| Hale Ray 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 330 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 8/27 | V Football | Branford (Scrim.) | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 10:00 a.m. | ||
| Sat., 8/27 | V Football | TBA | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 10:00 a.m. | ||
| Tue., 8/30 | V Boys Soccer | Norwich Tech (Scrim.) | Away - Norwich Technical HS-NTHS Outdoor Athletic Complex [Directions] | 4:00 p.m. | ||
| Tue., 8/30 | V Girls Soccer | Shepaug Valley (Scrim.) | Away - Shepaug Valley HS-Shepaug Valley Varsity Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 8/30 | V Girls Volleyball | Maloney (Scrim.) | Home - Nathan Hale Ray HS-Gym [Directions] | 3:30 p.m. | ||
| Thu., 9/1 | V Girls Volleyball | Bacon Academy (Scrim.) | Away - Bacon Academy-Gym [Directions] | 4:45 p.m. | ||
| Fri., 9/2 | V Boys Cross Country | Cromwell (Scrim.) | Away - Cromwell HS-cross country course [Directions] | 3:45 p.m. | ||
| Fri., 9/2 | V Football | Foran (Scrim.) | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 5:00 p.m. | ||
| Fri., 9/2 | V Girls Cross Country | Cromwell (Scrim.) | Away - Cromwell HS-cross country course [Directions] | 3:45 p.m. | ||
| Sat., 9/3 | V Boys Soccer | Putnam (Scrim.) | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 11:00 a.m. | ||
| Sat., 9/3 | V Girls Volleyball | Glastonbury Jamboree | Away - Glastonbury HS-Gym | 8:00 a.m. | ||
| Tue., 9/6 | V Boys Soccer | Parish Hill (Scrim.) | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | Rainout | ||
| Tue., 9/6 | V Girls Volleyball | Naugatuck (Scrim.) | Home - Nathan Hale Ray HS-Gym [Directions] | 4:30 p.m. | ||
| Thu., 9/8 | V Boys Cross Country | Middletown | Away - Veterans Memorial Park, Middletown, CT [Directions] | 3:30 p.m. | ||
| Thu., 9/8 | V Football | Capital/Achievement | Away - Annie Fisher Turf Field [Directions] | 6:00 p.m. | L 19-43 | |
| Thu., 9/8 | V Girls Cross Country | Middletown | Away - Veterans Memorial Park, Middletown, CT [Directions] | 3:30 p.m. | ||
| Thu., 9/8 | V Girls Soccer | Valley Regional | Home - North Branford HS-NBHS Front Field [Directions] | 6:30 p.m. | L 0-3 | |
| Thu., 9/8 | V Girls Volleyball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 9/8 | JV Girls Volleyball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 4:30 p.m. | ||
| Fri., 9/9 | V Boys Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 3:45 p.m. | L 7-0 | |
| Sat., 9/10 | V Girls Cross Country | Simsbury, Daniel Hand, South Windsor | Away - Stratton Brook State Park [Directions] | 10:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 12:00 p.m. | ||||||
| Mon., 9/12 | JV Football | Capital/Achievement | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 4:30 p.m. | ||
| Mon., 9/12 | V Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | 3:45 p.m. | L 4-0 | |
| Mon., 9/12 | V Girls Volleyball | Valley Regional | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 9/12 | JV Girls Volleyball | Valley Regional | Home - Nathan Hale Ray HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 9/13 | V Boys Cross Country | Portland | Away - Camp Ingersoll [Directions] | 3:30 p.m. | ||
| Tue., 9/13 | V Boys Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 4:00 p.m. | L 8-1 | |
| Tue., 9/13 | V Girls Cross Country | Portland | Away - Camp Ingersoll [Directions] | 3:30 p.m. | ||
| Wed., 9/14 | V Girls Volleyball | East Hampton | Away - East Hampton HS-Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Wed., 9/14 | JV Girls Volleyball | East Hampton | Away - East Hampton HS-Gym [Directions] | 4:30 p.m. | ||
| Thu., 9/15 | V Girls Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 3-1 | |
| Fri., 9/16 | V Football | Valley Regional/Old Lyme | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 6:30 p.m. | L 12-61 | |
| Fri., 9/16 | V Boys Soccer | Haddam-Killingworth | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 6:00 p.m. | L 4-1 | |
| Fri., 9/16 | V Girls Volleyball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:00 p.m. | W 3-1 | |
| Fri., 9/16 | JV Girls Volleyball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 3:30 p.m. | ||
| Sat., 9/17 | V Boys Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 9:00 a.m. | ||
| Sat., 9/17 | JV Football | Valley Regional/Old Lyme | Home - Coginchaug Regional HS-Field #1 - Brookside Field @ CRHS [Directions] | 10:00 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | CT River Valley Invitational | Away - Cromwell HS-cross country course | 8:30 a.m. | ||
