| Old Saybrook 2015-16 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 659 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Cromwell | Home - Old Saybrook HS [Directions] | Cancelled | Cancelled | |
| TBA | JV Baseball | Morgan | Home - Old Saybrook HS [Directions] | TBA | ||
| TBA | JV Baseball | Portland | Away - Portland HS [Directions] | TBA | ||
| TBA | FR Boys Basketball | Creed | Away - Fair Haven School | 4:30 p.m. | ||
| TBA | FR Boys Basketball | North Branford | Away - North Branford HS [Directions] | TBA | ||
| TBA | JV Football | Enfield | Away - Enfield HS [Directions] | TBA | ||
| TBA | V Boys Ice Hockey | Jamboree | Home - DiLungo Rink [Directions] | 1:00 p.m. | ||
| TBA | JV Boys Soccer | North Branford | Home - Old Saybrook HS [Directions] | Cancelled | Cancelled | |
| TBA | V Girls Gymnastics | Valley Regional, Daniel Hand | Away - Flip Flop Gym [Directions] | Cancelled | Cancelled | |
| TBA | JV Girls Soccer | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | Coginchaug | Home - Old Saybrook HS [Directions] | TBA | ||
| Sat., 8/29 | V Football | Stonington (Scrim.) | Away [Directions] | 10:00 a.m. | ||
| Sat., 8/29 | V Football | Stonington (Scrim.) | Away - Stonington HS [Directions] | TBA | ||
| Tue., 9/1 | V Boys Soccer | New London (Scrim.) | Away - Canamella Field [Directions] | 3:30 p.m. | ||
| Wed., 9/2 | V Field Hockey | Fitch (Scrim.) | Home - Old Saybrook HS [Directions] | 3:30 p.m. | ||
| Wed., 9/2 | JV Field Hockey | Fitch (Scrim.) | Home - Old Saybrook HS [Directions] | 3:30 p.m. | ||
| Thu., 9/3 | V Football | Woodland (Scrim.) | Away - Woodland Football Field [Directions] | 4:30 p.m. | ||
| Thu., 9/3 | V Boys Soccer | Maloney (Scrim.) | Home - Old Saybrook HS [Directions] | 4:30 p.m. | ||
| Thu., 9/3 | V Girls Soccer | Daniel Hand (Scrim.) | Away - Surf Club [Directions] | 3:30 p.m. | ||
| Fri., 9/4 | V Boys Cross Country | Hale Ray (Scrim.) | Away [Directions] | 3:30 p.m. | ||
| Fri., 9/4 | V Football | VGW Techs (Scrim.) | Home - Peters Complex [Directions] | 5:30 p.m. | ||
| Fri., 9/4 | JV Boys Soccer | Morgan (Scrim.) | Away [Directions] | 3:45 p.m. | ||
| Fri., 9/4 | V Girls Cross Country | Hale Ray (Scrim.) | Away [Directions] | 3:30 p.m. | ||
| Fri., 9/4 | V Girls Soccer | Haddam-Killingworth (Scrim.) | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Sat., 9/5 | V Boys Soccer | North Haven (Scrim.) | Away [Directions] | 3:00 p.m. | ||
| Tue., 9/8 | V Girls Soccer | Montville (Scrim.) | Away [Directions] | 3:30 p.m. | ||
| Wed., 9/9 | V Field Hockey | Waterford (Scrim.) | Away - Miner Lane Field # 3 [Directions] | 3:45 p.m. | ||
| Wed., 9/9 | JV Field Hockey | Waterford (Scrim.) | Away [Directions] | 3:45 p.m. | ||
| Fri., 9/11 | V Boys Cross Country | Guilford | Away - Hammonasett Park [Directions] | 3:30 p.m. | ||
| Fri., 9/11 | V Football | North Branford | Away - Colafati Field - NBHS [Directions] | 6:30 p.m. | W 40-37 | |
| Fri., 9/11 | V Girls Cross Country | Guilford | Away - Hammonasett Park [Directions] | 3:30 p.m. | ||
| Fri., 9/11 | V Girls Soccer | East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | L 1-2 | |
| Sat., 9/12 | V Football | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:00 p.m. | W 29-22 | |
| Sat., 9/12 | JV Football | North Branford | Home - Peters Complex [Directions] | 10:30 a.m. | ||
| Sat., 9/12 | V Boys Soccer | East Hampton | Away - East Hampton HS [Directions] | 3:00 p.m. | W 1-0 | Non-Seeding Game |
| Sat., 9/12 | JV Girls Soccer | East Hampton | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Mon., 9/14 | JV Football | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Mon., 9/14 | JV Boys Soccer | East Hampton | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Mon., 9/14 | V Field Hockey | North Branford | Away - North Branford HS [Directions] | 3:45 p.m. | L 0-2 | |
| Mon., 9/14 | JV Field Hockey | North Branford | Away - North Branford HS [Directions] | 5:15 p.m. | L 1-2 | |
| Wed., 9/16 | V Boys Soccer | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | T 0-0 | |
| Wed., 9/16 | JV Boys Soccer | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Wed., 9/16 | V Girls Soccer | Old Lyme | Home - Old Saybrook HS [Directions] | 3:45 p.m. | L 0-4 | |
| Wed., 9/16 | JV Girls Soccer | Old Lyme | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Fri., 9/18 | V Football | Valley Regional/Old Lyme | Away - VRHS Football Field [Directions] | 6:30 p.m. | W 40-0 | |
| Fri., 9/18 | V Girls Soccer | North Branford/Hale Ray | Away - North Branford HS [Directions] | 3:45 p.m. | W 3-2 | |
| Fri., 9/18 | V Girls Swimming and Diving | East Lyme, Norwich Free Academy | Away - East Lyme HS [Directions] | 3:30 p.m. | ||
| Sat., 9/19 | V Boys Cross Country | Cromwell | Away [Directions] | 9:00 a.m. | ||
| Sat., 9/19 | V Football | Creed | Away - Wilbur Cross Athletic Complex | 12:00 p.m. | W 27-25 | |
| Sat., 9/19 | JV Football | Valley Regional/Old Lyme | Home - Peters Complex [Directions] | 10:30 a.m. | ||
| Sat., 9/19 | V Boys Soccer | North Branford | Away - North Branford HS [Directions] | 10:30 a.m. | W 6-0 | |
| Sat., 9/19 | V Girls Cross Country | Cromwell | Away [Directions] | 9:00 a.m. | ||
| Sat., 9/19 | V Field Hockey | East Lyme | Away - ELHS Turf Field [Directions] | 6:30 p.m. | L 1-2 | |
| Sat., 9/19 | JV Field Hockey | East Lyme | Away - ELHS Turf Field [Directions] | 5:00 p.m. | L 2-3 | |
| Sat., 9/19 | JV Girls Soccer | North Branford/Hale Ray | Home - Old Saybrook HS [Directions] | 10:30 a.m. | ||
| Mon., 9/21 | JV Football | Creed | Away - Blake Field | 4:00 p.m. | ||
| Mon., 9/21 | V Field Hockey | North Haven | Home - Old Saybrook HS [Directions] | 4:00 p.m. | W 5-0 | |
| Mon., 9/21 | JV Field Hockey | North Haven | Home - Old Saybrook HS [Directions] | 5:15 p.m. | W 6-0 | |
| Tue., 9/22 | V Boys Cross Country | Run To The Sun Invitational | Away - Coginchaug | 3:30 p.m. | ||
| Tue., 9/22 | V Girls Cross Country | Run To The Sun Invitational | Away - Coginchaug | 3:30 p.m. | ||
| Tue., 9/22 | V Field Hockey | Morgan | Away - Indian River Complex [Directions] | 6:30 p.m. | W 1-0 | |
| Tue., 9/22 | JV Field Hockey | Morgan | Away - Indian River Complex [Directions] | 5:00 p.m. | T 1-1 | |
| Tue., 9/22 | V Girls Soccer | Portland | Home - Old Saybrook HS [Directions] | 3:45 p.m. | T 2-2 | |
| Thu., 9/24 | V Boys Soccer | Portland | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 5-0 | |
| Thu., 9/24 | V Field Hockey | Westbrook/Old Lyme Coop | Away - Westbrook HS [Directions] | 3:15 p.m. | L 0-2 | |
| Thu., 9/24 | JV Field Hockey | Westbrook/Old Lyme Coop | Away - Westbrook HS [Directions] | Cancelled | Cancelled | |
| Fri., 9/25 | V Football | North Branford | Away - Colafati Field - NBHS [Directions] | 6:30 p.m. | L 7-33 | |
| Fri., 9/25 | JV Boys Soccer | Portland | Away - Portland HS [Directions] | 3:45 p.m. | ||
| Fri., 9/25 | V Girls Soccer | Valley Regional | Home - Old Saybrook HS [Directions] | 3:45 p.m. | L 1-2 | |
| Sat., 9/26 | V Football | Creed | Home - Peters Complex [Directions] | 2:00 p.m. | W 21-12 | |
| Sat., 9/26 | V Boys Soccer | Valley Regional | Home - Old Saybrook HS [Directions] | 10:30 a.m. | W 3-0 | |
| Sat., 9/26 | JV Girls Soccer | Valley Regional | Away - Valley Regional HS [Directions] | 10:30 a.m. | ||
| Mon., 9/28 | JV Football | North Branford | Home - Old Saybrook HS [Directions] | 4:00 p.m. | ||
| Mon., 9/28 | JV Football | Creed | Away - Blake Field | 4:00 p.m. | ||
| Mon., 9/28 | JV Boys Soccer | Valley Regional | Away - Valley Regional HS [Directions] | 3:45 p.m. | ||
| Mon., 9/28 | V Girls Soccer | Cromwell | Home - Old Saybrook HS [Directions] | 3:45 p.m. | T 2-2 | |
| Tue., 9/29 | V Boys Cross Country | League Meet #1 | Home - Old Saybrook HS [Directions] | 3:30 p.m. | ||
| Tue., 9/29 | V Boys Soccer | Cromwell | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 2-0 | |
| Tue., 9/29 | V Girls Cross Country | League Meet #1 | Home - Old Saybrook HS [Directions] | 3:30 p.m. | ||
| Tue., 9/29 | V Field Hockey | Valley Regional | Away - Valley Regional Hockey Field [Directions] | 3:45 p.m. | L 2-4 | |
| Tue., 9/29 | JV Field Hockey | Valley Regional | Away - Valley Regional Hockey Field [Directions] | 5:15 p.m. | T 1-1 | |
| Tue., 9/29 | JV Girls Soccer | Cromwell | Away - Cromwell HS [Directions] | 3:45 p.m. | ||
| Tue., 9/29 | V Girls Swimming and Diving | Fitch/Stonington/Wheeler/NL, Waterford | Away - UCONN Avery Point [Directions] | 4:00 p.m. | ||
| Thu., 10/1 | V Boys Cross Country | Husky Run Invite | Away - Indian River - Clinton | 3:30 p.m. | ||
| Thu., 10/1 | V Football | Enfield | Home - Peters Complex [Directions] | 5:30 p.m. | W 42-13 | |
