| Old Saybrook 2017-18 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 555 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Coginchaug | Home - Old Saybrook HS [Directions] | Cancelled | Non-seeding | |
| TBA | JV Baseball | North Branford | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| TBA | JV Baseball | Westbrook | Away - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | 2:45 | |
| TBA | JV Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | TBA | 2:45 p.m. | |
| TBA | JV Baseball | Portland | Away - Portland HS [Directions] | TBA | ||
| TBA | JV Baseball | Portland | Away - Portland HS [Directions] | TBA | 2:30 | |
| TBA | JV Baseball | Creed | Away - West Rock Park | TBA | 2:30 | |
| TBA | JV Football | Coginchaug/Hale Ray/East Hampton | Away - Field #1 - Brookside Field @ CRHS [Directions] | TBA | ||
| TBA | JV Boys Soccer | Old Lyme | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| TBA | JV Boys Soccer | East Hampton | Home - Old Saybrook HS [Directions] | 4:00 p.m. | non-seeding | |
| TBA | FR Boys Soccer | Hale Ray | Away - Hale-Ray HS, Nevers Field [Directions] | Cancelled | ||
| TBA | JV Field Hockey | Weston | Away - WHS Turf Field [Directions] | TBA | 9:30 | |
| TBA | JV Girls Lacrosse | Old Lyme | Home - Old Saybrook HS [Directions] | 11:15 a.m. | ||
| TBA | JV Girls Lacrosse | Waterford | Away - Alumni Turf Field [Directions] | 5:30 p.m. | ||
| TBA | JV Girls Lacrosse | North Branford | Home - Old Saybrook HS Turf Field [Directions] | 6:15 p.m. | ||
| TBA | JV Girls Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS Turf Field [Directions] | Cancelled | ||
| TBA | JV Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall Field [Directions] | TBA | ||
| TBA | JV Girls Soccer | Valley Regional | Away - Valley Regional HS [Directions] | TBA | non-seeding | |
| TBA | JV Softball | North Branford | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | Morgan | Away - Morgan [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | Hale Ray | Away - Hale-Ray HS, Lou Milardo Field [Directions] | 3:45 p.m. | 2:30 pm | |
| TBA | JV Softball | Morgan | Home - Westbrook HS Field #5 - Softball [Directions] | TBA | ||
| Fri., 9/8 | V Boys Cross Country | Middletown | Away [Directions] | 3:00 p.m. | ||
| Fri., 9/8 | V Football | Stafford/East Windsor/Somers | Away - Stafford High, Lighted field behind school [Directions] | L 0-36 | 4:00 x 2 | |
| Fri., 9/8 | V Football | Gilbert/Northwestern/Housy | Away - Gilbert [Directions] | W 49-14 | ||
| Fri., 9/8 | FR Boys Soccer | North Haven | Home - Old Saybrook HS [Directions] | 3:45 p.m. | Playing North Haven JV | |
| Fri., 9/8 | V Girls Cross Country | Middletown | Away [Directions] | 3:00 p.m. | 1:55 | |
| Fri., 9/8 | V Girls Soccer | Portland | Away - Portland HS [Directions] | W 2-1 | non-seeding | |
| Sat., 9/9 | V Boys Cross Country | Martha's Vineyard Invitational | Away | 10:00 a.m. | ||
| Sat., 9/9 | JV Football | Stafford/East Windsor/Somers | Home - Peters Complex [Directions] | 10:30 a.m. | ||
| Sat., 9/9 | JV Football | Gilbert/Northwestern/Housy | Home - Old Saybrook HS Turf Field [Directions] | 1:00 p.m. | ||
| Sat., 9/9 | V Boys Soccer | Norwich Free Academy | Home - Old Saybrook HS Turf Field [Directions] | W 6-0 | ||
| Sat., 9/9 | JV Boys Soccer | Norwich Free Academy | Home - Old Saybrook HS [Directions] | 10:00 a.m. | ||
| Sat., 9/9 | V Girls Cross Country | Martha's Vineyard Invitational | Away | 10:00 a.m. | ||
| Mon., 9/11 | V Boys Soccer | North Branford | Home - Old Saybrook HS Turf Field [Directions] | W 5-0 | ||
| Mon., 9/11 | V Field Hockey | Westbrook/Old Lyme Coop | Home - Old Saybrook HS Turf Field [Directions] | L 1-0 | ||
| Mon., 9/11 | JV Field Hockey | Westbrook/Old Lyme Coop | Home - Old Saybrook HS Turf Field [Directions] | 5:15 p.m. | ||
| Mon., 9/11 | JV Girls Soccer | Portland | Away - Portland [Directions] | 3:45 p.m. | non-seeding | |
| Tue., 9/12 | JV Boys Soccer | North Branford | Away - North Branford HS [Directions] | Cancelled | ||
| Tue., 9/12 | V Girls Soccer | North Branford/Hale Ray | Home - Old Saybrook HS Turf Field [Directions] | L 1-0 | ||
| Wed., 9/13 | V Field Hockey | Haddam-Killingworth | Home - Old Saybrook HS Turf Field [Directions] | W 3-2 | ||
| Wed., 9/13 | JV Field Hockey | Haddam-Killingworth | Home - Old Saybrook HS Turf Field [Directions] | 5:15 p.m. | ||
| Wed., 9/13 | JV Girls Soccer | North Branford/Hale Ray | Away - North Branford HS [Directions] | 3:45 p.m. | ||
| Thu., 9/14 | V Boys Soccer | Portland | Home - Old Saybrook HS Turf Field [Directions] | W 6-0 | ||
| Thu., 9/14 | FR Boys Soccer | East Lyme | Away [Directions] | 3:45 p.m. | Game vs. EL JV at Bridebrook Keser Field | |
| Fri., 9/15 | V Football | Valley Regional/Old Lyme | Away - VRHS Football Field [Directions] | L 7-48 | 5:00 x 2 | |
| Fri., 9/15 | JV Boys Soccer | Portland | Away - Portland HS [Directions] | 3:45 p.m. | ||
| Fri., 9/15 | V Girls Soccer | Portland | Away - Portland HS [Directions] | L 2-0 | ||
| Fri., 9/15 | V Girls Swimming and Diving | East Lyme, Lyman Memorial | Home - East Lyme HS Pool [Directions] | 3:45 p.m. | 2:30pm | |
| Sat., 9/16 | V Boys Cross Country | Connecticut Valley Invitational | Away | 10:00 a.m. | Cromwell | |
| Sat., 9/16 | V Football | Nonnewaug | Home - Old Saybrook HS Turf Field [Directions] | W 35-12 | ||
| Sat., 9/16 | JV Football | Valley Regional/Old Lyme | Home - Peters Complex [Directions] | 10:30 a.m. | ||
| Sat., 9/16 | V Girls Cross Country | Cromwell | Away [Directions] | 10:00 a.m. | 8:30 | |
| Sat., 9/16 | V Field Hockey | Waterford | Away - Alumni Turf Field [Directions] | L 3-0 | ||
| Sat., 9/16 | JV Girls Soccer | Portland | Home - Old Saybrook HS [Directions] | 11:00 a.m. | ||
| Mon., 9/18 | JV Football | Nonnewaug | Away - Nonnewaug HS Football Field [Directions] | 3:45 p.m. | ||
| Mon., 9/18 | V Boys Soccer | Valley Regional | Away - VRHS Football Field [Directions] | W 4-1 | ||
| Mon., 9/18 | FR Boys Soccer | Sacred Heart | Away - Waterville Park | 3:45 p.m. | ||
| Tue., 9/19 | JV Boys Soccer | Valley Regional | Home - Old Saybrook HS [Directions] | 3:45 p.m. | Freshmen/Sophomore Game vs. Valley JV | |
| Tue., 9/19 | V Field Hockey | Valley Regional | Away - Valley Regional Hockey Field [Directions] | OT-L 1-0 | ||
| Tue., 9/19 | JV Field Hockey | Valley Regional | Away - Valley Regional Hockey Field [Directions] | 5:30 p.m. | ||
| Tue., 9/19 | V Girls Soccer | Valley Regional | Home - Old Saybrook HS Turf Field [Directions] | T 0-0 | ||
| Wed., 9/20 | JV Girls Soccer | Valley Regional | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Thu., 9/21 | V Boys Cross Country | Run to the Sun | Away | 3:00 p.m. | Durham | |
| Thu., 9/21 | FR Boys Soccer | Xavier | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Thu., 9/21 | V Girls Cross Country | Coginchaug | Away [Directions] | 3:00 p.m. | 1:45 | |
| Thu., 9/21 | V Girls Soccer | Old Lyme | Away - Old Lyme HS [Directions] | L 3-0 | Non-League | |
| Fri., 9/22 | V Football | Haddam-Killingworth | Home - Peters Complex [Directions] | L 7-21 | ||
