| Old Saybrook 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 604 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 8/28 | V Football | Bristol Eastern, New Britain, Newington (Scrim.) | Away - Bristol Eastern HS-Alumni Field-Turf [Directions] | 9:00 a.m. | ||
| Mon., 8/30 | JV Boys Soccer | Morgan (Scrim.) | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 10:00 a.m. | ||
| Wed., 9/1 | V Football | St. Paul Catholic (Scrim.) | Away - St. Paul Catholic HS-McPhee Field / Stadium Field [Directions] | Canceled | Cancelled | |
| Wed., 9/1 | V Girls Soccer | Bacon Academy (Scrim.) | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:00 p.m. | ||
| Thu., 9/2 | V Football | East Haven (Scrim.) | Away - East Haven HS-EHHS Turf Field & Track [Directions] | 3:30 p.m. | ||
| Fri., 9/3 | V Boys Soccer | TBA, Jonathan Law, Litchfield, Masuk, Montville, Northwestern, Wilton | Away - Not Listed-Kelley Martin Tighe Memorial Field | 4:00 p.m. | ||
| Sat., 9/4 | V Boys Cross Country | Old Lyme (Scrim.) | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 9:30 a.m. | ||
| Sat., 9/4 | V Girls Cross Country | Old Lyme (Scrim.) | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 9:30 a.m. | ||
| Sat., 9/4 | V Field Hockey | Field Hockey Pre-Season Play Day | Away - Farmington HS-Turf Field | 10:00 a.m. | ||
| Sat., 9/4 | V Girls Soccer | Bacon Academy, Chariho (RI), Ledyard (Scrim.) | Away - Bacon Academy-Football/Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 9/4 | V Girls Soccer | Bacon Academy, Chariho (RI), Ledyard | Away - Bacon Academy-Football/Soccer Field [Directions] | 11:45 a.m. | ||
| Sat., 9/4 | V Girls Soccer | Bacon Academy, Chariho (RI), Ledyard | Away - Bacon Academy-Football/Soccer Field [Directions] | 1:30 p.m. | ||
| Wed., 9/8 | JV Girls Soccer | Montville (Scrim.) | Away - Montville HS-Grass Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/10 | V Football | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | 6:30 p.m. | L 22-27 | |
| Fri., 9/10 | V Football | Cromwell/Portland | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | L 8-36 | |
| Fri., 9/10 | V Boys Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 3:45 p.m. | W 3-1 | |
| Fri., 9/10 | JV Boys Soccer | East Hampton | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | Postponed | ||
| Fri., 9/10 | V Field Hockey | Waterford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 4-0 | |
| Fri., 9/10 | JV Field Hockey | Waterford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | W 4-0 | |
| Fri., 9/10 | V Girls Soccer | East Hampton | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:45 p.m. | W 6-0 | |
| Fri., 9/10 | V Girls Swimming and Diving | Windsor Locks/Ellington/E.Granby/E.Windsor | Home - Lyme-Old Lyme HS-East Lyme High School [Directions] | 4:00 p.m. | ||
| Sat., 9/11 | JV Football | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | Canceled | Cancelled | |
| Sat., 9/11 | JV Football | Cromwell/Portland | Away - Pierson Park, Cromwell [Directions] | Canceled | Cancelled | |
| Sat., 9/11 | V Field Hockey | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 10:00 a.m. | W 1-0 | |
| Sat., 9/11 | JV Field Hockey | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:30 a.m. | W 10-4 | |
| Mon., 9/13 | V Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 p.m. | W 2-1 | |
| Tue., 9/14 | V Boys Cross Country | Morgan, Old Lyme, Valley Regional | Away - Indian River Complex-XC Course [Directions] | 3:45 p.m. | ||
| Tue., 9/14 | V Girls Cross Country | Morgan, Old Lyme, Valley Regional | Away - Indian River Complex-XC Course [Directions] | 3:45 p.m. | ||
| Tue., 9/14 | V Girls Soccer | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | L 0-1 | |
| Wed., 9/15 | V Field Hockey | Suffield | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 4-1 | |
| Wed., 9/15 | JV Field Hockey | Suffield | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:30 p.m. | L 0-1 | |
| Wed., 9/15 | JV Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 p.m. | ||
| Thu., 9/16 | JV Boys Soccer | East Hampton | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:45 p.m. | ||
| Thu., 9/16 | V Field Hockey | East Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 2-1 | |
| Thu., 9/16 | JV Field Hockey | East Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:15 p.m. | W 2-0 | |
| Thu., 9/16 | V Girls Soccer | North Branford/Hale Ray | Away - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | W 6-0 | |
| Fri., 9/17 | V Football | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | 6:30 p.m. | W 36-22 | |
| Fri., 9/17 | V Girls Swimming and Diving | Guilford | Away - Guilford HS-Branford YMCA [Directions] | 3:30 p.m. | ||
| Sat., 9/18 | V Boys Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 8:30 a.m. | ||
| Sat., 9/18 | V Football | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | ||
| Sat., 9/18 | JV Football | Haddam-Killingworth | Home - Peters Complex-Football Field [Directions] | 10:30 a.m. | ||
| Sat., 9/18 | V Girls Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 8:30 a.m. | ||
| Sat., 9/18 | V Girls Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 8:30 a.m. | ||
| Sat., 9/18 | V Field Hockey | Fitch | Away - Groton MS-Groton Middle School-Turf Feld [Directions] | 11:00 a.m. | W 3-0 | |
| Sat., 9/18 | JV Field Hockey | Fitch | Away - Groton MS-Groton Middle School-Turf Feld [Directions] | 9:00 a.m. | W 2-1 | |
| Mon., 9/20 | JV Football | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | Canceled | Cancelled | |
| Mon., 9/20 | V Boys Soccer | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 4-1 | |
| Mon., 9/20 | V Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | W 2-1 | |
| Mon., 9/20 | JV Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 5:15 p.m. | T 1-1 | |
| Mon., 9/20 | JV Girls Soccer | Old Lyme | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:45 p.m. | ||
| Tue., 9/21 | JV Boys Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Middle Field [Directions] | 3:45 p.m. | ||
| Tue., 9/21 | V Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:45 p.m. | T 0-0 | |
| Tue., 9/21 | V Girls Swimming and Diving | Ledyard/St. Bernard | Away - Ledyard HS-Vitale Aquatic [Directions] | 3:30 p.m. | ||
| Wed., 9/22 | V Boys Cross Country | Coginchaug - Going to the Sun Cross Country Meet | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:15 p.m. | ||||||
| Wed., 9/22 | V Girls Cross Country | Coginchaug - Going to the Sun Cross Country Meet | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:30 p.m. | ||
| Thu., 9/23 | V Boys Soccer | Hale Ray | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:45 p.m. | W 3-0 | |
| Thu., 9/23 | V Field Hockey | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | T 2-2 | |
| Thu., 9/23 | JV Field Hockey | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | L 0-2 | |
| Thu., 9/23 | V Girls Swimming and Diving | Fitch/Stonington/Wheeler/NL | Away - UCONN Avery Point-Pool [Directions] | 3:45 p.m. | ||
| Fri., 9/24 | V Girls Soccer | Hale Ray | Away - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 4:00 p.m. | W Forfeit | |
| Sat., 9/25 | V Football | Coginchaug/Hale Ray/East Hampton | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | L 0-40 | |
| Sat., 9/25 | V Football | CREC Coop | Home - Peters Complex-Football Field [Directions] | 1:00 p.m. | W 54-6 | Game will be continued from the point of interruption |
| Sat., 9/25 | JV Football | CREC Coop | Away - Civic Leadership HS-Civic Leadership Turf Field [Directions] | Canceled | Cancelled | |
| Mon., 9/27 | JV Football | Coginchaug/Hale Ray/East Hampton | Away - Coginchaug Regional HS-Brookside Field [Directions] | 4:00 p.m. | ||
| Mon., 9/27 | V Boys Soccer | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:45 p.m. | W 4-3 | |
| Mon., 9/27 | V Field Hockey | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 3:45 p.m. | L 1-2 | |
| Mon., 9/27 | JV Field Hockey | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 5:15 p.m. | L 0-1 | |
| Mon., 9/27 | JV Girls Soccer | St. Bernard | Away - St. Bernard School-Upper Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/28 | V Boys Cross Country | LEAGUE MEET #1 Small Schools | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:30 p.m. | ||