| Thu., 10/1 | V Girls Cross Country | Husky Run Invite | Away - Indian River - Clinton | 3:30 p.m. | ||
| Thu., 10/1 | V Field Hockey | North Branford | Home - Old Saybrook HS [Directions] | 3:45 p.m. | L 1-4 | |
| Thu., 10/1 | JV Field Hockey | North Branford | Home - Old Saybrook HS [Directions] | 5:15 p.m. | W 2-0 | |
| Thu., 10/1 | V Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | T 2-2 | |
| Sat., 10/3 | V Boys Soccer | Bacon Academy | Away - Football/ Soccer Field [Directions] | 3:00 p.m. | L 0-5 | Non Seeding Game |
| Mon., 10/5 | V Boys Soccer | Hale Ray | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 5-0 | |
| Mon., 10/5 | V Girls Soccer | Lyman Memorial | Away - Lyman Memorial Soccer Complex [Directions] | 6:30 p.m. | W 2-0 | |
| Tue., 10/6 | V Boys Cross Country | Cougar Invite | Away - North Branford | 3:30 p.m. | ||
| Tue., 10/6 | JV Boys Soccer | Hale Ray | Away - Hale-Ray HS, Nevers Field [Directions] | 3:45 p.m. | ||
| Tue., 10/6 | V Girls Cross Country | Cougar Invite | Away - North Branford | 3:30 p.m. | ||
| Tue., 10/6 | V Girls Soccer | Hale Ray | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 7-1 | |
| Wed., 10/7 | V Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 4:00 p.m. | W 4-1 | |
| Wed., 10/7 | V Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | L 0-3 | |
| Wed., 10/7 | JV Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:15 p.m. | W 4-1 | |
| Wed., 10/7 | JV Girls Soccer | Hale Ray | Away - Hale-Ray HS [Directions] | 3:45 p.m. | ||
| Thu., 10/8 | V Boys Soccer | Coginchaug | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 8-1 | |
| Fri., 10/9 | JV Boys Soccer | Coginchaug | Away - Field #2 - Middle Field @ CRHS [Directions] | 3:45 p.m. | ||
| Fri., 10/9 | V Field Hockey | Westbrook/Old Lyme Coop | Home - Old Saybrook HS [Directions] | 3:45 p.m. | L 0-1 | |
| Fri., 10/9 | JV Field Hockey | Westbrook/Old Lyme Coop | Home - Old Saybrook HS [Directions] | 5:15 p.m. | W 1-0 | |
| Fri., 10/9 | V Girls Soccer | Coginchaug | Home - Old Saybrook HS [Directions] | 3:45 p.m. | L 1-2 | |
| Sat., 10/10 | V Boys Cross Country | Wickham Park Invitational | Away - Wickham Park | 9:30 a.m. | ||
| Sat., 10/10 | V Football | Nonnewaug | Home - Old Saybrook HS [Directions] | 12:00 p.m. | W 27-26 | |
| Sat., 10/10 | V Football | Canton | Home - Peters Complex [Directions] | 1:30 p.m. | W 48-14 | Homecoming |
| Sat., 10/10 | JV Boys Soccer | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 4:00 p.m. | ||
| Sat., 10/10 | V Girls Cross Country | Wickham Park Invitational | Away - Wickham Park | 9:30 a.m. | ||
| Sat., 10/10 | JV Girls Soccer | Coginchaug | Away - CRHS Stadium Field & Track [Directions] | 10:30 a.m. | ||
| Mon., 10/12 | JV Football | Nonnewaug | Away - Nonnewaug HS Football Field [Directions] | 11:00 a.m. | ||
| Mon., 10/12 | V Boys Soccer | Morgan | Away - Indian River Complex [Directions] | 2:00 p.m. | L 1-4 | |
| Mon., 10/12 | V Girls Soccer | Morgan | Away - Indian River Complex [Directions] | 4:00 p.m. | L 0-1 | |
| Mon., 10/12 | JV Girls Soccer | Portland | Away - Portland HS [Directions] | 10:30 a.m. | ||
| Tue., 10/13 | V Boys Cross Country | League Meet #2 - Mega-Meet | Away - Indian River - Clinton | 3:30 p.m. | ||
| Tue., 10/13 | JV Boys Soccer | Morgan | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Tue., 10/13 | V Girls Cross Country | League Meet #2 - Mega-Meet | Away - Indian River - Clinton | 3:30 p.m. | ||
| Tue., 10/13 | V Field Hockey | Morgan | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 4-1 | |
| Tue., 10/13 | JV Field Hockey | Morgan | Home - Old Saybrook HS [Directions] | 5:15 p.m. | W 6-2 | |
| Wed., 10/14 | V Field Hockey | Sheehan | Home - Old Saybrook HS [Directions] | 4:00 p.m. | W 6-0 | |
| Wed., 10/14 | JV Field Hockey | Sheehan | Home - Old Saybrook HS [Directions] | 5:15 p.m. | W 2-0 | |
| Wed., 10/14 | JV Girls Soccer | Morgan | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Thu., 10/15 | V Boys Soccer | Westbrook | Away - Westbrook HS [Directions] | 3:30 p.m. | W 7-0 | |
| Thu., 10/15 | V Girls Soccer | Griswold | Away - Griswold [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 10/16 | V Field Hockey | Valley Regional | Home - Old Saybrook HS [Directions] | 4:15 p.m. | L 0-1 | |
| Fri., 10/16 | JV Field Hockey | Valley Regional | Home - Old Saybrook HS [Directions] | 5:45 p.m. | W 2-1 | |
| Fri., 10/16 | V Girls Soccer | Westbrook | Away - Westbrook HS [Directions] | 3:30 p.m. | W 6-1 | |
| Fri., 10/16 | JV Girls Soccer | Westbrook | Away - Westbrook HS [Directions] | 5:00 p.m. | ||
| Fri., 10/16 | V Girls Swimming and Diving | Ledyard/St. Bernard | Away - East Lyme HS [Directions] | 3:30 p.m. | ||
| Sat., 10/17 | V Football | Coventry/Windham Tech/Bolton/Lyman | Home - Old Saybrook HS [Directions] | 12:00 p.m. | W 27-6 | |
| Sat., 10/17 | V Football | Coginchaug/Hale Ray/East Hampton | Away - CRHS Stadium Field & Track [Directions] | 1:00 p.m. | W 34-0 | |
| Sat., 10/17 | JV Boys Soccer | Westbrook | Away - Westbrook HS [Directions] | Cancelled | Cancelled | |
| Mon., 10/19 | JV Football | Coventry/Windham Tech/Bolton/Lyman | Away - Larry A. Pietrantonio Athletic Field Complex [Directions] | 4:00 p.m. | ||
| Mon., 10/19 | JV Football | Coginchaug/Hale Ray/East Hampton | Home - Peters Complex [Directions] | 4:00 p.m. | ||
| Mon., 10/19 | V Boys Soccer | East Hampton | Home - Old Saybrook HS [Directions] | 3:45 p.m. | T 1-1 | |
| Tue., 10/20 | JV Boys Soccer | East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | ||
| Tue., 10/20 | V Field Hockey | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 3:45 p.m. | L 0-1 | |
| Tue., 10/20 | JV Field Hockey | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 5:15 p.m. | W 3-0 | |
| Tue., 10/20 | V Girls Swimming and Diving | East Lyme | Away - East Lyme HS Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/21 | JV Boys Soccer | Cromwell | Away - Cromwell HS [Directions] | 3:45 p.m. | ||
| Wed., 10/21 | V Girls Soccer | East Hampton | Home - Old Saybrook HS [Directions] | 3:45 p.m. | L 1-2 | |
| Thu., 10/22 | V Boys Cross Country | Shoreline Conference Championships | Away - Indian River - Clinton | 2:30 p.m. | ||
| Thu., 10/22 | V Boys Soccer | Old Lyme | Home - Old Saybrook HS [Directions] | 3:30 p.m. | L 1-4 | Non-Seeding Game |
| Thu., 10/22 | JV Boys Soccer | Old Lyme | Home - Old Saybrook HS [Directions] | 5:00 p.m. | ||
| Thu., 10/22 | V Girls Cross Country | Shoreline Conference Championships | Away - Indian River - Clinton | 2:30 p.m. | ||
| Fri., 10/23 | V Football | Enfield | Away - Enfield High Turf Field [Directions] | 7:00 p.m. | W 33-20 | |
| Fri., 10/23 | V Field Hockey | Suffield | Home - Old Saybrook HS [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 10/23 | JV Field Hockey | Suffield | Home - Old Saybrook HS [Directions] | 5:15 p.m. | L 2-3 | |
| Fri., 10/23 | V Girls Soccer | Old Lyme | Away - Old Lyme HS [Directions] | 3:30 p.m. | L 2-4 | |
| Fri., 10/23 | JV Girls Soccer | Old Lyme | Away - Old Lyme HS [Directions] | Cancelled | Cancelled | |
| Fri., 10/23 | V Girls Swimming and Diving | EnricoFermi | Away - Fermi High Pool | 6:30 p.m. | ||
| Sat., 10/24 | V Boys Soccer | Portland | Away - Portland HS [Directions] | 6:00 p.m. | L 2-3 | Non-Seeding Game |
| Sat., 10/24 | JV Girls Soccer | Lyman Memorial | Home - Old Saybrook HS [Directions] | Cancelled | Cancelled | |
| Mon., 10/26 | JV Football | Enfield | Home - Old Saybrook HS [Directions] | 4:00 p.m. | ||
| Mon., 10/26 | JV Football | Canton | Away - Canton H.S. Grass [Directions] | Cancelled | Cancelled | |
| Mon., 10/26 | V Boys Soccer | Waterford | Away - Alumni Turf Field [Directions] | 7:00 p.m. | L 1-2(OT) | Non-Seeding Game |
| Mon., 10/26 | JV Boys Soccer | Waterford | Away - Miner Lane Field # 1 [Directions] | 3:30 p.m. | ||
| Mon., 10/26 | V Field Hockey | Norwich Free Academy | Away - NFA Turf Field [Directions] | 6:30 p.m. | W 3-2(OT) | |
| Mon., 10/26 | JV Field Hockey | Norwich Free Academy | Away - NFA Turf Field [Directions] | 5:00 p.m. | W 7-1 | |
| Mon., 10/26 | V Girls Soccer | Portland | Away - Portland HS [Directions] | 7:00 p.m. | L 0-3 | |
| Tue., 10/27 | V Boys Cross Country | OSHS Freshman/Sophomore Invite | Home - Old Saybrook HS [Directions] | 3:30 p.m. | ||
| Tue., 10/27 | JV Boys Soccer | Portland | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Tue., 10/27 | V Girls Cross Country | OSHS Freshman/Sophomore Invite | Home - Old Saybrook HS [Directions] | 3:30 p.m. | ||