| Sat., 9/17 | V Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 10:00 a.m. | L 0-5 | |
| Mon., 9/19 | V Girls Volleyball | Morgan | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 9/19 | JV Girls Volleyball | Morgan | Home - Nathan Hale Ray HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 9/20 | V Boys Soccer | Portland | Away - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | L 5-0 | |
| Wed., 9/21 | V Boys Cross Country | Coginchaug - Going to the Sun Cross Country Meet | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:30 p.m. | ||||||
| Wed., 9/21 | V Girls Cross Country | Coginchaug - Going to the Sun Cross Country Meet | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:30 p.m. | ||
| Thu., 9/22 | V Boys Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:45 p.m. | L 2-1 | |
| Fri., 9/23 | V Football | Ellington | Away - Ellington HS-Main Field [Directions] | 6:30 p.m. | L 6-35 | |
| Fri., 9/23 | V Girls Volleyball | Cromwell | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 9/23 | JV Girls Volleyball | Cromwell | Home - Nathan Hale Ray HS-Gym [Directions] | 4:30 p.m. | ||
| Sat., 9/24 | V Boys Cross Country | Ocean State Invitational | Away - Not Listed | 10:00 a.m. | ||
| Sat., 9/24 | JV Football | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 10:00 a.m. | ||
| Sat., 9/24 | V Girls Cross Country | Ocean State Invitational | Away - Not Listed | 10:00 a.m. | ||
| Mon., 9/26 | JV Football | Ellington | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | Canceled | Cancelled | |
| Tue., 9/27 | V Boys Soccer | Westbrook | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 6:00 p.m. | L 4-1 | |
| Tue., 9/27 | V Girls Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 7:00 p.m. | L 3-0 | |
| Wed., 9/28 | V Boys Cross Country | Coginchaug, Old Lyme, TBA, Portland | Home - Nathan Hale Ray HS-HS XC Course [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Cross Country | Shoreline Conference Small Schools Meet | Home - Nathan Hale Ray HS-HS XC Course [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Volleyball | Haddam-Killingworth | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 3-2 | |
| Wed., 9/28 | JV Girls Volleyball | Haddam-Killingworth | Home - Nathan Hale Ray HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 9/30 | V Boys Cross Country | Nonnewaug | Away - Nonnewaug HS [Directions] | 3:00 p.m. | ||
| Fri., 9/30 | V Boys Soccer | Valley Regional | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 6:00 p.m. | L 6-0 | |
| Fri., 9/30 | V Girls Cross Country | Nonnewaug | Away - Nonnewaug HS [Directions] | 3:00 p.m. | ||
| Fri., 9/30 | V Girls Volleyball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Fri., 9/30 | JV Girls Volleyball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/1 | V Football | Old Saybrook | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 2:00 p.m. | W 31-0 | |
| Sat., 10/1 | V Girls Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 9:45 a.m. | L 4-0 | |
| Mon., 10/3 | JV Football | Old Saybrook, MSW | Away - Peters Complex-Football Field [Directions] | 6:00 p.m. | ||
| Mon., 10/3 | V Girls Soccer | Harding | Away - Warren Harding HS-Lewis Field [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 10/3 | V Girls Volleyball | North Branford | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 3-0 | |
| Mon., 10/3 | JV Girls Volleyball | North Branford | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/5 | V Girls Soccer | Westbrook | Home - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | T 2-2 | Non League Game |
| Wed., 10/5 | V Girls Volleyball | Putnam | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/5 | JV Girls Volleyball | Putnam | Home - Nathan Hale Ray HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/7 | V Football | Stafford/East Windsor/Somers | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 6:30 p.m. | L 12-33 | |
| Fri., 10/7 | V Boys Soccer | Old Lyme | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 3:45 p.m. | L 5-0 | |
| Fri., 10/7 | V Girls Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 2:30 p.m. | L 0-6 | |
| Fri., 10/7 | V Girls Volleyball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/7 | JV Girls Volleyball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/8 | V Boys Cross Country | Wickham Invitational | Away - Wickham Park | 10:00 a.m. | ||