| Tue., 9/28 | V Girls Cross Country | LEAGUE MEET #1 Small Schools | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:30 p.m. | ||
| Tue., 9/28 | V Girls Soccer | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | L 2-1 | |
| Tue., 9/28 | V Girls Swimming and Diving | Waterford | Away - Waterford HS-Pool - WHS [Directions] | 3:45 p.m. | ||
| Wed., 9/29 | JV Girls Soccer | Valley Regional | Away - Valley Regional HS-JV Girls Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 9/30 | V Boys Soccer | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | T 1-1 | |
| Thu., 9/30 | V Field Hockey | Westbrook/Old Lyme Coop | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 10/1 | V Football | Valley Regional/Old Lyme | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | W 20-15 | |
| Fri., 10/1 | JV Boys Soccer | Morgan | Away - Morgan School-Soccer/Lax Field [Directions] | 3:45 p.m. | ||
| Fri., 10/1 | V Girls Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 3:45 p.m. | L 0-1 | |
| Fri., 10/1 | JV Girls Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 5:15 p.m. | ||
| Sat., 10/2 | V Football | CREC Coop | Away - Civic Leadership HS-Civic Leadership Turf Field [Directions] | 11:00 a.m. | L 6-20 | |
| Sat., 10/2 | JV Football | Valley Regional/Old Lyme | Away - Valley Regional HS-Practice Football Field [Directions] | 10:00 a.m. | ||
| Sat., 10/2 | V Boys Soccer | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 4:00 p.m. | W 3-2 | |
| Sat., 10/2 | JV Boys Soccer | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | Canceled | Cancelled | |
| Mon., 10/4 | JV Football | CREC Coop | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 10/5 | ||||||
| Mon., 10/4 | V Field Hockey | Morgan | Away - Indian River Complex-Turf Field [Directions] | 4:45 p.m. | W 3-0 | |
| Mon., 10/4 | JV Field Hockey | Morgan | Away - Indian River Complex-Turf Field [Directions] | 3:45 p.m. | W 3-0 | |
| Tue., 10/5 | V Boys Cross Country | North Branford, Haddam-Killingworth, Old Lyme, Morgan, Valley Regional | Away - Totoket Valley Park - North Branford-Totoket Park - North Branford | 3:30 p.m. | ||
| Tue., 10/5 | V Boys Soccer | Portland | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 4:30 p.m. | W 2-1 | |
| Tue., 10/5 | V | Shoreline Conference Unified Soccer Tournament | Away - Cromwell HS-Soccer field 2 | 3:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Westbrook HS | ||||||
| Tue., 10/5 | V Girls Cross Country | North Branford, Haddam-Killingworth, Old Lyme, Morgan, Valley Regional | Away - Totoket Valley Park - North Branford-Totoket Park - North Branford | 3:30 p.m. | ||
| Thu., 10/7 | V Field Hockey | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 4-0 | |
| Thu., 10/7 | JV Field Hockey | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | ||
| Thu., 10/7 | V Girls Soccer | Westbrook | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:45 p.m. | W 4-1 | |
| Thu., 10/7 | V Girls Swimming and Diving | Suffield | Away - Windsor Locks HS-Pool- No diving [Directions] | 4:00 p.m. | ||
| Fri., 10/8 | V Boys Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | W 5-0 | |
| Fri., 10/8 | V Girls Soccer | Norwich Free Academy | Away - Norwich Free Academy-Turf [Directions] | 7:00 p.m. | T 0-0 | |
| Fri., 10/8 | JV Girls Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | ||
| Sat., 10/9 | JV Football | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 10:00 a.m. | ||
| Sat., 10/9 | JV Boys Soccer | Westbrook | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | ||
| Mon., 10/11 | V Boys Soccer | Norwich Free Academy | Away - Norwich Free Academy-Turf Field [Directions] | 10:00 a.m. | W 3-0 | |
| Mon., 10/11 | V Field Hockey | North Branford | Away - North Branford HS-NBHS Back Field [Directions] | 10:00 a.m. | L 0-3 | |
| Mon., 10/11 | JV Field Hockey | North Branford | Away - North Branford HS-NBHS Back Field [Directions] | 11:15 a.m. | ||
| Mon., 10/11 | V Girls Soccer | North Branford/Hale Ray | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 10:00 a.m. | W 7-0 | |
| Tue., 10/12 | V Girls Swimming and Diving | Norwich Free Academy | Away - UCONN Avery Point-Pool [Directions] | 7:00 p.m. | ||
| Wed., 10/13 | V Boys Soccer | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | W 7-0 | |
| Thu., 10/14 | V Boys Cross Country | SLC Mega Meet | Away - East Hampton HS-Cross Country Course | 2:30 p.m. | ||
| Thu., 10/14 | V Girls Cross Country | Shoreline Conference Mega Meet | Away - East Hampton HS-Cross Country Course | 3:30 p.m. | ||
| Thu., 10/14 | V Field Hockey | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | L 0-1 | |
| Thu., 10/14 | JV Field Hockey | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | ||
| Thu., 10/14 | V Girls Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 6:00 p.m. | T 1-1 | |
| Thu., 10/14 | V Girls Swimming and Diving | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Pool - no diving [Directions] | 4:00 p.m. | ||
| Fri., 10/15 | V Boys Soccer | Coginchaug | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 6-1 | |
| Fri., 10/15 | V Girls Soccer | East Lyme | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:45 p.m. | L 0-3 | |
| Sat., 10/16 | V Football | Gilbert/Northwestern/Housy | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | L 0-42 | |
| Sat., 10/16 | V Football | SMSA Coop | Away - Hartford Public HS-Turf field [Directions] | 12:00 p.m. | W 44-42 | |
| Sat., 10/16 | V Boys Soccer | East Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:00 p.m. | W 2-0 | |
| Mon., 10/18 | JV Football | SMSA Coop | Home - Peters Complex-Football Field [Directions] | Canceled | Cancelled | |
| Mon., 10/18 | JV Football | Gilbert/Northwestern/Housy | Away - Gilbert School-Football Field [Directions] | 4:00 p.m. | ||
| Mon., 10/18 | V Field Hockey | Westbrook/Old Lyme Coop | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 2-0 | |
| Tue., 10/19 | V Boys Soccer | Cromwell | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 10/19 | V Girls Soccer | Cromwell | Away - Cromwell HS-Main field [Directions] | 3:45 p.m. | T 1-1 | |
| Tue., 10/19 | V Girls Swimming and Diving | Windsor Locks/Ellington/E.Granby/E.Windsor | Away - Windsor Locks HS-Pool- No diving [Directions] | 5:00 p.m. | ||
| Wed., 10/20 | JV Boys Soccer | Cromwell | Away - Cromwell HS-soccer field 1 [Directions] | 3:45 p.m. | ||
| Wed., 10/20 | JV Girls Soccer | St. Bernard | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Thu., 10/21 | V Boys Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 7:00 p.m. | T 1-1 | |
| Thu., 10/21 | V Girls Soccer | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:30 p.m. | T 0-0 | |
| Thu., 10/21 | JV Girls Soccer | Morgan | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 4:00 p.m. | ||
| Fri., 10/22 | V Football | Cromwell/Portland | Away - Pierson Park, Cromwell [Directions] | 6:00 p.m. | L 8-52 | |
| Fri., 10/22 | V Football | Coginchaug/Hale Ray/East Hampton | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | W 50-20 | |
| Fri., 10/22 | V Girls Swimming and Diving | Haddam-Killingworth | Home - East Lyme HS-East Lyme Aquatics Center [Directions] | 3:30 p.m. | ||
| Sat., 10/23 | V Boys Cross Country | Shoreline Cross Country Championship | Away - East Hampton HS-Cross Country Course | 10:45 a.m. | ||
| Sat., 10/23 | JV Football | Cromwell/Portland | Home - Old Saybrook HS-Old Saybrook HS Back Field [Directions] | 11:00 a.m. | ||
| Sat., 10/23 | JV Football | Coginchaug/Hale Ray/East Hampton | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 11:00 a.m. | ||
| Sat., 10/23 | V Boys Soccer | Valley Regional | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 11:00 a.m. | W 5-3 | |
| Sat., 10/23 | V Girls Cross Country | Shoreline Cross Country Championship | Away - East Hampton HS-Cross Country Course | 10:00 a.m. | ||
| Sat., 10/23 | V Field Hockey | Norwich Free Academy | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 2:00 p.m. | W 4-0 | |
| Sat., 10/23 | JV Field Hockey | Norwich Free Academy | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:30 p.m. | ||
| Mon., 10/25 | JV Boys Soccer | Valley Regional | Away - Valley Regional HS-JV Boys Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 10/25 | V Girls Soccer | Wheeler | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 2-1 | |
