., 1/28 | JV Boys Basketball | North Branford | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/28 | V Boys Ice Hockey | Northeastern Shamrocks | Home - Newington Ice Arena-Blue Rink [Directions] | 6:00 p.m. | L 1-3 | |
| Fri., 1/28 | V Boys Indoor Track | Shoreline Coaches Invite | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Fri., 1/28 | V Girls Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 5:30 p.m. | L 34-64 | |
| Fri., 1/28 | JV Girls Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/28 | V Girls Gymnastics | Valley Regional | Away - ABC Gymnastics [Directions] | 3:30 p.m. | 138.95 | |
| Fri., 1/28 | V Girls Indoor Track | Shoreline Coaches Invite | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Tue., 2/1 | V Boys Basketball | Portland | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | L 42-60 | |
| Tue., 2/1 | JV Boys Basketball | Portland | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/1 | V Girls Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 6:00 p.m. | L 34-39 | |
| Tue., 2/1 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | L 1-3 | |
| Wed., 2/2 | V Girls Basketball | Hale Ray | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:00 p.m. | W 41-25 | |
| Thu., 2/3 | Miscellaneous Events | Early Dismissal - PD | Home - Westbrook HS [Directions] | 12:15 p.m. | ||
| Sat., 2/5 | FR Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 1:30 p.m. | ||
| Sat., 2/5 | V Boys Ice Hockey | Conard | Home - Champions Skating Rink - Cromwell-Upper Rink [Directions] | 3:30 p.m. | W 3-1 | |
| Sat., 2/5 | V Boys Indoor Track | Shoreline Conference Indoor Track Championship | Away - Hillhouse HS-Field House | 10:00 a.m. | ||
| Sat., 2/5 | V Girls Indoor Track | Shoreline Conference Indoor Track Championship | Away - Coginchaug Regional HS-Floyd Little Athletic Center - Hillhouse HS | 10:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Hillhouse HS-Field House | ||||||
| Tue., 2/8 | FR Boys Basketball | North Branford | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/8 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:30 p.m. | L 3-6 | |
| Tue., 2/8 | V Girls Basketball | Old Lyme | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | L 40-27 | |
| Tue., 2/8 | JV Girls Basketball | Old Lyme | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | ||
| Tue., 2/8 | V Girls Gymnastics | Valley Regional, TBA | Away - Flip Flop Gymnastics [Directions] | 2:00 p.m. | 136.9 | |
| Tue., 2/8 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Ice Arena-Red Rink [Directions] | 4:25 p.m. | L 0-2 | |
| Wed., 2/9 | V Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 7:00 p.m. | L 56-82 | |
| Wed., 2/9 | JV Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/10 | V Girls Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 58-32 | |
| Fri., 2/11 | V Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 45-58 | |
| Fri., 2/11 | JV Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/11 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - The Frederick Gunn School-Ice Rink [Directions] | 7:30 p.m. | L 1-4 | |
| Fri., 2/11 | V Girls Basketball | Old Saybrook | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 46-28 | |
| Fri., 2/11 | V Girls Gymnastics | Shoreline Tournament | Away - ABC Gymnastics | 3:00 p.m. | ||
| Fri., 2/11 | V Girls Gymnastics | Shoreline Tournament | Home - ABC Gymnastics [Directions] | 3:00 p.m. | 133.35 | |
| Fri., 2/11 | V Girls Gymnastics | Valley Regional | Away - ABC Gymnastics [Directions] | 3:00 p.m. | 133.35 | |
| Sat., 2/12 | FR Boys Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/12 | V Boys Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/12 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Northford Ice Pavilion-Red [Directions] | 7:40 p.m. | L 1-3 | |
