| Old Saybrook 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 461 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| 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 | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:30 p.m. | W 4-1 | |
| Thu., 9/8 | JV Field Hockey | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | ||
| Thu., 9/8 | V Girls Soccer | Portland | Away - Portland HS-Varsity Soccer FIeld [Directions] | 4:00 p.m. | L 2-1 | |
| Fri., 9/9 | V Boys Soccer | Portland | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | W 4-1 | |
| Fri., 9/9 | JV Girls Soccer | Portland | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 4:00 p.m. | ||
| Sat., 9/10 | V Football | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 1:00 p.m. | L 0-30 | |
| Sat., 9/10 | JV Boys Soccer | Portland | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 10:00 a.m. | ||
| Mon., 9/12 | JV Football | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | Canceled | Cancelled | |
| Tue., 9/13 | V Boys Soccer | Hale Ray | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 8-1 | |
| Tue., 9/13 | V Girls Swimming and Diving | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Pool - no diving [Directions] | 4:00 p.m. | ||
| 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 Girls Cross Country | Morgan, Old Lyme, Valley Regional | Away - Indian River Complex-XC Course [Directions] | 3:45 p.m. | ||
| Wed., 9/14 | V Field Hockey | Westbrook/Old Lyme Coop | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | W 1-0 | |
| Wed., 9/14 | JV Field Hockey | Westbrook/Old Lyme Coop | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Wed., 9/14 | JV Girls Soccer | Valley Regional | Away - Valley Regional HS-JV Girls Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 9/15 | V Boys Soccer | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 6:00 p.m. | W 6-0 | |
| Thu., 9/15 | V Girls Soccer | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | T 0-0 | |
| Fri., 9/16 | V Football | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 6:30 p.m. | L 7-48 | |
| Fri., 9/16 | JV Boys Soccer | Valley Regional | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | V Field Hockey | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | L 2-4 | |
| Fri., 9/16 | JV Field Hockey | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| 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 | |
| Sat., 9/17 | V Girls Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 8:30 a.m. | ||
| Sat., 9/17 | V Field Hockey | Waterford | Away - Waterford HS-Alumni Turf Field/Track [Directions] | 12:15 p.m. | W 3-2 | |
| Sat., 9/17 | JV Field Hockey | Waterford | Away - Waterford HS-Alumni Turf Field/Track [Directions] | 1:30 p.m. | ||
| Mon., 9/19 | JV Football | North Branford | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | Canceled | Cancelled | |
| Mon., 9/19 | V Field Hockey | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 3:45 p.m. | L 0-2 | |
| Mon., 9/19 | JV Field Hockey | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 5:15 p.m. | ||
| Mon., 9/19 | V Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | 3:45 p.m. | T 1-1 | |
| Tue., 9/20 | V Boys Soccer | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 9/20 | JV Girls Soccer | Old Lyme | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Girls Swimming and Diving | Ledyard/St. Bernard | Away - Ledyard HS-Vitale Aquatic [Directions] | 3:30 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 Girls Cross Country | Coginchaug - Going to the Sun Cross Country Meet | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:30 p.m. | ||
| Thu., 9/22 | V Girls Soccer | Westbrook | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | W 2-1 | |
| 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 | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 9/23 | V Field Hockey | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:30 p.m. | W 1-0 | |
| Fri., 9/23 | JV Field Hockey | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Fri., 9/23 | V Girls Swimming and Diving | Guilford | Home - East Lyme HS-East Lyme Aquatics Center [Directions] | 4:00 p.m. | ||
| Sat., 9/24 | V Football | Capital/Achievement | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | L 19-48 | |
| Sat., 9/24 | JV Football | Valley Regional/Old Lyme | Home - Peters Complex-Football Field [Directions] | 10:30 a.m. | ||
| Sat., 9/24 | V Boys Soccer | Valley Regional | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 2:00 p.m. | W 11-0 | |
| Sat., 9/24 | V Field Hockey | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 3:00 p.m. | T 0-0 | |
| Sat., 9/24 | JV Field Hockey | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 1:30 p.m. | ||
| Sat., 9/24 | V Girls Soccer | Norwich Free Academy | Away - Norwich Free Academy-Turf Field [Directions] | 12:00 p.m. | L 0-1 | |
| Mon., 9/26 | JV Football | Capital/Achievement | Away - Annie Fisher Turf Field [Directions] | Canceled | Cancelled | |
| Tue., 9/27 | V Field Hockey | Granby Memorial | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 9/27 | JV Field Hockey | Granby Memorial | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:30 p.m. | ||
| Tue., 9/27 | V Girls Soccer | North Branford/Hale Ray | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 7:00 p.m. | W 3-0 | |
| Wed., 9/28 | V Girls Cross Country | Shoreline Conference Small Schools Meet | Away - Nathan Hale Ray HS-HS XC Course | 4:00 p.m. | ||
| Wed., 9/28 | JV Girls Soccer | Valley Regional | Away - Valley Regional HS-JV Girls Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 9/29 | V Field Hockey | Morgan | Away - Indian River Complex-Turf Field [Directions] | 6:30 p.m. | W 3-0 | |
