| Old Saybrook 2020-21 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 356 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 10/1 | V Boys Cross Country | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:45 p.m. | ||
| Thu., 10/1 | V Boys Soccer | East Hampton | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 2-0 | |
| Thu., 10/1 | V Girls Cross Country | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 4:15 p.m. | ||
| Thu., 10/1 | JV Girls Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 3:45 p.m. | ||
| Fri., 10/2 | JV Boys Soccer | East Hampton | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | ||
| Fri., 10/2 | V Field Hockey | Westbrook/Old Lyme Coop | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | W 4-0 | |
| Fri., 10/2 | V Girls Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 3:45 p.m. | L 1-3 | |
| Fri., 10/2 | V Girls Swimming and Diving | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Pool - no diving [Directions] | 4:00 p.m. | ||
| Mon., 10/5 | V Boys Soccer | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 2-0 | |
| Mon., 10/5 | V Field Hockey | Morgan | Away - Indian River Complex-Turf Field [Directions] | 3:45 p.m. | W 3-1 | |
| Mon., 10/5 | JV Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 p.m. | ||
| Tue., 10/6 | V Boys Cross Country | Hale Ray, North Branford | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | ||
| Tue., 10/6 | V Girls Cross Country | Hale Ray, North Branford | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | ||
| Tue., 10/6 | V Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 p.m. | L 0-3 | |
| Thu., 10/8 | V Boys Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:45 p.m. | L 1-4 | |
| Thu., 10/8 | V Field Hockey | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 9-0 | |
| Thu., 10/8 | JV Field Hockey | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:15 p.m. | ||
| Fri., 10/9 | JV Boys Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Middle Field [Directions] | 3:45 p.m. | ||
| Fri., 10/9 | V Girls Soccer | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | L 3-0 | |
| Fri., 10/9 | V Girls Swimming and Diving | Haddam-Killingworth, Middletown | Away - Haddam Killingworth HS (HK)-HKHS Pool - no diving [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Soccer | Hale Ray | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 6-0 | |
| Wed., 10/14 | V Boys Cross Country | Morgan | Away - Indian River Complex-XC Course [Directions] | 3:45 p.m. | ||
| Wed., 10/14 | V Girls Cross Country | Morgan | Away - Indian River Complex-XC Course [Directions] | 4:15 p.m. | ||
| Wed., 10/14 | V Field Hockey | North Branford | Away - North Branford HS-NBHS Back Field [Directions] | 5:00 p.m. | L 3-4 | |
| Wed., 10/14 | JV Field Hockey | North Branford | Away - North Branford HS-NBHS Back Field [Directions] | 3:45 p.m. | ||
| Thu., 10/15 | V Boys Soccer | Valley Regional | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:45 p.m. | W 5-0 | |
| Thu., 10/15 | V Field Hockey | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 3-1 | |
| Fri., 10/16 | JV Boys Soccer | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Postponed | ||
| Fri., 10/16 | V Girls Swimming and Diving | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Pool - no diving [Directions] | 4:00 p.m. | ||
| Sat., 10/17 | V Field Hockey | North Branford (Scrim.) | Away - North Branford HS-NBHS Back Field [Directions] | Canceled | Cancelled | |
| Sat., 10/17 | JV Field Hockey | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | ||
| Sat., 10/17 | JV Girls Soccer | Coginchaug | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | Postponed | ||
| Sun., 10/18 | V Boys Soccer | Hale Ray | Away - Nathan Hale-Ray MS-Nathan Hale-Ray MS Soccer fields [Directions] | 1:00 p.m. | W 5-0 | |
| Mon., 10/19 | V Football | MSW | Away - Peters Complex-Football Field [Directions] | 3:45 p.m. | L 041 | |
| Mon., 10/19 | V Football | Old Saybrook | Home - Peters Complex-Football Field [Directions] | 3:45 p.m. | W 41-0 | |
| Mon., 10/19 | V Boys Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 3:45 p.m. | L 0-1 | |
| Mon., 10/19 | V Field Hockey | Westbrook/Old Lyme Coop | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | T 0-0 | |
| Mon., 10/19 | JV Field Hockey | Westbrook/Old Lyme Coop | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | ||
| Mon., 10/19 | JV Girls Soccer | Morgan | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:45 p.m. | ||
| Tue., 10/20 | V Boys Cross Country | Old Lyme | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:45 p.m. | ||
| Tue., 10/20 | V Girls Cross Country | Old Lyme | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 4:15 p.m. | ||
| Tue., 10/20 | V Girls Soccer | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | L 0-1 | |
| Thu., 10/22 | JV Boys Soccer | Portland | Away - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/22 | V Field Hockey | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 5-1 | |