| Tue., 10/27 | JV Girls Soccer | Portland | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Tue., 10/27 | V Girls Swimming and Diving | Ledyard/St. Bernard | Away - Mashantucket Community Center [Directions] | 6:00 p.m. | ||
| Thu., 10/29 | V Field Hockey | Waterford | Away - Alumni Turf Field [Directions] | 7:00 p.m. | W 3-0 | |
| Thu., 10/29 | JV Field Hockey | Waterford | Away - Alumni Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 10/29 | JV Girls Soccer | East Hampton | Away - East Hampton HS [Directions] | Cancelled | Cancelled | |
| Fri., 10/30 | V Football | Granby/Canton | Home - Peters Complex [Directions] | 6:30 p.m. | L 41-49 | |
| Fri., 10/30 | V Girls Swimming and Diving | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 4:00 p.m. | ||
| Sat., 10/31 | V Boys Cross Country | CIAC Class SS Championship | Away - Wickham Park | TBA | ||
| Sat., 10/31 | V Football | Lewis Mills | Away - Lewis Mills Track [Directions] | 1:00 p.m. | L 7-27 | |
| Sat., 10/31 | JV Football | Granby/Canton | Away - Granby Memorial HS [Directions] | 10:30 a.m. | ||
| Sat., 10/31 | V Girls Cross Country | CIAC Class SS Championship | Away - Wickham Park | TBA | ||
| Mon., 11/2 | V Boys Cross Country | Freshman Invite | Away - Valley Regional | 3:30 p.m. | ||
| Mon., 11/2 | JV Football | Lewis Mills | Home - Old Saybrook HS [Directions] | 4:00 p.m. | ||
| Mon., 11/2 | V Girls Cross Country | Freshman Invite | Away - Valley Regional | 3:30 p.m. | ||
| Tue., 11/3 | V Boys Soccer | Old Lyme | Away - Old Lyme HS [Directions] | 2:00 p.m. | L 0-2 | |
| Fri., 11/6 | V Boys Cross Country | CIAC State Open Championships | Away - Wickham Park | 1:30 p.m. | ||
| Fri., 11/6 | V Football | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 6:30 p.m. | W 20-6 | |
| Fri., 11/6 | V Girls Cross Country | CIAC State Open Championships | Away - Wickham Park | 1:30 p.m. | ||
| Fri., 11/6 | V Girls Swimming and Diving | HK Invitational | Away - Haddam-Killingworth HS | 4:00 p.m. | ||
| Sat., 11/7 | V Football | Valley Regional/Old Lyme | Home - Old Saybrook HS [Directions] | 1:30 p.m. | L 13-27 | |
| Sat., 11/7 | JV Football | Haddam-Killingworth | Home - Peters Complex [Directions] | 10:30 a.m. | ||
| Mon., 11/9 | JV Football | Valley Regional/Old Lyme | Away - Valley Regional HS [Directions] | 3:30 p.m. | ||
| Tue., 11/10 | V Boys Soccer | Terryville | Home - Old Saybrook HS Turf Field [Directions] | 2:00 p.m. | W 2-0 | |
| Tue., 11/10 | V Boys Soccer | Terryville | Home - Old Saybrook HS Turf Field [Directions] | Cancelled | Cancelled | |
| Tue., 11/10 | V Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 2:00 p.m. | ||
| Tue., 11/10 | V Field Hockey | Haddam-Killingworth | Away [Directions] | 2:00 p.m. | ||
| Fri., 11/13 | V Football | Stafford/East Windsor/Somers | Away - SHS Football Field [Directions] | 6:30 p.m. | W 34-20 | |
| Fri., 11/13 | V Football | Ellington | Home - Peters Complex [Directions] | 6:30 p.m. | W 44-14 | senior night |
| Sat., 11/14 | V Boys Cross Country | New England Championships | Away - TBA | TBA | ||
| Sat., 11/14 | JV Football | Stafford/East Windsor/Somers | Home - Old Saybrook HS [Directions] | 10:30 a.m. | ||
| Sat., 11/14 | JV Football | Ellington | Away - Ellington HS [Directions] | 10:30 a.m. | ||
| Sat., 11/14 | V Boys Soccer | Notre Dame-Fairfield | Home [Directions] | 2:00 p.m. | ||
| Sat., 11/14 | V Boys Soccer | Notre Dame-Fairfield | Home [Directions] | 2:00 p.m. | ||
| Sat., 11/14 | V Girls Cross Country | New England Championships | Away - TBA | TBA | ||
| Wed., 11/18 | JV Football | Old Saybrook | Home - Peters Complex [Directions] | 3:45 p.m. | ||
| Wed., 11/18 | JV Football | MSW | Away - Peters Complex [Directions] | 3:45 p.m. | ||
| Thu., 11/26 | V Football | MSW | Home - Old Saybrook HS [Directions] | 10:30 a.m. | L 22-49 | |
| Thu., 11/26 | V Football | Old Saybrook | Away - Old Saybrook HS [Directions] | 10:30 a.m. | W 49-22 | |
| Tue., 12/1 | V Football | CIAC Playoff - Trinity Catholic - Boyle Field (Stamford High School) | Away | 6:00 p.m. | ||
| Fri., 12/4 | V Girls Ice Hockey | Simsbury (Scrim.) | Away - International Skating Center [Directions] | 7:20 p.m. | ||
| Sat., 12/5 | V Girls Basketball | East Haven (Scrim.) | Away [Directions] | 3:00 p.m. | ||
| Tue., 12/8 | V Boys Basketball | St. Bernard (Scrim.) | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Wed., 12/9 | V Boys Ice Hockey | New Canaan (Scrim.) | Home - DiLungo Rink [Directions] | 3:30 p.m. | ||
| Wed., 12/9 | V Girls Ice Hockey | Guilford Coop (Scrim.) | Home - Northford Ice Pavilion [Directions] | 4:15 p.m. | ||
| Thu., 12/10 | V Boys Basketball | Montville (Scrim.) | Home [Directions] | 5:00 p.m. | ||
| Fri., 12/11 | V Girls Basketball | East Lyme (Scrim.) | Home - Old Saybrook HS [Directions] | 3:30 p.m. | ||
| Fri., 12/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | 5:30 p.m. | W 1-0 | |
| Sat., 12/12 | V Boys Basketball | Griswold (Scrim.) | Home - Old Saybrook HS [Directions] | 12:00 p.m. | ||
| Sat., 12/12 | V Boys Ice Hockey | Notre Dame-Fairfield (Scrim.) | Home - DiLungo Rink [Directions] | 3:30 p.m. | ||
| Sat., 12/12 | V Girls Ice Hockey | Lauralton Hall | Home - Northford Ice Pavilion [Directions] | 4:30 p.m. | W 9-1 | |
| Tue., 12/15 | V Boys Basketball | Stonington (Scrim.) | Away - SHS Main Gymnasium [Directions] | TBA | ||
| Tue., 12/15 | V Boys Ice Hockey | Guilford (Scrim.) | Away [Directions] | 5:00 p.m. | @Hudson street | |
| Tue., 12/15 | V Girls Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 7:00 p.m. | L 26-27 | |
| Tue., 12/15 | JV Girls Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 5:30 p.m. | ||
| Wed., 12/16 | V Boys Basketball | E.O. Smith (Scrim.) | Home [Directions] | 5:00 p.m. | ||
| Wed., 12/16 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats (Scrim.) | Home - DiLungo Rink [Directions] | 6:00 p.m. | ||
| Wed., 12/16 | V Boys Indoor Track | SLC League Development Meet | Away - Hillhouse | 4:30 p.m. | ||
| Wed., 12/16 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Northford Ice Pavilion [Directions] | 5:30 p.m. | L 0-2 | |
| Wed., 12/16 | V Girls Indoor Track | SLC League Development Meet | Away - Hillhouse | 4:30 p.m. | ||
| Fri., 12/18 | V Girls Basketball | Portland | Home - Old Saybrook HS [Directions] | 7:00 p.m. | L 34-44 | |
| Fri., 12/18 | JV Girls Basketball | Portland | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Fri., 12/18 | JV Girls Ice Hockey | Shelton | Away - Shelton [Directions] | 4:15 p.m. | ||
| Sat., 12/19 | V Boys Indoor Track | Reindeer Relays | Away | 9:30 a.m. | ||
| Sat., 12/19 | V Boys Indoor Track | Reindeer Relays | Away | 9:30 a.m. | ||
| Sat., 12/19 | V Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | 4:15 p.m. | L 1-3 | |
| Sat., 12/19 | V Girls Indoor Track | Reindeer Relays | Away - Wilton HS | 9:30 a.m. | ||
| Sat., 12/19 | V Girls Indoor Track | Reindeer Relays | Away - Wilton HS | 9:30 a.m. | ||
| Mon., 12/21 | V Boys Basketball | Old Lyme | Home - Old Saybrook HS [Directions] | 7:00 p.m. | W 50-42 | |
| Mon., 12/21 | JV Boys Basketball | Old Lyme | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Mon., 12/21 | V Boys Ice Hockey | Newington Coop | Home - DiLungo Rink [Directions] | 6:00 p.m. | W 7-1 | |
| Mon., 12/21 | V Boys Swimming and Diving | Jonathan Law | Away - Foran HS Pool [Directions] | 4:00 p.m. | Win 88-70 | |
| Mon., 12/21 | V Girls Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 7:00 p.m. | W 46-34 | |
| Mon., 12/21 | JV Girls Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Wed., 12/23 | V Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 7:00 p.m. | W 65-50 | |
| Wed., 12/23 | JV Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Wed., 12/23 | V Boys Ice Hockey | Wilton | Home - DiLungo Rink [Directions] | 6:00 p.m. | W 11-2 | |
| Wed., 12/23 | V Girls Basketball | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 7:00 p.m. | L 31-55 | |
| Wed., 12/23 | JV Girls Basketball | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Sat., 12/26 | V Boys Basketball | Valley Regional | Home - Old Saybrook HS [Directions] | 7:00 p.m. | W 55-42 | Shoreline Holiday Tournament |
| Sat., 12/26 | V Boys Ice Hockey | Westhill/Stamford | Home - DiLungo Rink [Directions] | 1:00 p.m. | T 3-3 | Stamford co-op with Westhill |
| Mon., 12/28 | V Boys Basketball | Waterford | Home - Old Saybrook HS [Directions] | 7:00 p.m. | L 44-58 | Shoreline Holiday Tournament |
| Mon., 12/28 | V Boys Swimming and Diving | West Haven | Away - WHHS Pool [Directions] | 4:00 p.m. | Win 92-69 | |
| Mon., 12/28 | V Girls Basketball | St. Bernard | Away - St. Bernard Gymnasium [Directions] | 6:30 p.m. | L 17-30 | |