| Tue., 10/26 | V Boys Cross Country | Frosh/Soph Invitational | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 10/27 | ||||||
| Tue., 10/26 | V Girls Cross Country | Frosh/Soph Invitational | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 10/27 | ||||||
| Tue., 10/26 | JV Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Middle Field [Directions] | Canceled | Cancelled | |
| Wed., 10/27 | V Field Hockey | Granby Memorial | Away - Granby Memorial HS-Stadium Field [Directions] | 5:00 p.m. | L 0-2 | |
| Wed., 10/27 | JV Field Hockey | Granby Memorial | Away - Granby Memorial HS-Granby [Directions] | 6:30 p.m. | ||
| Wed., 10/27 | V Girls Soccer | Portland | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | T 2-2 | |
| Sat., 10/30 | V Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | 10:00 a.m. | L 0-2 | |
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class S Championship | Away - Wickham Park | 2:05 p.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class S Championship | Away - Wickham Park | 2:35 p.m. | ||
| Mon., 11/1 | V Field Hockey | North Branford | Away - Indian River Complex [Directions] | 4:00 p.m. | ||
| Tue., 11/2 | V Boys Soccer | Portland | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:00 p.m. | W 3-0 | |
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | Coventry/Windham Tech/Bolton/Lyman | Away - Coventry HS-Football Field [Directions] | 6:30 p.m. | W 41-21 | |
| Fri., 11/5 | V Boys Soccer | Morgan | Home - Portland HS-Default Facility [Directions] | 6:00 p.m. | T 1-1 | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | V Football | Ellington | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 1:00 p.m. | L 6-42 | |
| Sat., 11/6 | JV Football | Coventry/Windham Tech/Bolton/Lyman | Home - Peters Complex-Football Field [Directions] | 10:30 a.m. | ||
| Mon., 11/8 | JV Football | Ellington | Away - Ellington HS-Main Field [Directions] | 6:00 p.m. | ||
| Mon., 11/8 | V Girls Soccer | Ellis Tech/Putnam | Away - Ellis R V Tech School-Soccer Field [Directions] | 2:00 p.m. | W 6-0 | |
| Tue., 11/9 | V Field Hockey | New Fairfield | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 2:00 p.m. | ||
| Wed., 11/10 | V Girls Soccer | St. Bernard | Away - St. Bernard School-Delaporta Field [Directions] | 2:00 p.m. | W 1-0 | |
| Thu., 11/11 | V Boys Soccer | Portland | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 2:00 p.m. | W 1-0 | |
| Thu., 11/11 | V Field Hockey | Thomaston | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 4:30 p.m. | ||
| Thu., 11/11 | V Girls Swimming and Diving | CIAC Class M Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Fri., 11/12 | V Football | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 6:30 p.m. | W 46-6 | |
| Fri., 11/12 | V Girls Soccer | Somers | Away - Somers HS-Somers High School Turf Field [Directions] | 4:00 p.m. | L 0-1 | |
| Sat., 11/13 | V Football | Valley Regional/Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 10:30 a.m. | L 7-41 | |
| Sat., 11/13 | JV Football | North Branford | Home - Peters Complex-Football Field [Directions] | Canceled | Cancelled | |
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class M Qualifying Meet | Away - East Hartford | 4:00 p.m. | ||
| Sun., 11/14 | V Boys Soccer | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 1:00 p.m. | W 4-3 | |
| Mon., 11/15 | JV Football | Valley Regional/Old Lyme | Away - Valley Regional HS-Practice Football Field [Directions] | 3:00 p.m. | ||
| Tue., 11/16 | V Girls Swimming and Diving | CIAC Class M Swimming Championships | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 11/18 | V Boys Soccer | Somers | Home - Veteran's Stadium-Willow Brook Park-New Britain HS [Directions] | 7:00 p.m. | W 5-3 | |
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 11/19 | V Football | Coventry/Windham Tech/Bolton/Lyman | Away - Coventry HS-Football Field [Directions] | 6:30 p.m. | L 8-40 | |
| Fri., 11/19 | V Football | Ellington | Away - Ellington HS-Main Field [Directions] | 6:30 p.m. | L 26-28 | |
| Sat., 11/20 | JV Football | Valley Regional/Old Lyme | Home - Peters Complex-Football Field [Directions] | Canceled | Cancelled | |
| Sat., 11/20 | JV Football | Coventry/Windham Tech/Bolton/Lyman | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Sun., 11/21 | V Boys Soccer | Canton | Home - Dillon Stadium [Directions] | 6:30 p.m. | W 4-1 | |
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Wed., 11/24 | V Football | MSW | Away - Peters Complex-Football Field [Directions] | 6:30 p.m. | L 8-46 | |
| Wed., 11/24 | V Football | Old Saybrook | Home - Peters Complex-Football Field [Directions] | 6:30 p.m. | W 46-8 | Senior Night |
| Tue., 11/30 | V Football | Bloomfield | Away - Bloomfield HS-Phil Rubin Stadium- Turf Field & Track [Directions] | 6:30 p.m. | ||
| Sat., 12/4 | V Boys Ice Hockey | Hamden (Scrim.) | Away - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | ||
| Mon., 12/6 | V Boys Basketball | Griswold (Scrim.) | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 12/6 | V Boys Ice Hockey | Notre Dame-Fairfield (Scrim.) | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 5:30 p.m. | ||
| Mon., 12/6 | V Girls Basketball | East Haven (Scrim.) | Away - East Haven HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 12/8 | V Boys Basketball | Daniel Hand (Scrim.) | Away - Daniel Hand HS-Polson Gym/DHHS Campus [Directions] | 5:00 p.m. | ||
| Wed., 12/8 | V Boys Indoor Track | Shoreline Developmental Track Meet | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Wed., 12/8 | V Girls Basketball | St. Bernard (Scrim.) | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 12/8 | V Girls Ice Hockey | West Haven/SHA | Home - Northford Ice Pavilion-White [Directions] | 8:30 p.m. | L 2-3 | |
| Wed., 12/8 | V Girls Indoor Track | Shoreline Developmental Track Meet | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Sat., 12/11 | V Boys Basketball | St. Bernard (Scrim.) | Away - St. Bernard School-Powers Gym [Directions] | 12:00 p.m. | ||
| Mon., 12/13 | V Boys Basketball | Lyman Memorial (Scrim.) | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 12/13 | V Boys Ice Hockey | Cheshire | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | W 9-7 | |
| Tue., 12/14 | V Girls Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 35-43 | |
| Tue., 12/14 | JV Girls Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/15 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:50 p.m. | L 0-6 | |
| Thu., 12/16 | V Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 71-60 | |
| Thu., 12/16 | JV Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/16 | V Girls Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 46-28 | |
| Thu., 12/16 | JV Girls Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/17 | V Girls Ice Hockey | Guilford Coop | Home - Northford Ice Pavilion-White [Directions] | 8:30 p.m. | L 3-6 | |
| Sat., 12/18 | FR Boys Basketball | Valley Regional | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 12/18 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 7:30 p.m. | W 9-2 | |
| Mon., 12/20 | V Boys Ice Hockey | Woodstock Academy | Home - East Haven HS-Veterans Rink [Directions] | 8:45 p.m. | W 3-2 | |
| Mon., 12/20 | V Boys Swimming and Diving | Lyman Hall | Away - Sheehan HS-Sheehan HS Pool [Directions] | 5:00 p.m. | 98-79 | |
| Mon., 12/27 | V Girls Basketball | Norwich Tech | Away - Montville HS-Gym [Directions] | 1:00 p.m. | W 44-11 | |
| Tue., 12/28 | V Boys Swimming and Diving | Milford Boys Swimming & Diving Team | Away - Foran HS -Pool [Directions] | 10:00 a.m. | 90-79 | |
| Wed., 12/29 | V Girls Basketball | Montville | Away - Montville HS-Gym [Directions] | 1:00 p.m. | L 29-43 | |
| Wed., 12/29 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 5:00 p.m. | L 0-2 | |
| Thu., 12/30 | V Girls Gymnastics | Valley Regional, Mercy, TBA, Stonington | Away - Flip Flop Gymnastics [Directions] | 10:00 a.m. | 90.45 | |
| Tue., 1/4 | V Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 6:00 p.m. | W 44-28 | |
| Tue., 1/4 | JV Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/4 | V Boys Swimming and Diving | West Haven | Home - Madison Swim and Racquet [Directions] | 3:30 p.m. | 85-56 | |