| Fri., 9/22 | V Field Hockey | North Branford | Away - North Branford HS [Directions] | L 3-2 | ||
| Fri., 9/22 | JV Field Hockey | North Branford | Away - North Branford HS [Directions] | 5:15 p.m. | ||
| Sat., 9/23 | V Boys Cross Country | Ocean State Invitational | Away | 10:00 a.m. | Rhode Island | |
| Sat., 9/23 | V Football | Granby/Canton | Home - Old Saybrook HS Turf Field [Directions] | W 30-0 | ||
| Sat., 9/23 | JV Football | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 10:30 a.m. | 9:15 | |
| Sat., 9/23 | V Boys Soccer | Cromwell | Home - Old Saybrook HS Turf Field [Directions] | W 8-3 | ||
| Sat., 9/23 | JV Boys Soccer | Cromwell | Away - Cromwell HS [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | V Girls Cross Country | Ocean State Invitational | Away | 10:00 a.m. | ||
| Sat., 9/23 | V Girls Soccer | Cromwell | Home - Old Saybrook HS Turf Field [Directions] | L 2-3 | ||
| Sat., 9/23 | JV Girls Soccer | Cromwell | Home - Old Saybrook HS [Directions] | 11:00 a.m. | ||
| Mon., 9/25 | JV Football | Granby/Canton | Away - Granby Memorial HS [Directions] | 4:45 p.m. | ||
| Mon., 9/25 | V Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | W 1-0 | ||
| Tue., 9/26 | V Boys Cross Country | East Hampton, Hale Ray, Old Lyme, Creed | Away [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | JV Boys Soccer | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | FR Boys Soccer | Windham Tech | Away [Directions] | 3:45 p.m. | Playing JV Team | |
| Tue., 9/26 | V Girls Cross Country | East Hampton, Hale Ray, Old Lyme, Creed | Away [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Field Hockey | Granby Memorial | Home - Old Saybrook HS Turf Field [Directions] | L 3-0 | ||
| Tue., 9/26 | JV Field Hockey | Granby Memorial | Home - Old Saybrook HS Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 9/27 | V Boys Soccer | Hale Ray | Home - Old Saybrook HS Turf Field [Directions] | W 7-0 | ||
| Wed., 9/27 | JV Girls Soccer | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Thu., 9/28 | V Football | North Branford | Away - Colafati Field - NBHS [Directions] | L 2-41 | 5:00 x 2 | |
| Thu., 9/28 | JV Boys Soccer | Hale Ray | Away - Hale-Ray HS [Directions] | 3:45 p.m. | ||
| Thu., 9/28 | V Field Hockey | Morgan | Home - Old Saybrook HS Turf Field [Directions] | W 4-1 | ||
| Thu., 9/28 | JV Field Hockey | Morgan | Home - Old Saybrook HS Turf Field [Directions] | 5:15 p.m. | ||
| Thu., 9/28 | V Girls Swimming and Diving | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 4:00 p.m. | 2:45pm | |
| Fri., 9/29 | V Boys Cross Country | Husky Invitational | Away | 3:30 p.m. | ||
| Fri., 9/29 | V Girls Cross Country | Morgan | Away [Directions] | 3:45 p.m. | ||
| Sat., 9/30 | V Football | Lewis Mills | Home - Old Saybrook HS Turf Field [Directions] | W 34-14 | ||
| Sat., 9/30 | JV Football | North Branford | Home - Peters Complex [Directions] | Cancelled | ||
| Mon., 10/2 | JV Football | Lewis Mills | Home - Old Saybrook HS [Directions] | 3:45 p.m. | Grass Field | |
| Mon., 10/2 | FR Boys Soccer | Hale Ray | Away - Old Saybrook HS [Directions] | Cancelled | Playing Hale Ray JV | |
| Mon., 10/2 | V Girls Soccer | Coginchaug | Home - Old Saybrook HS Turf Field [Directions] | W 3-2 | ||
| Mon., 10/2 | JV Girls Soccer | Coginchaug | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Tue., 10/3 | V Boys Soccer | Coginchaug | Home - Old Saybrook HS Turf Field [Directions] | W 5-2 | ||
| Tue., 10/3 | V Field Hockey | Westbrook/Old Lyme Coop | Away - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | L 4-1 | ||
| Tue., 10/3 | JV Field Hockey | Westbrook/Old Lyme Coop | Away - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 5:15 p.m. | ||
| Wed., 10/4 | V Boys Cross Country | Cougar Invitational | Away - Totocket Park North Branford | 3:30 p.m. | ||
| Wed., 10/4 | JV Boys Soccer | Coginchaug | Away - Field #2 - Middle Field @ CRHS [Directions] | 3:45 p.m. | ||
| Wed., 10/4 | V Girls Cross Country | Cougar Invitational | Away - Totocket Park North Branford | 3:30 p.m. | ||
| Thu., 10/5 | FR Boys Soccer | Xavier | Away - Larry McHugh Field (Xavier H.S.) [Directions] | 6:30 p.m. | ||
| Thu., 10/5 | V Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | T 0-0 | ||
| Thu., 10/5 | JV Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:15 p.m. | ||
| Thu., 10/5 | V Girls Soccer | Morgan | Away - Indian River Complex [Directions] | L 4-1 | ||
| Fri., 10/6 | V Football | Valley Regional/Old Lyme | Away - VRHS Football Field [Directions] | W 34-13 | ||
| Fri., 10/6 | V Football | Nonnewaug | Home - Peters Complex [Directions] | L 22-30 | ||
| Fri., 10/6 | V Boys Soccer | Morgan | Away - Indian River Complex [Directions] | W 2-1 | ||
| Fri., 10/6 | JV Girls Soccer | Morgan | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Fri., 10/6 | V Girls Swimming and Diving | Sacred Heart | Away - Kennedy HS Pool | 7:00 p.m. | 5:00pm | |
| Sat., 10/7 | V Boys Cross Country | Wickham Invitational | Away | TBA | ||
| Sat., 10/7 | JV Football | Nonnewaug | Away - Nonnewaug HS Football Field [Directions] | Cancelled | 8:00 | |
| Sat., 10/7 | JV Boys Soccer | Morgan | Home - Old Saybrook HS Turf Field [Directions] | 11:30 a.m. | ||
| Sat., 10/7 | V Girls Cross Country | Wickham Invitational | Away | TBA | ||
| Sat., 10/7 | V Field Hockey | East Lyme | Away - ELHS Turf Field [Directions] | W 3-1 | ||
| Sat., 10/7 | JV Field Hockey | East Lyme | Away - ELHS Turf Field [Directions] | 1:00 p.m. | ||
| Sat., 10/7 | V Girls Soccer | Norwich Free Academy | Home - Old Saybrook HS Turf Field [Directions] | L 3-0 | ||
| Mon., 10/9 | JV Football | Valley Regional/Old Lyme | Home - Old Saybrook HS Turf Field [Directions] | 3:45 p.m. | ||
| Mon., 10/9 | FR Boys Soccer | Sacred Heart | Home - Old Saybrook HS Turf Field [Directions] | 11:00 a.m. | ||
| Tue., 10/10 | V Boys Soccer | Westbrook | Away - Westbrook HS Field #2 - Track/Soccer [Directions] | W 4-0 | ||
| Tue., 10/10 | V Field Hockey | Waterford | Home - Old Saybrook HS Turf Field [Directions] | T 0-0- | ||
| Tue., 10/10 | JV Girls Soccer | Westbrook | Home - Old Saybrook HS [Directions] | Cancelled | ||
| Tue., 10/10 | V Girls Swimming and Diving | Windsor Locks/Ellington/E.Granby/E.Windsor | Home [Directions] | 4:30 p.m. | ||
| Wed., 10/11 | V Girls Soccer | Westbrook | Away - Westbrook HS Field #2 - Track/Soccer [Directions] | W 6-1 | ||
| Thu., 10/12 | V Boys Cross Country | Old Lyme | Away [Directions] | 3:45 p.m. | ||
| Thu., 10/12 | V Girls Cross Country | Old Lyme | Away [Directions] | 3:45 p.m. | ||
| Thu., 10/12 | V Girls Soccer | East Hampton | Home - Old Saybrook HS Turf Field [Directions] | W 1-0 | ||
| Thu., 10/12 | JV Girls Soccer | East Hampton | Home - Old Saybrook HS [Directions] | 4:30 p.m. | ||
| Fri., 10/13 | V Boys Soccer | East Hampton | Home - Old Saybrook HS Turf Field [Directions] | W 4-0 | ||
| Fri., 10/13 | FR Boys Soccer | East Lyme | Home - Old Saybrook HS [Directions] | 3:45 p.m. | game played vs. EL JV | |
| Fri., 10/13 | V Field Hockey | Valley Regional | Home - Old Saybrook HS [Directions] | L 1-0 | ||
| Fri., 10/13 | JV Field Hockey | Valley Regional | Home - Old Saybrook HS Turf Field [Directions] | 5:15 p.m. | ||