| Sat., 10/8 | JV Football | Stafford/East Windsor/Somers | Away - Stafford HS-Lighted Stadium Field (behind the school) [Directions] | 10:00 a.m. | ||
| Sat., 10/8 | V Girls Cross Country | Wickham Invitational | Away - Wickham Park | 10:00 a.m. | ||
| Sat., 10/8 | V Girls Soccer | Cromwell | Home - North Branford HS-NBHS Front Field [Directions] | 12:00 p.m. | L 7-0 | |
| Mon., 10/10 | V Girls Volleyball | East Hampton | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | L 3-0 | |
| Mon., 10/10 | JV Girls Volleyball | East Hampton | Home - Nathan Hale Ray HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 10/11 | V Boys Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 4:45 p.m. | L 3-0 | |
| Tue., 10/11 | V Girls Soccer | Old Saybrook | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 6:00 p.m. | L 3-0 | |
| Wed., 10/12 | V Girls Volleyball | Coginchaug | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 3-2 | |
| Wed., 10/12 | JV Girls Volleyball | Coginchaug | Home - Nathan Hale Ray HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/14 | V Girls Soccer | Haddam-Killingworth | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 6:00 p.m. | L 6-2 | |
| Fri., 10/14 | V Girls Volleyball | Morgan | Away - Morgan School-Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Fri., 10/14 | JV Girls Volleyball | Morgan | Away - Morgan School-Gym [Directions] | 6:45 p.m. | ||
| Mon., 10/17 | V Girls Soccer | Morgan | Home - North Branford HS-NBHS Front Field [Directions] | 3:00 p.m. | L 3-0 | |
| Mon., 10/17 | V Girls Volleyball | Aerospace | Away - Academy of Aerospace and Engineering-Gym 1 [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/17 | JV Girls Volleyball | Aerospace | Away - Academy of Aerospace and Engineering-Gym 1 [Directions] | Canceled | Cancelled | |
| Wed., 10/19 | V Boys Soccer | Cromwell | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 5:30 p.m. | L 9-0 | |
| Wed., 10/19 | V Girls Soccer | Portland | Away - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | L 0-6 | |
| Wed., 10/19 | V Girls Volleyball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/19 | JV Girls Volleyball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | V Boys Cross Country | Shoreline Cross Country Championship | Away - Hammonasset Park | 1:30 p.m. | ||
| Thu., 10/20 | V Boys Cross Country | Shoreline Championship-Hammonassett State Park | Away - Not Listed | 2:30 p.m. | ||
| Thu., 10/20 | V Boys Soccer | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | W 4-1 | |
| Thu., 10/20 | V Girls Cross Country | Shoreline Cross Country Championship | Away - Hammonasset Park | 1:30 p.m. | ||
| Thu., 10/20 | V Girls Cross Country | Shoreline Championship-Hammonassett State Park | Away - Not Listed | 2:30 p.m. | ||
| Fri., 10/21 | V Girls Volleyball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 10/21 | JV Girls Volleyball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 6:00 p.m. | ||
| Sat., 10/22 | V Football | MSW | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 1:00 p.m. | L 39-58 | |
| Sat., 10/22 | V Boys Soccer | Amistad | Away - Amistad HS-Stadium [Directions] | 11:00 a.m. | L 4-1 | |
| Mon., 10/24 | JV Girls Volleyball | Portland | Home - Nathan Hale Ray HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/25 | V Boys Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 6:00 p.m. | L 8-0 | |
| Tue., 10/25 | V Girls Soccer | Harding | Home - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | W 10-1 | |
| Tue., 10/25 | V | ValleyReg, HaddamKillingworth, NorthBranford | Away - Valley Regional HS-JV Girls Soccer Field [Directions] | 3:30 p.m. | ||
| Wed., 10/26 | V Girls Soccer | Coginchaug | Home - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | L 4-0 | |
| Wed., 10/26 | V Girls Volleyball | Old Lyme | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/26 | JV Girls Volleyball | Old Lyme | Home - Nathan Hale Ray HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/28 | V Football | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | 6:30 p.m. | L 6-56 | |
| Fri., 10/28 | V Girls Volleyball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 5:15 p.m. | W 3-0 | |
| Fri., 10/28 | JV Girls Volleyball | Guilford | Away - Guilford HS-Main gym at GHS [Directions] | 3:45 p.m. | ||
| Sat., 10/29 | V Boys Cross Country | CIAC Class S Championship | Away - Wickham Park | 11:55 a.m. | ||
| Sat., 10/29 | V Boys Cross Country | Class S State Championship | Away - Wickham Park | 12:00 p.m. | ||