| Tue., 1/4 | V Girls Basketball | Westbrook | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:00 p.m. | L 34-40 | |
| Wed., 1/5 | V Boys Indoor Track | Shoreline League Meet #1 | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Wed., 1/5 | V Girls Indoor Track | Shoreline League Meet #1 | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Thu., 1/6 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 5:15 p.m. | W 9-1 | |
| Sat., 1/8 | FR Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | Postponed | ||
| Sat., 1/8 | V Boys Ice Hockey | Glastonbury | Away - Koeppel Community Sports Center - Trinity College-Albert Creighton Williams '64 Rink [Directions] | 7:30 p.m. | W 5-3 | |
| Sat., 1/8 | V Girls Gymnastics | Foran, Mercy | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 10:00 a.m. | 127.50 | |
| Sat., 1/8 | V Girls Ice Hockey | Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 1:30 p.m. | L 2-5 | |
| Mon., 1/10 | V Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 7:00 p.m. | L 57-76 | |
| Mon., 1/10 | JV Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 5:30 p.m. | ||
| Mon., 1/10 | V Boys Indoor Track | HK Invite | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:45 p.m. | ||||||
| Mon., 1/10 | V Girls Basketball | Morgan | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 31-52 | |
| Mon., 1/10 | JV Girls Basketball | Morgan | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 1/10 | V Girls Indoor Track | HK Invite | Away - Floyd Little Athletic Center-Field House | 4:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Hillhouse HS-Field House | ||||||
| Tue., 1/11 | V Boys Swimming and Diving | Notre Dame-West Haven | Away - Albertus Magnus-Cosgrove Marcus Messer Athletic Center [Directions] | 4:00 p.m. | 85-80 | |
| Wed., 1/12 | V Boys Basketball | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 62-54 | |
| Wed., 1/12 | JV Boys Basketball | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | Canceled | Cancelled | |
| Wed., 1/12 | V Boys Ice Hockey | West Haven Coop | Away - West Haven HS-Bennett Rink [Directions] | 6:00 p.m. | L 0-4 | |
| Thu., 1/13 | V Boys Indoor Track | Shoreline League Meet #2 | Away - TBA-connell memorial rink | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Hillhouse HS-Field House | ||||||
| Thu., 1/13 | V Girls Gymnastics | Daniel Hand | Away - Polson MS, Small Gym-Polson Middle School/DHHS Campus [Directions] | 3:30 p.m. | ||
| Thu., 1/13 | V Girls Indoor Track | Shoreline League Meet #2 | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Fri., 1/14 | V Boys Basketball | North Branford | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 54-41 | |
| Fri., 1/14 | JV Boys Basketball | North Branford | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/14 | V Girls Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 7:00 p.m. | L 21-59 | |
| Fri., 1/14 | JV Girls Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/14 | V Girls Ice Hockey | Masuk Coop | Home - Northford Ice Pavilion-Red [Directions] | 4:00 p.m. | L 1-5 | |
| Sat., 1/15 | FR Boys Basketball | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | Postponed | ||
| Sat., 1/15 | V Boys Ice Hockey | Eastern CT Eagles | Away - Norwich - Rose Garden-RoseGarden Arena [Directions] | 5:10 p.m. | W 3-0 | |
| Sat., 1/15 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | W 5-1 | |
| Mon., 1/17 | V Boys Ice Hockey | Branford | Away - Northford Ice Pavilion-Red [Directions] | 8:45 p.m. | W 8-2 | |
| Tue., 1/18 | V Boys Basketball | Valley Regional | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | W 42-35 | |
| Tue., 1/18 | V Boys Swimming and Diving | Waterford/Ledyard | Away - Waterford HS - official -Pool - WHS [Directions] | 3:45 p.m. | 91-77 | |
| Tue., 1/18 | V Girls Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 4:00 p.m. | L 25-59 | |
| Tue., 1/18 | JV Girls Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/19 | V Girls Gymnastics | Norwich Free Academy, Old Lyme | Away - Thames Valley Gymnastics [Directions] | 2:00 p.m. | ||
| Wed., 1/19 | V Girls Ice Hockey | Guilford Coop | Away - Northford Ice Pavilion-Blue [Directions] | 3:15 p.m. | L 3-4 | |
| Fri., 1/21 | V Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 7:00 p.m. | L 71-47 | |
| Fri., 1/21 | JV Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/21 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion-Red [Directions] | 8:30 p.m. | W 4-3 | |
| Fri., 1/21 | V Boys Swimming and Diving | Cheshire | Away - Cheshire Community Pool [Directions] | 7:00 p.m. | 97-81 | |
| Fri., 1/21 | V Girls Basketball | Cromwell | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 26-64 | |
| Fri., 1/21 | JV Girls Basketball | Cromwell | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/21 | V Girls Gymnastics | Old Lyme, Killingly, Woodstock Academy | Away - ABC Gymnastics [Directions] | 3:00 p.m. | ||
| Sat., 1/22 | V Boys Basketball | Stonington | Away - Stonington HS-SHS Main Gym [Directions] | 5:30 p.m. | L 63-80 | |
| Sat., 1/22 | JV Boys Basketball | Stonington | Away - Stonington HS-SHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/22 | FR Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/22 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Home - Northford Ice Pavilion-White [Directions] | 7:45 p.m. | W 5-0 | |
| Sat., 1/22 | V Girls Basketball | Old Lyme | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:00 p.m. | L 18-36 | |
| Sat., 1/22 | JV Girls Basketball | Old Lyme | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 1/22 | V Girls Gymnastics | Valley Regional, Hamden, Mercy, TBA | Away - Flip Flop Gymnastics [Directions] | TBA | 130.85 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Mon., 1/24 | JV Boys Basketball | Valley Regional | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | Canceled | Cancelled | |
| Mon., 1/24 | V Boys Ice Hockey | Amity | Home - Northford Ice Pavilion-Red [Directions] | 8:45 p.m. | L 3-6 | |
| Mon., 1/24 | V Girls Gymnastics | Stonington, East Lyme/Waterford/St Bernard, Old Lyme | Away - Stonington HS-Aux Gym [Directions] | 6:30 p.m. | ||
| Tue., 1/25 | V Boys Basketball | East Hampton | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 62-54 | |
| Tue., 1/25 | JV Boys Basketball | East Hampton | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/25 | V Girls Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 7:00 p.m. | L 19-53 | |
| Tue., 1/25 | JV Girls Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/25 | V | Unified Basketball Tournament | Away - Westbrook HS-Westbrook HS Gym | 3:00 p.m. | ||
| Wed., 1/26 | V Boys Basketball | Old Lyme | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 49-32 | |
| Wed., 1/26 | JV Boys Basketball | Old Lyme | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/26 | V Girls Ice Hockey | Avon | Away - Newington Ice Arena-Blue Rink [Directions] | 5:10 p.m. | L 0-6 | |
| Fri., 1/28 | V Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 7:00 p.m. | W 52-43 | |
| Fri., 1/28 | JV Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:30 p.m. | ||
| Fri., 1/28 | V Boys Indoor Track | Shoreline Coaches Invite | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Fri., 1/28 | V Girls Basketball | Haddam-Killingworth | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 38-45 | |
| Fri., 1/28 | JV Girls Basketball | Haddam-Killingworth | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/28 | V Girls Gymnastics | Old Lyme, Valley Regional | Away - ABC Gymnastics [Directions] | 3:00 p.m. | ||
| Fri., 1/28 | V Girls Gymnastics | Valley Regional | Away - ABC Gymnastics [Directions] | 3:30 p.m. | 138.95 | |
| Fri., 1/28 | V Girls Indoor Track | Shoreline Coaches Invite | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Mon., 1/31 | V Girls Gymnastics | Woodstock Academy, Killingly, Old Lyme, Stonington | Away - Deary's Gymnastics [Directions] | 6:00 p.m. | ||
| Tue., 2/1 | V Boys Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 60-46 | |
| Tue., 2/1 | JV Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/1 | JV Boys Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/1 | V Girls Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 54-23 | |
| Tue., 2/1 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | L 1-3 | |
