| Hale Ray 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 389 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 8/28 | V Football | Branford (Scrim.) | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 10:00 a.m. | ||
| Sat., 8/28 | V Football | Coginchaug Jamboree | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 10:00 a.m. | ||
| Tue., 8/31 | V Girls Volleyball | Bacon Academy (Scrim.) | Home - Nathan Hale Ray HS-Gym [Directions] | 3:30 p.m. | ||
| Wed., 9/1 | V Boys Soccer | St. Bernard (Scrim.) | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 4:00 p.m. | ||
| Wed., 9/1 | V Girls Volleyball | Naugatuck (Scrim.) | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 9/3 | V Boys Cross Country | TBA | Away - Pierson Park, Cromwell | 3:45 p.m. | ||
| Fri., 9/3 | V Boys Cross Country | Cromwell, Berlin, Granby Memorial (Scrim.) | Away - Cromwell HS-cross country course [Directions] | 4:00 p.m. | ||
| Fri., 9/3 | V Football | Foran (Scrim.) | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 5:00 p.m. | ||
| Fri., 9/3 | V Boys Soccer | Aerospace (Scrim.) | Away - Academy of Aerospace and Engineering-Soccer Field [Directions] | 3:30 p.m. | ||
| Fri., 9/3 | V Girls Cross Country | Cromwell, Avon, Granby Memorial (Scrim.) | Away - Cromwell HS-cross country course [Directions] | 4:00 p.m. | ||
| Sat., 9/4 | V Girls Volleyball | Glastonbury VB Jamboree | Away - Not Listed | 8:40 a.m. | ||
| Sat., 9/4 | V Girls Volleyball | Glastonbury (Scrim.) | Away - Glastonbury HS-Gym [Directions] | 9:00 a.m. | ||
| Tue., 9/7 | V Girls Soccer | East Haven (Scrim.) | Home - North Branford HS-NBHS Front Field [Directions] | 3:45 p.m. | ||
| Tue., 9/7 | V Girls Volleyball | Maloney (Scrim.) | Away - Maloney HS-Gym [Directions] | 3:30 p.m. | ||
| Wed., 9/8 | V Boys Cross Country | Scrimmage meet at Glastonbury HS | Away - Not Listed | 3:45 p.m. | ||
| Wed., 9/8 | V Boys Cross Country | Glastonbury, Portland, RHAM (Scrim.) | Away - JB Williams Park [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Wed., 9/8 | V Girls Cross Country | Glastonbury, Portland, RHAM (Scrim.) | Away - JB Williams Park [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Thu., 9/9 | V Girls Volleyball | Cromwell | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 9/9 | JV Girls Volleyball | Cromwell | Home - Nathan Hale Ray HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/10 | V Boys Cross Country | Middletown | Away - Veterans Memorial Park, Middletown, CT [Directions] | 3:30 p.m. | ||
| Fri., 9/10 | V Girls Soccer | Cromwell | Home - North Branford HS-NBHS Front Field [Directions] | 3:45 p.m. | L 1-9 | |
| Fri., 9/10 | V Girls Soccer | Valley Regional | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 4:00 p.m. | L 6-1 | |
| Sat., 9/11 | V Football | CREC Coop | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 1:00 p.m. | W 14-7 | |
| Mon., 9/13 | JV Football | CREC Coop | Away - Civic Leadership HS-Civic Leadership Turf Field [Directions] | 3:45 p.m. | ||
| Mon., 9/13 | V Girls Volleyball | East Hampton | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | L 3-2 | |
| Mon., 9/13 | JV Girls Volleyball | East Hampton | Home - Nathan Hale Ray HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Boys Cross Country | Portland, Coginchaug, East Hampton, TBA | Away - Camp Ingersoll [Directions] | 3:45 p.m. | ||
| Tue., 9/14 | V Boys Soccer | Morgan | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 4:00 p.m. | L 2-0 | |
| Tue., 9/14 | V Girls Cross Country | Portland, Coginchaug, East Hampton, TBA | Away - Camp Ingersoll [Directions] | 3:45 p.m. | ||
| Tue., 9/14 | V Girls Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 9/14 | V Girls Soccer | East Hampton | Home - North Branford HS-NBHS Front Field [Directions] | 3:45 p.m. | L 1-9 | |
| Wed., 9/15 | V Girls Volleyball | RHAM | Away - RHAM HS-Gym [Directions] | 6:00 p.m. | L 3-0 | |
| Wed., 9/15 | JV Girls Volleyball | RHAM | Away - RHAM HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 9/16 | V Girls Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 3-1 | |
| Thu., 9/16 | V Girls Soccer | Old Saybrook | Home - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | L 0-6 | |
| Fri., 9/17 | V Boys Soccer | Westbrook | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 6:00 p.m. | W 1-0 | |
| Fri., 9/17 | V Girls Volleyball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 6:30 p.m. | L 3-2 | |
| Fri., 9/17 | JV Girls Volleyball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:00 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 | Valley Regional/Old Lyme | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 1:00 p.m. | W 14-0 | |
| 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. | ||
| Mon., 9/20 | JV Football | Valley Regional/Old Lyme | Away - Valley Regional HS-Practice Football Field [Directions] | 3:45 p.m. | ||