| Mon., 12/28 | JV Girls Basketball | St. Bernard | Away - St. Bernard Gymnasium [Directions] | Cancelled | Cancelled | |
| Mon., 12/28 | V Girls Gymnastics | Valley Regional, Mercy | Away - Flip-Flop Gymnastics, Deep River [Directions] | 10:00 a.m. | 132.70 | |
| Tue., 12/29 | V Boys Indoor Track | Jack Long Invitational | Away - Hill House | 12:00 p.m. | ||
| Tue., 12/29 | V Girls Indoor Track | Jack Long Invitational | Away - Hill House | 12:00 p.m. | ||
| Wed., 12/30 | V Boys Basketball | Portland | Home - Old Saybrook HS [Directions] | 7:00 p.m. | W 66-48 | |
| Wed., 12/30 | JV Boys Basketball | Portland | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Wed., 12/30 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | 5:30 p.m. | T 2-2 | |
| Wed., 12/30 | V Boys Swimming and Diving | East Lyme NFA | Away - East Lyme HS [Directions] | 12:30 p.m. | Win 94-89 | |
| Wed., 12/30 | V Girls Basketball | Portland | Away - Portland HS [Directions] | 7:00 p.m. | L 30-55 | |
| Wed., 12/30 | JV Girls Basketball | Portland | Away - Portland HS [Directions] | 5:30 p.m. | ||
| Wed., 12/30 | V Girls Gymnastics | Valley Regional, Mercy, Stonington | Away - Flip-Flop Gymnastics, Deep River [Directions] | 10:00 a.m. | 135.40 | |
| Wed., 12/30 | V Girls Ice Hockey | West Haven/SHA | Home - Northford Ice Pavilion [Directions] | 3:00 p.m. | L 1-3 | |
| Sat., 1/2 | FR Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 9:00 a.m. | ||
| Sat., 1/2 | V Boys Ice Hockey | Cheshire | Home - DiLungo Rink [Directions] | 1:00 p.m. | L 5-1 | |
| Sat., 1/2 | V Boys Indoor Track | SLC Coaches Invitational | Away - Hillhouse | 10:00 a.m. | ||
| Sat., 1/2 | V Girls Basketball | Valley Regional | Away - Valley Regional HS [Directions] | 7:00 p.m. | L 43-58 | |
| Sat., 1/2 | JV Girls Basketball | Valley Regional | Away - Valley Regional HS [Directions] | 5:30 p.m. | ||
| Sat., 1/2 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Northford Ice Pavilion [Directions] | 4:30 p.m. | L 0-7 | |
| Sat., 1/2 | V Girls Indoor Track | SLC Coaches Invitational | Away - Hillhouse | 10:00 a.m. | ||
| Mon., 1/4 | V Boys Basketball | Creed | Away - Fair Haven School | 7:30 p.m. | W 65-52 | |
| Mon., 1/4 | JV Boys Basketball | Creed | Away - Fair Haven School | 6:00 p.m. | ||
| Mon., 1/4 | V Boys Ice Hockey | New Milford | Away - Canterbury School [Directions] | 7:30 p.m. | L 3-4 | |
| Mon., 1/4 | V Boys Indoor Track | Coginchaug, North Branford, Valley Regional, Haddam-Killingworth | Away - Hill House [Directions] | 4:15 p.m. | ||
| Mon., 1/4 | V Boys Swimming and Diving | Shelton | Away - Shelton Community Center Pool [Directions] | 4:00 p.m. | Win 87-83 | |
| Mon., 1/4 | V Girls Indoor Track | Coginchaug, North Branford, Valley Regional, Haddam-Killingworth | Away - Hill House [Directions] | 4:15 p.m. | ||
| Tue., 1/5 | V Girls Basketball | Creed | Home - Old Saybrook HS [Directions] | 7:00 p.m. | W 49-12 | |
| Tue., 1/5 | JV Girls Basketball | Creed | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Wed., 1/6 | V Boys Ice Hockey | North Haven | Away - Northford Ice Pavilion [Directions] | 8:15 p.m. | L 3-6 | |
| Wed., 1/6 | V Girls Ice Hockey | Guilford Coop | Away - East Haven Ice Rink [Directions] | 7:00 p.m. | L 2-5 | |
| Thu., 1/7 | V Boys Indoor Track | Glastonbury | Away - Glastonbury [Directions] | 4:00 p.m. | ||
| Thu., 1/7 | V Girls Gymnastics | Valley Regional, Stonington | Away - Flip Flop [Directions] | 7:00 p.m. | 134.15 | |
| Thu., 1/7 | V Girls Indoor Track | Glastonbury | Away - Glastonbury [Directions] | 4:00 p.m. | ||
| Fri., 1/8 | V Boys Basketball | Westbrook | Home - Old Saybrook HS [Directions] | 7:00 p.m. | W 62-55 | |
| Fri., 1/8 | JV Boys Basketball | Westbrook | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Fri., 1/8 | V Boys Swimming and Diving | Greater New Haven | Away - Gawrych Town Pool [Directions] | 4:00 p.m. | Win 98-72 | |
| Fri., 1/8 | V Girls Basketball | Westbrook | Away - Westbrook HS [Directions] | 5:45 p.m. | L 52-54(OT) | |
| Fri., 1/8 | JV Girls Basketball | Westbrook | Away - Westbrook HS [Directions] | Cancelled | Cancelled | |
| Sat., 1/9 | V Boys Ice Hockey | West Haven Coop | Away - Bennett Rink [Directions] | 1:00 p.m. | L 3-9 | |
| Sat., 1/9 | V Boys Indoor Track | Glastonbury | Away - Glastonbury [Directions] | 10:00 a.m. | ||
| Sat., 1/9 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Northford Ice Pavilion [Directions] | 3:15 p.m. | L 1-3 | |
| Sat., 1/9 | V Girls Indoor Track | Glastonbury | Away - Glastonbury [Directions] | 10:00 a.m. | ||
| Mon., 1/11 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - The Rinks at Shelton [Directions] | 8:00 p.m. | L 0-6 | |
| Tue., 1/12 | V Boys Basketball | Coginchaug | Home - Old Saybrook HS [Directions] | 7:00 p.m. | W 64-53 | |
| Tue., 1/12 | JV Boys Basketball | Coginchaug | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Tue., 1/12 | FR Boys Basketball | Coginchaug | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Tue., 1/12 | V Boys Indoor Track | SLC League Meet #1 | Away - Hillhouse | 4:30 p.m. | ||
| Tue., 1/12 | V Boys Swimming and Diving | Cheshire | Home - Madison Swim and Racquet Club [Directions] | 7:00 p.m. | Loss 70-92 | |
| Tue., 1/12 | V Girls Basketball | Coginchaug | Away - Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | L 25-38 | |
| Tue., 1/12 | JV Girls Basketball | Coginchaug | Away - Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Tue., 1/12 | V Girls Indoor Track | SLC League Meet #1 | Away - Hillhouse | 4:30 p.m. | ||
| Wed., 1/13 | FR Boys Basketball | Morgan | Away - Morgan HS [Directions] | 7:00 p.m. | ||
| Wed., 1/13 | V Boys Ice Hockey | Daniel Hand | Away - Northford Ice Pavilion [Directions] | 6:00 p.m. | L 2-3 | |
| Thu., 1/14 | V Girls Gymnastics | Valley Regional, Mercy, Foran | Away - Flip-Flop Gymnsatics, Deep River [Directions] | 7:00 p.m. | 132.05 | |
| Thu., 1/14 | JV Girls Ice Hockey | Hamden Coop | Away - Lou Astorino Ice Rink [Directions] | 3:45 p.m. | ||
| Fri., 1/15 | V Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 7:00 p.m. | W 52-35 | |
| Fri., 1/15 | JV Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 5:30 p.m. | ||
| Fri., 1/15 | V Girls Basketball | Hale Ray | Home - Old Saybrook HS [Directions] | 7:00 p.m. | W 55-50 | |
| Fri., 1/15 | JV Girls Basketball | Hale Ray | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Sat., 1/16 | FR Boys Basketball | Westbrook | Home - Old Saybrook HS [Directions] | 10:00 a.m. | ||
| Sat., 1/16 | V Boys Ice Hockey | Guilford | Home - DiLungo Rink [Directions] | 12:00 p.m. | L 5-4 | |
| Sat., 1/16 | V Boys Indoor Track | H-K Invitational | Away | 10:00 a.m. | ||
| Sat., 1/16 | V Boys Indoor Track | HK Invitational | Away - Hill House | 10:00 a.m. | ||
| Sat., 1/16 | V Boys Indoor Track | HK Invitational | Away - Hill House | 10:00 a.m. | ||
| Sat., 1/16 | V Boys Swimming and Diving | Fairfield Prep | Away - Weston MS [Directions] | 10:30 a.m. | Loss 83-95 | |
| Sat., 1/16 | V Girls Ice Hockey | Lauralton Hall | Away [Directions] | 4:30 p.m. | W 7-0 | |
| Sat., 1/16 | V Girls Indoor Track | H-K Invitational | Away | 10:00 a.m. | ||
| Mon., 1/18 | FR Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 10:00 a.m. | ||
| Mon., 1/18 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Northford Ice Pavilion [Directions] | 12:45 p.m. | L 0-4 | |
| Tue., 1/19 | V Boys Swimming and Diving | Amity | Away - Orange Community Center Pool [Directions] | 7:15 p.m. | Loss 81-96 | |
| Wed., 1/20 | V Boys Ice Hockey | Milford Coop | Home - DiLungo Rink [Directions] | 6:00 p.m. | T 4-4 | |
| Wed., 1/20 | V Girls Ice Hockey | Hall/Conard | Home [Directions] | 6:00 p.m. | L 0-5 | |
| Fri., 1/22 | V Boys Basketball | Morgan | Away - Morgan HS [Directions] | 7:00 p.m. | W 68-38 | |
| Fri., 1/22 | JV Boys Basketball | Morgan | Away - Morgan HS [Directions] | 5:30 p.m. | ||
| Fri., 1/22 | V Boys Indoor Track | SLC League Meet #2 | Away - Hillhouse | 4:30 p.m. | ||
| Fri., 1/22 | V Girls Basketball | Morgan | Home - Old Saybrook HS [Directions] | 7:00 p.m. | L 15-53 | |
| Fri., 1/22 | JV Girls Basketball | Morgan | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Fri., 1/22 | V Girls Indoor Track | SLC League Meet #2 | Away - Hillhouse | 4:30 p.m. | ||
| Mon., 1/25 | V Boys Swimming and Diving | Lyman Hall | Away - Sheehan Pool [Directions] | 5:00 p.m. | Win 110-76 | |
| Tue., 1/26 | V Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 7:00 p.m. | W 64-40 | |
| Tue., 1/26 | JV Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 5:30 p.m. | ||
| Tue., 1/26 | V Girls Basketball | East Hampton | Home - Old Saybrook HS [Directions] | 7:00 p.m. | L 29-38 | |
