| Portland 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 349 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 9/8 | V Boys Cross Country | Blue Dragon Invitational | Away - Palmer Field | 3:45 p.m. | ||
| Thu., 9/8 | V Football | MSW | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 6:00 p.m. | W 41-0 | |
| Thu., 9/8 | V Girls Cross Country | Blue Dragon Invitational | Away - Palmer Field | 3:45 p.m. | ||
| Thu., 9/8 | V Girls Soccer | Old Saybrook | Home - Portland HS-Varsity Soccer FIeld [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 9/9 | V Boys Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | L 4-1 | |
| Fri., 9/9 | JV Girls Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 4:00 p.m. | ||
| Sat., 9/10 | JV Boys Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 10:00 a.m. | ||
| Mon., 9/12 | V Girls Soccer | Haddam-Killingworth | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | T 1-1 | |
| Tue., 9/13 | V Boys Cross Country | Hale Ray | Home - Camp Ingersoll [Directions] | 3:30 p.m. | ||
| Tue., 9/13 | V Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 p.m. | L 1-0 | |
| Tue., 9/13 | V Girls Cross Country | Hale Ray | Home - Camp Ingersoll [Directions] | 3:30 p.m. | ||
| Tue., 9/13 | V Girls Swimming and Diving | Bristol Central/Eastern | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Tue., 9/13 | JV Girls Volleyball | East Granby | Away - East Granby HS-Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | JV Boys Soccer | Old Lyme | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | ||
| Thu., 9/15 | V Girls Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:45 p.m. | L 0-2 | |
| Fri., 9/16 | V Football | Capital/Achievement | Away - Annie Fisher Turf Field [Directions] | 6:30 p.m. | W 35-0 | |
| Fri., 9/16 | V Boys Soccer | Coginchaug | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | W 1-0 | |
| Fri., 9/16 | JV Girls Volleyball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/17 | V Boys Cross Country | Cromwell Invitational | Away - Pierson Park, Cromwell | 8:30 a.m. | ||
| Sat., 9/17 | JV Football | Capital/Achievement | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 10:00 a.m. | ||
| Sat., 9/17 | JV Boys Soccer | Coginchaug | Away - Coginchaug Regional HS-Field #2 - Middle Field @ CRHS [Directions] | 11:00 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 Cross Country | Cromwell Invitational | Away - Pierson Park, Cromwell | 8:30 a.m. | ||
| Sat., 9/17 | V Girls Soccer | Morgan | Home - Portland HS-Varsity Soccer FIeld [Directions] | 7:00 p.m. | L 0-1 | |
| Sat., 9/17 | JV Girls Soccer | Morgan | Home - Portland HS-Varsity Soccer FIeld [Directions] | 5:00 p.m. | ||
| Tue., 9/20 | V Boys Soccer | Hale Ray | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | W 5-0 | |
| Tue., 9/20 | V Girls Swimming and Diving | South Windsor | Away - Star Hill Pool-Pool [Directions] | 3:45 p.m. | L | |
| Wed., 9/21 | V Boys Cross Country | Coginchaug Invitational | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:45 p.m. | ||
| 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. | ||
| Wed., 9/21 | V Girls Cross Country | Coginchaug Invitational (Durham) | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:45 p.m. | ||
| Fri., 9/23 | V Football | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | 6:30 p.m. | W 35-0 | |
| Fri., 9/23 | V Girls Swimming and Diving | Middletown | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:00 p.m. | L | |
| Sat., 9/24 | JV Football | Haddam-Killingworth | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 10:00 a.m. | ||
| Sat., 9/24 | JV Boys Soccer | Valley Regional | Home - Portland HS-JV Soccer Field [Directions] | 11:00 a.m. | ||
| Mon., 9/26 | V Girls Soccer | Rocky Hill | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | L 1-3 | |
| Mon., 9/26 | JV Girls Volleyball | East Hampton | Away - East Hampton HS-Gym [Directions] | 3:30 p.m. | ||
| Tue., 9/27 | V Girls Soccer | Valley Regional | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | T 1-1 | |
| Wed., 9/28 | V Boys Cross Country | Hale Ray, Coginchaug, Old Lyme, TBA | Away - Nathan Hale Ray HS-HS XC Course [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Cross Country | Shoreline Conference Small Schools Meet | Away - Nathan Hale Ray HS-HS XC Course | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Swimming and Diving | Conard | Away - Cornerstone Aquatics Center-Pool [Directions] | 3:45 p.m. | L | |
| Thu., 9/29 | V Boys Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | 3:45 p.m. | T 1-1 | |
| Thu., 9/29 | V Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:45 p.m. | L 1-2 | |
| Thu., 9/29 | JV Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Middle Field [Directions] | 5:15 p.m. | ||