| Sat., 10/29 | JV Football | Haddam-Killingworth | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 11:00 a.m. | ||
| Sat., 10/29 | V Boys Soccer | Amistad (Scrim.) | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 6:30 p.m. | ||
| Sat., 10/29 | V Girls Cross Country | CIAC Class S Championship | Away - Wickham Park | 11:20 a.m. | ||
| Sat., 10/29 | V Girls Cross Country | Class S State Championship | Away - Wickham Park | 12:00 p.m. | ||
| Thu., 11/3 | V Girls Volleyball | Valley Regional | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 3-2 | |
| Fri., 11/4 | V Boys Cross Country | Cross Country State Open | Away - Wickham Park | 1:45 p.m. | ||
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | V Football | Cromwell/Portland | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 6:30 p.m. | L 0-55 | |
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Sat., 11/5 | V Girls Volleyball | East Hampton | Home - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 12:00 p.m. | L 3-1 | |
| Mon., 11/7 | JV Football | Cromwell/Portland | Away - Pierson Park (Cromwell, CT)-Football Field [Directions] | Canceled | Cancelled | |
| Wed., 11/9 | V Girls Volleyball | Immaculate | Home - Nathan Hale Ray HS-Gym [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 11/11 | V Girls Volleyball | Coventry | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | ||
| Sat., 11/12 | V Boys Cross Country | Cross Country New Englands- Pattagonsett HS -RI | Away - TBA | 12:00 p.m. | ||
| Sat., 11/12 | V Football | SMSA Coop | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 1:00 p.m. | L 14-59 | |
| Mon., 11/14 | V Girls Volleyball | Coginchaug | Home - East Hampton HS-Gym [Directions] | 6:00 p.m. | ||
| Sat., 11/19 | V Girls Volleyball | East Hampton | Home - East Haven HS-Gym [Directions] | 4:00 p.m. | ||
| Wed., 11/23 | V Football | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 6:00 p.m. | L 18-51 | |
| Sat., 12/3 | V Girls Basketball | Norwich Tech (Scrim.) | Home - Nathan Hale Ray HS-Gym [Directions] | 11:00 a.m. | ||
| Tue., 12/6 | V Girls Basketball | Windham (Scrim.) | Home - Nathan Hale Ray HS-Gym [Directions] | 3:30 p.m. | ||
| Wed., 12/7 | V Boys Basketball | Windham Tech (Scrim.) | Away - Windham Technical HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 12/7 | V Boys Indoor Track | Shoreline Conference Indoor Track Developmental | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 12/13 | ||||||
| Wed., 12/7 | V Girls Indoor Track | Shoreline Conference Indoor Track Developmental | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 12/13 | ||||||
| Thu., 12/8 | V Girls Basketball | Parish Hill (Scrim.) | Home - Nathan Hale Ray HS-Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/10 | V Girls Basketball | Windham Tech (Scrim.) | Away - Windham Technical HS-Gym [Directions] | 10:00 a.m. | ||
| Mon., 12/12 | V Boys Basketball | Bacon Academy (Scrim.) | Away - Bacon Academy-Gym [Directions] | 4:45 p.m. | ||
| Thu., 12/15 | V Boys Basketball | Old Saybrook | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | L 62-44 | |
| Thu., 12/15 | JV Boys Basketball | Old Saybrook | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/15 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:00 p.m. | L 47-22 | |
| Thu., 12/15 | V | Basketball | Away - Valley Regional HS-Valley Regional High School Gym | 3:30 p.m. | ||
| Fri., 12/16 | V Boys Indoor Track | Hillhouse Invitational | Away - Hillhouse HS-Field House | 4:00 p.m. | ||
| Sat., 12/17 | V Boys Indoor Track | Hillhouse Invitational | Away - Hillhouse HS-Field House | 10:00 a.m. | ||
| Mon., 12/19 | V Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 6:00 p.m. | L 68-60 | |
| Mon., 12/19 | JV Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | Postponed | ||
| Mon., 12/19 | V Girls Basketball | Old Lyme | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 50-27 | |
| Tue., 12/27 | V Boys Basketball | Plainfield | Home - Nathan Hale Ray HS-Gym [Directions] | 12:30 p.m. | W 65-31 | |
| Tue., 12/27 | JV Boys Basketball | Plainfield | Home - Nathan Hale Ray HS-Gym [Directions] | 11:00 a.m. | ||
| Fri., 12/30 | V Girls Basketball | Putnam | Home - Nathan Hale Ray HS-Gym [Directions] | 12:00 p.m. | W 44-26 | |
| Tue., 1/3 | V Boys Basketball | Coginchaug | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | L 54-45 | |