| Tue., 1/26 | JV Girls Basketball | East Hampton | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Wed., 1/27 | FR Boys Basketball | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 7:00 p.m. | ||
| Wed., 1/27 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft-Mays Rink [Directions] | 8:00 p.m. | W 4-3 | |
| Wed., 1/27 | V Girls Ice Hockey | Simsbury | Home [Directions] | 6:00 p.m. | L 0-9 | |
| Thu., 1/28 | V Boys Swimming and Diving | Branford | Away - Walsh Intermediate School - pool [Directions] | 4:00 p.m. | Loss 86-97 | |
| Thu., 1/28 | V Girls Gymnastics | Valley Regional, Mercy, Daniel Hand | Away - Polson Gymnastics Gym/DHHS Campus [Directions] | 6:00 p.m. | 137.35 | |
| Fri., 1/29 | V Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 7:00 p.m. | L 43-48 | |
| Fri., 1/29 | JV Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 5:30 p.m. | ||
| Fri., 1/29 | V Girls Basketball | Cromwell | Home - Old Saybrook HS [Directions] | 7:00 p.m. | L 23-68 | |
| Fri., 1/29 | JV Girls Basketball | Cromwell | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Fri., 1/29 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Ice Rink [Directions] | 8:30 p.m. | L 0-5 | |
| Sat., 1/30 | V Boys Basketball | Coginchaug | Away - Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | L 47-62 | |
| Sat., 1/30 | JV Boys Basketball | Coginchaug | Away - Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Mon., 2/1 | V Boys Ice Hockey | Staples | Home - DiLungo Rink [Directions] | 6:00 p.m. | L 3-0 | |
| Tue., 2/2 | V Boys Basketball | North Branford | Home - Old Saybrook HS [Directions] | 7:00 p.m. | W 52-47 | |
| Tue., 2/2 | JV Boys Basketball | North Branford | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Tue., 2/2 | FR Boys Basketball | North Branford | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Tue., 2/2 | V Boys Swimming and Diving | Hamden | Away - HHS Pool [Directions] | 4:00 p.m. | Win 95-88 | |
| Tue., 2/2 | V Girls Basketball | North Branford | Away - North Branford HS [Directions] | 7:00 p.m. | W 38-35 | |
| Tue., 2/2 | JV Girls Basketball | North Branford | Away - North Branford HS [Directions] | 5:30 p.m. | ||
| Wed., 2/3 | FR Boys Basketball | Westbrook | Away - Westbrook HS [Directions] | 7:00 p.m. | ||
| Wed., 2/3 | V Boys Ice Hockey | Simsbury | Away - ISCC [Directions] | 7:00 p.m. | L 1-5 | |
| Wed., 2/3 | V Girls Ice Hockey | Branford | Home - Northford Ice Pavilion [Directions] | 5:45 p.m. | T 2-2 | |
| Sat., 2/6 | FR Boys Basketball | Coginchaug | Away - Maynard Stender Gymnasium @ CRHS [Directions] | 12:00 p.m. | ||
| Sat., 2/6 | V Boys Ice Hockey | Amity | Home - DiLungo Rink [Directions] | 1:00 p.m. | T 3-3 | Senior Night |
| Sat., 2/6 | V Boys Indoor Track | SLC Conference Championships | Away - Hillhouse | 10:00 a.m. | ||
| Sat., 2/6 | V Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | 7:00 p.m. | L 15-45 | |
| Sat., 2/6 | JV Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | 5:30 p.m. | ||
| Sat., 2/6 | V Girls Ice Hockey | Northwest Catholic | Away - Champions Skating Center, Cromwell [Directions] | 2:20 p.m. | W 4-3(OT) | |
| Sat., 2/6 | V Girls Indoor Track | SLC Conference Championships | Away - Hillhouse | 10:00 a.m. | ||
| Tue., 2/9 | V Boys Swimming and Diving | Milford Boys Swimming & Diving Team | Away - Foran HS [Directions] | 6:30 p.m. | Win 100-70 | |
| Tue., 2/9 | V Girls Basketball | Old Lyme | Home - Old Saybrook HS [Directions] | 7:00 p.m. | L 45-46 | |
| Tue., 2/9 | JV Girls Basketball | Old Lyme | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Wed., 2/10 | V Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 7:00 p.m. | L 42-57 | |
| Wed., 2/10 | JV Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Wed., 2/10 | FR Boys Basketball | Morgan | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Wed., 2/10 | V Boys Ice Hockey | Hamden | Home - DiLungo Rink [Directions] | 6:00 p.m. | W 5-4 | |
| Wed., 2/10 | V Girls Ice Hockey | West Haven/SHA | Away - Bennett Rink [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 2/11 | V Boys Basketball | East Hampton | Home - Old Saybrook HS [Directions] | 7:00 p.m. | W 59-38 | |
| Thu., 2/11 | JV Boys Basketball | East Hampton | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Thu., 2/11 | V Boys Swimming and Diving | Sheehan/Lyman Hall | Home - Madison Swim and Racquet Club [Directions] | 5:00 p.m. | Win 92-76 | |
| Fri., 2/12 | V Boys Indoor Track | Class S State Meet | Away - Hillhouse | 4:00 p.m. | ||
| Fri., 2/12 | V Girls Indoor Track | Class S State Meet | Away - Hillhouse | 4:00 p.m. | ||
| Sat., 2/13 | FR Boys Basketball | Portland | Home - Old Saybrook HS [Directions] | 10:30 a.m. | ||
| Sat., 2/13 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion [Directions] | 5:45 p.m. | L 3-6 | |
| Sat., 2/13 | V Girls Basketball | Plainfield | Home - Old Saybrook HS [Directions] | 1:30 p.m. | L 26-45 | |
| Sat., 2/13 | JV Girls Basketball | Plainfield | Home - Old Saybrook HS [Directions] | 12:00 p.m. | ||
| Sat., 2/13 | V Girls Ice Hockey | Guilford Coop | Home - Northford Ice Pavilion [Directions] | 4:40 p.m. | W 2-1 | |
| Mon., 2/15 | V Boys Ice Hockey | Norwich Free Academy | Away - Norwich Ice Rink [Directions] | 10:00 a.m. | W 7-1 | |
| Tue., 2/16 | V Boys Basketball | Westbrook | Away - Westbrook HS [Directions] | 7:00 p.m. | L 58-64 | |
| Tue., 2/16 | JV Boys Basketball | Westbrook | Away - Westbrook HS [Directions] | 5:30 p.m. | ||
| Tue., 2/16 | V Boys Swimming and Diving | HK-Valley | Away - Haddam Killingworth HS [Directions] | 4:00 p.m. | Win 83-75 | |
| Tue., 2/16 | V Girls Basketball | Westbrook | Home - Old Saybrook HS [Directions] | 7:00 p.m. | W 47-32 | |
| Tue., 2/16 | JV Girls Basketball | Westbrook | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Tue., 2/16 | V Girls Gymnastics | Valley Regional, Mercy | Away - Flip-Flop Gymnastics, Deep River [Directions] | 3:30 p.m. | 136.3 | |
| Tue., 2/16 | V Girls Ice Hockey | Hamden Coop | Away - Lou Astorino Ice Rink [Directions] | 12:00 p.m. | L 0-9 | |
| Wed., 2/17 | V Boys Basketball | Creed | Home - Old Saybrook HS [Directions] | 7:00 p.m. | L 50-62 | |
| Wed., 2/17 | JV Boys Basketball | Creed | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Wed., 2/17 | FR Boys Basketball | Creed | Home - Old Saybrook HS [Directions] | 4:00 p.m. | ||
| Wed., 2/17 | V Girls Basketball | Creed | Away - Truman School | 6:30 p.m. | W 35-31 | |
| Wed., 2/17 | JV Girls Basketball | Creed | Away - Truman School | 5:00 p.m. | ||
| Wed., 2/17 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | 4:15 p.m. | W 5-4(OT) | |
| Thu., 2/18 | FR Boys Basketball | Valley Regional | Away - Valley Regional HS [Directions] | 5:00 p.m. | ||
| Thu., 2/18 | V Girls Gymnastics | Valley Regional | Away - Flip Flop Gym [Directions] | 7:00 p.m. | 136.35 | |
| Sat., 2/20 | FR Boys Basketball | East Hampton | Home - Old Saybrook HS [Directions] | 10:00 a.m. | ||
| Sat., 2/20 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | 6:00 p.m. | W 6-0 | |
| Sat., 2/20 | V Boys Indoor Track | CT State Open Meet | Away - Hillhouse | 12:00 p.m. | ||
| Sat., 2/20 | V Girls Indoor Track | CT State Open Meet | Away - Hillhouse | 12:00 p.m. | ||
| Mon., 2/22 | V Boys Basketball | Hale Ray | Home - Old Saybrook HS [Directions] | 7:00 p.m. | W 54-33 | |
| Mon., 2/22 | JV Boys Basketball | Hale Ray | Home - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Mon., 2/22 | V Girls Ice Hockey | SCC Semi-Final | Away - West Haven | 5:00 p.m. | ||
| Wed., 2/24 | V Boys Basketball | Portland | Away - Portland HS [Directions] | 7:00 p.m. | W 70-44 | |
| Wed., 2/24 | JV Boys Basketball | Portland | Away - Portland HS [Directions] | 5:30 p.m. | ||
| Wed., 2/24 | FR Boys Basketball | Portland | Away - Portland HS [Directions] | 3:45 p.m. | ||
| Thu., 2/25 | JV Girls Ice Hockey | East Haven | Away - East Haven [Directions] | 7:30 p.m. | ||
| Fri., 2/26 | V Boys Indoor Track | New England Championships | Away - Boston, MA | 10:30 a.m. | ||
| Fri., 2/26 | V Girls Ice Hockey | SCC Finals | Away - West Haven | Cancelled | Cancelled | |
| Fri., 2/26 | V Girls Indoor Track | New England Championships | Away - Boston, MA | 10:30 a.m. | ||
| Sat., 2/27 | FR Boys Basketball | Valley Regional | Home - Old Saybrook HS [Directions] | 10:00 a.m. | ||
| Sat., 2/27 | V Boys Ice Hockey | Branford | Away - NORTHFORD ICE PAVILION [Directions] | 5:45 p.m. | W 5-3 | |
| Mon., 2/29 | V Boys Swimming and Diving | SCC Trials- Division II | Away - Hamden [Directions] | 4:00 p.m. | ||
| Tue., 3/1 | V Boys Swimming and Diving | SCC Diving | Away - Hamden | 5:30 p.m. | ||