| Sat., 2/12 | V Girls Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Mon., 2/14 | V Boys Basketball | Coginchaug | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 64-48 | |
| Mon., 2/14 | JV Boys Basketball | Coginchaug | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/14 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 7:30 p.m. | W 3-2 | |
| Mon., 2/14 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 6:00 p.m. | L 38-20 | |
| Wed., 2/16 | V Boys Ice Hockey | JBWA | Home - Champions Skating Rink - Cromwell-Upper Rink [Directions] | 3:10 p.m. | L 0-6 | |
| Wed., 2/16 | V Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 6:00 p.m. | L 52-36 | |
| Wed., 2/16 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 2/17 | V Boys Basketball | Wheeler | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 60-46 | |
| Thu., 2/17 | JV Boys Basketball | Wheeler | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/17 | V Girls Gymnastics | Daniel Hand, H-K/Morgan/Westbrook, Mercy, Morgan, Valley Regional | Away - Polson MS, Small Gym-Polson Middle School/DHHS Campus | 6:30 p.m. | ||
| Thu., 2/17 | V Girls Gymnastics | Daniel Hand, Mercy, Morgan, Valley Regional, Westbrook | Away - Polson MS, Small Gym-Polson Middle School/DHHS Campus | 6:30 p.m. | 134.05 | |
| Thu., 2/17 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 3-2(OT) | |
| Fri., 2/18 | V Boys Basketball | Hale Ray | Home - Westbrook HS-Westbrook HS Gym [Directions] | 6:30 p.m. | L 75-52 | |
| Fri., 2/18 | JV Boys Basketball | Hale Ray | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:00 p.m. | ||
| Sat., 2/19 | FR Boys Basketball | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/19 | V Boys Ice Hockey | Guilford | Home - Newington Ice Arena-Blue Rink [Directions] | 7:00 p.m. | L 3-8 | |
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Girls Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 12:00 p.m. | ||
| Sat., 2/19 | V Girls Ice Hockey | Hamden Coop | Home - Northford Ice Pavilion-Red [Directions] | 2:30 p.m. | L 0-3 | |
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | V Boys Ice Hockey | Hall | Home - Newington Ice Arena-Red Rink [Directions] | 7:40 p.m. | L 3-4(OT) | |
| Mon., 2/21 | V Girls Gymnastics | Valley Regional, Mercy | Away - Flip Flop Gymnastics [Directions] | 10:00 a.m. | 132.45 | |
| Mon., 2/21 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Northford Ice Pavilion-Red [Directions] | 12:30 p.m. | ||
| Mon., 2/21 | Miscellaneous Events | Holiday - Presidents Day | Home - Westbrook HS [Directions] | 7:20 a.m. | ||
| Tue., 2/22 | Miscellaneous Events | Holiday - Presidents Day | Home - Westbrook HS [Directions] | 7:20 a.m. | ||
| Wed., 2/23 | V Boys Basketball | Cromwell | Home - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | L 64-44 | |
| Wed., 2/23 | JV Boys Basketball | Cromwell | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/23 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Away - Enfield Twin Rinks-Rink 2 [Directions] | 3:50 p.m. | L 3-6 | |
| Thu., 2/24 | FR Boys Basketball | Old Saybrook | Home - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/24 | V Boys Ice Hockey | Housatonic Coop | Home - Newington Ice Arena-Blue Rink [Directions] | 5:30 p.m. | L 3-7 | |
| Sat., 2/26 | V Boys Basketball | Whitney Tech | Away - Eli Whitney RVTS-Gym [Directions] | 12:30 p.m. | W 40-39 | |
| Sat., 2/26 | JV Boys Basketball | Whitney Tech | Away - Eli Whitney RVTS-Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/26 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall-Ice Rink [Directions] | 4:30 p.m. | L 1-6 | |
| Sat., 2/26 | V Girls Gymnastics | CIAC Class M Divisional Championship | Away - Richetelli Gymnasium @Jonathan Law | 10:00 a.m. | ||
| Mon., 2/28 | V Boys Ice Hockey | Hall | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 7:20 p.m. | L 0-2 | |