| Mon., 9/20 | V Girls Volleyball | Old Lyme | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 9/20 | JV Girls Volleyball | Old Lyme | Home - Nathan Hale Ray HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Boys Soccer | Portland | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 5:00 p.m. | L 5-0 | |
| Tue., 9/21 | V Girls Soccer | Portland | Away - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | L 0-6 | |
| Tue., 9/21 | V Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 p.m. | L 0-5 | |
| 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. | ||
| Wed., 9/22 | V Girls Volleyball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 6:30 p.m. | W 3-1 | |
| Wed., 9/22 | JV Girls Volleyball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 5:00 p.m. | ||
| Thu., 9/23 | V Boys Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:45 p.m. | L 3-0 | |
| Fri., 9/24 | V Girls Soccer | Old Lyme | Home - North Branford HS-NBHS Front Field [Directions] | 3:45 p.m. | L 0-8 | |
| Fri., 9/24 | V Girls Soccer | Old Saybrook | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 4:00 p.m. | L Forfeit | |
| Fri., 9/24 | V Girls Volleyball | Morgan | Away - Morgan HS-Gym 1 [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 9/24 | JV Girls Volleyball | Morgan | Away - Morgan HS-Gym 1 [Directions] | 5:30 p.m. | ||
| Sat., 9/25 | V Boys Cross Country | Ocean State Invitational | Away - Not Listed | 1:00 p.m. | ||
| Sat., 9/25 | V Football | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 11:00 a.m. | W 40-0 | |
| Mon., 9/27 | JV Football | Old Saybrook | Home - Coginchaug Regional HS-Brookside Field [Directions] | 4:00 p.m. | ||
| Mon., 9/27 | V Boys Soccer | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | W 6-0 | |
| Mon., 9/27 | V Girls Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:45 p.m. | L 9-0 | |
| Mon., 9/27 | V Girls Volleyball | North Branford | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 9/27 | JV Girls Volleyball | North Branford | Home - Nathan Hale Ray HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | V Boys Cross Country | LEAGUE MEET #1 Small Schools | Away - Old Saybrook HS-Old Saybrook Campus | 3:30 p.m. | ||
| Tue., 9/28 | V Girls Cross Country | LEAGUE MEET #1 Small Schools | Away - Old Saybrook HS-Old Saybrook Campus | 3:30 p.m. | ||
| Wed., 9/29 | V Girls Soccer | Hale Ray | Home - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | L 0-4 | |
| Wed., 9/29 | V Girls Soccer | North Branford/Hale Ray | Away - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | W 4-0 | |
| Thu., 9/30 | V Boys Soccer | Coginchaug | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 9/30 | V Girls Soccer | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:45 p.m. | L 7-1 | |
| Fri., 10/1 | V Boys Cross Country | Nonnewaug Invitational | Away - TBA | 3:30 p.m. | ||
| Fri., 10/1 | V Boys Cross Country | Nonnewaug Invitational | Away - Nonnewaug HS-XC Course | 4:00 p.m. | ||
| Fri., 10/1 | V Football | Stafford/East Windsor/Somers | Away - Stafford HS-Lighted Stadium Field (behind the school) [Directions] | 6:30 p.m. | W 21-14 | |
| Fri., 10/1 | V Girls Cross Country | Nonnewaug Invitational | Away - Nonnewaug HS-XC Course | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Fri., 10/1 | V Girls Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 5:00 p.m. | L 0-7 | |
| Fri., 10/1 | V Girls Volleyball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 6:15 p.m. | W 3-0 | |
| Fri., 10/1 | JV Girls Volleyball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:00 p.m. | ||
| Sat., 10/2 | JV Football | Stafford/East Windsor/Somers | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 11:00 a.m. | ||
| Mon., 10/4 | V Girls Soccer | Morgan | Home - North Branford HS-NBHS Front Field [Directions] | 3:45 p.m. | L 8-0 | |
| Mon., 10/4 | V Girls Volleyball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 10/4 | JV Girls Volleyball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Tue., 10/5 | V Boys Cross Country | Sheehan Invitational | Away - Not Listed | Canceled | Cancelled | |
| 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 | ||||||
| Wed., 10/6 | V Boys Soccer | Cromwell | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 5:30 p.m. | W 2-1 | |
| Wed., 10/6 | V Girls Volleyball | East Hampton | Away - East Hampton HS-Gym [Directions] | 5:30 p.m. | L 3-2 | |
| Wed., 10/6 | JV Girls Volleyball | East Hampton | Away - East Hampton HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/7 | V Girls Soccer | Portland | Home - North Branford HS-NBHS Front Field [Directions] | 3:45 p.m. | L 5-0 | |
| Thu., 10/7 | V Girls Soccer | East Hampton | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 4:00 p.m. | L 4-2 | |
| Fri., 10/8 | V Football | Haddam-Killingworth | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 6:30 p.m. | W 18-0 | |
| Fri., 10/8 | V Boys Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 3:45 p.m. | L 0-2 | |