| Wed., 3/2 | V Boys Ice Hockey | Staples (Scrim.) | Home - DiLungo Rink [Directions] | 6:40 p.m. | controlled practice | |
| Wed., 3/2 | V Boys Swimming and Diving | SCC Championships | Away - SCSU | 6:00 p.m. | ||
| Tue., 3/8 | V Boys Ice Hockey | Conard | Away - Veteran's Memorial Rink [Directions] | 8:00 p.m. | ||
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Fri., 3/11 | V Boys Ice Hockey | Branford | Away - Bennet Rink (west haven) [Directions] | 7:30 p.m. | ||
| Sat., 3/12 | V Boys Swimming and Diving | CIAC Class L Qualifying | Away - Kennedy HS [Directions] | 4:30 p.m. | ||
| Wed., 3/16 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Wesleyan Univ. [Directions] | 6:00 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Thu., 3/24 | V Baseball | St. Bernard (Scrim.) | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Thu., 3/24 | V Girls Lacrosse | Fitch (Scrim.) | Home - Old Saybrook HS Turf Field [Directions] | 3:30 p.m. | ||
| Sat., 3/26 | V Baseball | New London (Scrim.) | Home - Old Saybrook HS [Directions] | 12:00 p.m. | ||
| Sat., 3/26 | V Boys Lacrosse | St. Bernard-Wheeler (Scrim.) | Home - Old Saybrook HS Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 3/26 | V Softball | Branford (Scrim.) | Away - Branford HS-Softball Field [Directions] | 10:30 a.m. | ||
| Tue., 3/29 | V Girls Lacrosse | St. Bernard (Scrim.) | Home - Old Saybrook HS Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 3/29 | V Softball | Montville (Scrim.) | Home - Westbrook HS [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Baseball | Griswold (Scrim.) | Away - Griswold Baseball Field [Directions] | Cancelled | Cancelled | |
| Wed., 3/30 | V Baseball | Griswold (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Softball | Montville (Scrim.) | Home - Old Saybrook HS [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Girls Lacrosse | Mercy (Scrim.) | Away - Mercy [Directions] | 3:45 p.m. | ||
| Thu., 3/31 | V Softball | Wolcott (Scrim.) | Away - George Babcock Field, Wolcott HS [Directions] | 4:15 p.m. | ||
| Thu., 3/31 | V Girls Tennis | Mercy (Scrim.) | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Sat., 4/2 | V Boys Lacrosse | North Branford | Home - Old Saybrook HS Turf Field [Directions] | 2:00 p.m. | L 4-20 | |
| Sat., 4/2 | JV Boys Lacrosse | North Branford | Home - Old Saybrook HS [Directions] | 3:30 p.m. | ||
| Sat., 4/2 | V Boys Outdoor Track | Daniel Hand (Scrim.) | Home [Directions] | 10:00 a.m. | ||
| Sat., 4/2 | V Girls Outdoor Track | Daniel Hand (Scrim.) | Home - Old Saybrook HS Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 4/4 | V Softball | Haddam-Killingworth (Scrim.) | Away - Haddam Killingworth HS [Directions] | Cancelled | Cancelled | |
| Tue., 4/5 | V Girls Lacrosse | Waterford | Away - Alumni Turf Field [Directions] | 4:00 p.m. | W 12-10 | |
| Tue., 4/5 | JV Girls Lacrosse | Waterford | Away - Alumni Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 4/5 | V Softball | Wolcott Tech | Home - Westbrook HS [Directions] | 4:00 p.m. | W 11-1 | |
| Wed., 4/6 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | L 1-5 | |
| Wed., 4/6 | V Boys Outdoor Track | East Hampton, Valley Regional | Away - Valley Regional HS [Directions] | 3:45 p.m. | ||
| Wed., 4/6 | V Girls Outdoor Track | East Hampton, Valley Regional | Away - Valley Regional HS [Directions] | 3:45 p.m. | ||
| Wed., 4/6 | V Softball | Old Saybrook | Away - Old Saybrook HS [Directions] | 4:00 p.m. | W 17-2 | |
| Wed., 4/6 | V Softball | Westbrook/Old Saybrook | Home - Old Saybrook HS [Directions] | 4:00 p.m. | L 2-17 | |
| Wed., 4/6 | V Girls Tennis | Valley Regional | Away [Directions] | 3:45 p.m. | L 2-5 | |
| Fri., 4/8 | V Baseball | Portland | Away - Portland HS [Directions] | 3:45 p.m. | L 5-11 | |
| Fri., 4/8 | JV Baseball | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Fri., 4/8 | V Boys Lacrosse | Morgan | Home - Old Saybrook HS Turf Field [Directions] | 4:00 p.m. | L 2-14 | |
| Fri., 4/8 | JV Boys Lacrosse | Morgan | Away - Indian River Complex [Directions] | Cancelled | Cancelled | |
| Fri., 4/8 | V Boys Tennis | Coginchaug | Away - Tennis Courts @ CRHS [Directions] | 3:45 p.m. | W 6-1 | |
| Fri., 4/8 | V Softball | East Hampton | Home - Westbrook HS [Directions] | 4:00 p.m. | W 4-3 | |
| Fri., 4/8 | V Softball | Hale Ray | Away - Hale-Ray HS, Lou Milardo Field [Directions] | 4:00 p.m. | L 1-13 | |
| Fri., 4/8 | V Girls Tennis | Coginchaug | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 4-3 | |
| Sat., 4/9 | V Baseball | Old Lyme | Away - Old Lyme HS [Directions] | 2:00 p.m. | L 2-14 | |
| Sat., 4/9 | JV Baseball | Portland | Home - Old Saybrook HS [Directions] | 11:00 a.m. | ||
| Sat., 4/9 | V Boys Lacrosse | New Milford | Home - Old Saybrook HS Turf Field [Directions] | 1:00 p.m. | L 0-15 | |
| Sat., 4/9 | V Boys Outdoor Track | East Hampton Invitational | Away - East Hampton | 9:00 a.m. | ||
| Sat., 4/9 | V Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:30 p.m. | L 9-13 | |
| Sat., 4/9 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:00 p.m. | ||
| Sat., 4/9 | V Girls Outdoor Track | East Hampton Invitational | Away - East Hampton | 9:00 a.m. | ||
| Sat., 4/9 | JV Softball | Hale Ray | Home - Old Saybrook HS [Directions] | 11:00 a.m. | ||
| Sat., 4/9 | V Girls Tennis | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 1:00 p.m. | W 6-1 | |
| Mon., 4/11 | V Baseball | ValleyReg/Westbrook | Home - Old Saybrook HS [Directions] | 4:00 p.m. | L 0-13 | |
| Mon., 4/11 | V Boys Lacrosse | Cromwell | Home - Old Saybrook HS Turf Field [Directions] | 3:45 p.m. | L 3-5 | |
| Mon., 4/11 | V Boys Tennis | East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | W 6-1 | |
| Mon., 4/11 | V Girls Lacrosse | Morgan | Away - Indian River Complex [Directions] | 4:00 p.m. | W 18-11 | |
| Mon., 4/11 | JV Girls Lacrosse | Morgan | Away - Indian River Complex [Directions] | 5:30 p.m. | ||
| Mon., 4/11 | V Softball | East Hampton | Away - East Hampton HS [Directions] | 4:00 p.m. | L 3-16(6) | |
| Mon., 4/11 | V Softball | Old Lyme | Home - Westbrook HS [Directions] | 4:00 p.m. | W 17-0 | |
| Mon., 4/11 | V Girls Tennis | East Hampton | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 4/13 | V Baseball | Creed | Home - Old Saybrook HS [Directions] | 4:00 p.m. | W 12-0 | |
| Wed., 4/13 | V Boys Golf | Fishers Island (NY) | Home - Fenwick [Directions] | 3:00 p.m. | Old Saybrook 176 Fishers Island 230 | |
| Wed., 4/13 | V Boys Outdoor Track | Coginchaug, Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | ||
| Wed., 4/13 | V Boys Tennis | Old Lyme | Home - Old Saybrook HS [Directions] | 3:45 p.m. | L 3-4 | |
| Wed., 4/13 | V Girls Outdoor Track | Coginchaug, Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | ||
| Wed., 4/13 | V Softball | Portland | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 10-9 | |
| Wed., 4/13 | V Softball | Hale Ray | Away - Hale-Ray HS, Lou Milardo Field [Directions] | 4:00 p.m. | L 1-11 | |
| Thu., 4/14 | JV Baseball | Creed | Away - East Shore Athletic Complex | 4:00 p.m. | ||
| Thu., 4/14 | V Boys Lacrosse | Old Lyme | Away - Old Lyme HS [Directions] | 4:00 p.m. | L 5-20 | |
| Thu., 4/14 | V Girls Lacrosse | Old Lyme | Home - Old Saybrook HS Turf Field [Directions] | 3:45 p.m. | L 3-7 | |
| Thu., 4/14 | JV Girls Lacrosse | Old Lyme | Home - Old Saybrook HS Turf Field [Directions] | 5:15 p.m. | ||
| Fri., 4/15 | V Baseball | Westbrook | Away - Westbrook HS [Directions] | 4:00 p.m. | L 14-4 | |
| Fri., 4/15 | V Softball | Old Lyme | Home - Old Saybrook HS [Directions] | 4:00 p.m. | W 29-17 | |
| Fri., 4/15 | V Softball | Portland | Away - Nolan Field Maple Ave. off Airline Ave [Directions] | 4:00 p.m. | W 4-3 | |
| Sat., 4/16 | JV Baseball | Westbrook | Home - Old Saybrook HS [Directions] | 11:00 a.m. | ||
| Sat., 4/16 | V Girls Lacrosse | Weston | Home - Old Saybrook HS Turf Field [Directions] | 12:00 p.m. | W 8-7 | |
| Sat., 4/16 | JV Girls Lacrosse | Weston | Home - Old Saybrook HS Turf Field [Directions] | Cancelled | Cancelled | |
| Mon., 4/18 | V Baseball | Coginchaug | Home - Old Saybrook HS [Directions] | 3:45 p.m. | L 3-4 | |
| Mon., 4/18 | V Boys Tennis | Morgan | Home - Old Saybrook HS [Directions] | 10:30 a.m. | W 7-0 | |
| Mon., 4/18 | V Softball | Cromwell | Away - Cromwell HS [Directions] | 4:00 p.m. | L 1-7 | |
| Mon., 4/18 | V Girls Tennis | Morgan | Away - Morgan HS [Directions] | 10:30 a.m. | W 6-1 | |
| Tue., 4/19 | JV Baseball | Coginchaug | Away - Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 3:45 p.m. | ||