| Tue., 1/3 | V Girls Basketball | Coginchaug | Home - Nathan Hale Ray HS-Gym [Directions] | 5:00 p.m. | L 55-25 | |
| Thu., 1/5 | V Boys Indoor Track | Shoreline League Meet 1 | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Thu., 1/5 | V Girls Indoor Track | Shoreline League Meet 1 | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Fri., 1/6 | V Boys Basketball | Westbrook | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 57-45 | |
| Fri., 1/6 | JV Boys Basketball | Westbrook | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | V Girls Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 6:00 p.m. | L 37-27 | |
| Sat., 1/7 | JV Boys Basketball | Coginchaug | Home - Nathan Hale Ray HS-Gym [Directions] | Postponed | ||
| Sat., 1/7 | V Girls Basketball | Derby | Home - Nathan Hale Ray HS-Gym [Directions] | 2:00 p.m. | W 43-19 | |
| Mon., 1/9 | V Girls Basketball | Aerospace | Away - Academy of Aerospace and Engineering-Gym 1 [Directions] | 6:30 p.m. | W 42-27 | |
| Tue., 1/10 | V Boys Basketball | East Hampton | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | L 58-47 | |
| Tue., 1/10 | JV Boys Basketball | East Hampton | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | V Girls Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 6:00 p.m. | L 75-19 | |
| Thu., 1/12 | V Boys Indoor Track | League meet # 2 | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Thu., 1/12 | V Girls Basketball | North Branford | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | L 58-26 | |
| Thu., 1/12 | JV Girls Basketball | North Branford | Home - Nathan Hale Ray HS-Gym [Directions] | Postponed | ||
| Fri., 1/13 | V Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 7:00 p.m. | W 46-44 | |
| Fri., 1/13 | JV Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/14 | JV Girls Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 4:30 p.m. | ||
| Mon., 1/16 | V Boys Basketball | Tourtellotte | Home - Nathan Hale Ray HS-Gym [Directions] | 12:30 p.m. | W 57-48 | |
| Mon., 1/16 | JV Boys Basketball | Tourtellotte | Home - Nathan Hale Ray HS-Gym [Directions] | 10:45 a.m. | ||
| Tue., 1/17 | V Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:00 p.m. | W 47-44 | |
| Tue., 1/17 | JV Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | Canceled | Cancelled | |
| Tue., 1/17 | V Girls Basketball | Haddam-Killingworth | Home - Nathan Hale Ray HS-Gym [Directions] | 4:00 p.m. | L 65-40 | |
| Tue., 1/17 | JV Girls Basketball | Haddam-Killingworth | Home - Nathan Hale Ray HS-Gym [Directions] | Postponed | ||
| Thu., 1/19 | V | LymeOldLyme | Away - Lyme-Old Lyme HS [Directions] | 3:00 p.m. | ||
| Fri., 1/20 | V Boys Basketball | Cromwell | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | L 36-30 | |
| Fri., 1/20 | JV Boys Basketball | Cromwell | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | V Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:30 p.m. | L 50-9 | |
| Fri., 1/20 | JV Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | Postponed | ||
| Sat., 1/21 | JV Girls Basketball | Morgan | Home - Nathan Hale Ray HS-Gym [Directions] | 10:00 a.m. | ||
| Mon., 1/23 | V Boys Indoor Track | Shoreline Coaches Invite | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Mon., 1/23 | V Girls Indoor Track | Shoreline Coaches Invite | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Tue., 1/24 | V Boys Basketball | Valley Regional | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | L 45-41 | |
| Tue., 1/24 | JV Boys Basketball | Valley Regional | Home - Nathan Hale Ray HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 6:00 p.m. | L 68-11 | |
| Fri., 1/27 | V Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 7:00 p.m. | L 76-53 | |
| Fri., 1/27 | JV Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | V Girls Basketball | Morgan | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | L 42-14 | |
| Mon., 1/30 | V Girls Basketball | Comp Sci | Away - Academy of Computer Science and Engineering HS-Gymnasium [Directions] | 5:00 p.m. | L 46-44 | |
| Tue., 1/31 | V Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 58-43 | |
| Tue., 1/31 | JV Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Old Saybrook | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | L 62-41 | |
| Fri., 2/3 | V Boys Basketball | Old Lyme | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 36-32 | |