| Thu., 10/22 | V Girls Soccer | Portland | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:45 p.m. | W 3-2 | |
| Fri., 10/23 | V Football | Coginchaug/Hale Ray/East Hampton | Home - Peters Complex-Football Field [Directions] | 3:45 p.m. | W 62-33 | Coginchaug White |
| Fri., 10/23 | V Boys Soccer | Portland | Away - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/23 | JV Girls Soccer | Coginchaug | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:30 p.m. | ||
| Fri., 10/23 | V Girls Swimming and Diving | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Pool - no diving [Directions] | Canceled | Cancelled | |
| Sat., 10/24 | V Football | Coginchaug/Hale Ray/East Hampton | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 10:30 a.m. | L 7-54 | |
| Sat., 10/24 | JV Field Hockey | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | ||
| Sat., 10/24 | V Girls Soccer | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 11:00 a.m. | T 2-2 | |
| Tue., 10/27 | V Boys Soccer | Westbrook | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 4-1 | |
| Tue., 10/27 | JV Girls Soccer | Old Lyme | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:45 p.m. | ||
| Wed., 10/28 | JV Boys Soccer | Coginchaug | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | Canceled | Cancelled | |
| Thu., 10/29 | V Girls Cross Country | East Hampton | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:45 p.m. | ||
| Fri., 10/30 | V Boys Soccer | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 10-0 | |
| Fri., 10/30 | JV Girls Soccer | North Branford/Hale Ray | Away - North Branford HS-NBHS Front Field [Directions] | Canceled | Cancelled | |
| Sat., 10/31 | V Football | Coginchaug/Hale Ray/East Hampton | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | L 14-40 | Coginchaug Blue |
| Sat., 10/31 | JV Boys Soccer | Westbrook | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | Postponed | ||
| Mon., 11/2 | V Field Hockey | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:45 p.m. | W 3-2(OT) | |
| Mon., 11/2 | JV Field Hockey | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 5:15 p.m. | ||
| Mon., 11/2 | V Girls Soccer | Coginchaug | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:00 p.m. | L 1-5 | |
| Tue., 11/3 | V Football | Coginchaug/Hale Ray/East Hampton | Home - Peters Complex-Football Field [Directions] | 3:45 p.m. | W 35-34 | Coginchaug Blue |
| Tue., 11/3 | V Boys Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:00 p.m. | Cancelled | |
| Wed., 11/4 | JV Boys Soccer | Coginchaug | Away - Coginchaug Regional HS-Field #2 - Middle Field @ CRHS [Directions] | Canceled | Cancelled | |
| Wed., 11/4 | V Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:15 p.m. | W 6-1 | |
| Wed., 11/4 | JV Field Hockey | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 5:00 p.m. | ||
| Wed., 11/4 | V Girls Soccer | North Branford/Hale Ray | Away - North Branford HS-NBHS Front Field [Directions] | 3:45 p.m. | W 3-1 | |
| Thu., 11/5 | V Field Hockey | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:00 p.m. | L 0-3 | |
| Thu., 11/5 | V Girls Soccer | Cromwell | Home - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:00 p.m. | T 1-1 | |
| Fri., 11/6 | V Football | MSW | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Fri., 11/6 | V Football | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Fri., 11/6 | V Boys Soccer | Cromwell | Away - Cromwell HS-Varsity field [Directions] | 3:15 p.m. | Cancelled | |
| Fri., 11/6 | JV Girls Soccer | Cromwell | Away - Cromwell HS-soccer field 1 [Directions] | 3:00 p.m. | ||
| Fri., 11/6 | V Girls Swimming and Diving | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Pool - no diving [Directions] | Canceled | Cancelled | |
| Sat., 11/7 | V Girls Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | Canceled | Cancelled | |
| Mon., 11/9 | V Girls Soccer | North Branford/Hale Ray | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 2:00 p.m. | W 1-0 | |
| Tue., 11/10 | V Field Hockey | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Tue., 11/10 | V Field Hockey | North Branford | Away - North Branford HS-NBHS Back Field [Directions] | 5:00 p.m. | ||
| Wed., 11/11 | V Boys Soccer | Hale Ray | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 2:00 p.m. | W 1-0 | |
| Wed., 11/11 | V Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | 2:00 p.m. | ||
| Fri., 11/13 | V Boys Soccer | East Hampton | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 2:00 p.m. | L 1-2 | |
| Wed., 2/10 | V Boys Ice Hockey | North Haven | Away - Northford Ice Pavilion-Red [Directions] | 8:30 p.m. | L 0-3 | |
| Wed., 2/10 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | W 4-2 | |
| Thu., 2/11 | V Boys Swimming and Diving | Greater New Haven | Away - Walter Gawrych Community Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/12 | V Boys Swimming and Diving | Cheshire, Greater New Haven | Home - Madison Swim and Racquet [Directions] | 7:30 p.m. | ||