| Tue., 3/1 | V Girls Basketball | Windsor Locks | Away - Windsor Locks HS-WLHS Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 3/3 | Miscellaneous Events | CIAC MS Unified Basketball State Tournament (WHS Gym & WMS Gym) | Home - Westbrook HS-Westbrook HS Gym [Directions] | 2:30 p.m. | CIAC Unified Sports State Tournament: Contacts: Paul Mengold; Bob Hale | |
| Fri., 3/4 | V Boys Basketball | East Haven (Scrim.) | Away - EAST HAVEN-gym [Directions] | 2:00 p.m. | ||
| Sat., 3/5 | V Girls Gymnastics | State Open | Away - New Milford | 10:00 a.m. | ||
| Sat., 3/5 | V Girls Ice Hockey | Woodstock Academy Coop | Home - Northford Ice Pavilion-Red [Directions] | 7:00 p.m. | ||
| Tue., 3/8 | V Boys Basketball | Capital Prep | Away - Capital Preparatory Magnet 2-Gym [Directions] | 6:30 p.m. | ||
| Thu., 3/10 | Miscellaneous Events | Early Dismissal - Parent Conferences | Home - Westbrook HS [Directions] | 12:15 p.m. | ||
| Fri., 3/11 | Miscellaneous Events | No School - PD Day | Home - Westbrook HS [Directions] | 7:20 a.m. | ||
| Wed., 3/23 | V Baseball | Haddam-Killingworth (Scrim.) | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 3/25 | V Baseball | Granby Memorial (Scrim.) | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 3/25 | V Boys Tennis | Waterford (Scrim.) | Away - Waterford HS-Tennis Courts - WHS [Directions] | 3:45 p.m. | ||
| Fri., 3/25 | V Girls Tennis | Waterford (Scrim.) | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:15 p.m. | ||
| Sat., 3/26 | V Baseball | Hopkinton (NH) (Scrim.) | Home - Valley Regional HS-Baseball Diamond [Directions] | 11:00 a.m. | ||
| Sat., 3/26 | V Boys Tennis | Guilford (Scrim.) | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 1:00 p.m. | ||
| Sat., 3/26 | V Girls Tennis | Guilford (Scrim.) | Away - Guilford Racquet & Swim Club [Directions] | 12:00 p.m. | ||
| Mon., 3/28 | V Baseball | Manchester (Scrim.) | Away - Mt. Nebo Park-Baseball Diamond [Directions] | 3:45 p.m. | Cancelled | |
| Wed., 3/30 | V Softball | Morgan (Scrim.) | Away - Morgan School-Softball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/1 | V Boys Tennis | Sheehan (Scrim.) | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 4/1 | V Girls Tennis | Sheehan (Scrim.) | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | ||
| Sat., 4/2 | V Baseball | Old Saybrook | Away - Old Saybrook HS-OSHS Baseball Field [Directions] | 10:00 a.m. | L 1-11 | |
| Sat., 4/2 | V Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 10:30 a.m. | W 6-5 | |
| Sat., 4/2 | JV Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 1:00 p.m. | L 7-1 | |
| Sat., 4/2 | V Softball | Old Saybrook | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 10:00 a.m. | W 15-14 | |
| Mon., 4/4 | V Baseball | Morgan | Away - Morgan School-Baseball Field [Directions] | 4:00 p.m. | W 7-5 | |
| Mon., 4/4 | V Baseball | Coginchaug | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 1-8 | |
| Mon., 4/4 | V Softball | Coginchaug | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L 1-21 (5) | |
| Tue., 4/5 | JV Baseball | Morgan | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Softball | Old Lyme | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L 0-14 (5) | |
| Thu., 4/7 | JV Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 4/8 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Baseball Diamond [Directions] | 4:00 p.m. | L 1-11 | |
| Fri., 4/8 | V Boys Tennis | East Hampton | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Fri., 4/8 | V Girls Tennis | East Hampton | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Sat., 4/9 | V Boys Outdoor Track | Wildcat Relays | Away - Lyme-Old Lyme HS-Track Field | 11:30 a.m. | ||
| Sat., 4/9 | V Girls Outdoor Track | Wildcat Relays | Away - Lyme-Old Lyme HS-Track Field | 11:30 a.m. | ||
| Mon., 4/11 | V Baseball | Cromwell | Away - Cromwell HS-Fran Monnes Baseball Field [Directions] | 4:00 p.m. | W 1-0 | |