| Tue., 4/19 | JV Boys Lacrosse | Vinal-Goodwin | Away - Vinal Tech Field [Directions] | 3:45 p.m. | ||
| Tue., 4/19 | V Girls Lacrosse | Stonington | Home - Old Saybrook HS Turf Field [Directions] | 3:45 p.m. | W 10-6 | |
| Tue., 4/19 | JV Girls Lacrosse | Stonington | Home - Old Saybrook HS Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 4/19 | V Softball | Coginchaug | Away - Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 3:30 p.m. | L 0-21 | |
| Wed., 4/20 | V Baseball | Hale Ray | Home - Old Saybrook HS [Directions] | 4:00 p.m. | W 20-3 | |
| Wed., 4/20 | V Boys Tennis | Westbrook | Away - Westbrook HS [Directions] | 3:45 p.m. | W 6-1 | |
| Wed., 4/20 | V Softball | North Branford | Home - Old Saybrook HS [Directions] | 11:00 a.m. | L 1-13 | |
| Wed., 4/20 | V Softball | Coginchaug | Home - Westbrook HS [Directions] | 3:45 p.m. | L 1-9 | |
| Wed., 4/20 | V Girls Tennis | Westbrook | Home - Old Saybrook HS [Directions] | 11:00 a.m. | L 3-4 | |
| Thu., 4/21 | JV Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Boys Lacrosse | Valley Regional | Away - Valley Regional Hockey Field [Directions] | 4:00 p.m. | L 5-20 | |
| Thu., 4/21 | V Girls Lacrosse | Valley Regional | Home - Old Saybrook HS Turf Field [Directions] | 4:00 p.m. | W 14-4 | |
| Thu., 4/21 | JV Softball | North Branford | Away - Totoket Park [Directions] | 11:00 a.m. | ||
| Fri., 4/22 | V Boys Tennis | Cromwell | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 6-1 | |
| Fri., 4/22 | V Girls Lacrosse | North Branford | Away - North Branford HS [Directions] | 4:00 p.m. | W 7-6 | |
| Fri., 4/22 | JV Girls Lacrosse | North Branford | Away - North Branford HS [Directions] | Cancelled | Cancelled | |
| Fri., 4/22 | V Softball | Cromwell | Away - Cromwell HS [Directions] | 3:45 p.m. | L 2-14 | |
| Fri., 4/22 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 4:00 p.m. | L 0-10 | |
| Sat., 4/23 | V Baseball | Bacon Academy | Away - BA Baseball Field [Directions] | 11:00 a.m. | L 4-9 | |
| Sat., 4/23 | V Boys Outdoor Track | Plainfield | Away - Plainfield [Directions] | 9:00 a.m. | ||
| Sat., 4/23 | V Girls Outdoor Track | Panther Invite | Away - Plainfield | 9:00 a.m. | ||
| Mon., 4/25 | V Baseball | Morgan | Away - Indian River Complex [Directions] | 3:45 p.m. | L 2-13 | |
| Mon., 4/25 | V Boys Golf | Valley Regional | Away [Directions] | 3:00 p.m. | Old Saybrook 203 Valley Regional 225 | |
| Mon., 4/25 | V Boys Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS Turf Field [Directions] | 4:15 p.m. | L 6-19 | |
| Mon., 4/25 | V Boys Tennis | North Branford | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 7-0 | |
| Mon., 4/25 | V Softball | Morgan | Home - Old Saybrook HS [Directions] | 3:45 p.m. | L 6-11 | |
| Mon., 4/25 | V Softball | North Branford | Home - Westbrook HS [Directions] | 3:45 p.m. | L 0-11 | |
| Mon., 4/25 | V Girls Tennis | North Branford | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 6-1 | |
| Wed., 4/27 | V Baseball | East Hampton | Home - Old Saybrook HS [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 4/27 | V Boys Golf | North Branford | Home - Fenwick [Directions] | 3:00 p.m. | Old Saybrook 178 North Branford 206 | |
| Wed., 4/27 | V Boys Outdoor Track | Morgan, Old Lyme | Home - Old Saybrook HS Turf Field [Directions] | 3:30 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 4/27 | V Girls Outdoor Track | Morgan, Old Lyme | Home - Old Saybrook HS Turf Field [Directions] | 3:30 p.m. | ||
| Wed., 4/27 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | L 1-24 | |
| Wed., 4/27 | V Softball | Valley Regional | Away - Valley Regional HS [Directions] | 3:45 p.m. | W 10-4 | |
| Wed., 4/27 | V Girls Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | W 5-2 | |
| Thu., 4/28 | JV Baseball | East Hampton | Away - East Hampton HS [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Boys Lacrosse | North Branford | Away - Colafati Field - NBHS [Directions] | 6:00 p.m. | L 0-18 | |
| Thu., 4/28 | V Boys Tennis | Portland | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/28 | V Girls Lacrosse | North Branford | Home - Old Saybrook HS Turf Field [Directions] | 3:45 p.m. | W 17-8 | |
| Thu., 4/28 | JV Girls Lacrosse | North Branford | Home - Old Saybrook HS Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 4/28 | JV Softball | Haddam-Killingworth | Home - Old Saybrook HS [Directions] | Cancelled | Cancelled | |
| Thu., 4/28 | V Girls Tennis | Portland | Away - Portland HS [Directions] | 3:45 p.m. | W 5-2 | |
| Fri., 4/29 | V Baseball | Cromwell | Home - Old Saybrook HS [Directions] | 4:00 p.m. | L 8-11 | |
| Fri., 4/29 | V Boys Golf | East Hampton | Away - Black Birch Country Club [Directions] | 3:00 p.m. | Old Saybrook 189 East Hampton 216 | |
| Fri., 4/29 | V Boys Outdoor Track | Stafford Relays | Away - Stafford | 4:00 p.m. | ||
| Fri., 4/29 | V Boys Tennis | Portland | Away - Portland HS [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 4/29 | V Girls Outdoor Track | Stafford Relays | Away - Stafford | 4:00 p.m. | ||
| Fri., 4/29 | V Softball | Morgan | Home - Westbrook HS [Directions] | 3:45 p.m. | L 1-13 | |
| Fri., 4/29 | V Softball | Valley Regional | Home - Old Saybrook HS [Directions] | 4:00 p.m. | L 1-14 | |
| Sat., 4/30 | JV Baseball | Old Lyme | Home - Old Saybrook HS [Directions] | 11:00 a.m. | ||
| Sat., 4/30 | V Boys Lacrosse | Montville | Away - Montville Turf Field [Directions] | 11:00 a.m. | L 9-11 | |
| Sat., 4/30 | JV Boys Lacrosse | Montville | Away - Montville Turf Field [Directions] | 12:30 p.m. | ||
| Sat., 4/30 | V Girls Lacrosse | Branford | Home - Old Saybrook HS Turf Field [Directions] | 12:00 p.m. | L 7-12 | |
| Sat., 4/30 | JV Girls Lacrosse | Branford | Home - Old Saybrook HS Turf Field [Directions] | 1:30 p.m. | ||
| Mon., 5/2 | V Baseball | North Branford | Away - North Branford HS [Directions] | 4:00 p.m. | L 1-7 | |
| Mon., 5/2 | V Boys Golf | St. Bernard | Home - Fenwick [Directions] | 3:00 p.m. | Old Saybrook 177 St. Bernard's No Score | |
| Mon., 5/2 | V Boys Tennis | Valley Regional | Away [Directions] | 3:45 p.m. | W 5-2 | |
| Mon., 5/2 | V Softball | Hale Ray | Home - Westbrook HS [Directions] | 4:00 p.m. | L 1-7 | |
| Mon., 5/2 | V Girls Tennis | Valley Regional | Home - Old Saybrook HS [Directions] | 3:45 p.m. | L 2-5 | |
| Tue., 5/3 | V Boys Golf | Hale Ray | Away [Directions] | 3:00 p.m. | Old Saybrook 185 Hale Ray 217 | |
| Tue., 5/3 | V Boys Lacrosse | Morgan | Away - Indian River [Directions] | 4:00 p.m. | L 1-16 | |
| Tue., 5/3 | V Boys Outdoor Track | Westbrook, Hale Ray, Creed | Away - Westbrook [Directions] | 3:30 p.m. | ||
| Tue., 5/3 | V Girls Lacrosse | Morgan | Home - Old Saybrook HS Turf Field [Directions] | 4:00 p.m. | L 10-11 | |
| Tue., 5/3 | JV Girls Lacrosse | Morgan | Home - Old Saybrook HS Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 5/3 | V Girls Outdoor Track | Westbrook, Hale Ray, Creed | Away - Westbrook [Directions] | 3:30 p.m. | ||
| Wed., 5/4 | V Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | 4:00 p.m. | W 11-0 | |
| Wed., 5/4 | V Boys Golf | Coginchaug | Home - Fenwick [Directions] | 3:00 p.m. | Coginchaug 183 Old Saybrook 184 | |
| Wed., 5/4 | V Girls Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 4:00 p.m. | L 11-16 | |
| Wed., 5/4 | JV Girls Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Thu., 5/5 | JV Baseball | Hale Ray | Home - Old Saybrook HS [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Boys Lacrosse | Cromwell | Away - Cromwell HS [Directions] | 3:45 p.m. | L 8-10 | |
| Thu., 5/5 | JV Softball | Valley Regional | Away - Valley Regional HS [Directions] | 4:00 p.m. | ||
| Fri., 5/6 | V Boys Golf | Wheeler | Away - Stonington Country Club [Directions] | 3:00 p.m. | Old Saybrook 183 Wheeler 194 | |
| Sat., 5/7 | V Boys Outdoor Track | Coginchaug Relays | Away - Coginchaug | 1:30 p.m. | ||
| Sat., 5/7 | V Girls Lacrosse | Ellington | Away - Ellington HS [Directions] | 2:00 p.m. | W 12-9 | |
| Sat., 5/7 | JV Girls Lacrosse | Ellington | Away - Ellington HS [Directions] | 3:30 p.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Coginchaug Relays | Away - Coginchaug | 1:30 p.m. | ||
| Mon., 5/9 | V Baseball | East Hampton | Away - East Hampton HS [Directions] | 4:00 p.m. | W 1-0 | |
| Mon., 5/9 | V Boys Golf | Old Lyme | Home - Fenwick [Directions] | 3:00 p.m. | Old Lyme 164 Old Saybrook 183 | |
| Mon., 5/9 | V Boys Lacrosse | Old Lyme | Home - Old Saybrook HS Turf Field [Directions] | 3:45 p.m. | L 3-16 | |
| Mon., 5/9 | V Boys Tennis | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | W 4-3 | |
| Mon., 5/9 | V Softball | East Hampton | Away - East Hampton HS [Directions] | 4:00 p.m. | W 4-3 | |