| Sat., 2/13 | FR Boys Basketball | Old Lyme | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | Canceled | Cancelled | |
| Sat., 2/13 | V Girls Gymnastics | Valley Regional, Morgan, Hale Ray | Away - Flip Flop Gymnastics [Directions] | 12:00 p.m. | 123.30 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 12:30 p.m. | ||||||
| Mon., 2/15 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | 4:00 p.m. | L 2-4 | |
| Mon., 2/15 | V Girls Gymnastics | Valley Regional, Morgan, Hale Ray | Away - Flip Flop Gymnastics [Directions] | 2:30 p.m. | 128.15 | |
| Tue., 2/16 | V Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 59-24 | |
| Tue., 2/16 | JV Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/16 | V Boys Swimming and Diving | Cheshire | Away - Cheshire Community Pool [Directions] | 3:00 p.m. | ||
| Tue., 2/16 | V Girls Basketball | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | W 47-43 | |
| Tue., 2/16 | JV Girls Basketball | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/17 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 2/19 | V Boys Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/19 | JV Boys Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | Postponed | ||
| Fri., 2/19 | V Girls Ice Hockey | Woodstock Academy Coop (Scrim.) | Away - Norwich - Rose Garden-RoseGarden Arena [Directions] | Postponed | ||
| Sat., 2/20 | V Boys Basketball | Westbrook | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 12:30 p.m. | W 54-48 | |
| Sat., 2/20 | JV Boys Basketball | Westbrook | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 2/20 | FR Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 2/20 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavilion-Red [Directions] | 5:15 p.m. | L 1-4 | |
| Sat., 2/20 | V Girls Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 2:30 p.m. | W 54-29 | |
| Sat., 2/20 | JV Girls Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 1:00 p.m. | ||
| Sat., 2/20 | V Girls Gymnastics | Valley Regional, Hale Ray | Away - Flip Flop Gymnastics [Directions] | 2:00 p.m. | 124.80 | |
| Sat., 2/20 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 1:00 p.m. | L 0-7 | |
| Sun., 2/21 | V Girls Ice Hockey | Guilford Coop | Home - Northford Ice Pavilion-White [Directions] | 6:50 p.m. | L 1-8 | |
| Mon., 2/22 | V Boys Basketball | Old Lyme | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | L 44-39 | |
| Mon., 2/22 | JV Boys Basketball | Old Lyme | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/22 | V Boys Swimming and Diving | Amity, TBA | Home - Madison Swim and Racquet [Directions] | 7:30 p.m. | ||
| Mon., 2/22 | V Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | L 50-21 | |
| Mon., 2/22 | JV Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/23 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 6:00 p.m. | W 55-45 | |
| Tue., 2/23 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 4:30 p.m. | ||
| Tue., 2/23 | V Boys Swimming and Diving | Amity | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | 3:20 p.m. | ||
| Tue., 2/23 | V Girls Basketball | Coginchaug | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | L 48-27 | |
| Tue., 2/23 | JV Girls Basketball | Coginchaug | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 2/25 | V Boys Basketball | Morgan | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | L 76-29 | |
| Thu., 2/25 | JV Boys Basketball | Morgan | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 2/25 | V Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | 6:00 p.m. | L 28-60 | |
| Thu., 2/25 | JV Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | 4:30 p.m. | ||
| Fri., 2/26 | V Boys Ice Hockey | Branford | Away - Northford Ice Pavilion-Red [Directions] | Postponed | ||
| Fri., 2/26 | V Boys Swimming and Diving | Xavier | Away - Woodrow Wilson MS-Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/26 | V Boys Swimming and Diving | Greater New Haven, Shelton | Home - Madison Swim and Racquet [Directions] | 7:30 p.m. | ||
| Sat., 2/27 | FR Boys Basketball | Coginchaug | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 2/27 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 9:00 p.m. | L 2-3 | |
| Sat., 2/27 | V Girls Gymnastics | Old Lyme | Away - ABC Gymnastics [Directions] | 12:45 p.m. | 134.30 | |
| Sat., 2/27 | V Girls Ice Hockey | Guilford Coop | Away - Northford Ice Pavilion [Directions] | 6:15 p.m. | L 6-9 | |
| Sun., 2/28 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Northford Ice Pavilion-White [Directions] | 6:50 p.m. | L 2-5 | |
| Mon., 3/1 | V Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 6:00 p.m. | W 58-33 | |
| Mon., 3/1 | JV Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 4:30 p.m. | ||
| Mon., 3/1 | V Girls Basketball | North Branford | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:00 p.m. | L 52-39 | |
| Mon., 3/1 | JV Girls Basketball | North Branford | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 3/2 | V Boys Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | W 59-55 | |