| Mon., 4/11 | V Baseball | Hale Ray | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 1-16 | |
| Mon., 4/11 | V Boys Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Mon., 4/11 | V Girls Tennis | Old Lyme | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 4/12 | JV Baseball | Cromwell | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 13-3 | |
| Tue., 4/12 | V Boys Outdoor Track | East Hampton, Portland | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | ||
| Tue., 4/12 | V Girls Outdoor Track | East Hampton, Portland | Home - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | ||
| Wed., 4/13 | V Baseball | ValleyReg/Westbrook | Away - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | L 1-25 | |
| Wed., 4/13 | V Baseball | Westbrook | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 25-1 | |
| Wed., 4/13 | V Boys Tennis | Portland | Away - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 4/13 | V Softball | Valley Regional | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L 0-22 | |
| Wed., 4/13 | V Girls Tennis | Portland | Away - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/14 | V Baseball | Cromwell | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 0-13 | |
| Thu., 4/14 | V Boys Tennis | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Thu., 4/14 | V Softball | Cromwell | Away - Cromwell HS-Softball Diamond [Directions] | 4:00 p.m. | L 0-22 | |
| Thu., 4/14 | V Girls Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 4/15 | Miscellaneous Events | No School - April Vacation | Home - Westbrook HS [Directions] | 7:20 a.m. | ||
| Mon., 4/18 | V Baseball | Old Saybrook | Away - Old Saybrook HS-OSHS Baseball Field [Directions] | 11:00 a.m. | L 1-2 | |
| Mon., 4/18 | V Baseball | East Hampton | Away - Legion Field - Moodus-Baseball Diamond [Directions] | 4:00 p.m. | L 0-17 | |
| Mon., 4/18 | V Boys Tennis | Valley Regional | Away - Valley Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Mon., 4/18 | V Softball | East Hampton | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L 19-2 | |
| Mon., 4/18 | V Girls Tennis | Valley Regional | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 11:00 a.m. | W 5-2 | |
| Mon., 4/18 | Miscellaneous Events | No School - April Vacation | Home - Westbrook HS [Directions] | 7:20 a.m. | ||
| Tue., 4/19 | JV Baseball | East Hampton | Home - Valley Regional HS-Baseball Diamond [Directions] | 11:00 a.m. | ||
| Tue., 4/19 | Miscellaneous Events | No School - April Vacation | Home - Westbrook HS [Directions] | 7:20 a.m. | ||
| Wed., 4/20 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Baseball Diamond [Directions] | 4:00 p.m. | W 16-1 | |
| Wed., 4/20 | V Baseball | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 0-15 | |
| Wed., 4/20 | V Boys Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Wed., 4/20 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Varsity Softball Field [Directions] | 4:00 p.m. | L 0-18 | |
| Wed., 4/20 | V Girls Tennis | Morgan | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 11:00 a.m. | W 7-0 | |
| Wed., 4/20 | Miscellaneous Events | No School - April Vacation | Home - Westbrook HS [Directions] | 7:20 a.m. | ||
| Thu., 4/21 | JV Baseball | Old Lyme | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | Cancelled | |
| Thu., 4/21 | V Boys Tennis | Coginchaug | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 5-0 | |
| Thu., 4/21 | Miscellaneous Events | No School - April Vacation | Home - Westbrook HS [Directions] | 7:20 a.m. | ||
| Fri., 4/22 | V Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | W 13-0 | |
| Fri., 4/22 | V Baseball | Morgan | Away - Morgan School-Baseball Field [Directions] | 4:00 p.m. | L 6-16 | |
| Fri., 4/22 | V Softball | Morgan | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L 3-28 | |
| Fri., 4/22 | V Girls Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 11:00 a.m. | W 6-1 | |