| Thu., 9/29 | JV Field Hockey | Morgan | Away - Indian River Complex-Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 9/30 | V Football | Capital/Achievement | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | L 28-35 | |
| Fri., 9/30 | V Girls Soccer | Morgan | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 6:30 p.m. | L 0-1 | |
| Fri., 9/30 | V Girls Swimming and Diving | Haddam-Killingworth | Home - East Lyme HS-East Lyme Aquatics Center [Directions] | 3:30 p.m. | ||
| Sat., 10/1 | V Football | Coginchaug/Hale Ray/East Hampton | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 2:00 p.m. | L 0-31 | |
| 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 | JV Football | Coginchaug/Hale Ray/East Hampton, MSW | Home - Peters Complex-Football Field [Directions] | 6:00 p.m. | ||
| Mon., 10/3 | V Field Hockey | Westbrook/Old Lyme Coop | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:30 p.m. | W 3-2 | |
| Mon., 10/3 | JV Field Hockey | Westbrook/Old Lyme Coop | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | ||
| Mon., 10/3 | V Girls Soccer | St. Bernard | Away - St. Bernard School-Delaporta Field [Directions] | 3:45 p.m. | L 2-0 | |
| 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 Boys Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 3:45 p.m. | W 2-1 | |
| Tue., 10/4 | V Girls 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 Girls Soccer | Montville | Away - Montville HS-Montville Turf Field [Directions] | 6:00 p.m. | T 0-0 | |
| Thu., 10/6 | V Boys Soccer | Cromwell | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | W 5-0 | |
| Thu., 10/6 | V Field Hockey | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 4:00 p.m. | L 1-5 | |
| Thu., 10/6 | JV Field Hockey | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 5:15 p.m. | ||
| Fri., 10/7 | V Football | Rockville | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | L 14-54 | |
| Fri., 10/7 | JV Boys Soccer | Cromwell | Away - Cromwell HS-Soccer field 2 [Directions] | 3:45 p.m. | ||
| Fri., 10/7 | V Field Hockey | Suffield | Away - Suffield HS-Ted Beneski Turf Field [Directions] | 6:30 p.m. | L 1-2 | |
| Fri., 10/7 | JV Field Hockey | Suffield | Away - Suffield HS-Ted Beneski Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 10/7 | V Girls Soccer | Cromwell | Away - Cromwell HS-Main field [Directions] | 6:00 p.m. | L 0-5 | |
| Sat., 10/8 | V Football | CREC Coop | Away - Academy of Computer Science and Engineering HS- Academy of Computer Science and Engineering Turf Field [Directions] | 11:00 a.m. | L 14-20 | |
| Sat., 10/8 | V Boys Soccer | Norwich Free Academy | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | W 3-2 | |
| Sat., 10/8 | JV Girls Soccer | Cromwell | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | Postponed | ||
| Tue., 10/11 | JV Football | Old Saybrook, CREC Coop | Away - Old Saybrook HS-Westbrook High School [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | JV Football | MSW, CREC Coop | Home - Old Saybrook HS-Westbrook High School [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Field Hockey | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | W 1-0 | |
| Tue., 10/11 | V Girls Soccer | North Branford/Hale Ray | Away - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/11 | V Girls Swimming and Diving | Waterford | Away - Waterford HS-Pool - WHS [Directions] | 3:45 p.m. | ||
| Fri., 10/14 | V Boys Soccer | Canton | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | T 2-2 | |
| Fri., 10/14 | V Girls Soccer | East Hampton | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:30 p.m. | L 3-2 | |
| Sat., 10/15 | JV Football | North Branford, MSW | Away - North Branford HS-NBHS Colafati Field [Directions] | 10:00 a.m. | ||
| 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 | Fitch | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | W 2-1 | |
| Sat., 10/15 | JV Field Hockey | Fitch | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 12:30 p.m. | ||
| Mon., 10/17 | V Boys Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:45 p.m. | W 4-0 | |
| Tue., 10/18 | JV Boys Soccer | Coginchaug | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | Postponed | ||
| Tue., 10/18 | V Girls Soccer | Coginchaug | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/18 | JV Girls Soccer | Coginchaug | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:30 p.m. | ||
| Tue., 10/18 | V Girls Swimming and Diving | Fitch/Stonington/Wheeler/NL | Away - UCONN Avery Point-Pool [Directions] | 3:45 p.m. | ||
| Wed., 10/19 | V Boys Soccer | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:30 p.m. | W 12-0 | |
| Thu., 10/20 | V Boys Cross Country | Shoreline Cross Country Championship | Away - Hammonasset Park | 1:30 p.m. | ||
| Thu., 10/20 | V Boys Soccer | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | W 4-0 | |
| Thu., 10/20 | V Girls Cross Country | Shoreline Cross Country Championship | Away - Hammonasset Park | 1:30 p.m. | ||
| Fri., 10/21 | JV Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | 3:45 p.m. | ||
| Fri., 10/21 | V Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 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 | |
| Sat., 10/22 | V Football | Cromwell/Portland | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | L 0-42 | |
| Sat., 10/22 | V Boys Soccer | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 4:00 p.m. | T 2-2 | |
| Sat., 10/22 | V Field Hockey | Norwich Free Academy | Away - Norwich Free Academy-Turf Field [Directions] | 12:00 p.m. | W 3-0 | |
| Mon., 10/24 | JV Football | Cromwell/Portland, MSW | Away - Pierson Park (Cromwell, CT)-Football Field [Directions] | Canceled | Cancelled | |
| 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 | Fitch | Away - Groton MS-Groton Middle School-Turf Feld [Directions] | 4:00 p.m. | W 4-0 | |
| Mon., 10/24 | V Girls Soccer | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | L 0-2 | |