| Tue., 3/2 | JV Boys Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 3/2 | V Boys Swimming and Diving | Shelton | Away - Shelton Community Center Pool [Directions] | 3:30 p.m. | ||
| Tue., 3/2 | V Boys Swimming and Diving | Greater New Haven | Away - Walter Gawrych Community Pool [Directions] | 4:00 p.m. | ||
| Thu., 3/4 | V Boys Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 5:30 p.m. | W 49-46 | |
| Thu., 3/4 | JV Boys Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 4:00 p.m. | ||
| Thu., 3/4 | V Girls Basketball | Valley Regional | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | L 62-37 | |
| Thu., 3/4 | JV Girls Basketball | Valley Regional | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 3/4 | V Girls Ice Hockey | West Haven/SHA | Home - Northford Ice Pavilion-Red [Directions] | 2:45 p.m. | L 0-5 | |
| Fri., 3/5 | V Boys Swimming and Diving | Cheshire | Away - Cheshire Community Pool [Directions] | 3:00 p.m. | ||
| Fri., 3/5 | V Boys Swimming and Diving | Cheshire, Fairfield Prep | Home - Madison Swim and Racquet [Directions] | 7:30 p.m. | ||
| Fri., 3/5 | V Girls Ice Hockey | Jonathan Law | Home - Northford Ice Pavilion-White [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 3/6 | FR Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 9:00 a.m. | ||
| Sat., 3/6 | V Boys Ice Hockey | Guilford | Away - West Haven HS-Bennett Rink [Directions] | 1:00 p.m. | ||
| Sat., 3/6 | V Girls Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 12:00 p.m. | L 37-43 | |
| Sat., 3/6 | V Girls Ice Hockey | Hamden Coop | Home - Northford Ice Pavilion-Blue [Directions] | 6:15 p.m. | L 1-3 | |
| Mon., 3/8 | V Boys Basketball | Cromwell | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | L 53-36 | |
| Mon., 3/8 | JV Boys Basketball | Cromwell | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 3/8 | V Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:30 p.m. | L 33-58 | |
| Mon., 3/8 | JV Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 3/9 | V Boys Swimming and Diving | Fairfield Prep | Away - Fairfield University-Rec Plex [Directions] | 3:45 p.m. | ||
| Wed., 3/10 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion-Red [Directions] | 3:50 p.m. | Cancelled | |
| Wed., 3/10 | V Boys Indoor Track | Hale Ray | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:00 p.m. | ||
| Wed., 3/10 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | ||
| Wed., 3/10 | V Girls Indoor Track | Hale Ray | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 3:00 p.m. | ||
| Thu., 3/11 | V Boys Basketball | East Hampton | Away - East Hampton [Directions] | 6:00 p.m. | L 62-52 | |
| Thu., 3/11 | JV Boys Basketball | East Hampton | Away - East Hampton [Directions] | 4:30 p.m. | ||
| Thu., 3/11 | V Girls Basketball | East Hampton | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | L 14-64 | |
| Thu., 3/11 | JV Girls Basketball | East Hampton | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 3/12 | V Boys Swimming and Diving | Amity | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | 3:20 p.m. | ||
| Fri., 3/12 | V Boys Swimming and Diving | Amity | Home - Madison Swim and Racquet [Directions] | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 7:30 p.m. | ||||||
| Sat., 3/13 | FR Boys Basketball | Morgan | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 3/13 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Northford Ice Pavilion-Blue [Directions] | TBA | Cancelled | |
| Sat., 3/13 | V Girls Gymnastics | Valley Regional, Morgan, Hale Ray | Away - Flip Flop Gymnastics [Directions] | 12:45 p.m. | 122.85 | |
| Mon., 3/15 | V Boys Basketball | Haddam-Killingworth | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | L 68-50 | |
| Mon., 3/15 | JV Boys Basketball | Haddam-Killingworth | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 3/15 | V Boys Ice Hockey | Sheehan | Away - Northford Ice Pavilion-Red [Directions] | Canceled | Cancelled | |
| Mon., 3/15 | V Girls Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:30 p.m. | L 36-49 | |
| Mon., 3/15 | JV Girls Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 4:00 p.m. | ||
| Mon., 3/15 | V Girls Ice Hockey | Jonathan Law | Away - Milford Ice Pavillion-Ice Rink [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 3/16 | V Boys Indoor Track | Old Lyme | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | Canceled | Cancelled | |
| Tue., 3/16 | V Boys Swimming and Diving | Xavier | Away - Woodrow Wilson MS-Pool [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 7:00 p.m. | ||||||
| Tue., 3/16 | V Girls Indoor Track | Old Lyme | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | Canceled | Cancelled | |
| Wed., 3/17 | V Boys Ice Hockey | Daniel Hand | Away - Northford Ice Pavilion-Red [Directions] | Canceled | Cancelled | |
| Thu., 3/18 | V Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 6:00 p.m. | W 54-46 | |
| Thu., 3/18 | JV Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 4:30 p.m. | ||