| Sat., 10/14 | V Boys Soccer | East Lyme | Home - Old Saybrook HS Turf Field [Directions] | W 5-1 | ||
| Sat., 10/14 | JV Boys Soccer | East Hampton | Away - East Hampton HS [Directions] | 10:30 a.m. | ||
| Mon., 10/16 | V Field Hockey | Farmington | Away - Farmington HS [Directions] | W 3-2 | 2:15 | |
| Mon., 10/16 | JV Field Hockey | Farmington | Away - Farmington HS [Directions] | 5:15 p.m. | 2:15 | |
| Mon., 10/16 | V Girls Soccer | Old Lyme | Home - Old Saybrook HS Turf Field [Directions] | L 6-0 | ||
| Tue., 10/17 | V Boys Soccer | Old Lyme | Home - Old Saybrook HS Turf Field [Directions] | W 8-1 | ||
| Tue., 10/17 | JV Girls Soccer | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | ||
| Wed., 10/18 | JV Boys Soccer | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | ||
| Wed., 10/18 | V Field Hockey | North Branford | Home - Old Saybrook HS Turf Field [Directions] | L 3-2 | ||
| Wed., 10/18 | JV Field Hockey | North Branford | Home - Old Saybrook HS Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 10/19 | JV Boys Soccer | Valley Regional | Away - Valley Regional HS [Directions] | 3:45 p.m. | JV team vs. Valley JV | |
| Thu., 10/19 | V Girls Soccer | Cromwell | Away - Cromwell HS [Directions] | L 0-4 | 2:30 pm | non-seeding |
| Thu., 10/19 | JV Girls Soccer | Cromwell | Away - Cromwell HS [Directions] | 4:00 p.m. | non-seeding | |
| Fri., 10/20 | V Boys Cross Country | Shoreline Championship | Away | 2:30 p.m. | Lyme Old Lyme | |
| Fri., 10/20 | V Football | Cromwell/Portland | Away - Pierson Park, Cromwell [Directions] | L 6-12 | ||
| Fri., 10/20 | V Football | Ellington | Home - Peters Complex [Directions] | L 7-33 | ||
| Fri., 10/20 | V Boys Soccer | Cromwell | Away - Cromwell HS [Directions] | W 2-1 | 4:15 p.m. | non-seeding |
| Fri., 10/20 | V Girls Cross Country | Shoreline Champion | Away - Lyme-Old Lyme | 2:30 p.m. | 1:00 | |
| Fri., 10/20 | V Girls Swimming and Diving | Fitch/Stonington/Wheeler/NL | Away - UCONN Avery Point [Directions] | 3:30 p.m. | 2:30pm | |
| Sat., 10/21 | JV Football | Ellington | Away - Ellington HS [Directions] | Cancelled | 8:00 | |
| Sat., 10/21 | JV Football | Cromwell/Portland | Home - Old Saybrook HS Turf Field [Directions] | Cancelled | ||
| Sat., 10/21 | JV Boys Soccer | Cromwell | Home - Old Saybrook HS [Directions] | 10:00 a.m. | non-seeding | |
| Sat., 10/21 | V Girls Soccer | Woodstock Academy | Away - Bentley Turf Field [Directions] | L 0-3 | ||
| Sat., 10/21 | JV Girls Soccer | Woodstock Academy | Away - Bentley Main Soccer Field [Directions] | 1:00 p.m. | ||
| Mon., 10/23 | V Boys Soccer | East Hampton | Away - East Hampton HS [Directions] | W 8-1 | 2:30 | non-seeding |
| Mon., 10/23 | V Field Hockey | Morgan | Away - Indian River Complex [Directions] | W 4-2 | ||
| Mon., 10/23 | JV Field Hockey | Morgan | Away - Indian River Complex [Directions] | 5:00 p.m. | ||
| Mon., 10/23 | V Girls Soccer | Valley Regional | Away - Valley VRHS Football Field [Directions] | W 2-1 | non-seeding | |
| Tue., 10/24 | V Boys Cross Country | Fresh/Soph | Home - Old Saybrook HS [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | V Girls Cross Country | Freshman/Sophomore Invite | Home - Old Saybrook HS [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | V Girls Swimming and Diving | Lyman Memorial | Away - Windham HS - Pool [Directions] | 4:00 p.m. | 2:30pm | |
| Wed., 10/25 | V Field Hockey | Weston | Away - WHS Turf Field [Directions] | L 0-2 | 9:30 | |
| Wed., 10/25 | V Girls Soccer | Haddam-Killingworth | Home - Old Saybrook HS Turf Field [Directions] | T 1-1 | ||
| Thu., 10/26 | V Boys Soccer | Morgan | Home - Old Saybrook HS Turf Field [Directions] | W 7-0 | non-seeding | |
| Fri., 10/27 | JV Boys Soccer | Morgan | Away - Morgan HS [Directions] | 3:45 p.m. | non-seeding | |
| Fri., 10/27 | V Girls Swimming and Diving | Suffield | Away - Windsor Locks HS Pool (No Diving Board) [Directions] | 4:30 p.m. | 2:30pm | |
| Sat., 10/28 | V Football | Coginchaug/Hale Ray/East Hampton | Home - Old Saybrook HS Turf Field [Directions] | W 37-0 | ||
| Sat., 10/28 | V Football | Lewis Mills | Home - Peters Complex [Directions] | L 0-29 | Homecoming | |
| Sat., 10/28 | FR Boys Soccer | Westbrook | Home - Old Saybrook HS [Directions] | 10:00 a.m. | Playing Westbrook JV | |
| Mon., 10/30 | V Boys Cross Country | Freshman @ John Winthrop | Away | 3:30 p.m. | ||
| Mon., 10/30 | JV Football | Lewis Mills | Home - Peters Complex [Directions] | Cancelled | ||
| Fri., 11/3 | V Football | North Branford | Away - Colafati Field - NBHS [Directions] | W 55-25 | ||
| Fri., 11/3 | V Football | Cromwell/Portland | Home - Peters Complex [Directions] | L 8-33 | ||
| Sat., 11/4 | JV Football | Cromwell/Portland | Away - Pierson Park, Cromwell [Directions] | Cancelled | 9:00 | |
| Sat., 11/4 | JV Football | North Branford | Home - Old Saybrook HS Turf Field [Directions] | 10:30 a.m. | ||
| Fri., 11/10 | V Football | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | L 7-14 | ||
| Fri., 11/10 | V Football | Coginchaug/Hale Ray/East Hampton | Away - CRHS Stadium Field & Track [Directions] | L 21-42 | 5:00 x 2 | |
| Sat., 11/11 | JV Football | Coginchaug/Hale Ray/East Hampton | Home - Peters Complex [Directions] | Cancelled | ||
| Sat., 11/11 | JV Football | Haddam-Killingworth | Home - Old Saybrook HS Turf Field [Directions] | 9:00 a.m. | ||
| Sat., 11/18 | JV Football | Old Saybrook | Home - Peters Complex [Directions] | Cancelled | ||
| Sat., 11/18 | JV Football | MSW | Away - Peters Complex [Directions] | Cancelled | ||
| Thu., 11/23 | V Football | MSW | Home - Old Saybrook HS Turf Field [Directions] | W 35-0 | ||
| Thu., 11/23 | V Football | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | L 0-35 | 9:00 x 2 | |
| Tue., 12/12 | V Girls Basketball | Westbrook | Home - Old Saybrook HS [Directions] | W 40-31 | ||
| Wed., 12/13 | V Girls Ice Hockey | East Catholic Coop | Home - Northford Ice Pavilion [Directions] | W 2-1 (OT) | 2:15 p.m. | |
| Thu., 12/14 | V Girls Basketball | Creed | Away - Truman School | W 38-31 | ||
| Thu., 12/14 | JV Girls Basketball | Creed | Away - Truman School | 5:00 p.m. | ||
| Sat., 12/16 | V Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | L 53-45 | ||
| Sat., 12/16 | JV Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Sat., 12/16 | FR Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 9:00 a.m. | ||
| Sat., 12/16 | V Boys Ice Hockey | Farmington Valley | Away - Avon Old Farms School [Directions] | L 0-6 | 5:30pm | |
| Sat., 12/16 | V Girls Basketball | Old Lyme | Home - Old Saybrook HS [Directions] | L 58-28 | ||
| Sat., 12/16 | JV Girls Basketball | Old Lyme | Home - Old Saybrook HS [Directions] | 2:00 p.m. | ||
| Sat., 12/16 | FR Girls Basketball | Old Lyme | Home - Old Saybrook HS [Directions] | 12:30 p.m. | ||
| Sat., 12/16 | V Girls Ice Hockey | West Haven/SHA | Home - Northford Ice Pavilion [Directions] | L 1-0 | 5:30 p.m. | |
| Mon., 12/18 | V Boys Basketball | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | W 61-35 | ||