| Fri., 2/3 | JV Boys Basketball | Old Lyme | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/3 | V Boys Indoor Track | Shoreline Conference Indoor Track Championship | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Fri., 2/3 | V Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 6:00 p.m. | W 54-36 | |
| Fri., 2/3 | V Girls Indoor Track | Shoreline Conference Indoor Track Championship | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Tue., 2/7 | V Boys Basketball | Portland | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | L 64-46 | |
| Tue., 2/7 | JV Boys Basketball | Portland | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 26-36 | |
| Tue., 2/7 | JV Girls Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | Postponed | ||
| Thu., 2/9 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Thu., 2/9 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/10 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | L 49-61 | |
| Fri., 2/10 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:00 p.m. | L 21-54 | |
| Sat., 2/11 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 11:30 a.m. | ||
| Sat., 2/11 | JV Girls Basketball | Coginchaug | Home - Nathan Hale Ray HS-Gym [Directions] | 11:00 a.m. | ||
| Mon., 2/13 | V Girls Gymnastics | Shoreline Conference Championship | Away - ABC Gymnastics | 6:30 p.m. | ||
| Tue., 2/14 | V Girls Basketball | Westbrook | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | L 32-29 | |
| Wed., 2/15 | V Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | L 52-40 | |
| Wed., 2/15 | JV Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/16 | V Boys Basketball | Grasso Tech | Away - Grasso Tech-Grasso Gymnasium [Directions] | 6:30 p.m. | W 53-39 | |
| Thu., 2/16 | JV Boys Basketball | Grasso Tech | Away - Grasso Tech-Grasso Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 2/17 | V Girls Basketball | Portland | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 40-19 | |
| Sat., 2/18 | V Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 2:00 p.m. | L 40-67 | |
| Sat., 2/18 | JV Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 12:30 p.m. | ||
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/20 | V Boys Basketball | Wheeler | Away - Wheeler HS-Gym [Directions] | 7:00 p.m. | L 78-67 | |
| Mon., 2/20 | JV Boys Basketball | Wheeler | Away - Wheeler HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 3/1 | V Girls Basketball | Thomaston | Away - Thomaston HS-Gym [Directions] | 6:30 p.m. | L 49-12 | |
| Thu., 3/2 | JV Boys Basketball | Windham | Home - Nathan Hale Ray HS-Gym [Directions] | 3:45 p.m. | ||
| Mon., 3/6 | V Boys Basketball | Coventry | Away - Coventry [Directions] | 6:30 p.m. | ||
| Wed., 3/22 | V Baseball | Hillhouse/Career (Scrim.) | Away - West Rock Park - Amhryn Field [Directions] | 4:00 p.m. | ||
| Sat., 3/25 | V Softball | RHAM (Scrim.) | Away - RHAM HS-Softball Diamond [Directions] | 10:00 a.m. | Cancelled | |
| Mon., 3/27 | V Baseball | RHAM (Scrim.) | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | ||
| Tue., 3/28 | V Softball | Bacon Academy (Scrim.) | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 3:45 p.m. | ||
| Wed., 3/29 | V Baseball | Bacon Academy (Scrim.) | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | ||
| Thu., 3/30 | V Softball | Ledyard (Scrim.) | Away - Ledyard HS-Ellen Mahoney Softball Complex [Directions] | 3:45 p.m. | ||
| Mon., 4/3 | V Baseball | Portland | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | W 8-5 | |
| Mon., 4/3 | V Softball | Portland | Away - Portland HS-MS Softball Field [Directions] | 4:00 p.m. | W 29-0 | |
| Tue., 4/4 | JV Baseball | Portland | Away - Portland HS-Portland HS [Directions] | 4:00 p.m. | ||
| Wed., 4/5 | V Baseball | Coginchaug | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:15 p.m. | L 10-2 | |
| Wed., 4/5 | V Softball | Coginchaug | Away - Coginchaug Regional HS-Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 3:15 p.m. | W 11-7 | |
| Thu., 4/6 | V Baseball | Westbrook | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 4/6 | V Softball | Westbrook/Old Saybrook | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 4:00 p.m. | W 24-1 | |
| Sat., 4/8 | JV Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 10:00 a.m. | ||
| Tue., 4/11 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Gloria Maddocks Field [Directions] | 12:00 p.m. | L 7-0 | |
| Tue., 4/11 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 2:00 p.m. | L 3-2 | |
| Tue., 4/11 | JV Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 3:30 p.m. | ||