| Thu., 3/18 | V Girls Basketball | Westbrook | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | W 55-41 | |
| Thu., 3/18 | JV Girls Basketball | Westbrook | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 3/19 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 7:30 p.m. | ||
| Sat., 3/20 | V Boys Basketball | Hale Ray | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 3:00 p.m. | L 52-37 | |
| Sat., 3/20 | FR Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 10:00 a.m. | ||
| Sat., 3/20 | V Boys Swimming and Diving | SCC Dive Championship | Away - Sheehan HS-Sheehan HS Pool | 10:00 a.m. | ||
| Sat., 3/20 | V Girls Basketball | Portland | Home - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:00 p.m. | ||
| Sun., 3/21 | V Girls Gymnastics | Coginchaug, Old Lyme | Away - Haddam Killingworth HS (HK)-Gymnastics [Directions] | 12:00 p.m. | 125.40 | |
| Thu., 3/25 | V Boys Swimming and Diving | SCC | Home - TBA [Directions] | 6:30 p.m. | ||
| Sat., 4/3 | V Baseball | Guilford (Scrim.) | Away - Guilford HS-Baseball Diamond [Directions] | 11:00 a.m. | ||
| Tue., 4/6 | V Boys Tennis | Westbrook (Scrim.) | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:30 p.m. | ||
| Tue., 4/6 | V Girls Tennis | Westbrook (Scrim.) | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:30 p.m. | ||
| Wed., 4/7 | V Boys Outdoor Track | Old Lyme (Scrim.) | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:30 p.m. | ||
| Wed., 4/7 | V Girls Outdoor Track | Old Lyme (Scrim.) | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:30 p.m. | ||
| Thu., 4/8 | V Baseball | ValleyReg/Westbrook (Scrim.) | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/8 | V Softball | Valley Regional (Scrim.) | Away - Valley Regional HS-Joseph Camarota Memorial Field [Directions] | 4:00 p.m. | ||
| Sat., 4/10 | V Baseball | Westbrook | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 11:00 a.m. | W 13-1 | |
| Sat., 4/10 | V Boys Tennis | Old Lyme | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 11:00 a.m. | L 0-5 | |
| Sat., 4/10 | V Girls Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 11:00 a.m. | L 0-7 | |
| Mon., 4/12 | V Baseball | Old Lyme | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 11:00 a.m. | W 4-2 | |
| Mon., 4/12 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 11:00 a.m. | L 1-16 | |
| Mon., 4/12 | V Girls Tennis | Coginchaug | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 11:00 a.m. | L 0-7 | |
| Tue., 4/13 | V Boys Golf | Cromwell | Away - TPC River Highlands [Directions] | 3:00 p.m. | Cromwell 194- Old Saybrook 220. Medalist Garrett Brady (38) | |
| Tue., 4/13 | V Boys Lacrosse | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | L 10-18 | |
| Tue., 4/13 | V Girls Lacrosse | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | 10:00 a.m. | W 8 - 7 [Detailed Results] | |
| Wed., 4/14 | V Baseball | Hale Ray | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 11:00 a.m. | L 11-8 | |
| Wed., 4/14 | V Boys Tennis | Valley Regional | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 4/14 | V Softball | Hale Ray | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | W 8-4 | |
| Wed., 4/14 | V Girls Tennis | Valley Regional | Away - Valley Regional HS-Tennis Courts [Directions] | 11:00 a.m. | L 0-7 | |
| Sat., 4/17 | V Girls Lacrosse | Old Lyme | Away - Lyme-Old Lyme HS-Middle Field [Directions] | 10:00 a.m. | W 13-8 [Detailed Results] | |
| Sun., 4/18 | V Baseball | Portland | Away - Portland HS-Portland HS [Directions] | 1:00 p.m. | W 10-2 | |
| Mon., 4/19 | V Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 4:00 p.m. | L 4-0 | |
| Mon., 4/19 | V Boys Golf | Morgan | Away - Clinton Country Club [Directions] | 3:00 p.m. | Morgan 185, Old Saybrook 212. | |
| Mon., 4/19 | V Boys Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Mon., 4/19 | V Softball | Coginchaug | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | L 0-11 | |
| Mon., 4/19 | V Girls Tennis | Morgan | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Tue., 4/20 | V Boys Golf | Valley Regional | Away - Black Hall Golf Club [Directions] | 3:00 p.m. | Valley 216, Old Saybrook 220. Co-medalist Medalist Garrett Brady (46) | |
| Tue., 4/20 | V Boys Lacrosse | Cromwell | Away - Cromwell HS-Lacrosse Field [Directions] | 4:00 p.m. | W 13-8 | |
| Tue., 4/20 | V Boys Outdoor Track | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:30 p.m. | ||
| Tue., 4/20 | V Girls Lacrosse | Cromwell | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 21 -- 2 [Detailed Results] | |
| Tue., 4/20 | V Girls Outdoor Track | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:30 p.m. | ||
| Wed., 4/21 | V Boys Tennis | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Thu., 4/22 | V Boys Golf | Haddam-Killingworth | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:00 p.m. | Saybrook 194, HK 226. Drew Kulmann Medalist (46) | |
| Thu., 4/22 | V Boys Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | L 2-14 | |