| Fri., 10/8 | V Girls Volleyball | Haddam-Killingworth | Home - Nathan Hale Ray HS-Gym [Directions] | 6:30 p.m. | L 3-2 | |
| Fri., 10/8 | JV Girls Volleyball | Haddam-Killingworth | Home - Nathan Hale Ray HS-Gym [Directions] | 5:00 p.m. | ||
| Sat., 10/9 | V Boys Cross Country | Wickham Invitational | Away - Wickham Park | 11:00 a.m. | ||
| Sat., 10/9 | JV Football | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | 10:00 a.m. | ||
| Sat., 10/9 | V Girls Soccer | Norwich Free Academy | Away - Norwich Free Academy-Turf Field [Directions] | 10:00 a.m. | L 5-0 | |
| Mon., 10/11 | V Girls Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 10:00 a.m. | L 7-0 | |
| Mon., 10/11 | V Girls Volleyball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 3:30 p.m. | W 3-1 | |
| Mon., 10/11 | JV Girls Volleyball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 2:00 p.m. | ||
| Tue., 10/12 | V Boys Soccer | Haddam-Killingworth | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 4:00 p.m. | L 1-0 | |
| Tue., 10/12 | V Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 p.m. | L 6-1 | |
| Wed., 10/13 | JV Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | Canceled | Cancelled | |
| Wed., 10/13 | V Girls Volleyball | Valley Regional | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | L 3-2 | |
| Wed., 10/13 | JV Girls Volleyball | Valley Regional | Home - Nathan Hale Ray HS-Gym [Directions] | 4:00 p.m. | ||
| 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 Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:45 p.m. | L 1-5 | |
| Fri., 10/15 | V Boys Soccer | Old Lyme | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 6:00 p.m. | L 1-0 | |
| Fri., 10/15 | V Girls Soccer | Cromwell | Away - Cromwell HS-Main field [Directions] | 3:00 p.m. | L 0-4 | |
| Fri., 10/15 | V Girls Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | L 4-0 | |
| Fri., 10/15 | V Girls Volleyball | Morgan | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/15 | JV Girls Volleyball | Morgan | Home - Nathan Hale Ray HS-Gym [Directions] | 4:30 p.m. | ||
| Mon., 10/18 | V Girls Soccer | Westbrook | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 4:00 p.m. | W 4-2 | |
| Mon., 10/18 | V Girls Soccer | Coginchaug | Home - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | L 7-0 | |
| Tue., 10/19 | V Boys Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | T 2-2 | |
| Tue., 10/19 | V Girls Volleyball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Tue., 10/19 | JV Girls Volleyball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/21 | V Boys Soccer | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:45 p.m. | L 4-0 | |
| Thu., 10/21 | V Girls Soccer | Norwich Free Academy | Home - North Branford HS-NBHS Front Field [Directions] | 3:45 p.m. | L 2-0 | |
| Fri., 10/22 | V Boys Cross Country | TBA, TBA, TBA, Valley Regional, Westbrook | Away - TBA-connell memorial rink | 2:30 p.m. | ||
| Fri., 10/22 | V Boys Cross Country | SLC Championship | Away - TBA | 2:30 p.m. | ||
| Fri., 10/22 | V Football | MSW | Away - Peters Complex-Football Field [Directions] | 6:30 p.m. | L 20-50 | |
| Fri., 10/22 | V Girls Cross Country | Shoreline Cross Country Championship | Away - TBA-Grandville HS | 2:30 p.m. | ||
| Fri., 10/22 | V Girls Volleyball | Coginchaug | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 3-0 | |
| Fri., 10/22 | JV Girls Volleyball | Coginchaug | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 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 | MSW | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 11:00 a.m. | ||
| 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 | JV Girls Volleyball | East Haven JV Volleyball Invite | Away - East Haven HS-Gym | 8:00 a.m. | ||
| Mon., 10/25 | V Boys Soccer | North Branford | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 6:45 p.m. | W 6-1 | |
| Mon., 10/25 | V Girls Soccer | North Branford/Hale Ray | Home - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 5:00 p.m. | W 5-0 | |
| Mon., 10/25 | V Girls Soccer | Hale Ray | Away - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 5:00 p.m. | L 0-6 | |
| Fri., 10/29 | V Football | Rockville | Away - Rockville HS-Stadium Field [Directions] | 6:30 p.m. | L 6-42 | |
| Sat., 10/30 | V Boys Cross Country | Class S State Meet | Away - Wickham Park | 2:05 p.m. | ||
| Sat., 10/30 | JV Football | Rockville | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 11:00 a.m. | ||
| 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 Girls Volleyball | Old Lyme | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 11/3 | V Girls Volleyball | East Hampton | Away - East Hampton HS-Gym [Directions] | 6:30 p.m. | W 3-2 | |
| Thu., 11/4 | V Boys Soccer | Old Lyme (Scrim.) | Away - Lyme-Old Lyme HS-Track Field [Directions] | 2:45 p.m. | Cancelled | |