| Wed., 2/2 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall-Ice Rink [Directions] | 8:00 p.m. | L 2-5 | |
| Thu., 2/3 | FR Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 6:30 p.m. | ||
| Sat., 2/5 | FR Boys Basketball | East Hampton | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/5 | V Boys Ice Hockey | Lyman Hall | Home - Northford Ice Pavilion-White [Directions] | 2:20 p.m. | L 1-2 | |
| Sat., 2/5 | V Boys Indoor Track | Shoreline Conference Indoor Track Championship | Away - Hillhouse HS-Field House | 10:00 a.m. | ||
| Sat., 2/5 | V Girls Basketball | Coginchaug | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 2:00 p.m. | L 28-51 | |
| Sat., 2/5 | JV Girls Basketball | Coginchaug | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 12:30 p.m. | ||
| Sat., 2/5 | V Girls Indoor Track | Shoreline Conference Indoor Track Championship | Away - Coginchaug Regional HS-Floyd Little Athletic Center - Hillhouse HS | 10:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Hillhouse HS-Field House | ||||||
| Tue., 2/8 | V Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 55-43 | |
| Tue., 2/8 | JV Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/8 | V Boys Ice Hockey | E.O. Smith-Tolland | Away - UConn Storrs-Freitas Ice Forum [Directions] | 4:45 p.m. | T 4-4(OT) | |
| Tue., 2/8 | V Boys Swimming and Diving | East Lyme NFA | Away - East Lyme HS-East Lyme Aquatics Center [Directions] | 3:30 p.m. | Cancelled | |
| Tue., 2/8 | V Boys Swimming and Diving | Fairfield Prep, Xavier | Away - Fairfield University-Rec Plex [Directions] | 7:00 p.m. | 63-113 - vs X 75-110 - vs Prep | |
| Tue., 2/8 | V Girls Basketball | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 31-52 | |
| Tue., 2/8 | JV Girls Basketball | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/8 | V Girls Gymnastics | Valley Regional, TBA | Away - Flip Flop Gymnastics [Directions] | 2:00 p.m. | 136.9 | |
| Tue., 2/8 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Ice Arena-Red Rink [Directions] | 4:25 p.m. | L 0-2 | |
| Wed., 2/9 | V Boys Basketball | Ledyard | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 76-37 | |
| Wed., 2/9 | V Boys Ice Hockey | Guilford | Away - Blake Field - New Haven-Walker Rink [Directions] | 8:15 p.m. | L 1-3 | |
| Wed., 2/9 | V Girls Basketball | Ledyard | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:00 p.m. | L 23-45 | |
| Thu., 2/10 | V Girls Basketball | Fitch | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 26-49 | |
| Thu., 2/10 | JV Girls Basketball | Fitch | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/11 | V Boys Basketball | Westbrook | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 58-45 | |
| Fri., 2/11 | JV Boys Basketball | Westbrook | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/11 | V Boys Swimming and Diving | Greater New Haven | Away - Walter Gawrych Community Pool [Directions] | 4:00 p.m. | 78-95 | |
| Fri., 2/11 | V Girls Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | L 28-46 | |
| Fri., 2/11 | V Girls Gymnastics | Shoreline Tournament | Home - ABC Gymnastics [Directions] | 3:00 p.m. | 133.35 | |
| Fri., 2/11 | V Girls Gymnastics | Valley Regional | Away - ABC Gymnastics [Directions] | 3:00 p.m. | 133.35 | |
| Fri., 2/11 | V Girls Gymnastics | Shoreline Tournament | Away - ABC Gymnastics | 3:00 p.m. | ||
| Sat., 2/12 | V Boys Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/12 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Northford Ice Pavilion-Red [Directions] | 7:40 p.m. | L 1-3 | |
| Sat., 2/12 | V Girls Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Mon., 2/14 | V Boys Basketball | Montville | Away - Montville HS-Gym [Directions] | 7:00 p.m. | W 68-59 | |
| Mon., 2/14 | JV Boys Basketball | Montville | Away - Montville HS-Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/14 | FR Boys Basketball | Montville | Away - Montville HS-Gym [Directions] | 3:45 p.m. | ||
| Mon., 2/14 | JV Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/14 | V Girls Gymnastics | Old Lyme, Norwich Free Academy | Away - ABC Gymnastics [Directions] | 2:30 p.m. | ||
| Tue., 2/15 | V Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:00 p.m. | L 61-55 | |
| Tue., 2/15 | JV Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/15 | V Boys Swimming and Diving | Amity | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | 6:45 p.m. | 84-90 | |
| Tue., 2/15 | V Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 7:00 p.m. | L 22-47 | |
| Wed., 2/16 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | L 31-52 | |
| Wed., 2/16 | JV Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Wed., 2/16 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 2/17 | V Girls Gymnastics | Daniel Hand, Mercy, Morgan, Valley Regional, Westbrook | Away - Polson MS, Small Gym-Polson Middle School/DHHS Campus | 6:30 p.m. | 134.05 | |
| Thu., 2/17 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 3-2(OT) | |
| Fri., 2/18 | V Boys Basketball | Coginchaug | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 51-49 | |
| Fri., 2/18 | JV Boys Basketball | Coginchaug | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/18 | V Girls Gymnastics | Old Lyme, Stonington | Away - ABC Gymnastics [Directions] | 3:00 p.m. | ||
| Sat., 2/19 | FR Boys Basketball | Coginchaug | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/19 | V Boys Ice Hockey | North Haven | Home - Northford Ice Pavilion-White [Directions] | 4:30 p.m. | L 2-5 | |
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Girls Ice Hockey | Hamden Coop | Home - Northford Ice Pavilion-Red [Directions] | 2:30 p.m. | L 0-3 | |
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | V Boys Basketball | Wheeler | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 2:30 p.m. | W 52-36 | |
| Mon., 2/21 | JV Boys Basketball | Wheeler | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 1:00 p.m. | ||
| Mon., 2/21 | JV Boys Ice Hockey | Guilford (Scrim.) | Away - [CIAC] People's United Center-Quinnipiac [Directions] | 3:45 p.m. | ||
| Mon., 2/21 | V Girls Gymnastics | Valley Regional, Mercy | Away - Flip Flop Gymnastics [Directions] | 10:00 a.m. | 132.45 | |
| Mon., 2/21 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Northford Ice Pavilion-Red [Directions] | 12:30 p.m. | ||
| Tue., 2/22 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | W 55-44 | |
| Tue., 2/22 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Tue., 2/22 | V Boys Swimming and Diving | Shelton | Home - Madison Swim and Racquet [Directions] | 5:00 p.m. | ||
| Wed., 2/23 | V Boys Ice Hockey | Eastern CT Eagles | Away - Norwich - Rose Garden-RoseGarden Arena [Directions] | 7:40 p.m. | W 5-1 | |
| Thu., 2/24 | FR Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/24 | V Boys Swimming and Diving | Xavier | Away - Middletown YMCA [Directions] | Canceled | Cancelled | |
| Sat., 2/26 | V Boys Basketball | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | L 49-41 | |
| Sat., 2/26 | V Boys Ice Hockey | Daniel Hand | Away - Northford Ice Pavilion-Red [Directions] | 5:15 p.m. | L 1-4 | |
| Sat., 2/26 | V Boys Swimming and Diving | SCC Dive Championship | Away - Sheehan HS-Sheehan HS Pool | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 12:00 p.m. | ||||||
| Sat., 2/26 | V Girls Gymnastics | CIAC Class M Divisional Championship | Away - Richetelli Gymnasium @Jonathan Law | 10:00 a.m. | ||
| Mon., 2/28 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft School-Mays [Directions] | 7:30 p.m. | L 3-4(OT) | |
| Mon., 2/28 | V Boys Swimming and Diving | Cheshire, Amity, Fairfield Prep, H-K/Morgan/Valley, Hamden, Foran/Law, Lyman Hall/Coginchaug, N.Haven/E.Haven/N.Bran/Guil, Notre Dame-West Haven, Sheehan, Shelton, West Haven, Xavier | Away - Cheshire Community Pool | 4:00 p.m. | ||
| Tue., 3/1 | V Boys Ice Hockey | Westhill/Stamford | Home - Northford Ice Pavilion-White [Directions] | 8:45 p.m. | L 1-5 | |
| Wed., 3/2 | V Boys Swimming and Diving | SCC Championship Meet | Away - Southern CT State University-pool | 4:30 p.m. | ||
| Sat., 3/5 | V Girls Gymnastics | State Open | Away - New Milford | 10:00 a.m. | ||
| Sat., 3/5 | V Girls Ice Hockey | Woodstock Academy Coop | Home - Northford Ice Pavilion-Red [Directions] | 7:00 p.m. | ||