| Fri., 4/22 | Miscellaneous Events | No School - April Vacation | Home - Westbrook HS [Directions] | 7:20 a.m. | ||
| Sat., 4/23 | JV Baseball | Rocky Hill | Home - Valley Regional HS-Baseball Diamond [Directions] | 11:00 a.m. | W 12-2 | |
| Sat., 4/23 | JV Baseball | Hale Ray | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:00 p.m. | ||
| Mon., 4/25 | V Baseball | Coginchaug | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | L 2-6 | |
| Mon., 4/25 | V Boys Tennis | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | W 4-1 | |
| Mon., 4/25 | V Softball | North Branford | Away - North Branford HS-NBHS Softball Field [Directions] | 4:00 p.m. | L 0-21 | |
| Mon., 4/25 | V Girls Tennis | Old Saybrook | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 4/26 | JV Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 4:00 p.m. | W 6-6 | |
| Wed., 4/27 | V Baseball | North Branford | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 9-8 | |
| Wed., 4/27 | V Baseball | Old Saybrook | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 4-19 | |
| Wed., 4/27 | V Boys Outdoor Track | Old Lyme, Hale Ray | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:30 p.m. | ||
| Wed., 4/27 | V Girls Outdoor Track | Old Lyme, Hale Ray | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:30 p.m. | ||
| Wed., 4/27 | V Softball | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:00 p.m. | L 12-24 | |
| Wed., 4/27 | V Girls Tennis | North Branford | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/28 | JV Baseball | Old Lyme, Old Saybrook | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | JV Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Baseball | Morgan | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 12-3 | |
| Fri., 4/29 | V Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 4:00 p.m. | L 1-11 | |
| Fri., 4/29 | V Softball | Coginchaug | Away - Coginchaug Regional HS-Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 4:00 p.m. | L 0-18 | |
| Sat., 4/30 | V Baseball | Portland | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 11:00 a.m. | L 1-12 | |
| Sat., 4/30 | JV Baseball | Morgan | Away - Morgan School-Baseball Field [Directions] | 10:30 a.m. | L 2-7 | |
| Sat., 4/30 | V Boys Outdoor Track | Ellington Relays Invite | Away - Ellington HS-Track | 11:00 a.m. | ||
| Sat., 4/30 | V Girls Outdoor Track | Ellington Relays Invite | Away - Ellington HS-Track | 11:00 a.m. | ||
| Sat., 4/30 | JV Girls Tennis | JV Tennis Match Versus Coginchaug and Cromwell | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 9:30 a.m. | ||
| Mon., 5/2 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 4:00 p.m. | W 13-3 | |
| Mon., 5/2 | V Girls Tennis | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | W 6-0 | |
| Tue., 5/3 | V Baseball | Portland | Away - Portland HS-Portland HS [Directions] | 4:00 p.m. | L 3-5 | |
| Tue., 5/3 | JV Baseball | Haddam-Killingworth | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 5-1 | |
| Tue., 5/3 | V Boys Outdoor Track | Haddam-Killingworth, Valley Regional | Away - Haddam Killingworth HS (HK)-HKHS Track [Directions] | 3:30 p.m. | ||
| Tue., 5/3 | V Girls Outdoor Track | Haddam-Killingworth, Valley Regional | Away - Haddam Killingworth HS (HK)-HKHS Track [Directions] | 3:30 p.m. | ||
| Thu., 5/5 | V Baseball | Cromwell | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 5/5 | V Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:45 p.m. | L 2-7 | |
| Thu., 5/5 | V Boys Tennis | Old Saybrook | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Fri., 5/6 | JV Baseball | Cromwell | Away - Cromwell HS-Fran Monnes Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/6 | V Boys Tennis | Portland | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 6-0 | |
| Fri., 5/6 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 4:00 p.m. | L 1-18 | |