| 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 Swimming and Diving | Suffield | Away - Suffield Academy [Directions] | 7:00 p.m. | ||
| Wed., 10/26 | V Boys Cross Country | Middle School Invitational | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:45 p.m. | ||
| Thu., 10/27 | V Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | W 1-0 | |
| Thu., 10/27 | JV Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 5:15 p.m. | ||
| Thu., 10/27 | V Girls Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 3:30 p.m. | L 0-2 | |
| Fri., 10/28 | V Boys Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 3:00 p.m. | L 3-2 | |
| Fri., 10/28 | JV Girls Soccer | Morgan | Away - Morgan School-Soccer/Lax Field [Directions] | 3:00 p.m. | ||
| Wed., 11/2 | V Girls Swimming and Diving | Windsor Locks/Ellington/E.Granby/E.Windsor | Away - Windsor Locks HS-Pool- No diving [Directions] | 5:00 p.m. | ||
| Fri., 11/4 | V Football | Granby/Canton | Away - Granby Memorial HS-Stadium Field [Directions] | 6:30 p.m. | L 22-38 | |
| Sat., 11/5 | V Football | Coventry/Windham Tech/Bolton/Lyman | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 1:00 p.m. | L 18-34 | |
| Mon., 11/7 | JV Football | Coventry/Windham Tech/Bolton/Lyman, MSW | Away - Coventry HS-Football Field [Directions] | 5:00 p.m. | ||
| Mon., 11/7 | JV Football | Coventry/Windham Tech/Bolton/Lyman, Old Saybrook | Away - Coventry HS-Football Field [Directions] | 5:00 p.m. | ||
| Thu., 11/10 | V Football | Ellington | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | L 28-48 | |
| Thu., 11/10 | V Football | Windsor Locks/Suffield/East Granby | Away - Windsor Locks HS-Patrick Scelza Field [Directions] | 6:30 p.m. | L 6-45 | |
| Mon., 11/14 | JV Football | MSW, Windsor Locks/Suffield/East Granby | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 4:30 p.m. | ||
| Mon., 11/14 | JV Football | Old Saybrook, Windsor Locks/Suffield/East Granby | Away - Old Saybrook HS-Old Saybrook Campus [Directions] | 4:30 p.m. | ||
| Wed., 11/16 | V Football | Valley Regional/Old Lyme | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 6:30 p.m. | L 8-46 | |
| 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 | MSW, Valley Regional/Old Lyme | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | Canceled | Cancelled | |
| 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 | MSW | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | L 14-32 | |
| Wed., 11/23 | V Football | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | W 32-14 | |
| Fri., 12/9 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Northford-Red [Directions] | 3:45 p.m. | W 54 | |
| Mon., 12/12 | V Girls Basketball | St. Bernard | Away - St. Bernard School-Powers Gym [Directions] | 7:00 p.m. | W 57-38 | |
| Mon., 12/12 | JV Girls Basketball | St. Bernard | Away - St. Bernard School-Powers Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/14 | V Boys Ice Hockey | E.O. Smith-Tolland | Home - East Haven HS-Veterans Rink [Directions] | 5:30 p.m. | W 4-0 | |
| 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 | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 62-44 | |
| Thu., 12/15 | JV Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/15 | V Girls Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:00 p.m. | W 47-22 | |
| Sat., 12/17 | V Boys Basketball | Wheeler | Away - Wheeler HS-Gym [Directions] | 5:30 p.m. | W 58-51 | |
| Sat., 12/17 | JV Boys Basketball | Wheeler | Away - Wheeler HS-Gym [Directions] | 4:00 p.m. | ||
| Sat., 12/17 | V Boys Ice Hockey | Cheshire | Home - East Haven HS-Veterans Rink [Directions] | 1:00 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 | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 63-34 | |
| Tue., 12/20 | JV Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/20 | V Boys Swimming and Diving | Sheehan/Lyman Hall | Away - Sheehan HS-Sheehan HS Pool [Directions] | 5:30 p.m. | Daniel Hand 86 Sheehan 71 | |
| Tue., 12/20 | V Girls Basketball | Westbrook | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 46-24 | |
| Tue., 12/20 | JV Girls Basketball | Westbrook | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 12/21 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | 6:00 p.m. | L 2-5 | |
| Wed., 12/21 | V Girls Ice Hockey | Masuk Coop | Home - Northford-Red [Directions] | 4:00 p.m. | W 7-4 | |
| Thu., 12/22 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | L 43-15 | |
| Thu., 12/22 | JV Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Thu., 12/22 | V Girls Gymnastics | Valley Regional | Away - Flip Flop Gymnastics [Directions] | 4:30 p.m. | 130.25 | |
| Fri., 12/23 | V Boys Basketball | Coginchaug | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | W 70-40 | |
| Fri., 12/23 | JV Boys Basketball | Coginchaug | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 12/27 | V Girls Basketball | Montville | Away - Montville HS-Gym [Directions] | 11:00 a.m. | W 45-23 | |
| Thu., 12/29 | V Girls Basketball | St. Bernard | Home - Montville HS-Gym [Directions] | 1:00 p.m. | W 39-34 | |
| Thu., 12/29 | V Girls Gymnastics | Mercy, Stonington, Valley Regional | Away - Flip Flop Gymnastics [Directions] | 10:00 a.m. | 127.1 | |
| Tue., 1/3 | V Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 6:00 p.m. | W 55-35 | |
| Tue., 1/3 | JV Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/4 | V Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 7:00 p.m. | W 56-32 | |
| Wed., 1/4 | JV Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/4 | V Boys Ice Hockey | Branford | Home - East Haven HS-Veterans Rink [Directions] | 6:00 p.m. | W 6-2 | |
| Wed., 1/4 | V Girls Gymnastics | Old Lyme, East Lyme/Waterford/St Bernard | Away - ABC Gymnastics [Directions] | 2:30 p.m. | ||