| Mon., 12/18 | JV Boys Basketball | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Mon., 12/18 | FR Boys Basketball | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 4:00 p.m. | ||
| Mon., 12/18 | V Boys Ice Hockey | New Milford | Away - Canterbury School [Directions] | L 1-4 | 5:00 pm | |
| Tue., 12/19 | V Boys Swimming and Diving | N.Haven/E.Haven/N.Bran/Guil | Away - Gawrych Town Pool [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 12/19 | V Girls Basketball | Haddam-Killingworth | Away - Haddam-Killingworth HS [Directions] | W 35-32 | ||
| Tue., 12/19 | JV Girls Basketball | Haddam-Killingworth | Away - Haddam-Killingworth HS [Directions] | 5:30 p.m. | ||
| Wed., 12/20 | V Girls Ice Hockey | Masuk Coop | Home - Northford Ice Pavilion [Directions] | W 9-0 | 2:15 p.m. | |
| Thu., 12/21 | V Boys Basketball | Valley Regional | Home - Old Saybrook HS [Directions] | W 62-53 | ||
| Thu., 12/21 | JV Boys Basketball | Valley Regional | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Thu., 12/21 | FR Boys Basketball | Valley Regional | Home - Old Saybrook HS [Directions] | 4:00 p.m. | ||
| Thu., 12/21 | V Boys Indoor Track | Old Saybrook Qualifier Meet | Away - Hillhouse | 5:00 p.m. | ||
| Thu., 12/21 | V Girls Basketball | Valley Regional | Away - Valley Regional HS [Directions] | L 46-42 | ||
| Thu., 12/21 | JV Girls Basketball | Valley Regional | Away - Valley Regional HS [Directions] | 5:30 p.m. | ||
| Fri., 12/22 | V Boys Swimming and Diving | West Haven | Away - WHHS Pool [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Sat., 12/23 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft-Mays Rink [Directions] | T 1-1(OT) | 4:15 pm | |
| Wed., 12/27 | FR Boys Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | 2:00 p.m. | ||
| Wed., 12/27 | V Boys Swimming and Diving | Holy Cross | Away - Kennedy HS [Directions] | 4:00 p.m. | 2pm | |
| Wed., 12/27 | V Girls Basketball | Plainfield | Away - Plainfield HS [Directions] | L 43-61 | ||
| Wed., 12/27 | JV Girls Basketball | Plainfield | Away - Plainfield HS [Directions] | 4:30 p.m. | ||
| Wed., 12/27 | V Girls Ice Hockey | Guilford Coop | Away - East Haven Ice Rink [Directions] | W 2-1 | 5:45 p.m. | |
| Thu., 12/28 | V Boys Basketball | Portland | Away - Portland HS [Directions] | W 68-55 | ||
| Thu., 12/28 | JV Boys Basketball | Portland | Away - Portland HS [Directions] | 5:30 p.m. | ||
| Thu., 12/28 | FR Boys Basketball | Portland | Away - Portland HS [Directions] | 4:00 p.m. | ||
| Thu., 12/28 | V Boys Indoor Track | H-K Invitational | Away - Hillhouse | 11:30 a.m. | ||
| Fri., 12/29 | V Girls Basketball | Portland | Home - Old Saybrook HS [Directions] | W 54-50 | ||
| Fri., 12/29 | JV Girls Basketball | Portland | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Sat., 12/30 | FR Boys Basketball | Cromwell | Home - Old Saybrook HS [Directions] | 10:00 a.m. | ||
| Tue., 1/2 | V Boys Basketball | Creed | Away - Fair Haven School | W 55-50 | ||
| Tue., 1/2 | JV Boys Basketball | Creed | Away - Fair Haven School | 6:00 p.m. | ||
| Tue., 1/2 | V Girls Basketball | Creed | Home - Old Saybrook HS [Directions] | W 31-23 | ||
| Tue., 1/2 | JV Girls Basketball | Creed | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | V Boys Basketball | Westbrook | Home - Old Saybrook HS [Directions] | W 55-39 | ||
| Wed., 1/3 | JV Boys Basketball | Westbrook | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | V Boys Ice Hockey | Staples | Home - DiLungo Rink [Directions] | W 4-0 | ||
| Wed., 1/3 | V Boys Indoor Track | Meet @ Glastonbury Pole Vault Only | Away - Glastonbury | Cancelled | ||
| Wed., 1/3 | V Boys Indoor Track | SLC League Meet #1 | Away - Hillhouse | 5:00 p.m. | ||
| Wed., 1/3 | V Girls Ice Hockey | Lauralton Hall | Home - Northford Ice Pavilion [Directions] | W 11-0 | 2:15 p.m. | |
| Sat., 1/6 | V Boys Ice Hockey | Cheshire | Home - DiLungo Rink [Directions] | W 3-2(OT) | ||
| Sat., 1/6 | V Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | L 1-2 | 12:30 p.m. | |
| Mon., 1/8 | V Boys Basketball | Coginchaug | Home - Old Saybrook HS [Directions] | W 51-44 | ||
| Mon., 1/8 | JV Boys Basketball | Coginchaug | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Mon., 1/8 | FR Boys Basketball | Coginchaug | Home - Old Saybrook HS [Directions] | Cancelled | ||
| Tue., 1/9 | V Boys Indoor Track | Bacon Academy Meet | Away - Wesleyan | Cancelled | ||
| Tue., 1/9 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | L 17-54 | ||
| Tue., 1/9 | JV Girls Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | 5:30 p.m. | ||
| Wed., 1/10 | FR Boys Basketball | Morgan | Home - Old Saybrook HS [Directions] | 7:30 p.m. | ||
| Wed., 1/10 | V Boys Ice Hockey | Daniel Hand | Away - Northford Ice Pavilion [Directions] | W 5-3 | 2:30 | |
| Thu., 1/11 | V Boys Basketball | Hale Ray | Home - Old Saybrook HS [Directions] | W 58-42 | ||
| Thu., 1/11 | JV Boys Basketball | Hale Ray | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Thu., 1/11 | V Boys Indoor Track | Glastonbury Pole Vault Only | Away - Glastonbury | 4:30 p.m. | ||
| Thu., 1/11 | V Boys Swimming and Diving | Fairfield Prep | Away - Recreation Complex, Fairfield University [Directions] | 4:00 p.m. | 2:10 p.m. | |
| Fri., 1/12 | V Girls Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | W 42-23 | ||
| Fri., 1/12 | JV Girls Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 5:30 p.m. | ||
| Fri., 1/12 | V Girls Ice Hockey | Suffield Coop | Away - Northford Ice Pavilion [Directions] | L 3-4 | 9:00 a.m. | |
| Sat., 1/13 | V Boys Basketball | Morgan | Away - Morgan HS [Directions] | W 69-52 | ||
| Sat., 1/13 | JV Boys Basketball | Morgan | Away - Morgan HS [Directions] | 5:30 p.m. | ||
| Sat., 1/13 | FR Boys Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/13 | V Boys Ice Hockey | West Haven Coop | Away - Bennett Rink [Directions] | W 2-1(OT) | 10:00 am | |
| Sat., 1/13 | V Boys Indoor Track | SCC Coaches Invitational | Away - Hillhouse | 9:00 a.m. | ||
| Sat., 1/13 | V Boys Indoor Track | Glastonbury Invitational | Away | 9:30 a.m. | 9th/10th graders only | |
| Sat., 1/13 | FR Girls Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | 12:00 p.m. | ||
| Sat., 1/13 | V Girls Ice Hockey | Lauralton Hall | Away - Wonderland of Ice [Directions] | W 5-0 | 11:30am | |
| Mon., 1/15 | V Boys Swimming and Diving | Amity | Away - Orange Community Center Pool [Directions] | 7:20 p.m. | 5:30 p.m. | |
| Tue., 1/16 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Northford Ice Pavilion [Directions] | W 1-0 | 2:15 p.m. | |
| Wed., 1/17 | FR Boys Basketball | Creed | Home - Old Saybrook HS [Directions] | 7:00 p.m. | ||
| Wed., 1/17 | V Girls Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | L 38-41 | ||
| Wed., 1/17 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners Ice Rink [Directions] | W 4-1 | 1:45 p.m. | |
| Thu., 1/18 | V Boys Indoor Track | Glastonbury Pole Vault | Away | 4:30 p.m. | ||
| Thu., 1/18 | V Boys Swimming and Diving | Cheshire | Away - Cheshire Community pool [Directions] | 7:00 p.m. | 5:00 p.m. | |
| Fri., 1/19 | V Boys Basketball | Amistad | Away - AF Amistad HS [Directions] | W 62-55 | ||