| Fri., 5/6 | V Girls Tennis | Portland | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Sat., 5/7 | JV Baseball | East Hampton | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Sat., 5/7 | V Boys Outdoor Track | Coginchaug - Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 10:00 a.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Coginchaug - Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 10:00 a.m. | ||
| Mon., 5/9 | V Baseball | Haddam-Killingworth | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 9-1 | |
| Mon., 5/9 | V Baseball | Old Lyme | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 0-11 | |
| Mon., 5/9 | V Boys Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 3:45 p.m. | W 4-0 | |
| Mon., 5/9 | V Softball | Acad. of the Holy Family | Home - Academy of the Holy Family [Directions] | 4:15 p.m. | W 29-11 | |
| Mon., 5/9 | V Girls Tennis | Coginchaug | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 5/10 | JV Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 4:00 p.m. | W 15-3 | |
| Tue., 5/10 | V Boys Outdoor Track | Coginchaug, Morgan, North Branford | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:30 p.m. | ||
| Tue., 5/10 | V Boys Tennis | Old Lyme | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 4:15 p.m. | L 3-4 | |
| Tue., 5/10 | V Girls Outdoor Track | Coginchaug, North Branford | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:45 p.m. | ||
| Wed., 5/11 | V Baseball | East Hampton | Away - East Hampton HS-Baseball Field [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 5/11 | JV Baseball | Old Lyme, Old Saybrook | Away - Lyme-Old Lyme HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/11 | V Softball | Hale Ray | Home - Portland HS-PHS Softball Diamond [Directions] | 4:45 p.m. | L 1-22 | |
| Wed., 5/11 | V Girls Tennis | North Branford | Away - North Branford HS-NBHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Thu., 5/12 | V Baseball | Canton | Home - Valley Regional HS-Baseball Diamond [Directions] | 5:00 p.m. | W 10-0 | |
| Thu., 5/12 | V Softball | Bassick | Away - Bassick HS-Went Field [Directions] | 4:15 p.m. | W 28-9 | |
| Fri., 5/13 | V Boys Outdoor Track | Running Rams Invitational | Away - Old Saybrook HS-Old Saybrook Track (HS) | 3:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Fri., 5/13 | V Boys Tennis | Cromwell | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 6-0 | |
| Fri., 5/13 | V Girls Outdoor Track | Running Rams Invitational | Away - Old Saybrook HS-Old Saybrook Track (HS) | 3:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Fri., 5/13 | V Girls Tennis | Cromwell | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | Non-league game |
| Sat., 5/14 | V Baseball | Whitney Tech | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 11:00 a.m. | L 2-4 | |
| Sat., 5/14 | V Baseball | Woodstock Academy | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 7-5 | |
| Sat., 5/14 | V Softball | Hale Ray | Away - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 11:00 a.m. | L 1-20 | |
| Sun., 5/15 | V Girls Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 1:00 p.m. | L 1-6 | |
| Mon., 5/16 | V Baseball | East Hampton | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 15-0 | |
| Mon., 5/16 | V Baseball | North Branford | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 3-14 | |
| Mon., 5/16 | V Boys Tennis | Morgan | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Mon., 5/16 | V Girls Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 5/17 | V Boys Tennis | Cromwell | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 5/17 | V Softball | Stafford | Away - Stafford HS-Varsity Softball Field (corner of Levinthal Run and County Rd) [Directions] | 4:15 p.m. | L 1-16 | |
| Tue., 5/17 | V Girls Tennis | Cromwell | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/18 | V Baseball | St. Bernard | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 0-11 | |