| 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 Indoor Track | Shoreline League Meet 1 | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Fri., 1/6 | V Boys Basketball | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 56-51 | |
| Fri., 1/6 | JV Boys Basketball | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | V Boys Swimming and Diving | Shelton | Away - Shelton Community Center Pool [Directions] | 3:30 p.m. | Shelton 90 Daniel Hand 77 | |
| Fri., 1/6 | V Girls Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 40-22 | |
| Fri., 1/6 | JV Girls Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| 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 | Coginchaug | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 3:00 p.m. | ||
| Sat., 1/7 | V Boys Ice Hockey | Glastonbury | Home - East Haven HS-Veterans Rink [Directions] | 1:00 p.m. | W 3-1 | |
| Sat., 1/7 | V Girls Ice Hockey | Hall/Conard | Home - Northford-Red [Directions] | 7:00 p.m. | L 2-8 | |
| Tue., 1/10 | V Boys Basketball | Morgan | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 74-54 | |
| Tue., 1/10 | JV Boys Basketball | Morgan | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | V Boys Swimming and Diving | Waterford/Ledyard | Away - Waterford HS-Pool - WHS [Directions] | 3:45 p.m. | Daniel Hand 69 Watertown 62 | |
| Tue., 1/10 | V Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | 7:00 p.m. | L 39-26 | |
| Tue., 1/10 | JV Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/11 | V Boys Ice Hockey | West Haven Coop | Home - East Haven HS-Veterans Rink [Directions] | 5:45 p.m. | L 2-3 | |
| Wed., 1/11 | V Girls Gymnastics | Jonathan Law, Mercy, Valley Regional | Away - Jonathan Law HS-North Gymnasium [Directions] | 6:00 p.m. | 101.9 | |
| Thu., 1/12 | V Boys Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 5:00 p.m. | W 82-45 | |
| Thu., 1/12 | JV Boys Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/13 | V Girls Basketball | East Hampton | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 51-19 | |
| Fri., 1/13 | JV Girls Basketball | East Hampton | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 1/14 | FR Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/14 | V Boys Ice Hockey | Eastern CT Eagles | Home - East Haven HS-Veterans Rink [Directions] | 1:00 p.m. | W 4-1 | |
| Sat., 1/14 | V Boys Indoor Track | NCCC Invitational #1 | Away - Hartford Public HS-Field House | 1:00 p.m. | ||
| Sat., 1/14 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Cromwell-Lower Rink [Directions] | 7:30 p.m. | L 1-7 | |
| Sat., 1/14 | V Girls Indoor Track | NCCC Invitational #1 | Away - Hartford Public HS-Field House | 1:00 p.m. | ||
| Mon., 1/16 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 1:45 p.m. | L 2-4 | |
| Mon., 1/16 | V Boys Swimming and Diving | Amity | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | 10:45 a.m. | Amity 95 Daniel Hand 77 | |
| Tue., 1/17 | V Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 5:30 p.m. | W 59-47 | |
| Tue., 1/17 | JV Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/17 | V Girls Basketball | North Branford | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:00 p.m. | L 57-48 | |
| Tue., 1/17 | JV Girls Basketball | North Branford | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 1/18 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | W 7-1 | |
| 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 | Haddam-Killingworth | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 53-34 | |
| Fri., 1/20 | JV Boys Basketball | Haddam-Killingworth | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | West Haven | Away - West Haven HS-Swimming Pool [Directions] | 3:45 p.m. | Daniel Hand 93 West Haven 75 | |
| Fri., 1/20 | V Girls Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 7:00 p.m. | L 28-75 | |
| Fri., 1/20 | JV Girls Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:30 p.m. | ||
| 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 | V Boys Basketball | Stonington | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:30 p.m. | W 74-59 | |
| Sat., 1/21 | JV Boys Basketball | Stonington | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 3:00 p.m. | ||
| Sat., 1/21 | FR Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/21 | V Boys Ice Hockey | North Branford | Home - East Haven HS-Patsy DiLungo Rink [Directions] | 1:00 p.m. | T 1-1 | |
| 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 | Cromwell | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 69-51 | |
| Tue., 1/24 | JV Boys Basketball | Cromwell | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 7:00 p.m. | L 59-28 | |
| Tue., 1/24 | JV Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:30 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 Boys Ice Hockey | Masuk | Home - East Haven HS-Veterans Rink [Directions] | 6:00 p.m. | L 5-3 | |
| Fri., 1/27 | V Boys Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 7:00 p.m. | W 54-46 | |
| Fri., 1/27 | JV Boys Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | V Boys Swimming and Diving | Fairfield Prep | Away - Fairfield University-Pool [Directions] | 6:30 p.m. | Fairfield Prep 95 Hand 66 | |
| Fri., 1/27 | V Girls Basketball | Valley Regional | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:00 p.m. | L 58-32 | |
| Fri., 1/27 | JV Girls Basketball | Valley Regional | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | Canceled | Cancelled | |
| Sat., 1/28 | FR Boys Basketball | Haddam-Killingworth | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 1/28 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Simsbury - ISCC-NHL [Directions] | 7:50 p.m. | W 5-3 | |
| Sat., 1/28 | V Girls Ice Hockey | Suffield Coop | Home - Northford-Red [Directions] | 2:30 p.m. | L 5-4 | |