| Fri., 11/5 | V Boys Cross Country | State Open | Away - Wickham Park | 1:30 p.m. | ||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/5 | V Girls Volleyball | Haddam-Killingworth | Away - Morgan School-Gym [Directions] | 6:00 p.m. | L 3-0 | |
| Mon., 11/8 | V Girls Volleyball | SMSA | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Tue., 11/9 | V Boys Soccer | St. Bernard | Away - St. Bernard School-Delaporta Field [Directions] | 2:00 p.m. | W 1-0 | |
| Tue., 11/9 | V Girls Volleyball | Comp Sci | Away - Civic Leadership HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 11/11 | V Boys Soccer | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 4:00 p.m. | L 6-1 | |
| Fri., 11/12 | V Girls Volleyball | Lyman Memorial | Away - Lyman Memorial HS-Gym [Directions] | 6:00 p.m. | L 3-0 | |
| Sat., 11/13 | V Boys Cross Country | New England Championship | Away - Not Listed | TBA | ||
| Sat., 11/13 | V Football | Cromwell/Portland | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 1:00 p.m. | L 6-49 | |
| Mon., 11/15 | JV Football | Cromwell/Portland | Away - Pierson Park, Cromwell [Directions] | Canceled | Cancelled | |
| Fri., 11/19 | V Football | Granby/Canton | Away - Granby Memorial HS-Stadium Field [Directions] | 6:30 p.m. | L 0-17 | |
| Sat., 11/20 | JV Football | Granby/Canton | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 11:00 a.m. | ||
| Wed., 11/24 | V Football | North Branford | Home - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 6:00 p.m. | L 6-46 | |
| Mon., 12/6 | V Girls Basketball | Vinal Tech (Scrim.) | Home - Nathan Hale Ray HS-Gym [Directions] | 3:00 p.m. | ||
| Tue., 12/7 | V Boys Basketball | Windham Tech (Scrim.) | Home - Nathan Hale Ray HS-Gym [Directions] | 4:30 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 Indoor Track | Shoreline Developmental Track Meet | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Sat., 12/11 | V Boys Basketball | Windham (Scrim.) | Home - Nathan Hale Ray HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 12/11 | V Girls Basketball | East Windsor (Scrim.) | Away - East Windsor Senior HS-Gym [Directions] | 10:00 a.m. | ||
| Mon., 12/13 | V Girls Basketball | Coventry | Away - Coventry HS-Gym [Directions] | 7:00 p.m. | L 34-55 | |
| Mon., 12/13 | JV Girls Basketball | Coventry | Away - Coventry HS-Hurlock Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 12/16 | V Boys Basketball | Old Saybrook | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | L 71-60 | |
| Thu., 12/16 | JV Boys Basketball | Old Saybrook | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/16 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 28-46 | |
| Thu., 12/16 | JV Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/17 | V Boys Indoor Track | Hillhouse Invitational | Away - Hillhouse HS-Field House | 4:30 p.m. | ||
| Fri., 12/17 | V Girls Indoor Track | Hillhouse Invitational | Away - Hillhouse HS-Field House | 4:30 p.m. | ||
| Sat., 12/18 | V Boys Basketball | Wheeler | Home - Nathan Hale Ray HS-Gym [Directions] | 4:30 p.m. | W 58-41 | |
| Sat., 12/18 | JV Boys Basketball | Wheeler | Home - Nathan Hale Ray HS-Gym [Directions] | 3:00 p.m. | ||
| Sat., 12/18 | V Boys Indoor Track | Hillhouse Invitational | Away - Hillhouse HS-Field House | 10:00 a.m. | ||
| Sat., 12/18 | V Girls Indoor Track | Hillhouse Invitational | Away - Hillhouse HS-Field House | 10:00 a.m. | ||
| Wed., 12/22 | JV Girls Basketball | Bolton | Home - Nathan Hale Ray HS-Gym [Directions] | Postponed | ||
| Thu., 12/23 | V Boys Basketball | Westbrook | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 67-41 | |
| Thu., 12/23 | JV Boys Basketball | Westbrook | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/28 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | W 74-52 | |
| Tue., 12/28 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Thu., 12/30 | V Boys Basketball | Ellis Tech | Home - Nathan Hale Ray HS-Gym [Directions] | 12:30 p.m. | W 94-27 | |
| Thu., 12/30 | JV Boys Basketball | Ellis Tech | Home - Nathan Hale Ray HS-Gym [Directions] | 11:00 a.m. | ||
| Tue., 1/4 | V Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 6:00 p.m. | W 59-56 | |
| Tue., 1/4 | JV Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | Postponed | ||
| 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 Basketball | Aerospace | Away - Academy of Aerospace and Engineering-Gym 1 [Directions] | 6:00 p.m. | L 26-38 | |
| Wed., 1/5 | V Girls Indoor Track | Shoreline League Meet #1 | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Fri., 1/7 | JV Boys Basketball | Portland | Home - Nathan Hale Ray HS-Gym [Directions] | Canceled | Cancelled | |
| Sat., 1/8 | V Boys Basketball | Portland | Home - Nathan Hale Ray HS-Gym [Directions] | 4:00 p.m. | L 63-43 | |
| 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 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 Girls Basketball | East Hampton | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | L 54-18 | |