| Mon., 3/7 | V Boys Ice Hockey | Farmington Valley Generals | Away - Avon Old Farms-Jennings Rink [Directions] | 6:00 p.m. | ||
| Tue., 3/8 | V Boys Basketball | East Granby | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:30 p.m. | W 48-39 | |
| Thu., 3/10 | V Boys Basketball | Achievement First | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:30 p.m. | L 81-52 | |
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class M Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sun., 3/13 | V Boys Swimming and Diving | CIAC Class M Qualifying Meet | Away - Cornerstone Pool | 1:00 p.m. | ||
| Wed., 3/16 | V Boys Swimming and Diving | CIAC Class M Swimming Championships | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Fri., 3/25 | V Baseball | Morgan (Scrim.) | Away - Morgan School-Baseball Field [Directions] | 4:30 p.m. | ||
| Sat., 3/26 | V Baseball | Waterford (Scrim.) | Away - Waterford HS-Alumni Baseball Field [Directions] | 12:00 p.m. | ||
| Sat., 3/26 | V Softball | East Lyme (Scrim.) | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 11:00 a.m. | ||
| Wed., 3/30 | V Baseball | Guilford (Scrim.) | Away - Guilford HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Boys Lacrosse | St. Bernard-Wheeler (Scrim.) | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Softball | Morgan (Scrim.) | Away - Morgan School-Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Softball | Norwich Free Academy (Scrim.) | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 3:45 p.m. | ||
| Sat., 4/2 | V Baseball | Westbrook | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 10:00 a.m. | W 11-1 | |
| Sat., 4/2 | V Boys Lacrosse | Ledyard-Griswold | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 1:00 p.m. | W 11-5 | |
| Sat., 4/2 | V Girls Lacrosse | Ledyard | Away - Ledyard HS-Bill Mignault Field [Directions] | 11:00 a.m. | W 4 - 13 | |
| Sat., 4/2 | V Softball | Westbrook/Old Saybrook | Away - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 10:00 a.m. | L 14-15 | |
| Sat., 4/2 | V Softball | Old Saybrook | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 10:00 a.m. | W 15-14 | |
| Mon., 4/4 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Baseball Diamond [Directions] | 4:00 p.m. | W 9-3 | |
| Mon., 4/4 | V Softball | Old Lyme | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:00 p.m. | L 2-21 | |
| Mon., 4/4 | V Softball | Coginchaug | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L 1-21 (5) | |
| Mon., 4/4 | V Girls Tennis | North Branford | Away - North Branford HS-NBHS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 4/5 | V Boys Lacrosse | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 4:00 p.m. | L 6-13 | |
| Tue., 4/5 | JV Boys Lacrosse | North Branford | Away - North Branford HS-NBHS Back Field [Directions] | 5:30 p.m. | ||
| Tue., 4/5 | V Boys Outdoor Track | Morgan, Old Lyme | Away - Peters Complex-Track [Directions] | 3:45 p.m. | ||
| Tue., 4/5 | V Girls Lacrosse | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 14 - 12 | |
| Tue., 4/5 | JV Girls Lacrosse | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:15 p.m. | ||
| Tue., 4/5 | V Girls Outdoor Track | Morgan, Old Lyme | Away - Peters Complex-Track [Directions] | 3:45 p.m. | ||
| Tue., 4/5 | V Softball | Old Lyme | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L 0-14 (5) | |
| Wed., 4/6 | V Boys Lacrosse | Maloney-Platt | Away - Maloney HS-Turf Field [Directions] | 4:00 p.m. | W 12-1 | |
| Fri., 4/8 | V Boys Tennis | Old Lyme | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 7-0 [Detailed Results] | |
| Fri., 4/8 | V Girls Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 4/9 | V Boys Outdoor Track | Wildcat Relays | Away - Lyme-Old Lyme HS-Track Field | 11:30 a.m. | ||
| Sat., 4/9 | V Girls Lacrosse | Waterford | Away - Waterford HS-Alumni Turf Field/Track [Directions] | 11:30 a.m. | W 9 - 8 | |
| Sat., 4/9 | JV Girls Lacrosse | Waterford | Away - Waterford HS-Alumni Turf Field/Track [Directions] | 10:00 a.m. | ||
| Sat., 4/9 | V Girls Outdoor Track | Wildcat Relays | Away - Lyme-Old Lyme HS-Track Field | 11:30 a.m. | ||
| Mon., 4/11 | V Baseball | Coginchaug | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | W 5-0 | |
| Mon., 4/11 | V Boys Golf | Haddam-Killingworth | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | Old Saybrook 182, H-K 192. Drew Kulmann medalist, 42 | |
| Mon., 4/11 | V Softball | Coginchaug | Away - Coginchaug Regional HS-Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 4:00 p.m. | L 0-18 | |
| Tue., 4/12 | V Boys Golf | North Branford | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | Tie, 184-184. Drew Kulmann Medalist (41) | |
| Tue., 4/12 | V Boys Lacrosse | Cromwell | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 16-4 | |
| Tue., 4/12 | JV Boys Lacrosse | Cromwell | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:15 p.m. | ||
| Tue., 4/12 | V Girls Lacrosse | Cromwell | Away - Cromwell HS-Lacrosse Field [Directions] | 4:00 p.m. | W 19 - 10 | |
| Tue., 4/12 | JV Girls Lacrosse | Cromwell | Away - Cromwell HS-Lacrosse Field [Directions] | 5:30 p.m. | ||
| Wed., 4/13 | V Baseball | Morgan | Away - Morgan School-Baseball Field [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 4/13 | V Boys Golf | Valley Regional | Away - Black Hall Golf Club [Directions] | 3:00 p.m. | Valley 199, Saybrook 202. | |
| Wed., 4/13 | V Boys Outdoor Track | North Branford, Cromwell | Away - North Branford HS-NBHS Track [Directions] | 3:45 p.m. | ||
| Wed., 4/13 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 3:45 p.m. | L 3-2 [Detailed Results] | |
| Wed., 4/13 | V Girls Outdoor Track | North Branford, Cromwell | Away - North Branford HS-NBHS Track [Directions] | 3:45 p.m. | ||
| Wed., 4/13 | V Softball | Morgan | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:00 p.m. | L 0-13 | |
| Wed., 4/13 | V Softball | Valley Regional | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L 0-22 | |
| Wed., 4/13 | V Girls Tennis | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Thu., 4/14 | V Boys Golf | Cromwell | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | Cromwell 175, Old Saybrook 185 | |
| Thu., 4/14 | V Boys Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 4:00 p.m. | L 3-8 | |
| Thu., 4/14 | JV Boys Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | Canceled | Cancelled | |
| Thu., 4/14 | V Boys Tennis | Valley Regional | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 6-1 [Detailed Results] | |
| Thu., 4/14 | V Girls Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 16 - 2 | |
| Thu., 4/14 | JV Girls Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:15 p.m. | ||
| Thu., 4/14 | V Softball | Cromwell | Away - Cromwell HS-Softball Diamond [Directions] | 4:00 p.m. | L 0-22 | |
| Thu., 4/14 | V Girls Tennis | Valley Regional | Away - Valley Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 4/15 | V Baseball | North Branford | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 11:00 a.m. | W 6-1 | |
| Fri., 4/15 | V Girls Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 4/15 | JV Girls Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 4/18 | V Baseball | ValleyReg/Westbrook | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 11:00 a.m. | W 2-1 | |
| Mon., 4/18 | V Boys Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 10:00 a.m. | L 7-0 [Detailed Results] | |
| Mon., 4/18 | V Softball | Valley Regional | Away - Valley Regional HS-Joseph Camarota Memorial Field [Directions] | 11:00 a.m. | L 1-15 | |
| Mon., 4/18 | V Softball | East Hampton | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L 19-2 | |
| Mon., 4/18 | V Girls Tennis | Morgan | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 11:00 a.m. | L 2-5 | |
| Tue., 4/19 | V Boys Lacrosse | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | 3:45 p.m. | L 8-14 | |
| Tue., 4/19 | JV Boys Lacrosse | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | Canceled | Cancelled | |
| Tue., 4/19 | V Girls Lacrosse | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 10:00 a.m. | W 12 - 7 | |
| Tue., 4/19 | JV Girls Lacrosse | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Wed., 4/20 | V Baseball | Cromwell | Away - Cromwell HS-Fran Monnes Baseball Field [Directions] | 4:00 p.m. | L 8-3 | |