| Mon., 1/30 | V Boys Swimming and Diving | Hamden | Home - Madison Swim and Racquet [Directions] | 4:00 p.m. | Hamden 88 Daniel Hand 76 | |
| Mon., 1/30 | V Girls Basketball | Norwich Tech | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:00 p.m. | W 59-37 | |
| Mon., 1/30 | V Girls Gymnastics | Old Lyme, East Lyme/Waterford/St Bernard, Killingly, Woodstock Academy | Away - ABC Gymnastics [Directions] | 2:00 p.m. | ||
| Tue., 1/31 | V Boys Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 58-43 | |
| Tue., 1/31 | JV Boys Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 62-41 | |
| Wed., 2/1 | V Boys Ice Hockey | Sheehan | Home - East Haven HS-Veterans Rink [Directions] | 6:15 p.m. | W 3-1 | |
| 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 | V Boys Basketball | Bacon Academy | Away - Bacon Academy-Gym [Directions] | 6:00 p.m. | L 59-32 | |
| Thu., 2/2 | JV Boys Basketball | Bacon Academy | Away - Bacon Academy-Gym [Directions] | 4:30 p.m. | ||
| Thu., 2/2 | FR Boys Basketball | Bacon Academy | Away - Bacon Academy-Gym [Directions] | Canceled | Cancelled | |
| Fri., 2/3 | V Boys Basketball | Westbrook | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 53-29 | |
| Fri., 2/3 | JV Boys Basketball | Westbrook | Home - 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 | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | W 46-34 | |
| 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. | ||
| Sat., 2/4 | FR Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 2/4 | V Boys Ice Hockey | Lyman Hall | Away - Northford-Red [Directions] | 5:00 p.m. | W 2-1 | |
| Sat., 2/4 | V Girls Gymnastics | TBA, Waterford | Away - TBA-Albermale Field | 4:30 p.m. | ||
| 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 Ice Hockey | Daniel Hand | Home - East Haven HS-Veterans Rink [Directions] | 7:00 p.m. | W 3-0 | |
| Mon., 2/6 | V Boys Swimming and Diving | Greater New Haven | Away - Walter Gawrych Community Pool [Directions] | 4:00 p.m. | GNH 91 Daniel Hand 80 | |
| Tue., 2/7 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | L 65-64 | |
| Tue., 2/7 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Coginchaug | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 50-27 | |
| Tue., 2/7 | JV Girls Basketball | Coginchaug | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/8 | V Boys Ice Hockey | Guilford | Home - East Haven HS-Veterans Rink [Directions] | 6:00 p.m. | L 5-6 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 Swimming and Diving | Xavier, Notre Dame-West Haven | Away - CCSU-Swimming Pool [Directions] | 5:30 p.m. | Xavier 51 Daniel Hand 43 Daniel Hand 60 Notre Dame 34 | |
| Fri., 2/10 | V Boys Basketball | Old Lyme | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 34-26 | |
| Fri., 2/10 | V Girls Basketball | Old Lyme | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:00 p.m. | W 52-26 | |
| Sat., 2/11 | FR Boys Basketball | Valley Regional | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 2/13 | V Boys Swimming and Diving | Cheshire, TBA | Away - Cheshire Community Pool [Directions] | 7:00 p.m. | Daniel Hand 89 Cheshire 72 | |
| Mon., 2/13 | V Girls Gymnastics | Shoreline Conference Championship | Away - ABC Gymnastics | 6:30 p.m. | ||
| Mon., 2/13 | V Girls Gymnastics | Shoreline Conference Championship | Away - ABC Gymnastics | 6:30 p.m. | 87.35 | |
| Tue., 2/14 | V Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 58-46 | |
| Tue., 2/14 | JV Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/14 | V Girls Basketball | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 54-25 | |
| Tue., 2/14 | JV Girls Basketball | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| 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 Ice Hockey | Watertown-Pomperaug | Home - East Haven HS-Veterans Rink [Directions] | 7:30 p.m. | T 2-2 OT | |
| Wed., 2/15 | V Girls Gymnastics | Old Lyme, East Lyme/Waterford/St Bernard, Norwich Free Academy | Away - ABC Gymnastics [Directions] | 2:30 p.m. | ||
| 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 | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/18 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Northford-Red [Directions] | 2:30 p.m. | L 7-4 | |
| Mon., 2/20 | V Boys Basketball | Montville | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 67-66 OT | |
| Mon., 2/20 | JV Boys Basketball | Montville | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | Montville | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/20 | V Girls Gymnastics | Valley Regional, Mercy | Away - Flip Flop Gymnastics [Directions] | 10:00 a.m. | 104.35 | |
| Wed., 2/22 | V Boys Ice Hockey | Eastern CT Eagles | Away - Norwich - Rose Garden-RoseGarden Arena [Directions] | 8:30 p.m. | Cancelled | |
| Sat., 2/25 | FR Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/25 | V Boys Ice Hockey | Woodstock Academy | Away - Pomfret School-Jahn Rink [Directions] | 7:15 p.m. | L 3-5 | |
| Sun., 2/26 | V Boys Ice Hockey | North Haven | Home - East Haven HS-Veterans Rink [Directions] | 7:00 p.m. | L 3-8 | |
| Mon., 2/27 | V Boys Swimming and Diving | SCC Qualifying Meet | Away - Cheshire Community Pool | 4:00 p.m. | ||
| Mon., 2/27 | V Girls Ice Hockey | Suffield Coop | Home - Northford-White [Directions] | 3:30 p.m. | L 6-7 | |
| Wed., 3/1 | V Boys Swimming and Diving | SCC Championship Meet | Away - SCSU-Field House | 4:30 p.m. | ||
| Mon., 4/3 | V Baseball | Westbrook | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | W 14-4 | |
| Mon., 4/3 | V Boys Tennis | Cromwell | Away - Watrous park [Directions] | 3:45 p.m. | L 5-0 [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 | Cromwell | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Tue., 4/4 | V Boys Lacrosse | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 4:00 p.m. | W 7-8 | |