| Wed., 5/18 | V Softball | Acad. of the Holy Family | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:15 p.m. | W 11-2 | |
| Fri., 5/20 | V Baseball | Waterford | Away - Waterford HS-Alumni Baseball Field [Directions] | 4:00 p.m. | W 4-1 | |
| Fri., 5/20 | JV Baseball | Waterford | Away - Leary Park-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Sat., 5/21 | V Baseball | Whitney Tech | Away - Eli Whitney RVTS-Baseball Diamond [Directions] | 11:00 a.m. | L 2-3 | |
| Sat., 5/21 | V Baseball | Putnam | Home - Valley Regional HS-Baseball Diamond [Directions] | 12:00 p.m. | W 11-1 | |
| Sat., 5/21 | V Baseball | Portland | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 13-0 | Valley will be the home team. |
| Mon., 5/23 | V Baseball | Hillhouse/Career | Home - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | L 2-13 | |
| Mon., 5/23 | V Baseball | East Hampton | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 15-1 | |
| Mon., 5/23 | V Boys Tennis | Shoreline Conference Tennis Tournament - First Round | Away - Westbrook HS-Westbrook HS / MS Tennis Courts | 9:00 a.m. | ||
| Mon., 5/23 | V Softball | Bassick | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:30 p.m. | W Forfeit | |
| Mon., 5/23 | V Girls Tennis | Shoreline Conference Tennis Tournament - First Round | Away - Old Saybrook HS | 9:00 a.m. | ||
| Tue., 5/24 | V Baseball | North Branford | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | W 8-3 | |
| Wed., 5/25 | V Boys Outdoor Track | Shoreline Conference Championship | Away - Old Saybrook HS-Old Saybrook Track (HS) | 2:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:30 p.m. | ||||||
| Wed., 5/25 | V Girls Outdoor Track | Shoreline Conference Championship | Away - Old Saybrook HS-Old Saybrook Track (HS) | 2:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:30 p.m. | ||||||
| Wed., 5/25 | V Softball | Stafford | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:15 p.m. | L 1-20 | |
| Thu., 5/26 | JV Baseball | Hale Ray | Home - Valley Regional HS-Baseball Diamond [Directions] | 5:00 p.m. | ||
| Thu., 5/26 | V | ValleyReg, Branford, TBA, NathanHaleRay | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:00 p.m. | ||
| Fri., 5/27 | V Baseball | Old Saybrook | Away - Palmer Field-Baseball Diamond [Directions] | 7:00 p.m. | ||
| Mon., 5/30 | Miscellaneous Events | Holiday - Memorial Day | Home - Westbrook HS [Directions] | 7:20 a.m. | ||
| Tue., 5/31 | V Baseball | East Windsor/International | Home - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/31 | V Boys Tennis | East Catholic | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Girls Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/31 | V Girls Tennis | Lyman Memorial | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 2:00 p.m. | ||
| Wed., 6/1 | V Baseball | Plainfield | Home - Valley Regional HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Wed., 6/1 | V Boys Tennis | Litchfield | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 1:00 p.m. | ||
| Thu., 6/2 | V Girls Tennis | Shepaug Valley | Home - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 12:00 p.m. | ||
| Fri., 6/3 | V Boys Tennis | Granby Memorial | Away - Granby Memorial HS-Tennis Courts [Directions] | 12:00 p.m. | ||
| Fri., 6/3 | V Girls Tennis | Holy Cross | Away - Tennis Club of Trumbull-Gym 1 [Directions] | 11:30 a.m. | ||
| Fri., 6/3 | Miscellaneous Events | Jr/Sr Prom | Home - Westbrook HS [Directions] | 6:00 p.m. | ||
| Sat., 6/4 | V Baseball | Oxford | Home - Valley Regional HS-Baseball Diamond [Directions] | 2:00 p.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | Miscellaneous Events | Sr. Field Trip to Holiday Hill | Home - Westbrook HS [Directions] | 7:20 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||