| Tue., 1/11 | JV Girls Basketball | East Hampton | Home - Nathan Hale Ray HS-Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/12 | V Girls Basketball | Coginchaug | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | L 56-16 | |
| Wed., 1/12 | JV Girls Basketball | Coginchaug | Home - Nathan Hale Ray HS-Gym [Directions] | Canceled | Cancelled | |
| Thu., 1/13 | V Boys Indoor Track | Shoreline League Meet #2 | Away - TBA | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to New Haven Athletic Center/Hillhouse HS | ||||||
| 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 Indoor Track | Shoreline League Meet #2 | Away - TBA | 5:00 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 | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 7:00 p.m. | W 75-34 | |
| Fri., 1/14 | JV Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:30 p.m. | ||
| Fri., 1/14 | V Girls Basketball | Haddam-Killingworth | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | L 52-20 | |
| Fri., 1/14 | JV Girls Basketball | Haddam-Killingworth | Home - Nathan Hale Ray HS-Gym [Directions] | Canceled | Cancelled | |
| Tue., 1/18 | V Boys Basketball | Morgan | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 75-67 | |
| Tue., 1/18 | JV Boys Basketball | Morgan | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/18 | V Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | 7:00 p.m. | L 50-27 | |
| Tue., 1/18 | JV Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/21 | V Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 7:00 p.m. | W 66-48 | |
| Fri., 1/21 | JV Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/21 | V Girls Basketball | North Branford | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | L 69-43 | |
| Fri., 1/21 | JV Girls Basketball | North Branford | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/22 | V Boys Indoor Track | SCC Coaches Invitational | Away - Hillhouse HS-Field House | 9:00 a.m. | ||
| Sat., 1/22 | JV Girls Basketball | Haddam-Killingworth | Home - Nathan Hale Ray HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/22 | V Girls Indoor Track | SCC Coaches Invitational | Away - Hillhouse HS-Field House | 2:00 p.m. | ||
| Mon., 1/24 | V Boys Basketball | Grasso Tech | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | W 67-44 | |
| Mon., 1/24 | JV Boys Basketball | Grasso Tech | Home - Nathan Hale Ray HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/25 | V Boys Basketball | Valley Regional | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 57-47 | |
| Tue., 1/25 | JV Boys Basketball | Valley Regional | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/25 | V Girls Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 6:00 p.m. | L 18-58 | |
| Tue., 1/25 | JV Girls Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | Canceled | Cancelled | |
| Tue., 1/25 | V | Unified Basketball Tournament | Away - Westbrook HS-Westbrook HS Gym | 3:00 p.m. | ||
| Fri., 1/28 | V Boys Basketball | Cromwell | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | L 60-52 | |
| Fri., 1/28 | JV Boys Basketball | Cromwell | Home - Nathan Hale Ray HS-Gym [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 | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 7:00 p.m. | L 19-69 | |
| Fri., 1/28 | JV Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/28 | V Girls Indoor Track | Shoreline Coaches Invite | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Tue., 2/1 | V Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 60-46 | |
| Tue., 2/1 | JV Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/1 | JV Boys Basketball | Old Saybrook | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/1 | V Girls Basketball | Old Saybrook | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | L 54-23 | |
| Wed., 2/2 | V Girls Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 6:00 p.m. | L 25-41 | |
| Sat., 2/5 | JV Boys Basketball | Wamogo | Home - Nathan Hale Ray HS-Gym [Directions] | Canceled | Cancelled | |
| 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 | Wamogo | Home - Nathan Hale Ray HS-Gym [Directions] | 2:30 p.m. | L 45-41 | |
| 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 | ||||||
| Mon., 2/7 | V Boys Basketball | Grasso Tech | Away - Grasso Tech-Grasso Gymnasium [Directions] | 6:00 p.m. | W 73-50 | |
| Mon., 2/7 | JV Boys Basketball | Grasso Tech | Away - Grasso Tech-Grasso Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 2/7 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 6:00 p.m. | L 23-54 | |
| Mon., 2/7 | JV Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 4:30 p.m. | ||
| Mon., 2/7 | V Girls Indoor Track | Last Chance Qualifier | Away - Hillhouse HS-Field House | 3:30 p.m. | ||
| Wed., 2/9 | V Girls Basketball | Old Lyme | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | L 53-32 | |
| Wed., 2/9 | JV Girls Basketball | Old Lyme | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/10 | V Boys Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 7:00 p.m. | L 57-59 | |