| Tue., 4/4 | JV Boys Lacrosse | North Branford | Away - North Branford HS-NBHS Back Field [Directions] | 5:30 p.m. | ||
| Tue., 4/4 | V Girls Lacrosse | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | L 12-11 [Detailed Results] | |
| Tue., 4/4 | JV Girls Lacrosse | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Wed., 4/5 | V Baseball | Portland | Away - Portland HS-Portland HS [Directions] | 4:00 p.m. | L 8-4 | |
| Wed., 4/5 | V Boys Outdoor Track | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 3:30 p.m. | ||
| Wed., 4/5 | V Girls Outdoor Track | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 3:30 p.m. | ||
| Wed., 4/5 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 4:00 p.m. | L 20-0 | |
| Thu., 4/6 | V Boys Lacrosse | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | L 8-9 | |
| Thu., 4/6 | JV Boys Lacrosse | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:30 p.m. | ||
| Thu., 4/6 | V Boys Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 4:00 p.m. | L 7-0 [Detailed Results] | |
| Thu., 4/6 | V Girls Lacrosse | Morgan | Away - Indian River Complex-Turf Field [Directions] | 3:45 p.m. | W 14 - 8 [Detailed Results] | |
| Thu., 4/6 | JV Girls Lacrosse | Morgan | Away - Indian River Complex-Turf Field [Directions] | Canceled | Cancelled | |
| Thu., 4/6 | V Softball | Hale Ray | Away - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 4:00 p.m. | L 25-1 | |
| Thu., 4/6 | V Girls Tennis | Old Lyme | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Sat., 4/8 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Gloria Maddocks Field [Directions] | 10:30 a.m. | L 7-6 | |
| Sat., 4/8 | V Boys Lacrosse | Ledyard-Griswold | Away - Ledyard HS-Bill Mignault Field [Directions] | 10:00 a.m. | W 12-3 | |
| Sat., 4/8 | JV Boys Lacrosse | Ledyard-Griswold | Away - Ledyard HS-Bill Mignault Field [Directions] | 11:30 a.m. | ||
| Sat., 4/8 | V Boys Outdoor Track | Hammonasset Freshman Invite | Away - Daniel Hand HS-DHHS Track | 9:00 a.m. | ||
| Sat., 4/8 | V Girls Lacrosse | Ledyard | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 10:00 a.m. | L 11-10 [Detailed Results] | |
| Sat., 4/8 | JV Girls Lacrosse | Ledyard | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Sat., 4/8 | V Girls Outdoor Track | Hammonasset Freshman Invite | Away - Daniel Hand HS-DHHS Track | 9:00 a.m. | ||
| Mon., 4/10 | V Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 4:00 p.m. | W 8-5 | |
| Mon., 4/10 | V Boys Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 2:00 p.m. | L 3-2 [Detailed Results] | |
| Mon., 4/10 | V Girls Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 3:45 p.m. | L 3-4 | |
| Tue., 4/11 | V Boys Lacrosse | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 11-4 | |
| Tue., 4/11 | JV Boys Lacrosse | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Tue., 4/11 | V Girls Lacrosse | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | 10:30 a.m. | W 17 - 3 [Detailed Results] | |
| Tue., 4/11 | JV Girls Lacrosse | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | Canceled | Cancelled | |
| Wed., 4/12 | V Baseball | Hale Ray | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | W 7-3 | |
| Wed., 4/12 | V Boys Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 4:00 p.m. | L 7-0 [Detailed Results] | |
| 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 | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 2:00 p.m. | L 0-7 | |
| Thu., 4/13 | V Girls Lacrosse | Fitch | Away - Groton MS-Groton Middle School-Turf Feld [Directions] | 11:00 a.m. | W 22 - 10 [Detailed Results] | |
| Thu., 4/13 | JV Girls Lacrosse | Fitch | Away - Groton MS-Groton Middle School-Turf Feld [Directions] | Canceled | Cancelled | |
| Fri., 4/14 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | L 1-0 | |
| Fri., 4/14 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Varsity Softball Field [Directions] | 2:30 p.m. | L 15-0 | |
| Sat., 4/15 | V Boys Lacrosse | St. Bernard-Wheeler | Away - St. Bernard School-Delaporta Field [Directions] | 11:00 a.m. | L 8-9 | |
| Tue., 4/18 | V Baseball | East Hampton | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 4/18 | V Boys Golf | Portland | Away - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Tue., 4/18 | V Boys Lacrosse | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 3:45 p.m. | W 13-12 | |
| Tue., 4/18 | JV Boys Lacrosse | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 5:15 p.m. | ||
| Tue., 4/18 | V Boys Tennis | Portland | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 4-1 [Detailed Results] | |
| Tue., 4/18 | V Girls Lacrosse | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:30 p.m. | W 23 - 6 [Detailed Results] | |
| 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 | Portland | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Wed., 4/19 | V Boys Outdoor Track | Old Lyme, Valley Regional | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:30 p.m. | ||
| Wed., 4/19 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 3:45 p.m. | L 7-0 [Detailed Results] | |
| Wed., 4/19 | V Girls Outdoor Track | Old Lyme, Valley Regional | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:30 p.m. | ||
| Wed., 4/19 | V Girls Tennis | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 4/20 | V Baseball | ValleyReg/Westbrook | Away - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | L 11-1 | |
| Thu., 4/20 | V Boys Golf | North Branford | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | ||
| Thu., 4/20 | V Boys Golf | Haddam-Killingworth | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | ||
| Thu., 4/20 | V Boys Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:30 p.m. | L 15-6 | |
| Thu., 4/20 | JV Boys Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Thu., 4/20 | V Girls Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 4:00 p.m. | W 14 - 8 [Detailed Results] | |