| Thu., 4/22 | V Girls Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 4:00 p.m. | W 17 - 13 [Detailed Results] | |
| Thu., 4/22 | V Girls Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Fri., 4/23 | V Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 4:00 p.m. | L 13-6 | |
| Fri., 4/23 | V Boys Tennis | Cromwell | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Fri., 4/23 | V Softball | Cromwell | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | Forfeit | L Forfeit | |
| Fri., 4/23 | V Softball | Morgan | Away - Morgan School-Softball Field [Directions] | 4:45 p.m. | L 8-4 | |
| Fri., 4/23 | V Girls Tennis | Cromwell | Away - Watrous park [Directions] | 3:45 p.m. | L 1-6 | |
| Sat., 4/24 | V Baseball | Morgan | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 11:00 a.m. | L 5-4 | |
| Sat., 4/24 | V Softball | Westbrook/Old Saybrook | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | W Forfeit | |
| Sat., 4/24 | V Softball | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | L Forfeit | |
| Mon., 4/26 | V Baseball | ValleyReg/Westbrook | Away - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | L 8-7 | |
| Mon., 4/26 | V Boys Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | L 0-6 | |
| Mon., 4/26 | V Softball | East Hampton | Away - East Hampton HS-Softball Field [Directions] | 3:45 p.m. | L Forfeit | |
| Mon., 4/26 | V Softball | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | L 3-12 | |
| Mon., 4/26 | V Girls Tennis | Westbrook | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 4/27 | V Boys Lacrosse | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | L 10-17 | |
| Wed., 4/28 | V Boys Outdoor Track | Hale Ray | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:00 p.m. | ||
| Wed., 4/28 | V Boys Tennis | Portland | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 0-6 | |
| Wed., 4/28 | V Girls Outdoor Track | Hale Ray | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:00 p.m. | ||
| Wed., 4/28 | V Softball | Haddam-Killingworth | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L Forfeit | |
| Wed., 4/28 | V Softball | Cromwell | Away - Cromwell HS-Softball Diamond [Directions] | 4:00 p.m. | L 0-12 | |
| Wed., 4/28 | V Girls Tennis | Portland | Away - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Thu., 4/29 | JV Baseball | Cromwell | Away - Cromwell HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Thu., 4/29 | V Boys Golf | Hale Ray | Away - Nathan Hale Ray HS-Black Birch [Directions] | 3:30 p.m. | ||
| Thu., 4/29 | V Boys Lacrosse | Morgan | Away - Indian River Complex-Turf Field [Directions] | 4:00 p.m. | L 7-16 | |
| Thu., 4/29 | V Girls Lacrosse | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 14-5 [Detailed Results] | |
| Fri., 4/30 | V Baseball | East Hampton | Away - East Hampton HS-Baseball Field [Directions] | 3:45 p.m. | L 9-7 | |
| Fri., 4/30 | V Boys Golf | Coginchaug | Away - Coginchaug-Lyman Orchards Golf course [Directions] | 3:40 p.m. | Coginchaug 197, Old Saybrook 214. Colin Murphy Medalist (39) | |
| Fri., 4/30 | V Softball | East Hampton | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | L 9-14 | |
| Fri., 4/30 | V Softball | Morgan | Away - Morgan School-Softball Field [Directions] | 4:00 p.m. | L Forfeit | |
| Sat., 5/1 | V Girls Lacrosse | Watertown | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | W 10-5 [Detailed Results] | |
| Sat., 5/1 | V Girls Tennis | North Branford | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 10:00 a.m. | W 4-3 | |
| Mon., 5/3 | V Baseball | Haddam-Killingworth | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | L 2-0 | |
| Mon., 5/3 | V Boys Golf | Valley Regional | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:00 p.m. | Old Saybrook 191, Valley Regional, 243 | |
| Mon., 5/3 | V Boys Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | L 1-17 | |
| Mon., 5/3 | V Boys Tennis | East Hampton | Home - Old Saybrook HS [Directions] | 3:45 p.m. | L 1-6 | |
| Mon., 5/3 | V Softball | North Branford | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L Forfeit | |
| Mon., 5/3 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Varsity Softball Field [Directions] | 4:00 p.m. | L 1-5 | |
| Mon., 5/3 | V Girls Tennis | East Hampton | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | Cancelled | |
| Tue., 5/4 | V Boys Golf | Coginchaug | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:00 p.m. | Coginchaug 172, Old Saybrook 193. Colin Murphy medalist (38) | |
| Tue., 5/4 | V Boys Lacrosse | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 4:00 p.m. | L 9-20 | |
| Tue., 5/4 | V Girls Lacrosse | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 19-10 [Detailed Results] | |
| Wed., 5/5 | V Softball | Old Saybrook | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L Forfeit | |
| Wed., 5/5 | V Softball | Westbrook/Old Saybrook | Away - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | W Forfeit | |