| Wed., 4/20 | V Boys Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 11:00 a.m. | W 3-0 [Detailed Results] | |
| Wed., 4/20 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Varsity Softball Field [Directions] | 4:00 p.m. | L 0-18 | |
| Wed., 4/20 | V Girls Tennis | Coginchaug | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:00 p.m. | W 4-3 | |
| Thu., 4/21 | V Boys Lacrosse | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | L 3-15 | |
| Thu., 4/21 | JV Boys Lacrosse | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:15 p.m. | ||
| Thu., 4/21 | V Girls Lacrosse | Morgan | Away - Indian River Complex-Turf Field [Directions] | 4:00 p.m. | W 6 - 5 | |
| Thu., 4/21 | JV Girls Lacrosse | Morgan | Away - Indian River Complex-Turf Field [Directions] | Canceled | Cancelled | |
| Fri., 4/22 | V Baseball | East Hampton | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | L 9-6 | |
| Fri., 4/22 | V Softball | Morgan | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L 3-28 | |
| Mon., 4/25 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 4:00 p.m. | L 4-1 | |
| Mon., 4/25 | JV Boys Lacrosse | Guilford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Tennis | Westbrook | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 4-1 [Detailed Results] | |
| Mon., 4/25 | V Softball | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:00 p.m. | L 0-21 | |
| Mon., 4/25 | V Softball | North Branford | Away - North Branford HS-NBHS Softball Field [Directions] | 4:00 p.m. | L 0-21 | |
| Mon., 4/25 | V Girls Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/26 | V Boys Golf | Morgan | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | Morgan 172, Old Saybrook 188. | |
| Tue., 4/26 | V Boys Lacrosse | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | L 6-13 | |
| Tue., 4/26 | JV Boys Lacrosse | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:15 p.m. | ||
| Tue., 4/26 | V Girls Lacrosse | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 4:00 p.m. | L 11-13 | |
| Tue., 4/26 | JV Girls Lacrosse | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 5:15 p.m. | ||
| Wed., 4/27 | V Baseball | Westbrook | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | W 19-4 | |
| Wed., 4/27 | V Boys Outdoor Track | Valley Regional, Portland | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Cromwell | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 4-2 [Detailed Results] | |
| Wed., 4/27 | V Girls Outdoor Track | Valley Regional, Portland | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Softball | Westbrook/Old Saybrook | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:00 p.m. | W 24-12 (5) | |
| Wed., 4/27 | V Softball | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:00 p.m. | L 12-24 | |
| Thu., 4/28 | JV Baseball | Westbrook, Old Lyme | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Boys Lacrosse | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | L 7-9 | |
| Thu., 4/28 | JV Boys Lacrosse | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:15 p.m. | ||
| Thu., 4/28 | V Girls Lacrosse | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 6:00 p.m. | W 11-10 | |
| Thu., 4/28 | JV Girls Lacrosse | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Girls Tennis | Cromwell | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Fri., 4/29 | V Baseball | Old Lyme | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | W 4-3 | |
| Fri., 4/29 | V Boys Tennis | Coginchaug | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | W 5-0 [Detailed Results] | |
| Fri., 4/29 | V Softball | Coginchaug | Away - Coginchaug Regional HS-Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 4:00 p.m. | L 0-18 | |
| Mon., 5/2 | V Baseball | Hale Ray | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | W 9-8 | |
| Mon., 5/2 | V Boys Golf | North Branford | Away - Indian Springs Golf Course-Indian Springs CC [Directions] | 3:00 p.m. | NB 177, Old Saybrook 199 | |
| Mon., 5/2 | V Girls Lacrosse | St. Bernard | Away - St. Bernard School-Lacrosse Field [Directions] | 4:00 p.m. | W 15-2 | |
| Mon., 5/2 | V Softball | Hale Ray | Away - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 3:30 p.m. | L 4-17 | |
| Mon., 5/2 | V Softball | Hale Ray | Away - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 5:30 p.m. | L 5-17 | |
| Mon., 5/2 | V Girls Tennis | Westbrook | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 0-6 | |
| Tue., 5/3 | JV Baseball | TBA, Old Lyme | Away - TBA-connell memorial rink | 4:00 p.m. | ||
| Tue., 5/3 | V Boys Golf | Coginchaug | Away - Coginchaug-Lyman Orchards Golf course [Directions] | 3:00 p.m. | old Saybrook 189, Coginchaug 185 | |
| Tue., 5/3 | JV Boys Lacrosse | East Lyme | Away - East Lyme HS-Back Soccer Field [Directions] | 3:30 p.m. | ||
| Tue., 5/3 | V Boys Outdoor Track | Coginchaug, Hale Ray | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:30 p.m. | ||
| Tue., 5/3 | V Boys Tennis | East Hampton | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 6-1 [Detailed Results] | |
| Tue., 5/3 | V Girls Outdoor Track | Coginchaug, Hale Ray | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:30 p.m. | ||
| Tue., 5/3 | V Girls Tennis | East Hampton | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Thu., 5/5 | V Baseball | Portland | Away - Portland HS-Portland HS [Directions] | 4:30 p.m. | W 15-7 | |
| Thu., 5/5 | V Boys Golf | Haddam-Killingworth | Away - Black Birch Golf Course [Directions] | 3:00 p.m. | old Saybrook 194- HK 185 | |
| Thu., 5/5 | V Boys Lacrosse | Cromwell | Away - Cromwell HS-Lacrosse Field [Directions] | 4:00 p.m. | W 11-8 | |
| Thu., 5/5 | JV Boys Lacrosse | Cromwell | Away - Cromwell HS-Lacrosse Field [Directions] | 5:30 p.m. | ||
| Thu., 5/5 | V Boys Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 4:00 p.m. | L 6-1 [Detailed Results] | |
| Thu., 5/5 | V Girls Lacrosse | Cromwell | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 19-11 | |
| Thu., 5/5 | JV Girls Lacrosse | Cromwell | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Fri., 5/6 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 4:00 p.m. | L 1-18 | |
| Sat., 5/7 | V Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | W 12-2 | |
| Sat., 5/7 | V Boys Outdoor Track | Coginchaug - Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 10:00 a.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Coginchaug - Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 10:00 a.m. | ||
| Mon., 5/9 | V Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 4:00 p.m. | L 2-1 | |
| Mon., 5/9 | V Boys Golf | Old Lyme | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | Old Lyme 205 - Old Saybrook 206 | |
| Mon., 5/9 | V Boys Lacrosse | Maloney-Platt | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:45 p.m. | W 13-6 | |
| Mon., 5/9 | V Boys Tennis | Portland | Away - Portland HS-Tennis Courts [Directions] | 4:15 p.m. | W 3-2 [Detailed Results] | |
| Mon., 5/9 | V Softball | Acad. of the Holy Family | Home - Academy of the Holy Family [Directions] | 4:15 p.m. | W 29-11 | |
| Mon., 5/9 | V Girls Tennis | Portland | Away - Portland HS-Tennis Courts [Directions] | 4:15 p.m. | L 3-4 | |
| Tue., 5/10 | V Boys Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | L 2-10 | |
| Tue., 5/10 | JV Boys Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Tue., 5/10 | V Boys Outdoor Track | Old Lyme, Morgan | Away - Lyme-Old Lyme HS-Track Field [Directions] | Canceled | Cancelled | |
| Tue., 5/10 | V Girls Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 4:00 p.m. | W 15 - 5 | |
| Tue., 5/10 | JV Girls Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | Canceled | Cancelled | |
| Tue., 5/10 | V Girls Outdoor Track | Old Lyme, Morgan | Away - Lyme-Old Lyme HS-Track Field [Directions] | Canceled | Cancelled | |
| Tue., 5/10 | V Softball | Morgan | Away - Morgan School-Softball Field [Directions] | 4:00 p.m. | L 4-16 | |
| Tue., 5/10 | JV Softball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS JV Softball Field [Directions] | Canceled | Cancelled | |
| Tue., 5/10 | V Girls Tennis | Old Lyme | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 5/11 | JV Baseball | Old Lyme, Westbrook | Away - Lyme-Old Lyme HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Boys Golf | Waterford | Away - Great Neck Country Club [Directions] | 3:00 p.m. | Waterford 182, Old Saybrook 196 | |