| Fri., 1/19 | JV Boys Basketball | Amistad | Away - AF Amistad HS [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Morgan | Home - Old Saybrook HS [Directions] | L 41-32 | ||
| Fri., 1/19 | JV Girls Basketball | Morgan | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Sat., 1/20 | FR Boys Basketball | North Branford | Away [Directions] | Cancelled | ||
| Sat., 1/20 | V Boys Ice Hockey | Guilford | Home - DiLungo Rink [Directions] | L 2-6 | ||
| Sat., 1/20 | V Boys Indoor Track | SLC Coaches Invitational | Away - Hillhouse | 10:00 a.m. | ||
| Sat., 1/20 | FR Girls Basketball | Norwich Free Academy | Home - Old Saybrook HS [Directions] | 10:00 a.m. | ||
| Sat., 1/20 | V Girls Ice Hockey | Avon Coop | Home - Northford Ice Pavilion [Directions] | W 3-2 | 1:15 p.m. | |
| Mon., 1/22 | V Boys Swimming and Diving | Notre Dame-West Haven | Away - Albertus Magnus College [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 1/22 | V Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | L 42-30 | ||
| Mon., 1/22 | JV Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | 4:00 p.m. | ||
| Mon., 1/22 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | L 3-1 | 2:30 p.m. | |
| Tue., 1/23 | V Boys Basketball | East Hampton | Home - Old Saybrook HS [Directions] | L 64-53 | ||
| Tue., 1/23 | JV Boys Basketball | East Hampton | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Wed., 1/24 | V Boys Ice Hockey | Milford Coop | Home - DiLungo Rink [Directions] | W 4-0 | ||
| Wed., 1/24 | V Girls Ice Hockey | Northwest Catholic | Away - Champions Skating Center, Cromwell [Directions] | W 3-2 (OT) | 2:00 p.m. | |
| Thu., 1/25 | V Girls Basketball | Cromwell | Home - Old Saybrook HS [Directions] | L 54-40 | ||
| Thu., 1/25 | JV Girls Basketball | Cromwell | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | V Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | L 77-64 | ||
| Fri., 1/26 | JV Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 3:30 p.m. | ||
| Fri., 1/26 | V Boys Indoor Track | SLC League Meet #2 | Away - Hillhouse | 4:30 p.m. | ||
| Fri., 1/26 | V Girls Ice Hockey | Masuk Coop | Away - The Rinks at Shelton [Directions] | W 6-1 | 2:00 p.m. | |
| Sat., 1/27 | FR Boys Basketball | Westbrook | Home - Old Saybrook HS [Directions] | 9:00 a.m. | ||
| Sat., 1/27 | V Boys Ice Hockey | Newtown/New Fairfield | Home - DiLungo Rink [Directions] | W 9-3 | ||
| Sat., 1/27 | V Girls Basketball | Valley Regional | Home - Old Saybrook HS [Directions] | L 49-35 | Non-League | |
| Sat., 1/27 | JV Girls Basketball | Valley Regional | Home - Old Saybrook HS [Directions] | 5:30 p.m. | Non-League | |
| Sat., 1/27 | V Girls Ice Hockey | Northwest Catholic | Home - Northford Ice Pavilion [Directions] | L 4-0 | 1:15 p.m. | |
| Mon., 1/29 | V Boys Swimming and Diving | Shelton | Home - Madison Swim and Racquet Club [Directions] | 4:00 p.m. | ||
| Mon., 1/29 | V Girls Basketball | North Branford | Home - Old Saybrook HS [Directions] | L 39-41 | ||
| Mon., 1/29 | JV Girls Basketball | North Branford | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | V Boys Basketball | North Branford | Away - North Branford HS [Directions] | L 38-66 | ||
| Tue., 1/30 | JV Boys Basketball | North Branford | Away - North Branford HS [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | V Girls Ice Hockey | West Haven/SHA | Away - Bennett Rink [Directions] | L 2-0 | 3:00 p.m. | |
| Wed., 1/31 | V Boys Ice Hockey | Hall | Away - Veteran's Memorial Rink [Directions] | L 0-3 | 5:15 pm | |
| Thu., 2/1 | V Girls Basketball | Hale Ray | Home - Old Saybrook HS [Directions] | W 48-34 | ||
| Thu., 2/1 | JV Girls Basketball | Hale Ray | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Fri., 2/2 | V Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | W 61-51 | ||
| Fri., 2/2 | JV Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 5:30 p.m. | ||
| Fri., 2/2 | FR Boys Basketball | Hale Ray | Away [Directions] | 4:00 p.m. | ||
| Fri., 2/2 | V Boys Swimming and Diving | Jonathan Law | Away - Foran HS Pool [Directions] | 4:00 p.m. | 2:30pm | |
| Sat., 2/3 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | W 47-43 | Non League | |
| Sat., 2/3 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | 5:30 p.m. | Non League | |
| Sat., 2/3 | V Boys Ice Hockey | Amity | Home - DiLungo Rink [Directions] | L 1-2(OT) | ||
| Sat., 2/3 | V Boys Indoor Track | SLC Conference Championship | Away - Hillhouse | 10:00 a.m. | ||
| Sat., 2/3 | V Girls Ice Hockey | Hamden Coop | Home - Northford Ice Pavilion [Directions] | T 1-1 (OT) | 6:15 p.m. | |
| Mon., 2/5 | FR Boys Basketball | Creed | Away - Fair Haven School | 5:00 p.m. | ||
| Mon., 2/5 | V Girls Basketball | Portland | Away - Portland HS [Directions] | L 46-59 | ||
| Mon., 2/5 | JV Girls Basketball | Portland | Away - Portland HS [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | V Boys Basketball | Portland | Home - Old Saybrook HS [Directions] | W 66-54 | ||
| Tue., 2/6 | JV Boys Basketball | Portland | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | V Boys Swimming and Diving | Branford | Away - Walsh Intermediate School - pool [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Wed., 2/7 | FR Boys Basketball | North Branford | Home - Old Saybrook HS [Directions] | Cancelled | ||
| Thu., 2/8 | V Boys Swimming and Diving | Xavier | Away - Freeman Athletic Center, Wesleyan University [Directions] | 7:30 p.m. | 5:30 p.m. | |
| Fri., 2/9 | V Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | L 73-58 | ||
| Fri., 2/9 | JV Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | V Girls Basketball | East Hampton | Home - Old Saybrook HS [Directions] | L 43-22 | ||
| Fri., 2/9 | JV Girls Basketball | East Hampton | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Sat., 2/10 | FR Boys Basketball | Coginchaug | Home - Old Saybrook HS [Directions] | 11:30 a.m. | ||
| Sat., 2/10 | V Boys Ice Hockey | Hall | Home - DiLungo Rink [Directions] | L 2-4 | ||
| Sat., 2/10 | FR Girls Basketball | Coginchaug | Home - Old Saybrook HS [Directions] | 10:00 a.m. | ||
| Sat., 2/10 | V Girls Ice Hockey | Guilford Coop | Home - Northford Ice Pavilion [Directions] | L 2-1 | 1:30 p.m. | |
| Mon., 2/12 | FR Boys Basketball | Morgan | Away - Morgan HS [Directions] | 7:00 p.m. | ||
| Mon., 2/12 | V Girls Basketball | Old Lyme | Away - Old Lyme HS [Directions] | L 24-70 | ||
| Mon., 2/12 | JV Girls Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Tue., 2/13 | V Boys Basketball | Old Lyme | Home - Old Saybrook HS [Directions] | L 53-50 | ||
| Tue., 2/13 | JV Boys Basketball | Old Lyme | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Tue., 2/13 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Northford Ice Pavilion [Directions] | L 5-3 | 2:15 p.m. | |
| Wed., 2/14 | V Boys Ice Hockey | Woodstock Academy | Home - DiLungo Rink [Directions] | W 5-2 | ||
| Fri., 2/16 | V Girls Ice Hockey | Simsbury | Away - Simsbury Farms CC [Directions] | L 2-1 (OT) | 1:15 p.m. | |
| Mon., 2/19 | V Boys Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | W 53-27 | ||
| Mon., 2/19 | JV Boys Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/20 | V Boys Ice Hockey | Woodstock Academy | Away - Jahn Hockey Rink - Pomfret School [Directions] | W 4-2 | 7:45am | |