| Thu., 2/10 | JV Boys Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/10 | V Girls Basketball | Westbrook | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | L 58-32 | |
| Fri., 2/11 | V Boys Basketball | Old Lyme | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 58-55 | |
| Fri., 2/11 | JV Boys Basketball | Old Lyme | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/11 | V Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 6:30 p.m. | L 11-44 | |
| Fri., 2/11 | JV Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:00 p.m. | ||
| 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 Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Mon., 2/14 | V Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 57-49 | |
| Mon., 2/14 | JV Boys Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/14 | V Girls Basketball | Bolton | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | L 51-21 | |
| Tue., 2/15 | V Girls Basketball | Portland | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | L 50-44 | |
| Tue., 2/15 | JV Girls Basketball | Portland | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/16 | JV Boys Basketball | Portland | Away - Portland HS-MS Gym [Directions] | Canceled | Cancelled | |
| Wed., 2/16 | V Girls Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 33-51 | |
| Wed., 2/16 | JV Girls Basketball | Portland | Away - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/18 | V Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 6:30 p.m. | W 75-52 | |
| Fri., 2/18 | JV Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 5:00 p.m. | ||
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Wed., 2/23 | V Boys Basketball | Coginchaug | Home - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 77-57 | |
| Wed., 2/23 | JV Boys Basketball | Coginchaug | Home - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Sat., 2/26 | V Boys Basketball | East Hampton | Home - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | L 59-55 | |
| Fri., 3/4 | V | TBA, Valley Regional | Home - Nathan Hale Ray HS-HS Gym [Directions] | 3:00 p.m. | ||
| Thu., 3/10 | V Boys Basketball | Windsor Locks | Home - Nathan Hale Ray HS-Gym [Directions] | 6:30 p.m. | L 49-48 | |
| Thu., 3/24 | V Softball | Lyman Memorial (Scrim.) | Away - Lyman Memorial HS-Softball Diamond [Directions] | 3:45 p.m. | Cancelled | |
| Sat., 3/26 | V Softball | E.O. Smith (Scrim.) | Away - E.O. Smith HS-Varsity Softball Field [Directions] | Canceled | Cancelled | |
| Tue., 3/29 | V Softball | Bacon Academy (Scrim.) | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 3:45 p.m. | Cancelled | |
| Wed., 3/30 | V Baseball | Suffield (Scrim.) | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | Canceled | Cancelled | |
| Thu., 3/31 | V Softball | Ledyard (Scrim.) | Away - Ledyard HS-Ellen Mahoney Softball Complex [Directions] | 4:00 p.m. | ||
| Sat., 4/2 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Baseball Diamond [Directions] | 12:00 p.m. | L 8-5 | |
| Sat., 4/2 | JV Baseball | Old Lyme | Home - Nathan Hale Ray HS-Baseball JV Field [Directions] | Postponed | ||
| Sat., 4/2 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 10:30 a.m. | L 8-4 | |
| Mon., 4/4 | V Baseball | Portland | Away - Portland HS-Portland HS [Directions] | 4:00 p.m. | W 6-4 (10) | |
| 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 Outdoor Track | Wildcat Relays | Away - Lyme-Old Lyme HS-Track Field | 11:30 a.m. | ||
| Mon., 4/11 | V Baseball | Westbrook | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | W 16-1 | |
| Mon., 4/11 | V Softball | Somers | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 4:30 p.m. | L 7-5 | |
| Tue., 4/12 | JV Baseball | Lyman Memorial | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Boys Outdoor Track | Valley Regional, Morgan | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Girls Outdoor Track | Valley Regional, Morgan | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Baseball | East Hampton | Away - Legion Park [Directions] | 4:00 p.m. | W 12-3 | |
| Wed., 4/13 | V Boys Golf | Morgan | Away - Clinton Country Club [Directions] | 3:00 p.m. | Hale-Ray 196 Morgan 179 | |
| Wed., 4/13 | V Softball | East Hampton | Away - East Hampton HS-Softball Field [Directions] | 3:45 p.m. | L 11-4 | |
| Thu., 4/14 | JV Baseball | East Hampton | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | ||
| Fri., 4/15 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 1:00 p.m. | L 12-2 | |
| Fri., 4/15 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 4/15 | JV Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 4/15 | V Softball | Haddam-Killingworth | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 11:00 a.m. | L 9-1 | |
| Sat., 4/16 | JV Baseball | Haddam-Killingworth | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 11:00 a.m. | ||