| Thu., 5/6 | V Baseball | Westbrook | Home - Old Saybrook HS [Directions] | 4:00 p.m. | W 16-6 | |
| Thu., 5/6 | V Boys Golf | Hale Ray | Away - Nathan Hale Ray HS-Black Birch [Directions] | 3:00 p.m. | Hale Ray 207, Old Saybrook 221 | |
| Thu., 5/6 | V Boys Lacrosse | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 4:00 p.m. | L 8-14 | |
| Thu., 5/6 | V Boys Tennis | Coginchaug | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 5/6 | V Girls Lacrosse | North Branford | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 13-11 | |
| Thu., 5/6 | V Softball | Coginchaug | Away - Coginchaug Regional HS-Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 4:00 p.m. | L Forfeit | |
| Thu., 5/6 | V Girls Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 3:30 p.m. | W 4-3 | |
| Fri., 5/7 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Baseball Diamond [Directions] | 4:00 p.m. | L 17-2 | |
| Fri., 5/7 | V Boys Outdoor Track | Portland | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:00 p.m. | ||
| Fri., 5/7 | V Girls Outdoor Track | Portland | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:00 p.m. | ||
| Fri., 5/7 | V Softball | Coginchaug | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L Forfeit | |
| Fri., 5/7 | V Softball | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | L 3-15 | |
| Sat., 5/8 | V Baseball | Cromwell | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 1:00 p.m. | L 6-8 | |
| Mon., 5/10 | V Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | L 0-5 | |
| Mon., 5/10 | V Softball | Hale Ray | Away - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 6:30 p.m. | L 1-2 | |
| Mon., 5/10 | V Girls Tennis | Valley Regional | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | Cancelled | |
| Tue., 5/11 | V Boys Golf | Old Lyme | Away - Black Hall Golf Club [Directions] | 3:00 p.m. | Old Lyme 190, Old Saybrook 205 | |
| Tue., 5/11 | V Boys Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 5/11 | V Softball | Valley Regional | Away - Valley Regional HS-Joseph Camarota Memorial Field [Directions] | 3:45 p.m. | L Forfeit | |
| Tue., 5/11 | V Softball | North Branford | Away - North Branford HS-NBHS Softball Field [Directions] | 6:30 p.m. | L 1-7 | |
| Tue., 5/11 | V Girls Tennis | Old Lyme | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Wed., 5/12 | V Baseball | Portland | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:30 p.m. | W 3-2 | Game needs to be played later due to a conflict with a track meet on the same day. |
| Wed., 5/12 | V Boys Golf | Morgan | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:00 p.m. | Morgan 182, Old Saybrook 195. Garrett Brady medalist (41) | |
| Wed., 5/12 | V Boys Outdoor Track | Cromwell | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 2:30 p.m. | ||
| Wed., 5/12 | V Girls Outdoor Track | Cromwell | Home - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 2:30 p.m. | ||
| Wed., 5/12 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 3:30 p.m. | L Forfeit | |
| Wed., 5/12 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 5:15 p.m. | L Forfeit | |
| Thu., 5/13 | V Boys Golf | North Branford | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:00 p.m. | North Branford 184, Old Saybrook 186. Jack O'Brien medalist (41) | |
| Thu., 5/13 | V Boys Lacrosse | Cromwell | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | L 4-8 | |
| Thu., 5/13 | V Boys Tennis | Morgan | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Thu., 5/13 | V Girls Lacrosse | Cromwell | Away - Cromwell HS-Lacrosse Field [Directions] | 4:00 p.m. | W 19-6 | |
| Thu., 5/13 | V Girls Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 5/14 | V Baseball | Coginchaug | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | L 4-5 | |
| Fri., 5/14 | V Softball | Hale Ray | Away - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 4:00 p.m. | L Forfeit | |
| Fri., 5/14 | V Softball | Coginchaug | Away - Coginchaug Regional HS-Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 5:00 p.m. | L 1-17 | |
| Sat., 5/15 | V Softball | Hale Ray | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 11:00 a.m. | L Forfeit | |
| Mon., 5/17 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 4:00 p.m. | L 0-4 | |
| Mon., 5/17 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Mon., 5/17 | V Softball | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | L 2-8 | |
| Mon., 5/17 | V Softball | North Branford | Away - North Branford HS-NBHS Softball Field [Directions] | 4:00 p.m. | L Forfeit | |
| Mon., 5/17 | V Girls Tennis | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Tue., 5/18 | V Boys Golf | East Hampton | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:00 p.m. | Cancelled | |
| Tue., 5/18 | V Boys Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 5:30 p.m. | L 3-16 | |
| Tue., 5/18 | V Boys Outdoor Track | East Hampton | Away - East Hampton HS-Track [Directions] | 3:30 p.m. | ||