| Mon., 5/9 | V Softball | Hale Ray | Home - Old Saybrook HS [Directions] | 4:00 p.m. | L 2-26 | |
| Mon., 5/9 | V Girls Tennis | Old Lyme | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 5/10 | JV Baseball | East Hampton | Home - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Tue., 5/10 | V Boys Golf | Morgan | Away - CCC [Directions] | 3:00 p.m. | Morgan 169 Old Saybrook 189 | |
| Tue., 5/10 | V Boys Outdoor Track | Hale Ray, Cromwell, Portland | Home - Old Saybrook HS Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 5/10 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | W 4-3 | |
| Tue., 5/10 | V Girls Lacrosse | Old Lyme | Away - Old Lyme HS [Directions] | 4:00 p.m. | L 8-13 | |
| Tue., 5/10 | JV Girls Lacrosse | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Tue., 5/10 | V Girls Outdoor Track | Hale Ray, Cromwell, Portland | Home - Old Saybrook HS Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 5/10 | V Softball | Portland | Home - Westbrook HS [Directions] | 4:00 p.m. | W 5-4 | |
| Tue., 5/10 | JV Softball | Hale Ray | Away - Hale-Ray HS, Lou Milardo Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Baseball | Old Lyme | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 4-3 | |
| Wed., 5/11 | V Boys Golf | Fisher's Island Tournament | Away | 3:00 p.m. | ||
| Wed., 5/11 | V Softball | Westbrook/Old Saybrook | Away - Westbrook HS [Directions] | 4:00 p.m. | L 7-11 | |
| Wed., 5/11 | V Softball | Old Saybrook | Home - Westbrook HS [Directions] | 4:00 p.m. | W 11-7 | |
| Thu., 5/12 | JV Baseball | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | ||
| Thu., 5/12 | V Boys Tennis | Valley Regional | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 5/12 | V Softball | Portland | Away - Nolan Field Maple Ave. off Airline Ave [Directions] | 3:30 p.m. | L 6-7 | |
| Thu., 5/12 | V Softball | Old Lyme | Away - Old Lyme HS [Directions] | 4:00 p.m. | W 22-3 | share bus with JV Baseball to EH after OLHS drop |
| Thu., 5/12 | V Girls Tennis | Cromwell | Away - Cromwell HS [Directions] | 3:45 p.m. | L 3-4 | |
| Sat., 5/14 | V Boys Lacrosse | Bristol Central | Away - Bristol Central HS [Directions] | 12:00 p.m. | L 7-14 | |
| Sat., 5/14 | JV Boys Lacrosse | Bristol Central | Away - Bristol Central HS [Directions] | 1:30 p.m. | ||
| Sat., 5/14 | V Boys Outdoor Track | Runnin' Rams Invitational | Home - Old Saybrook HS Turf Field [Directions] | 8:30 a.m. | ||
| Sat., 5/14 | V Boys Tennis | Morgan | Away - Morgan HS [Directions] | 10:30 a.m.. | W 7-0 | |
| Sat., 5/14 | V Girls Outdoor Track | Runnin' Rams Invitational | Home - Old Saybrook HS Turf Field [Directions] | 8:30 a.m. | ||
| Sun., 5/15 | V Baseball | Portland | Home - Old Saybrook HS [Directions] | 1:00 p.m. | W 9-5 | |
| Mon., 5/16 | V Baseball | Westbrook | Home - Old Saybrook HS [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 5/16 | V Boys Golf | North Branford | Away - Indian Springs [Directions] | 3:00 p.m. | Old Saybrook 177 North Branford 203 | Non-League Match |
| Mon., 5/16 | V Boys Tennis | Westbrook | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 7-0 | |
| Mon., 5/16 | V Girls Lacrosse | Valley Regional | Away - Valley Regional Hockey Field [Directions] | 5:30 p.m. | W 16-6 | |
| Mon., 5/16 | V Softball | Old Lyme | Away - Old Lyme HS [Directions] | 4:00 p.m. | L 19-20 | |
| Mon., 5/16 | V Girls Tennis | Westbrook | Away - Westbrook HS [Directions] | 3:45 p.m. | W 4-3 | |
| Tue., 5/17 | JV Baseball | Westbrook | Away - Westbrook HS [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Boys Golf | Portland | Home - Fenwick [Directions] | 3:00 p.m. | Portland 159 Old Saybrook 178 | |
| Tue., 5/17 | V Boys Lacrosse | Valley Regional | Home - Old Saybrook HS Turf Field [Directions] | 4:00 p.m. | L 6-11 | |
| Tue., 5/17 | V Boys Outdoor Track | North Branford, Haddam-Killingworth | Away - Haddam-Killingworth HS [Directions] | 3:45 p.m. | ||
| Tue., 5/17 | V Boys Tennis | East Hampton | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 5/17 | V Girls Outdoor Track | North Branford, Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Tue., 5/17 | V Softball | East Hampton | Home - Old Saybrook HS [Directions] | 4:00 p.m. | L 11-13 | |
| Tue., 5/17 | V Girls Tennis | East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/18 | V Boys Golf | Old Lyme | Away - Black Hall Club Old Lyme [Directions] | 3:00 p.m. | Old Lyme 168 Old Saybrook 188 | |
| Wed., 5/18 | V Boys Tennis | Cromwell | Away - Old Saybrook HS [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/18 | V Softball | Wilbur Cross | Away - Blake Field I [Directions] | 4:00 p.m. | W 16-1 | |
| Wed., 5/18 | V Softball | Wheeler | Home - Old Saybrook HS [Directions] | 4:00 p.m. | L 3-12 | |
| Wed., 5/18 | V Girls Tennis | Cromwell | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 4-3 | |
| Thu., 5/19 | JV Baseball | Creed | Home - Old Saybrook HS [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Boys Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 4:00 p.m. | L 2-17 | |
| Thu., 5/19 | V Boys Outdoor Track | Warrior Invitational | Away | 3:30 p.m. | ||
| Thu., 5/19 | V Girls Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS Turf Field [Directions] | 4:00 p.m. | W 17-15 | |
| Thu., 5/19 | JV Girls Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 5/19 | V Girls Outdoor Track | Warrior Invitational | Away - Valley Regional | 3:30 p.m. | ||
| Thu., 5/19 | V Softball | West Haven | Home - Old Saybrook HS [Directions] | 4:00 p.m. | L 0-16 | |
| Thu., 5/19 | V Girls Tennis | Portland | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 6-1 | |
| Fri., 5/20 | JV Baseball | ValleyReg/Westbrook | Away - Valley Regional HS [Directions] | 3:45 p.m. | ||
| Fri., 5/20 | V Boys Golf | Haddam-Killingworth | Home - Fenwick [Directions] | 3:00 p.m. | Old Saybrook 175 HK 183 | |
| Fri., 5/20 | V Boys Tennis | North Branford | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 5/20 | V Girls Tennis | North Branford | Home - Old Saybrook HS [Directions] | 3:45 p.m. | W 6-1 | |
| Sat., 5/21 | V Baseball | Creed | Away - East Shore Athletic Complex | 11:00 a.m. | W 14-1 | |
| Sat., 5/21 | V Girls Tennis | Morgan | Home - Old Saybrook HS [Directions] | 10:30 a.m.. | W 6-1 | |
| Mon., 5/23 | V Baseball | St. Bernard | Home - Old Saybrook HS [Directions] | 3:45 p.m. | L 2-4 | |
| Mon., 5/23 | V Boys Tennis | Coginchaug | Home - Old Saybrook HS [Directions] | 4:15 p.m. | W 6-1 | |
| Mon., 5/23 | V Softball | Hillhouse | Home - Westbrook HS [Directions] | 4:00 p.m. | W 18-0 | |
| Mon., 5/23 | V Softball | Ledyard | Home - Old Saybrook HS [Directions] | 4:00 p.m. | L 0-14 | |
| Mon., 5/23 | V Girls Tennis | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 5/24 | JV Baseball | North Branford | Home - Old Saybrook HS [Directions] | Cancelled | Cancelled | |
| Tue., 5/24 | V Boys Golf | Cromwell | Home - Fenwick [Directions] | 3:00 p.m. | Morgan 156 Cromwell 167 Old Saybrook 174 | |
| Tue., 5/24 | V Boys Lacrosse | Rockville | Away - Rockville H.S. [Directions] | 5:30 p.m. | L 7-11 | |
| Tue., 5/24 | V Girls Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/24 | V Girls Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/24 | V Softball | St. Bernard | Home - Old Saybrook HS [Directions] | Cancelled | Cancelled | |
| Tue., 5/24 | V Softball | Windsor Locks | Away - Windsor Locks HS [Directions] | 4:30 p.m. | L 5-8 | |
| Tue., 5/24 | V Girls Tennis | Coginchaug | Away - Tennis Courts @ CRHS [Directions] | 2:30 p.m. | W 4-3 | |
| Wed., 5/25 | V Boys Golf | Wheeler | Home - Fenwick [Directions] | 3:00 p.m. | Old Saybrook 162 Wheeler 205 | |
| Wed., 5/25 | V Boys Outdoor Track | Shoreline Championships | Away - Hyde Leadership | 2:30 p.m. | ||
| Wed., 5/25 | V Girls Outdoor Track | Shoreline Championships | Away - Hyde Leadership | 2:30 p.m. | ||
| Thu., 5/26 | V Softball | Morgan | Away - Peters Complex [Directions] | 4:00 p.m. | SLC Softball Quarterfinals | |
| Tue., 5/31 | V Softball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:30 p.m. | L 1-9 | |
| Thu., 6/2 | V Boys Outdoor Track | Class S State Meet | Away - New Britain | 2:00 p.m. | ||
| Thu., 6/2 | V Girls Outdoor Track | Class S State Meet | Away - New Britain | 2:00 p.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | State Open Meet | Away - New Britain | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | State Open Meet | Away - New Britain | 1:30 p.m.m | ||
| Sat., 6/11 | V Boys Outdoor Track | New Englands | Away - New Britain | 9:00 a.m. | ||
| Sat., 6/11 | V Girls Outdoor Track | New Englands | Away | 9:00 a.m. | ||