| Wed., 4/12 | V Baseball | Old Saybrook | Away - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | L 7-3 | |
| Wed., 4/12 | V Boys Golf | Cromwell | Away - TPC River Highlands [Directions] | 1:00 p.m. | ||
| Fri., 4/14 | V Baseball | ValleyReg/Westbrook | Away - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | L 6-1 | |
| Sat., 4/15 | JV Baseball | Morgan | Away - Indian River Complex-Baseball Field [Directions] | 12:30 p.m. | ||
| Mon., 4/17 | JV Baseball | ValleyReg/Westbrook | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | ||
| Tue., 4/18 | V Baseball | Morgan | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | L 16-2 | |
| Tue., 4/18 | V Boys Outdoor Track | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track [Directions] | 3:45 p.m. | ||
| Tue., 4/18 | V Softball | Morgan | Away - Peters Complex-Lupone Softball Field [Directions] | 3:45 p.m. | W 11-4 | |
| Thu., 4/20 | V Baseball | Cromwell | Away - Cromwell HS-Fran Monnes Baseball Field [Directions] | 4:00 p.m. | L 7-4 | |
| Thu., 4/20 | V Boys Golf | Old Lyme | Away - Black Hall Golf Club [Directions] | 3:00 p.m. | ||
| Thu., 4/20 | V Softball | Berlin | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 4:00 p.m. | L 5-2 | |
| Fri., 4/21 | V Baseball | Windham | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | W 4-3 (8) | |
| Fri., 4/21 | V Boys Outdoor Track | Xavier | Away - Xavier HS-Track [Directions] | 5:00 p.m. | ||
| Sat., 4/22 | JV Baseball | Cromwell | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 11:00 a.m. | ||
| Mon., 4/24 | V Baseball | North Branford | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | L 13-1 | |
| Mon., 4/24 | V Softball | North Branford | Away - North Branford HS-NBHS Softball Field [Directions] | 4:00 p.m. | L 12-0 | |
| Tue., 4/25 | V Boys Outdoor Track | Coginchaug, Valley Regional | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:45 p.m. | ||
| Tue., 4/25 | V Girls Outdoor Track | Coginchaug, Valley Regional | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:45 p.m. | ||
| Wed., 4/26 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | L 9-0 | |
| Wed., 4/26 | V Softball | Haddam-Killingworth | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 3:45 p.m. | L 6-1 | |
| Thu., 4/27 | JV Baseball | Haddam-Killingworth | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | Postponed | ||
| Fri., 4/28 | V Baseball | East Hampton | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | L 15-3 | |
| Fri., 4/28 | V Boys Golf | Old Saybrook | Home - Nathan Hale Ray HS-Black Birch [Directions] | 3:00 p.m. | ||
| Fri., 4/28 | V Softball | East Hampton | Away - East Hampton HS-Softball Field [Directions] | 4:00 p.m. | W 11-3 | |
| Sat., 4/29 | V Boys Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 11:00 a.m. | ||
| Sat., 4/29 | V Girls Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 11:00 a.m. | ||
| Mon., 5/1 | V Baseball | Portland | Away - Portland HS-Portland HS [Directions] | 3:45 p.m. | L 8-1 | |
| Mon., 5/1 | V Boys Golf | Morgan | Away - Clinton Country Club [Directions] | 3:00 p.m. | ||
| Mon., 5/1 | V Softball | Portland | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 4:00 p.m. | W Forfeit | |
| Tue., 5/2 | V Boys Golf | Coginchaug | Away - Coginchaug-Lyman Orchards Golf course [Directions] | 3:00 p.m. | ||
| Tue., 5/2 | V Boys Outdoor Track | East Hampton | Away - East Hampton HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | East Hampton | Away - East Hampton HS-Track [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 4:00 p.m. | L 12-2 | |
| Wed., 5/3 | V Boys Golf | Haddam-Killingworth | Home - Nathan Hale Ray HS-Black Birch [Directions] | 3:00 p.m. | ||
| Wed., 5/3 | V Softball | Coginchaug | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 3:30 p.m. | L 5-2 | |
| Fri., 5/5 | V Baseball | Westbrook | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | L 4-0 | |
| Fri., 5/5 | V Boys Golf | East Hampton | Home - Nathan Hale Ray HS-Black Birch [Directions] | 3:00 p.m. | ||
| Fri., 5/5 | V Softball | Westbrook/Old Saybrook | Away - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | W 15-2 | |
| Sat., 5/6 | JV Baseball | Old Lyme, Old Saybrook, Westbrook | Away - Lyme-Old Lyme HS-Gloria Maddocks Field [Directions] | 10:00 a.m. | ||
| Sat., 5/6 | V Boys Outdoor Track | Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Sat., 5/6 | V Girls Outdoor Track | Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Sat., 5/6 | V Girls Outdoor Track | MIddletown JV Track Invitational | Away - Middletown HS-MHS Stadium | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 12:00 p.m. | ||||||