| Tue., 5/18 | V Girls Lacrosse | Haddam-Killingworth | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | W 17-8 | |
| Tue., 5/18 | V Girls Outdoor Track | East Hampton | Away - East Hampton HS-Track [Directions] | 3:30 p.m. | ||
| Wed., 5/19 | V Baseball | ValleyReg/Westbrook | Home - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | L 4-1 | |
| Wed., 5/19 | V Boys Tennis | Cromwell | Away - Watrous park [Directions] | 3:45 p.m. | L 1-6 | |
| Wed., 5/19 | V Softball | Morgan | Home - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 3:45 p.m. | L Forfeit | |
| Wed., 5/19 | V Softball | Valley Regional | Away - Valley Regional HS-Joseph Camarota Memorial Field [Directions] | 4:00 p.m. | L 10-11 | |
| Wed., 5/19 | V Girls Tennis | Cromwell | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Thu., 5/20 | V Boys Golf | Portland | Away - Portland Golf Course [Directions] | 2:45 p.m. | Old Saybrook 193, Portland 154. Medalist Luke Stennett (34) | |
| Thu., 5/20 | V Boys Lacrosse | Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | 4:00 p.m. | L 7-9 | |
| Thu., 5/20 | V Girls Lacrosse | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | W 15-8 | |
| Thu., 5/20 | V Softball | Morgan | Home - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:00 p.m. | W 11-3 | |
| Fri., 5/21 | V Boys Lacrosse | Valley Regional | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | L 4-16 | |
| Fri., 5/21 | V Boys Tennis | Valley Regional | Away - Valley Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Fri., 5/21 | V Girls Lacrosse | Valley Regional | Away - Valley Regional HS-Field Hockey / Lacrosse Field [Directions] | 4:00 p.m. | W 17-9 | |
| Fri., 5/21 | V Girls Tennis | Valley Regional | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Sat., 5/22 | V Boys Lacrosse | Morgan | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 1:00 p.m. | L 4-12 | |
| Sat., 5/22 | V Softball | Morgan | Away - Morgan School-Softball Field [Directions] | 4:30 p.m. | W 9-5 | |
| Mon., 5/24 | V Boys Golf | Old Lyme | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:00 p.m. | Old Lyme 182, Old Saybrook 191. Garrett Brady Medalist(39) | |
| Mon., 5/24 | V Girls Lacrosse | Morgan | Away - Indian River Complex-Turf Field [Directions] | 4:00 p.m. | W 12-9 | |
| Mon., 5/24 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/25 | V Boys Tennis | Valley Regional | Home - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 11:30 a.m. | ||
| Tue., 5/25 | V Girls Lacrosse | Old Lyme | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:30 p.m. | W 6-3 | |
| Wed., 5/26 | V Boys Outdoor Track | Shoreline Track Championship | Away - Lyme-Old Lyme HS-Track Field | 1:30 p.m. | ||
| Wed., 5/26 | V Boys Tennis | Portland | Away - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Wed., 5/26 | V Girls Outdoor Track | Shoreline Track Championship | Away - Lyme-Old Lyme HS-Track Field | 1:30 p.m. | ||
| Thu., 5/27 | V Boys Golf | Haddam-Killingworth | Away - Black Birch Golf Course [Directions] | 3:00 p.m. | Old Saybrook 191, HK 191. Garrett Brady medalist (42) | |
| Thu., 5/27 | V Girls Lacrosse | North Branford | Home - Indian River Complex-Turf Field [Directions] | 6:00 p.m. | L 3-9 | |
| Tue., 6/1 | V Girls Lacrosse | Rocky Hill | Home - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 5:00 p.m. | W 17 - 3 | |
| Wed., 6/2 | V Boys Golf | Portland | Home - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:00 p.m. | Portland 161, Old Saybrook 185. Luke Stennett Medalist (36) | |
| Thu., 6/3 | V Boys Outdoor Track | CIAC Class S Boys Outdoor Track Championship | Away - Willow Brook Park | 3:00 p.m. | ||
| Thu., 6/3 | V Girls Outdoor Track | CIAC Class S Girls Outdoor Track Championship | Away - Willow Brook Park | 3:00 p.m. | ||
| Tue., 6/8 | V Boys Golf | CIAC Boys Div. IV Golf Championship | Away - Fairview Farms | 8:00 a.m. | ||
| Wed., 6/9 | V Boys Outdoor Track | CIAC Open Boys Outdoor Track Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Wed., 6/9 | V Girls Outdoor Track | CIAC Open Girls Outdoor Track Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Sat., 6/12 | V Boys Golf | CIAC State Open Golf Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/14 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Manchester | 3:30 p.m. | ||
| Mon., 6/14 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Manchester | 3:30 p.m. | ||
| Tue., 6/15 | V Boys Outdoor Track | CIAC Boys Decathlon Championship Day 1 | Away - Manchester | 10:00 a.m. | ||
| Tue., 6/15 | V Girls Outdoor Track | CIAC Girls Heptathlon Championship Day 1 | Away - Manchester | 10:30 a.m. | ||
| Tue., 6/15 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Manchester | 3:30 p.m. | ||
| Wed., 6/16 | V Boys Outdoor Track | CIAC Boys Decathlon Championship Day 2 | Away - Manchester | 10:00 a.m. | ||
| Wed., 6/16 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Manchester | 3:30 p.m. | ||
| Wed., 6/16 | V Girls Outdoor Track | CIAC Girls Heptathlon Championship Day 2 | Away - Manchester | 10:00 a.m. | ||