| Wed., 2/21 | V Boys Basketball | Creed | Home - Old Saybrook HS [Directions] | W 60-57 | ||
| Wed., 2/21 | JV Boys Basketball | Creed | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Wed., 2/21 | V Boys Ice Hockey | Branford | Away - NORTHFORD ICE PAVILION [Directions] | L 0-2 | 2:30 | |
| Fri., 2/23 | V Boys Ice Hockey | New Fairfield | Away - Danbury Ice Arena [Directions] | L 0-2 | 1:00 pm | |
| Sat., 2/24 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion [Directions] | L 1-3 | 2:15pm | |
| Mon., 2/26 | V Boys Ice Hockey | North Haven | Away - Northford Ice Pavilion [Directions] | L 0-3 | 2:30 | |
| Wed., 2/28 | V Boys Ice Hockey | Westhill-Stamford | Home - DiLungo Rink [Directions] | W 4-2 | ||
| Sat., 3/31 | JV Baseball | Old Lyme | Home - Old Saybrook HS [Directions] | L 12-5 | ||
| Sat., 3/31 | V Boys Lacrosse | Griswold | Away - Lacrosse Field [Directions] | W 5-2 | ||
| Sat., 3/31 | V Softball | Plainfield | Home - Old Saybrook HS [Directions] | W 22-18 | ||
| Sat., 3/31 | JV Softball | Plainfield | Home - Old Saybrook HS [Directions] | W 23-4 | ||
| Tue., 4/3 | V Boys Lacrosse | North Branford | Home - Old Saybrook HS Turf Field [Directions] | L 12-4 | ||
| Thu., 4/5 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | L 12-7 | ||
| Thu., 4/5 | V Boys Golf | Portland | Away - PGC [Directions] | Old Saybrook 186, Portland 183 (non-league) | Non-League | |
| Thu., 4/5 | V Boys Lacrosse | Morgan | Home - Old Saybrook HS Turf Field [Directions] | L 2-1 | ||
| Thu., 4/5 | V Boys Outdoor Track | Westbrook, Morgan | Home - Westbrook HS [Directions] | 3:45 p.m. | ||
| Thu., 4/5 | V Boys Tennis | Valley Regional | Home - Old Saybrook HS [Directions] | W 4-3 | ||
| Thu., 4/5 | V Girls Lacrosse | Morgan | Away - Indian River Complex [Directions] | W 15-4 | ||
| Thu., 4/5 | JV Girls Lacrosse | Morgan | Away - Indian River Complex [Directions] | 5:00 p.m. | ||
| Thu., 4/5 | V Girls Outdoor Track | Westbrook, Morgan | Home - Westbrook HS [Directions] | 3:45 p.m. | ||
| Thu., 4/5 | V Softball | Old Lyme | Home - Westbrook HS Field #5 - Softball [Directions] | L 1-13 (5) | ||
| Thu., 4/5 | V Softball | Portland | Home - Old Saybrook HS [Directions] | W 20-2 | ||
| Sat., 4/7 | V Boys Lacrosse | St. Bernard-Wheeler | Away - Wheeler HS [Directions] | L 7-0 | ||
| Sat., 4/7 | V Co-ed Crew | Guilford | Away | Cancelled | ||
| Sat., 4/7 | V Softball | Valley Regional | Away - Valley Regional HS [Directions] | L 11-5 | ||
| Sat., 4/7 | V Softball | East Hampton | Home - Westbrook HS Field #5 - Softball [Directions] | W 12-6 | ||
| Sat., 4/7 | JV Softball | North Branford | Away - North Branford HS [Directions] | Cancelled | ||
| Sun., 4/8 | V Softball | North Branford | Away - North Branford HS [Directions] | L 12-0 | ||
| Mon., 4/9 | V Baseball | Valley Regional | Away - Valley Regional HS [Directions] | W 8-5 | 2:45 p.m. | |
| Mon., 4/9 | V Boys Golf | North Branford | Away [Directions] | Old Saybrook 174, North Branford 211 (league) | LEAGUE | |
| Mon., 4/9 | V Boys Tennis | Westbrook | Home - Old Saybrook HS [Directions] | W 6-1 | ||
| Mon., 4/9 | V Girls Lacrosse | Stonington | Home - Old Saybrook HS Turf Field [Directions] | W 10-7 | ||
| Mon., 4/9 | JV Girls Lacrosse | Stonington | Home - Old Saybrook HS Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 4/9 | V Girls Tennis | Westbrook | Away - Westbrook HS/MS Tennis Courts [Directions] | L 2-5 | ||
| Tue., 4/10 | V Boys Lacrosse | Cromwell | Home - Old Saybrook HS [Directions] | W 7-6 | ||
| Tue., 4/10 | V Softball | Cromwell | Home - Old Saybrook HS [Directions] | L 14-7 | ||
| Tue., 4/10 | V Softball | Portland | Away - Nolan Field [Directions] | W 15-7 | 2:30 pm | |
| Wed., 4/11 | V Baseball | Creed | Home - Old Saybrook HS [Directions] | W 12-1 | ||
| Wed., 4/11 | JV Baseball | Valley Regional | Away - Valley Regional HS [Directions] | W 6-4 | 2:45 p.m. | |
| Wed., 4/11 | V Boys Outdoor Track | Valley Regional, Old Lyme | Away - Valley Regional HS [Directions] | 3:45 p.m. | @ Valley Regional | |
| Wed., 4/11 | V Girls Outdoor Track | Valley Regional, Old Lyme | Away - Valley Regional HS [Directions] | 3:45 p.m. | @ Valley Regional | |
| Wed., 4/11 | V Softball | North Branford | Home - Westbrook HS Field #5 - Softball [Directions] | L 0-17 | ||
| Thu., 4/12 | JV Baseball | Creed | Away - West Rock Park | W 12-4 | 2:45 p.m. | |
| Thu., 4/12 | V Boys Lacrosse | Old Lyme | Home - Old Saybrook HS Turf Field [Directions] | L 7-3 | ||
| Thu., 4/12 | V Boys Tennis | Coginchaug | Home - Old Saybrook HS [Directions] | W 6-1 | ||
| Thu., 4/12 | V Girls Lacrosse | North Branford | Home - Old Saybrook HS Turf Field [Directions] | L 15-4 | ||
| Thu., 4/12 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | L 4-15 | ||
| Thu., 4/12 | V Softball | Valley Regional | Away - Valley Regional HS [Directions] | L 0-15 | 2:30 pm | |
| Thu., 4/12 | V Girls Tennis | Coginchaug | Away - Tennis Courts @ CRHS [Directions] | W 4-3 | ||
| Fri., 4/13 | V Baseball | Westbrook | Away - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | W 14-3 | 2:45 p.m. | |
| Fri., 4/13 | V Boys Tennis | East Hampton | Home - Old Saybrook HS [Directions] | W 4-3 | ||
| Fri., 4/13 | JV Softball | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Fri., 4/13 | V Girls Tennis | East Hampton | Away - East Hampton HS [Directions] | W 7-0 | ||
| Sat., 4/14 | JV Baseball | Westbrook | Home - Old Saybrook HS [Directions] | 11:00 a.m. | ||
| Sat., 4/14 | V Boys Lacrosse | Stonington | Away - Palmer Field (Turf) [Directions] | L 4-0 | ||
| Sat., 4/14 | V Softball | Morgan | Home - Old Saybrook HS [Directions] | W 5-2 | ||
| Sat., 4/14 | JV Softball | Morgan | Home - Old Saybrook HS [Directions] | 1:00 p.m. | ||
| Sat., 4/14 | V Girls Tennis | Valley Regional | Away - Valley Regional HS [Directions] | L 3-4 | ||
| Mon., 4/16 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | W 7-0 | ||
| Tue., 4/17 | V Baseball | Coginchaug | Home - Old Saybrook HS [Directions] | W 1-0 | ||
| Tue., 4/17 | JV Baseball | Coginchaug | Away - Field #1 - Brookside Field @ CRHS [Directions] | 3:45 p.m. | 2:30 p.m. | |
| Tue., 4/17 | V Girls Lacrosse | Old Lyme | Home - Old Saybrook HS [Directions] | L 9-8 | ||
| Tue., 4/17 | V Softball | Hale Ray | Home - Old Saybrook HS [Directions] | L 23-10 | ||
| Tue., 4/17 | V Softball | Cromwell | Home - Westbrook HS Field #5 - Softball [Directions] | L 0-15 | ||
| Tue., 4/17 | JV Softball | Hale Ray | Home - Old Saybrook HS [Directions] | 2:00 p.m. | ||
| Tue., 4/17 | V Girls Tennis | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | L 3-4 | ||
| Wed., 4/18 | V Baseball | Hale Ray | Home - Old Saybrook HS [Directions] | W 12-8 | ||
| Wed., 4/18 | V Boys Tennis | Old Lyme | Away - Old Lyme HS [Directions] | L 1-6 | ||
| Wed., 4/18 | V Softball | Coginchaug | Home - Old Saybrook HS [Directions] | L 15-2 | ||
| Wed., 4/18 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | L 1-15 | 2:30 pm | |
| Wed., 4/18 | V Girls Tennis | Old Lyme | Home - Old Saybrook HS Turf Field [Directions] | W 6-1 | ||