| 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 | Valley Regional | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 4:00 p.m. | L 7-0 [Detailed Results] | |
| 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 | Valley Regional | Away - Valley Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Sat., 4/22 | JV Baseball | Old Lyme, Morgan | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 9:00 a.m. | ||
| Sat., 4/22 | V Boys Lacrosse | Ledyard-Griswold | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 11:00 a.m. | W 14-5 | |
| Sat., 4/22 | JV Boys Lacrosse | Ledyard-Griswold | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 12:30 p.m. | ||
| Sat., 4/22 | V Girls Lacrosse | Ledyard | Away - Ledyard HS-Bill Mignault Field [Directions] | 9:00 a.m. | L 12 - 9 | |
| Mon., 4/24 | V Baseball | Morgan | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | W 3-2 | |
| Mon., 4/24 | V Boys Tennis | East Hampton | Away - East Hampton HS-Tennis Courts [Directions] | 4:00 p.m. | L 4-1 [Detailed Results] | |
| 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 | East Hampton | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/25 | V Boys Lacrosse | Cromwell | Away - Cromwell HS-Lacrosse Field [Directions] | 4:00 p.m. | W 17-8 | |
| Tue., 4/25 | JV Boys Lacrosse | Cromwell | Away - Cromwell HS-Lacrosse Field [Directions] | 5:30 p.m. | ||
| Tue., 4/25 | V Girls Lacrosse | Cromwell | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 24 - 8 | |
| Tue., 4/25 | JV Girls Lacrosse | Cromwell | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Wed., 4/26 | V Baseball | Cromwell | Away - Cromwell HS-Fran Monnes Baseball Field [Directions] | 4:00 p.m. | L 5-1 | |
| Wed., 4/26 | V Boys Lacrosse | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | 4:00 p.m. | W 13-3 | |
| Wed., 4/26 | JV Boys Lacrosse | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | Canceled | Cancelled | |
| Wed., 4/26 | V Boys Outdoor Track | Westbrook, Morgan | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | ||
| Wed., 4/26 | V Girls Lacrosse | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:30 p.m. | L 9 - 8 [Detailed Results] | |
| Wed., 4/26 | JV Girls Lacrosse | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Wed., 4/26 | V Girls Outdoor Track | Westbrook, Morgan | Away - 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 | North Branford | Away - North Branford HS-NBHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Thu., 4/27 | V Boys Golf | East Hampton | Away - Black Birch Golf Course [Directions] | 3:00 p.m. | ||
| 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 | North Branford | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | L 12-0 | |
| Fri., 4/28 | V Boys Golf | Hale Ray | Away - Nathan Hale Ray HS-Black Birch [Directions] | 3:00 p.m. | ||
| Fri., 4/28 | JV Boys Lacrosse | Guilford | Away - Guilford HS-Maturo Field [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Boys Tennis | Morgan | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:00 p.m. | L 7-0 [Detailed Results] | |
| 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 | Westbrook | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | W 6-3 | |
| Mon., 5/1 | V Boys Tennis | Cromwell | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 4:00 p.m. | L 6-0 [Detailed Results] | |
| 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 | Cromwell | Away - Watrous park [Directions] | 3:45 p.m. | L 3-4 | |
| Tue., 5/2 | V Boys Golf | Old Lyme | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | ||
| Tue., 5/2 | V Boys Lacrosse | Maloney-Platt | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 14-9 | |
| Tue., 5/2 | V Boys Outdoor Track | East Hampton | Away - East Hampton HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | East Hampton | Away - East Hampton HS-Track [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Baseball | Portland | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | W 9-1 | |
| Wed., 5/3 | V Boys Golf | Valley Regional | Away - Black Hall Golf Club [Directions] | 3:15 p.m. | ||
| Wed., 5/3 | V Boys Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 4:00 p.m. | L 7-0 [Detailed Results] | |
| 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 | Westbrook | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Thu., 5/4 | V Boys Lacrosse | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:30 p.m. | W 12-9 | |
| Thu., 5/4 | JV Boys Lacrosse | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | ||
| Thu., 5/4 | V Girls Lacrosse | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 6:00 p.m. | W 13 - 14 [Detailed Results] | |
| Thu., 5/4 | JV Girls Lacrosse | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | Canceled | Cancelled | |
| Fri., 5/5 | V Baseball | Old Lyme | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | L 12-0 | |
| Fri., 5/5 | V Boys Golf | Fitch | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | ||
| Fri., 5/5 | V Boys Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 3:45 p.m. | L 7-0 [Detailed Results] | |
| Fri., 5/5 | V Softball | Hale Ray | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L 16-2 | |
| Fri., 5/5 | V Girls Tennis | Morgan | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Sat., 5/6 | JV Baseball | Old Lyme, Hale Ray, Westbrook | Away - Lyme-Old Lyme HS-Gloria Maddocks Field [Directions] | 10:00 a.m. | ||
| Sat., 5/6 | V Girls Outdoor Track | MIddletown JV Track Invitational | Away - Middletown HS-MHS Stadium | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 12:00 p.m. | ||||||
| Mon., 5/8 | V Baseball | Coginchaug | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | W 8-5 | |
| Mon., 5/8 | V Boys Golf | North Branford | Away - Indian Springs Golf Course-Indian Springs CC [Directions] | 3:00 p.m. | ||