| Mon., 4/18 | V Baseball | Morgan | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 12:00 p.m. | L 11-3 | |
| Mon., 4/18 | JV Baseball | Morgan | Home - Nathan Hale Ray HS-Baseball JV Field [Directions] | Postponed | ||
| Mon., 4/18 | V Softball | Morgan | Away - Morgan School-Softball Field [Directions] | 11:00 a.m. | W 6-2 | |
| Tue., 4/19 | JV Baseball | Morgan | Away - Morgan School-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | V Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 4:00 p.m. | L 10-1 | |
| Wed., 4/20 | V Softball | North Branford | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 11:00 a.m. | L 11-1 | |
| Thu., 4/21 | JV Baseball | North Branford | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | V Baseball | ValleyReg/Westbrook | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | L 14-0 | |
| Fri., 4/22 | V Softball | Valley Regional | Away - Valley Regional HS-Joseph Camarota Memorial Field [Directions] | 11:00 a.m. | L 6-2 | |
| Sat., 4/23 | JV Baseball | ValleyReg/Westbrook | Away - Valley Regional HS-Baseball Diamond [Directions] | 3:00 p.m. | ||
| Sat., 4/23 | V Boys Outdoor Track | Coventry | Away - Coventry HS [Directions] | 9:00 a.m. | ||
| Sat., 4/23 | V Girls Outdoor Track | Coventry | Away - Coventry HS [Directions] | 9:00 a.m. | ||
| Sat., 4/23 | JV Softball | Valley Regional | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | Postponed | ||
| Mon., 4/25 | V Boys Golf | Haddam-Killingworth | Away - Black Birch Golf Course [Directions] | 3:00 p.m. | Hale-Ray 193 HK 175 | |
| Mon., 4/25 | V Softball | Cromwell | Away - Cromwell HS-Softball Diamond [Directions] | 4:00 p.m. | L 10-0 | |
| Tue., 4/26 | JV Baseball | Cromwell | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | Postponed | ||
| Tue., 4/26 | V Boys Golf | Norwich Tech | Away - Norwich Technical HS-Norwich Golf Course [Directions] | 3:15 p.m. | Hale-Ray 185 Norwich Tech 208 | |
| Wed., 4/27 | V Baseball | Old Lyme | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | W 9-8 | |
| Wed., 4/27 | V Boys Outdoor Track | Old Lyme, Westbrook | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:30 p.m. | ||
| Wed., 4/27 | V Girls Outdoor Track | Old Lyme, Westbrook | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:30 p.m. | ||
| Wed., 4/27 | V Softball | Old Lyme | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 4:00 p.m. | L 9-2 | |
| Thu., 4/28 | JV Baseball | Lyman Memorial | Away - Lyman Memorial HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Sat., 4/30 | V Baseball | Windham | Away - Windham HS-WHS Baseball Field [Directions] | 10:00 a.m. | W 8-3 | |
| Sat., 4/30 | JV Softball | North Branford | Away - North Branford HS-NBHS Softball Field [Directions] | 11:00 a.m. | ||
| Sat., 4/30 | JV Softball | North Branford | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | Canceled | Cancelled | |
| Mon., 5/2 | V Baseball | Old Saybrook | Away - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | L 9-8 | |
| Mon., 5/2 | V Softball | Old Saybrook | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 3:30 p.m. | W 17-5 | |
| Mon., 5/2 | V Softball | Old Saybrook | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 5:30 p.m. | W 17-4 | |
| Tue., 5/3 | V Boys Golf | Old Lyme | Away - Black Hall Golf Club [Directions] | 3:00 p.m. | Hale_Ray 196 Old Lyme 208 | |
| Tue., 5/3 | V Boys Outdoor Track | Old Saybrook, Coginchaug | Away - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:30 p.m. | ||
| Tue., 5/3 | V Girls Outdoor Track | Old Saybrook, Coginchaug | Away - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:30 p.m. | ||
| Thu., 5/5 | V Baseball | Westbrook | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:45 p.m. | W 7-2 | |
| Thu., 5/5 | V Boys Golf | North Branford | Home - Nathan Hale Ray HS-Black Birch [Directions] | 3:15 p.m. | Hale-Ray 196 North Branford 186 | |
| Thu., 5/5 | V Softball | Berlin | Away - Sage Park Berlin-Softball Field 1 [Directions] | 3:45 p.m. | L 11-5 | |
| Fri., 5/6 | V Boys Golf | Cromwell | Home - Nathan Hale Ray HS-Black Birch [Directions] | 2:15 p.m. | Hale-Ray 180 Cromwell 199 | |
| Sat., 5/7 | V Baseball | Old Saybrook | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | L 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. | ||
| Sat., 5/7 | V Softball | Coginchaug | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 4:00 p.m. | L 9-4 | |
| Mon., 5/9 | V Baseball | Portland | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | W 9-5 | |
| Mon., 5/9 | V Boys Golf | Coginchaug | Home - Nathan Hale Ray HS-Black Birch [Directions] | 3:15 p.m. | Hale-Ray 197 Coginchaug 218 | |
| Tue., 5/10 | JV Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | Postponed | ||
| Tue., 5/10 | V Boys Golf | East Hampton | Away - Black Birch Golf Course [Directions] | 3:00 p.m. | Hale-Ray 174 East Hampton 275 | |
| Tue., 5/10 | V Girls Outdoor Track | Haddam-Killingworth, Cromwell | Away - Haddam Killingworth HS (HK)-HKHS Track [Directions] | 3:30 p.m. | ||