| Thu., 4/19 | V Boys Lacrosse | Valley Regional | Home - Old Saybrook HS Turf Field [Directions] | L 5-0 | ||
| Fri., 4/20 | V Boys Tennis | North Branford | Away - Old Saybrook HS [Directions] | Cancelled | ||
| Fri., 4/20 | V Softball | Hale Ray | Away - Hale-Ray HS, Lou Milardo Field [Directions] | L 1-18 | 12:10 pm | |
| Fri., 4/20 | V Girls Tennis | North Branford | Away [Directions] | W 4-3 | ||
| Sat., 4/21 | V Co-ed Crew | Old Lyme | Home - Roger's Lake [Directions] | TBA | ||
| Sat., 4/21 | V Girls Lacrosse | Northwest Catholic | Away - Northwest Catholic HS [Directions] | W 13-10 | ||
| Sat., 4/21 | JV Girls Lacrosse | Northwest Catholic | Away - Northwest Catholic HS [Directions] | Cancelled | ||
| Sat., 4/21 | JV Softball | Hale Ray | Home - Westbrook HS Field #5 - Softball [Directions] | 10:30 a.m. | ||
| Mon., 4/23 | V Baseball | Morgan | Away - Morgan HS [Directions] | W 16-7 | 2:45 | |
| Mon., 4/23 | V Boys Golf | O'Brien Tech | Away - Orange Hills Country Club [Directions] | Old Saybrook 178, Emmett O’Brien Tech 237 (non-league) | Orange Hills Country Club | |
| Mon., 4/23 | V Boys Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | L 0-8 | ||
| Mon., 4/23 | V Boys Tennis | Cromwell | Away - Cromwell HS [Directions] | L 2-5 | ||
| Mon., 4/23 | V Girls Lacrosse | Valley Regional | Away - Valley Regional Hockey Field [Directions] | W 18-13 | ||
| Mon., 4/23 | V Softball | Westbrook/Old Saybrook | Away - Westbrook HS Field #5 - Softball [Directions] | W 13-6 | ||
| Mon., 4/23 | V Softball | Old Saybrook | Home - Westbrook HS Field #5 - Softball [Directions] | L 6-13 | ||
| Mon., 4/23 | V Girls Tennis | Cromwell | Home - Old Saybrook HS [Directions] | L 2-5 | ||
| Tue., 4/24 | JV Baseball | Morgan | Away - Morgan HS [Directions] | 3:45 p.m. | 2:45 | |
| Tue., 4/24 | V Boys Golf | Cromwell | Home - Fenwick [Directions] | Old Saybrook 160, Cromwell 170 (league) | League | |
| Tue., 4/24 | V Boys Outdoor Track | Haddam-Killingworth, Creed | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Tue., 4/24 | V Girls Lacrosse | Haddam-Killingworth | Away - Haddam-Killingworth HS [Directions] | W 19-7 | ||
| Tue., 4/24 | JV Girls Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:15 p.m. | ||
| Tue., 4/24 | V Girls Outdoor Track | Haddam-Killingworth, Creed | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Tue., 4/24 | JV Softball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Thu., 4/26 | V Boys Golf | Haddam-Killingworth | Home - Fenwick [Directions] | Old Saybrook 170, Haddam-Killingworth 204 (league) | League | |
| Thu., 4/26 | V Boys Lacrosse | North Branford | Away - North Branford HS [Directions] | L 2-7 | ||
| Thu., 4/26 | V Boys Tennis | Morgan | Home - Old Saybrook HS [Directions] | L 2-5 | ||
| Thu., 4/26 | V Girls Lacrosse | North Branford | Away - North Branford HS [Directions] | L 17-13 | ||
| Thu., 4/26 | JV Girls Lacrosse | North Branford | Away - North Branford HS [Directions] | 5:15 p.m. | ||
| Thu., 4/26 | V Softball | Morgan | Home - Westbrook HS Field #5 - Softball [Directions] | L 12-23 | ||
| Thu., 4/26 | JV Softball | East Hampton | Away [Directions] | Cancelled | ||
| Thu., 4/26 | V Girls Tennis | Morgan | Away - Morgan HS [Directions] | W 6-1 | ||
| Sat., 4/28 | V Baseball | Old Lyme | Home - Old Saybrook HS [Directions] | L 8-1 | 2:45 p.m. | |
| Sat., 4/28 | JV Baseball | Cromwell | Away - Fran Monnes Baseball Field @ Cromwell HS [Directions] | 10:30 a.m. | 9:00 | |
| Sat., 4/28 | V Softball | New London | Away - Bates Woods Field [Directions] | W 13-0 | ||
| Sun., 4/29 | V Baseball | Cromwell | Home - Old Saybrook HS [Directions] | W 4-3 | ||
| Mon., 4/30 | V Baseball | North Branford | Away - North Branford HS [Directions] | W 14-8 | 2:30 | |
| Mon., 4/30 | V Boys Golf | East Hampton | Away - Black Birch Country Club [Directions] | Old Saybrook 180, East Hampton 217 (league) | LEAGUE | |
| Mon., 4/30 | V Boys Tennis | Morgan | Away - Morgan HS [Directions] | L 2-5 | ||
| Mon., 4/30 | V Softball | Hale Ray | Home - Westbrook HS Field #5 - Softball [Directions] | L 1-20 | ||
| Mon., 4/30 | V Softball | Portland | Away - Nolan Field [Directions] | W 24-9 | ||
| Mon., 4/30 | V Girls Tennis | Morgan | Home - Old Saybrook HS [Directions] | W 7-0 | ||
| Tue., 5/1 | V Boys Lacrosse | Morgan | Away - Indian River Complex [Directions] | L 1-4 | ||
| Tue., 5/1 | V Boys Outdoor Track | Hale Ray, Old Lyme, North Branford | Away [Directions] | 3:45 p.m. | @ North Branford | |
| Tue., 5/1 | V Girls Lacrosse | Morgan | Home - Old Saybrook HS Turf Field [Directions] | W 20-8 | ||
| Tue., 5/1 | JV Girls Lacrosse | Morgan | Home - Old Saybrook HS Turf Field [Directions] | 5:15 p.m. | ||
| Tue., 5/1 | V Girls Outdoor Track | Hale Ray, Old Lyme, North Branford | Away [Directions] | 3:45 p.m. | @ North Branford | |
| Tue., 5/1 | V Softball | Coginchaug | Away - Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | L 2-18 | 2:30 pm | |
| Tue., 5/1 | JV Softball | Coginchaug | Away - Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 5:15 p.m. | ||
| Tue., 5/1 | V Girls Tennis | Portland | Home - Old Saybrook HS [Directions] | W 6-1 | ||
| Wed., 5/2 | V Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | L 15-1 | 2:30 | |
| Wed., 5/2 | V Boys Golf | Hale Ray | Away - Fox Hopyard [Directions] | Old Saybrook 169, Hale Ray 215 (league) | League | |
| Wed., 5/2 | V Boys Tennis | Coginchaug | Away - Tennis Courts @ CRHS [Directions] | W 4-3 | ||
| Wed., 5/2 | V Co-ed Crew | E.O. Smith | Home - Rogers Lake [Directions] | 3:00 p.m. | ||
| Wed., 5/2 | V Softball | Old Lyme | Home - Old Saybrook HS [Directions] | L 7-11 | ||
| Wed., 5/2 | V Softball | Portland | Home - Westbrook HS Field #5 - Softball [Directions] | W 10-8 | ||
| Wed., 5/2 | V Girls Tennis | Coginchaug | Home - Old Saybrook HS [Directions] | W 5-2 | ||
| Thu., 5/3 | JV Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | 3:00 p.m. | 2:30 | |
| Thu., 5/3 | JV Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | 3:00 p.m. | 2:30 | |
| Thu., 5/3 | V Boys Lacrosse | Cromwell | Away - Cromwell HS [Directions] | W 4-3 | ||
| Thu., 5/3 | V Girls Lacrosse | St. Bernard | Home - Old Saybrook HS Turf Field [Directions] | W 12-3 | ||
| Thu., 5/3 | V Softball | East Hampton | Away - East Hampton HS [Directions] | W 11-3 | ||
| Fri., 5/4 | V Baseball | Portland | Home - Old Saybrook HS [Directions] | W 5-2 | 2:30 | |
| Fri., 5/4 | V Boys Tennis | Westbrook | Away - Westbrook HS/MS Tennis Courts [Directions] | W 6-1 | ||
| Fri., 5/4 | V Girls Lacrosse | Waterford | Away - Alumni Turf Field [Directions] | W 17-12 | ||
| Fri., 5/4 | V Softball | East Hampton | Home - Old Saybrook HS [Directions] | W 14-2 | ||
| Fri., 5/4 | V Softball | Old Lyme | Away - Old Lyme HS [Directions] | L 3-19 | 2:30 pm | |
| Fri., 5/4 | V Girls Tennis | Westbrook | Home [Directions] | W 5-2 | ||
| Sat., 5/5 | JV Softball | Westbrook/Old Saybrook | Home - Old Saybrook HS [Directions] | 9:00 a.m. | ||
| Sat., 5/5 | JV Softball | Old Saybrook | Away - Old Saybrook HS [Directions] | 9:00 a.m. | 8:00 am | |