| Mon., 5/8 | V Boys Outdoor Track | North Branford, Portland | Away - North Branford HS-NBHS Track [Directions] | 4:15 p.m. | ||
| Mon., 5/8 | V Boys Tennis | Old Lyme | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 4:00 p.m. | L 6-1 [Detailed Results] | |
| Mon., 5/8 | V Girls Outdoor Track | North Branford, Portland | Away - North Branford HS-NBHS Track [Directions] | 4:15 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 | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 5/9 | V Boys Golf | Haddam-Killingworth | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | ||
| Tue., 5/9 | V Boys Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | 5:00 p.m. | L 6-12 | |
| Tue., 5/9 | JV Boys Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | Canceled | Cancelled | |
| Tue., 5/9 | V Girls Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:30 p.m. | W 20 - 10 [Detailed Results] | |
| Tue., 5/9 | JV Girls Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Tue., 5/9 | V Girls Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Wed., 5/10 | V Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | W 7-3 | |
| Wed., 5/10 | V Boys Golf | Fitch | Away - Shennecossett Golf Course [Directions] | 2:45 p.m. | ||
| Thu., 5/11 | V Baseball | Windsor Locks | Away - Veterans Memorial Park - Windsor Locks-Baseball Diamond [Directions] | 5:00 p.m. | W 5-4 | |
| Thu., 5/11 | V Boys Golf | Coginchaug | Away - Coginchaug-Lyman Orchards Golf course [Directions] | 3:00 p.m. | ||
| Thu., 5/11 | V Boys Lacrosse | Morgan | Away - Indian River Complex-Turf Field [Directions] | 6:30 p.m. | W 10-8 | |
| Thu., 5/11 | JV Boys Lacrosse | Morgan | Away - Indian River Complex-Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 5/11 | V Girls Lacrosse | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | W 6 [Detailed Results] | |
| Thu., 5/11 | JV Girls Lacrosse | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Fri., 5/12 | V Boys Outdoor Track | Ledyard | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 2:00 p.m. | ||
| Fri., 5/12 | V Boys Outdoor Track | Bacon Academy | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 2:00 p.m. | ||
| Fri., 5/12 | V Boys Outdoor Track | Hale Ray | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:30 p.m. | ||
| Fri., 5/12 | V Girls Outdoor Track | Ledyard | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 2:00 p.m. | ||
| Fri., 5/12 | V Girls Outdoor Track | Bacon Academy | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 2:00 p.m. | ||
| Fri., 5/12 | V Girls Outdoor Track | Morgan | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 2:00 p.m. | ||
| 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 |
| Mon., 5/15 | V Baseball | St. Bernard | Away - St. Bernard School-Baseball Diamond [Directions] | 4:00 p.m. | L 3-0 | |
| Mon., 5/15 | V Boys Outdoor Track | Cromwell, Haddam-Killingworth | Away - Cromwell HS-Don Luke Track [Directions] | 3:30 p.m. | ||
| Mon., 5/15 | V Girls Outdoor Track | Cromwell, Haddam-Killingworth | Away - Cromwell HS-Don Luke Track [Directions] | 3:30 p.m. | ||
| Mon., 5/15 | V Softball | Stonington | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:15 p.m. | L 26-6 | |
| Tue., 5/16 | V Boys Golf | Morgan | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | ||
| Tue., 5/16 | V Boys Lacrosse | Cromwell | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 14-7 | |
| Tue., 5/16 | JV Boys Lacrosse | Cromwell | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:30 p.m. | ||
| Tue., 5/16 | V Girls Lacrosse | Cromwell | Away - Cromwell HS-Lacrosse Field [Directions] | 4:00 p.m. | W 26 - 20 [Detailed Results] | |
| Tue., 5/16 | JV Girls Lacrosse | Cromwell | Away - Cromwell HS-Lacrosse Field [Directions] | Canceled | Cancelled | |
| 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 Baseball | Norwich Free Academy | Away - Dickenman Field-Baseball Diamond [Directions] | 4:00 p.m. | L 10-6 | |
| 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 Boys Golf | Cromwell | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | ||
| Thu., 5/18 | V Boys Lacrosse | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | W 13-10 | |
| Thu., 5/18 | JV Boys Lacrosse | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:30 p.m. | ||
| Thu., 5/18 | V Girls Lacrosse | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 4:00 p.m. | W 21 - 8 [Detailed Results] | |
| Fri., 5/19 | JV Boys Lacrosse | East Lyme | Away - Bridebrook Park-Berardo Field [Directions] | 4:00 p.m. | ||
| Fri., 5/19 | V Boys Outdoor Track | OSMS Track Invitational | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:45 p.m. | ||
| Fri., 5/19 | V Girls Outdoor Track | OSMS Track Invitational | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:45 p.m. | ||
| Sat., 5/20 | V Baseball | Griswold | Away - Griswold HS-Baseball Diamond [Directions] | 8:30 a.m. | L 13-10 | |
| Sat., 5/20 | V Girls Lacrosse | St. Bernard | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 10:00 a.m. | W 15 - 3 [Detailed Results] | |
| Mon., 5/22 | V Boys Golf | Waterford | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | ||
| Mon., 5/22 | V Softball | Stonington | Away - Stonington HS-Softball Field [Directions] | 2:30 p.m. | L 24-2 | |
| Wed., 5/24 | V Boys Outdoor Track | Shoreline Conference Outdoor Championship | Away - East Hampton HS-Track | 2:30 p.m. | ||
| Wed., 5/24 | V Girls Outdoor Track | Shoreline Conference Outdoor Championship | Away - East Hampton HS-Track | 2:30 p.m. | ||
| Fri., 5/26 | V Boys Golf | Hale Ray | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/30 | V Boys Golf | Haddam-Killingworth, TBA, North Branford | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | ||
| Tue., 5/30 | V | Shoreline Unified Field Day | Away - Lyme-Old Lyme HS | 3:00 p.m. | ||