| Wed., 5/11 | V Boys Outdoor Track | OSMS Middle School Track Invitational | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:45 p.m. | ||
| Wed., 5/11 | V Boys Tennis | Morgan | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 7-0 [Detailed Results] | |
| Wed., 5/11 | V Softball | Hale Ray | Home - Portland HS-PHS Softball Diamond [Directions] | 4:45 p.m. | L 1-22 | |
| Wed., 5/11 | V Softball | Coginchaug | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 5:15 p.m. | L 0-12 | |
| Wed., 5/11 | V Girls Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 3:45 p.m. | L 2-5 | |
| Thu., 5/12 | V Baseball | St. Bernard | Away - St. Bernard School-Baseball Diamond [Directions] | 2:00 p.m. | W 2-1 | |
| Thu., 5/12 | V Baseball | St. Bernard | Away - St. Bernard School-Baseball Diamond [Directions] | 4:00 p.m. | W 13-5 | |
| Thu., 5/12 | V Boys Lacrosse | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | L 7-8 | |
| Thu., 5/12 | JV Boys Lacrosse | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Thu., 5/12 | V Softball | North Branford | Away - North Branford HS-NBHS Softball Field [Directions] | 4:00 p.m. | L 7-21 | |
| Thu., 5/12 | V Softball | Bassick | Away - Bassick HS-Went Field [Directions] | 4:15 p.m. | W 28-9 | |
| Fri., 5/13 | V Boys Outdoor Track | Running Rams Invitational | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Fri., 5/13 | V Boys Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Fri., 5/13 | V Girls Lacrosse | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | 3:45 p.m. | W 12-10 | |
| Fri., 5/13 | JV Girls Lacrosse | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | Canceled | Cancelled | |
| Fri., 5/13 | V Girls Outdoor Track | Running Rams Invitational | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Fri., 5/13 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 4:00 p.m. | L 0-12 | |
| Sat., 5/14 | V Baseball | Portland | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 12:00 p.m. | W 5-1 | |
| Sat., 5/14 | V Boys Lacrosse | Ledyard-Griswold | Away - Ledyard HS-Bill Mignault Field [Directions] | 10:00 a.m. | W 14-4 | |
| Sat., 5/14 | V Girls Lacrosse | Ledyard | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 10:00 a.m. | W 13-7 | |
| Sat., 5/14 | V Softball | Hale Ray | Away - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 11:00 a.m. | L 1-20 | |
| Mon., 5/16 | V Boys Golf | Old Lyme | Away - Black Hall Golf Club [Directions] | 3:00 p.m. | Old Lyme 185, Old Saybrook 190 | |
| Pending change awaiting acceptance by one or more parties involved: Date to 5/26 | ||||||
| Mon., 5/16 | V Softball | East Hampton | Away - East Hampton HS-Softball Field [Directions] | 4:00 p.m. | L 5-18 | |
| Tue., 5/17 | JV Baseball | TBA, Old Lyme | Away - TBA | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Tue., 5/17 | V Boys Lacrosse | Morgan | Away - Indian River Complex-Turf Field [Directions] | 4:00 p.m. | L 12-18 | |
| Tue., 5/17 | JV Boys Lacrosse | Morgan | Away - Indian River Complex-Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 5/17 | V Boys Outdoor Track | East Lyme, Killingly | Away - East Lyme HS-Dick North Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 5/17 | V Boys Tennis | Portland | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | W 3-2 [Detailed Results] | |
| Tue., 5/17 | V Girls Lacrosse | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 12-6 | |
| Tue., 5/17 | JV Girls Lacrosse | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Tue., 5/17 | V Girls Outdoor Track | East Lyme, Killingly | Away - East Lyme HS-Dick North Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 5/17 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Varsity Softball Field [Directions] | 4:00 p.m. | L 0-21 | |
| Tue., 5/17 | V Softball | Stafford | Away - Stafford HS-Varsity Softball Field (corner of Levinthal Run and County Rd) [Directions] | 4:15 p.m. | L 1-16 | |
| Tue., 5/17 | V Girls Tennis | Portland | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Wed., 5/18 | V Boys Golf | Hale Ray | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:10 p.m. | Hale Ray 171, Old Saybrook 178 | |
| Wed., 5/18 | V Softball | Cromwell | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:00 p.m. | L 9-23 | |
| Wed., 5/18 | V Softball | Acad. of the Holy Family | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:15 p.m. | W 11-2 | |
| Thu., 5/19 | V Boys Golf | Portland | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | Portland 156, Old Saybrook 178 | |
| Thu., 5/19 | V Boys Lacrosse | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 6:00 p.m. | L 8-12 | |
| Thu., 5/19 | JV Boys Lacrosse | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Boys Outdoor Track | SLC Novice Meet | Away - Haddam Killingworth HS (HK)-HKHS Track | 3:30 p.m. | ||
| Thu., 5/19 | V Girls Lacrosse | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:15 p.m. | W 12-11 | |
| Thu., 5/19 | JV Girls Lacrosse | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Thu., 5/19 | V Girls Outdoor Track | SLC Novice Meet | Away - Haddam Killingworth HS (HK)-HKHS Track | 3:30 p.m. | ||
| Fri., 5/20 | V Boys Golf | East Hampton | Away - Black Birch Golf Course [Directions] | 3:00 p.m. | Old Saybrook 186, East Hampton 281 | |
| Fri., 5/20 | V Boys Outdoor Track | SLC Middle School Championship | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:30 p.m. | ||
| Fri., 5/20 | V Girls Outdoor Track | SLC Middle School Championship | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:45 p.m. | ||
| Sat., 5/21 | V Softball | Fitch | Away - Washington Park-Field 1- Varsity [Directions] | 11:00 a.m. | L 0-15 | |
| Mon., 5/23 | V Baseball | Old Lyme | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | W 10-1 | |
| Mon., 5/23 | V Boys Tennis | Shoreline Conference Tennis Tournament - First Round | Away - Westbrook HS-Westbrook HS / MS Tennis Courts | 9:00 a.m. | ||
| Mon., 5/23 | V Softball | Bassick | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:30 p.m. | W Forfeit | |
| Mon., 5/23 | V Girls Tennis | Shoreline Conference Tennis Tournament - First Round | Away - Old Saybrook HS | 9:00 a.m. | ||
| Tue., 5/24 | V Baseball | Cromwell | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | W 16-2 | |
| Tue., 5/24 | V Boys Golf | Shoreline Conference Golf Championship | Away - TPC River Highlands | 9:00 a.m. | ||
| Tue., 5/24 | V Girls Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 2:00 p.m. | W 16-4 | |
| Wed., 5/25 | V Boys Outdoor Track | Shoreline Conference Championship | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 2:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:30 p.m. | ||||||
| Wed., 5/25 | V Girls Outdoor Track | Shoreline Conference Championship | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 2:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:30 p.m. | ||||||
| Wed., 5/25 | V Softball | Stafford | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:15 p.m. | L 1-20 | |
| Thu., 5/26 | V Girls Lacrosse | Morgan | Away - Indian River Complex [Directions] | 5:00 p.m. | ||
| Fri., 5/27 | V Baseball | ValleyReg/Westbrook | Home - Palmer Field-Baseball Diamond [Directions] | 7:00 p.m. | W 4-2 | |
| Tue., 5/31 | V Baseball | Windsor Locks | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | L 5-2 | |
| Tue., 5/31 | V Boys Golf | Portland | Away - Portland Golf Course [Directions] | 2:30 p.m. | Portland 150 - Old Saybrook 171 | |
| Tue., 5/31 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/31 | V Girls Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 2:00 p.m. | W 17-7 | |
| Tue., 5/31 | V Girls Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Fri., 6/3 | V Girls Lacrosse | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 15-13 | |
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Golf | CIAC Division III Spring Championship | Away - Fairview Farms | 8:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Girls Lacrosse | Lauralton Hall | Home - Jonathan Law HS-Lacrosse Field [Directions] | 5:00 p.m. | L 9-8 | |
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Boys Golf | CIAC State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||