| Wed., 5/11 | V Baseball | Cromwell | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | L 7-6 | |
| Wed., 5/11 | V Boys Golf | Valley Regional | Away - Black Hall Golf Club [Directions] | 3:00 p.m. | Hale-Ray 186 Valley 209 | |
| Wed., 5/11 | V Softball | Westbrook/Old Saybrook | Away - Portland HS-PHS Softball Diamond [Directions] | 4:45 p.m. | W 21-1 | |
| Wed., 5/11 | V | Newington Track Meet | Away - Not Listed | 3:00 p.m. | ||
| Thu., 5/12 | V Baseball | Somers | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:15 p.m. | L 14-1 | |
| Thu., 5/12 | JV Baseball | Cromwell | Away - Cromwell HS-Fran Monnes Baseball Field [Directions] | Postponed | ||
| Thu., 5/12 | V Boys Golf | Portland | Home - Nathan Hale Ray HS-Tallwood GC [Directions] | 3:00 p.m. | Hale-Ray 188 Portland 170 | |
| Fri., 5/13 | V Baseball | Norwich Tech | Away - Norwich Technical HS-NTHS Outdoor Athletic Complex [Directions] | 4:00 p.m. | W 15-8 | |
| Fri., 5/13 | V Boys Outdoor Track | Running Rams Invitational | Away - Old Saybrook HS-Old Saybrook Track (HS) | 3:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Fri., 5/13 | V Girls Outdoor Track | Running Rams Invitational | Away - Old Saybrook HS-Old Saybrook Track (HS) | 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 | East Hampton | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 6:30 p.m. | L 16-3 | |
| Sat., 5/14 | JV Baseball | Norwich Tech | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 11:00 a.m. | ||
| Sat., 5/14 | V Softball | Westbrook/Old Saybrook | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 11:00 a.m. | W 20-1 | |
| Mon., 5/16 | V Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 3:30 p.m. | L 4-2 | |
| Mon., 5/16 | JV Baseball | East Hampton | Away - East Hampton HS-Baseball Field [Directions] | Postponed | ||
| Mon., 5/16 | V Boys Golf | Norwich Tech | Home - Nathan Hale Ray HS-Black Birch [Directions] | 3:15 p.m. | Hale-Ray 201 Norwich Tech 218 | |
| Mon., 5/16 | V Softball | Griswold | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 4:00 p.m. | W 14-8 | |
| Tue., 5/17 | V Baseball | Windsor Locks | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 5/17 | V Softball | Coginchaug | Away - Coginchaug Regional HS-Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 4:00 p.m. | W 8-7 | |
| Wed., 5/18 | JV Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/18 | V Boys Golf | Old Saybrook | Away - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:10 p.m. | Hale-Ray 171 Old Saybrook 177 | |
| Wed., 5/18 | V Softball | Morgan | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 3:15 p.m. | W 10-4 | |
| Thu., 5/19 | V Boys Outdoor Track | SLC Novice Meet | Away - Haddam Killingworth HS (HK)-HKHS Track | 3:30 p.m. | ||
| Sat., 5/21 | V Baseball | Coginchaug | Home - Nathan Hale Ray HS-Baseball # 1 [Directions] | 11:00 a.m. | L 16-4 | |
| Sat., 5/21 | JV Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | Postponed | ||
| Mon., 5/23 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/24 | V Boys Golf | Shoreline Conference Golf Championship | Away - TPC River Highlands | 9:00 a.m. | ||
| Tue., 5/24 | V Softball | East Windsor | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 3:45 p.m. | W 11-0 | |
| Wed., 5/25 | V Boys Golf | Old Lyme, Haddam-Killingworth | Away - Black Hall Golf Club [Directions] | 3:00 p.m. | Hale-Ray 187 HK 196 Old Lyme 189 | |
| Wed., 5/25 | V Boys Outdoor Track | Shoreline Conference Championship | Away - Old Saybrook HS-Old Saybrook Track (HS) | 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 | Away - Old Saybrook HS-Old Saybrook Track (HS) | 2:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:30 p.m. | ||||||
| Thu., 5/26 | JV Baseball | ValleyReg/Westbrook | Away - Valley Regional HS-Baseball Diamond [Directions] | 5:00 p.m. | ||
| Thu., 5/26 | V Boys Golf | Haddam-Killingworth | Home - Nathan Hale Ray HS-Black Birch [Directions] | 3:00 p.m. | ||
| Thu., 5/26 | V | ValleyReg, Branford, TBA, Westbrook | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:00 p.m. | ||
| Sun., 5/29 | V Softball | East Hampton (Scrim.) | Home - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 1:30 p.m. | ||
| Tue., 5/31 | V Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | 3:00 p.m. | ||
| Tue., 5/31 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/31 | V Girls Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/31 | V Softball | Parish Hill | Away - Parish Hill HS-Softball Diamond [Directions] | 2:30 p.m. | ||
| Wed., 6/1 | V Softball | Wheeler | Away - Wheeler HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 6/3 | V Softball | Cromwell | Away - Cromwell HS-Softball Field [Directions] | 3:30 p.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Tue., 6/7 | V Boys Golf | CIAC Division III Spring Championship | Away - Fairview Farms | 8:00 a.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. | ||