| Mon., 5/8 | V Baseball | Old Lyme | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | L 10-5 | |
| Mon., 5/8 | V Boys Outdoor Track | Cromwell, Westbrook | Away - Cromwell HS-Don Luke Track [Directions] | 3:30 p.m. | ||
| Mon., 5/8 | V Girls Outdoor Track | Cromwell, Westbrook | Away - Cromwell HS-Don Luke Track [Directions] | 3:30 p.m. | ||
| Mon., 5/8 | V Softball | Old Lyme | Home - Hale-Ray HS, Lou Milardo Field-HR softball 1 [Directions] | 4:00 p.m. | L 1-0 | |
| Tue., 5/9 | JV Baseball | Portland | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | ||
| Tue., 5/9 | JV Baseball | Portland | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Golf | Valley Regional | Home - Nathan Hale Ray HS-Black Birch [Directions] | 3:00 p.m. | ||
| Wed., 5/10 | V Baseball | Old Saybrook | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | L 7-3 | |
| Wed., 5/10 | V | Shoreline Unified Track Meet | Away - Coginchaug-CRHS Track | 3:00 p.m. | ||
| Thu., 5/11 | V Softball | Valley Regional | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 4:00 p.m. | W 6-5 | |
| Fri., 5/12 | V Baseball | Somers | Away - Somers HS-Baseball Diamond [Directions] | 4:15 p.m. | L 7-5 | |
| Fri., 5/12 | V Boys Outdoor Track | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:30 p.m. | ||
| Sat., 5/13 | JV Baseball | Morgan | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 10:00 a.m. | ||
| Sat., 5/13 | V Softball | Cromwell | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 11:00 a.m. | L 7-1 | |
| Mon., 5/15 | V Boys Golf | Haddam-Killingworth | Away - Black Birch Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 5/15 | V Softball | Valley Regional | Away - Valley Regional HS-Joseph Camarota Memorial Field [Directions] | 4:00 p.m. | L 12-5 | |
| Tue., 5/16 | V Baseball | Windham Tech | Away - Windham Technical HS-Currier Field [Directions] | 3:30 p.m. | L 8-7 | |
| Tue., 5/16 | V Boys Golf | Portland | Away - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Wed., 5/17 | V Baseball | Norwich Tech | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | L 10-3 | |
| Wed., 5/17 | V Boys Golf | East Hampton | Away - Tallwood Country Club [Directions] | 2:30 p.m. | ||
| Wed., 5/17 | V Boys Outdoor Track | Old Lyme, North Branford | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:30 p.m. | ||
| Wed., 5/17 | V Girls Outdoor Track | Old Lyme, North Branford | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:30 p.m. | ||
| Thu., 5/18 | V Boys Golf | North Branford | Home - Nathan Hale Ray HS-Black Birch [Directions] | 3:30 p.m. | ||
| Fri., 5/19 | JV Baseball | East Hampton | Away - East Hamprton HS [Directions] | 3:45 p.m. | ||
| Fri., 5/19 | V Softball | Morgan | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 6:30 p.m. | W 18-9 | |
| Mon., 5/22 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Varsity Softball Field [Directions] | 4:00 p.m. | L 15-2 | |
| Tue., 5/23 | V Boys Golf | Shoreline Conference Championship | Away - Stanley Golf Course | 9:00 a.m. | ||
| Wed., 5/24 | V Boys Outdoor Track | Shoreline Conference Outdoor Championship | Away - East Hampton HS-Track | 2:30 p.m. | ||
| Wed., 5/24 | V Girls Outdoor Track | Shoreline Conference Outdoor Championship | Away - East Hampton HS-Track | 2:30 p.m. | ||
| Thu., 5/25 | V Boys Golf | Norwich Tech | Home - Nathan Hale Ray HS-Black Birch [Directions] | 3:15 p.m. | ||
| Thu., 5/25 | V | Unified Sports - Outdoor Track | Away - Valley Regional HS-Richard B. Blythe Field | 3:30 p.m. | ||
| Fri., 5/26 | V Boys Golf | Old Saybrook | Away - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/30 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/30 | V Girls Outdoor Track | CIAC Class S Championships | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/30 | V Softball | Cromwell | Away - Cromwell HS-Softball Diamond [Directions] | 4:00 p.m. | L 10-1 | |
| Tue., 5/30 | V | Shoreline Unified Field Day | Away - Lyme-Old Lyme HS | 3:00 p.m. | ||
| Wed., 5/31 | V Boys Golf | Norwich Tech | Away - Norwich Technical HS-Norwich Golf Course [Directions] | 2:30 p.m. | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Tue., 6/6 | V Boys Golf | CIAC Division III Championship | Away - Stanley GC | 8:00 a.m. | ||
| Sat., 6/10 | V Boys Golf | CIAC State Open Championship | Away - Black Hall Club | 1:00 p.m. | ||