| Sat., 5/5 | JV Softball | East Hampton | Home - Old Saybrook HS [Directions] | Cancelled | ||
| Mon., 5/7 | V Baseball | East Hampton | Away - East Hampton HS [Directions] | W 5-4 | 2:30 | |
| Mon., 5/7 | V Softball | Old Saybrook | Away - Old Saybrook HS [Directions] | L 4-16 | 3:15 pm | |
| Mon., 5/7 | V Softball | Westbrook/Old Saybrook | Home - Old Saybrook HS [Directions] | W 16-4 | ||
| Tue., 5/8 | V Baseball | New London | Away - Sal Amanti Field [Directions] | L 8-2 | 5:15 | |
| Tue., 5/8 | V Boys Golf | Fishers Island (NY) | Away | 9:00 a.m. | ||
| Tue., 5/8 | V Boys Lacrosse | Old Lyme | Away - Old Lyme HS [Directions] | L 7-0 | ||
| Tue., 5/8 | V Boys Outdoor Track | Portland, East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | @ East Hampton | |
| Tue., 5/8 | V Girls Lacrosse | Old Lyme | Away - Old Lyme HS [Directions] | L 13-11 | ||
| Tue., 5/8 | JV Girls Lacrosse | Old Lyme | Away - Old Lyme HS [Directions] | 5:15 p.m. | ||
| Tue., 5/8 | V Girls Outdoor Track | Portland, East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | @ East Hampton | |
| Tue., 5/8 | JV Softball | Westbrook/Old Saybrook | Away - Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | ||
| Tue., 5/8 | JV Softball | Old Saybrook | Home - Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | ||
| Wed., 5/9 | V Baseball | Old Lyme | Away - Old Lyme HS [Directions] | W 8-6 | ||
| Wed., 5/9 | V Boys Golf | Morgan | Home - Fenwick [Directions] | Old Saybrook 171, Morgan 174 (league) | League | |
| Wed., 5/9 | V Boys Tennis | East Hampton | Away - East Hampton HS [Directions] | W 6-1 | ||
| Wed., 5/9 | V Co-ed Crew | Avon | Home - Rogers Lake [Directions] | 3:00 p.m. | ||
| Wed., 5/9 | V Softball | East Hampton | Away - East Hampton HS [Directions] | L 2-17 | 2:30 pm | |
| Wed., 5/9 | V Softball | Hale Ray | Away - Hale-Ray HS, Lou Milardo Field [Directions] | L 4-8 | ||
| Wed., 5/9 | V Girls Tennis | East Hampton | Home - Old Saybrook HS [Directions] | W 6-1 | ||
| Thu., 5/10 | JV Baseball | Old Lyme | Away - Old Lyme HS [Directions] | L 10-0 | 2:45 | |
| Thu., 5/10 | V Boys Golf | Coginchaug | Away - Lyman Orchards [Directions] | Old Saybrook 177, Coginchaug 172 (league) | League | |
| Thu., 5/10 | V Boys Tennis | Valley Regional | Away - Valley Regional HS [Directions] | W 6-1 | ||
| Thu., 5/10 | V Girls Lacrosse | Branford | Home - Old Saybrook HS [Directions] | L 7-2 | ||
| Thu., 5/10 | JV Girls Lacrosse | Branford | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Thu., 5/10 | V Softball | Acad. of the Holy Family | Away - Franklin Field [Directions] | W 16-0 | 2:30 pm | |
| Thu., 5/10 | JV Softball | Hale Ray | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Thu., 5/10 | V Girls Tennis | Valley Regional | Home - Old Saybrook HS [Directions] | L 2-5 | ||
| Fri., 5/11 | V Baseball | East Hampton | Home - Old Saybrook HS [Directions] | W 12-2 (5) | ||
| Fri., 5/11 | V Boys Golf | Hale Ray | Home - Fenwick [Directions] | Old Saybrook 168, Hale Ray 213 (non-league) | Non-League | |
| Fri., 5/11 | V Boys Tennis | Haddam-Killingworth | Away - Haddam-Killingworth HS [Directions] | W 7-0 | ||
| Fri., 5/11 | V Softball | Montville | Home - Old Saybrook HS [Directions] | L 2-1 | ||
| Fri., 5/11 | V Girls Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | W 5-2 | ||
| Sat., 5/12 | V Boys Outdoor Track | Runnin' Rams Invitational | Home - Old Saybrook HS Turf Field [Directions] | 8:30 a.m. | ||
| Sat., 5/12 | V Co-ed Crew | Regatta | Home - Rogers Lake [Directions] | 10:00 a.m. | ||
| Sat., 5/12 | V Girls Outdoor Track | Runnin' Rams Invitational | Home - Old Saybrook HS Turf Field [Directions] | 8:30 a.m. | ||
| Mon., 5/14 | V Baseball | Westbrook | Home - Old Saybrook HS [Directions] | W 10-1 | ||
| Mon., 5/14 | JV Baseball | New London | Away - Mercer Field [Directions] | L 12-0 | ||
| Mon., 5/14 | V Boys Golf | Valley Regional | Away - Fox Hopyard CC [Directions] | Old Saybrook 178, Valley Regional 230 (league) | League | |
| Mon., 5/14 | V Boys Tennis | Old Lyme | Home - Old Saybrook HS [Directions] | L 2-5 | ||
| Mon., 5/14 | V Softball | Acad. of the Holy Family | Home - Westbrook HS Field #5 - Softball [Directions] | W 18-6 | ||
| Mon., 5/14 | V Softball | Morgan | Away - Peters Complex [Directions] | W 8-7 | ||
| Mon., 5/14 | V Girls Tennis | Old Lyme | Away - Old Lyme HS [Directions] | L 1-6 | ||
| Tue., 5/15 | V Boys Golf | Old Lyme | Home - Fenwick [Directions] | Old Saybrook 166, Old Lyme 152 (league) | League | |
| Tue., 5/15 | V Boys Lacrosse | Valley Regional | Away - Valley Regional Hockey Field [Directions] | L 12-0 | ||
| Tue., 5/15 | V Girls Lacrosse | Valley Regional | Home - Old Saybrook HS Turf Field [Directions] | W 16-14 | ||
| Tue., 5/15 | V Softball | Old Lyme | Away - Old Lyme HS [Directions] | L 1-10 | ||
| Wed., 5/16 | V Boys Outdoor Track | Coginchaug, Cromwell | Away - Cromwell HS [Directions] | 3:45 p.m. | @ Cromwell | |
| Wed., 5/16 | V Boys Tennis | North Branford | Home - North Branford HS [Directions] | W 7-0 | ||
| Wed., 5/16 | V Girls Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS Turf Field [Directions] | W 15-6 | ||
| Wed., 5/16 | V Girls Outdoor Track | Coginchaug, Cromwell | Away - Cromwell HS [Directions] | 3:45 p.m. | @ Cromwell | |
| Wed., 5/16 | V Girls Tennis | North Branford | Home - Old Saybrook HS [Directions] | W 6-1 | ||
| Thu., 5/17 | V Baseball | Portland | Away - Portland HS [Directions] | W 9-1 | ||
| Thu., 5/17 | V Boys Golf | Cromwell | Away - TPC [Directions] | Old Saybrook 171, Cromwell 164 (non-league) | Non League | |
| Thu., 5/17 | V Boys Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS Turf Field [Directions] | L 5-6 | ||
| Thu., 5/17 | V Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall Field [Directions] | W 13-11 | ||
| Thu., 5/17 | JV Softball | Montville | Away - Montville H.S. [Directions] | 3:45 p.m. | ||
| Fri., 5/18 | V Baseball | Coginchaug | Away - Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | L 1-0 | 2:30 | Non-seeding |
| Fri., 5/18 | V Boys Tennis | Cromwell | Home - Old Saybrook HS [Directions] | L 2-5 | ||
| Fri., 5/18 | V Softball | Windsor Locks | Away - Windsor Locks HS [Directions] | L 2-17 | 2:20 pm | |
| Fri., 5/18 | JV Softball | Coginchaug | Away - JV Softball Field @ CRHS [Directions] | 3:45 p.m. | ||
| Fri., 5/18 | V Girls Tennis | Cromwell | Away - Cromwell HS [Directions] | W 4-3 | ||
| Sun., 5/20 | V Baseball | Creed | Home - Old Saybrook HS [Directions] | W 6-1 | 2:30 | |
| Mon., 5/21 | V Boys Golf | Portland | Home - Fenwick [Directions] | Old Saybrook 168, Portland 161 (league) | League | |
| Mon., 5/21 | V Boys Lacrosse | Bristol Central | Home - Old Saybrook HS Turf Field [Directions] | W 7-3 | ||
| Mon., 5/21 | V Girls Tennis | Portland | Away - Portland HS [Directions] | W 7-0 | ||
| Wed., 5/23 | V Softball | O'Brien Tech | Away - O'Brien Tech Athletic Complex [Directions] | W 22-10 | 2:00 pm | |
| Tue., 5/29 | V Boys Golf | Old Lyme | Away [Directions] | Old Saybrook 174, Old Lyme 177 (non-league) | ||
| Wed., 5/30 | V Boys Golf | North Branford | Home - Fenwick [Directions] | Old Saybrook 169, North Branford 198 (non-league) | ||