| Fri., 9/30 | V Boys Cross Country | Woods Trail Run Thetford, VT (10/1 - 10/2) | Away - Ft. Clarke Middle | 10:00 a.m. | ||
| Fri., 9/30 | V Football | North Branford | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 6:00 p.m. | W 27-13 | |
| Fri., 9/30 | V Girls Cross Country | Woods Trail Run (Thetford VT) 10/1, 10/2 | Away - Ft. Clarke Middle | 10:00 a.m. | ||
| Fri., 9/30 | V Girls Swimming and Diving | Plainville | Away - Plainville HS-Pool [Directions] | 4:00 p.m. | L | |
| Sat., 10/1 | JV Football | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | Postponed | ||
| Mon., 10/3 | V Girls Swimming and Diving | Enfield | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | W | |
| Tue., 10/4 | V Boys Soccer | E.O. Smith | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | L 3-0 | |
| Thu., 10/6 | V Boys Soccer | Westbrook | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:30 p.m. | ||||||
| Thu., 10/6 | V Girls Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | W 3-1 | |
| Thu., 10/6 | V Girls Swimming and Diving | Wethersfield, Bristol Eastern | Away - Wethersfield HS-Backman Pool [Directions] | 4:30 p.m. | L W | |
| Thu., 10/6 | JV Girls Volleyball | Morgan | Away - Morgan School-Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | V Football | Granby/Canton | Away - Granby Memorial HS-Stadium Field [Directions] | 6:30 p.m. | W 14-7 | |
| Sat., 10/8 | V Boys Cross Country | Wickham Invitational (Wickham Park) | Away - TBA | 11:00 a.m. | ||
| Sat., 10/8 | JV Football | Granby/Canton | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 10:00 a.m. | ||
| Sat., 10/8 | V Boys Soccer | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 11:00 a.m. | ||
| Sat., 10/8 | V Girls Cross Country | Wickham Invitational (Wcikham Park) | Away - Not Listed | 11:00 a.m. | ||
| Sat., 10/8 | JV Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 11:00 a.m. | ||
| Mon., 10/10 | V Boys Soccer | Morgan | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | ||
| Tue., 10/11 | V Girls Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 6:00 p.m. | L 1-2 | |
| Thu., 10/13 | V Boys Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | V Girls Soccer | Amistad | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | W 9-0 | |
| Fri., 10/14 | JV Boys Soccer | Cromwell | Away - Cromwell HS-soccer field 1 [Directions] | 3:45 p.m. | ||
| Fri., 10/14 | V Girls Swimming and Diving | Windsor | Away - Windsor HS-Jack O'Brien Stadium [Directions] | 4:00 p.m. | L | |
| Fri., 10/14 | JV Girls Volleyball | Amistad | Away - Amistad HS-Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/15 | V Boys Soccer | Cromwell | Away - Cromwell HS-Soccer Field [Directions] | 6:00 p.m. | ||
| Sat., 10/15 | V Girls Soccer | Cromwell | Home - Portland HS-Varsity Soccer FIeld [Directions] | 2:00 p.m. | L 1-4 | |
| Sat., 10/15 | JV Girls Soccer | Cromwell | Home - Portland HS-Portland HS [Directions] | 11:30 a.m. | ||
| Mon., 10/17 | V Boys Soccer | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | 6:00 p.m. | ||
| Mon., 10/17 | V Girls Swimming and Diving | Haddam-Killingworth | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Mon., 10/17 | JV Girls Volleyball | East Granby | Away - East Granby HS-Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | V Girls Soccer | North Branford/Hale Ray | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | W 6-0 | |
| Thu., 10/20 | V Boys Cross Country | Shoreline Cross Country Championship | Away - Hammonasset Park | 1:30 p.m. | ||
| Thu., 10/20 | V Boys Soccer | East Hampton | Home - Portland HS-Varsity Soccer FIeld [Directions] | 7:00 p.m. | ||
| Thu., 10/20 | V Girls Cross Country | Shoreline Cross Country Championship | Away - Hammonasset Park | 1:30 p.m. | ||
| Thu., 10/20 | V Girls Swimming and Diving | Bulkeley/HMTCA/Weaver | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | W | |
| Fri., 10/21 | JV Boys Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 3:45 p.m. | ||
| Fri., 10/21 | V Girls Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 10/21 | JV Girls Volleyball | Amistad | Away - Amistad HS-Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/22 | V Football | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 6:00 p.m. | W 42-0 | |
| Sat., 10/22 | V Boys Soccer | Haddam-Killingworth | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | ||
| Mon., 10/24 | JV Football | MSW, Old Saybrook | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | Canceled | Cancelled | |
| Mon., 10/24 | JV Girls Volleyball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/25 | V Boys Soccer | Coventry | Away - Coventry HS-Soccer field [Directions] | 6:00 p.m. | ||
| Tue., 10/25 | V Girls Soccer | Coventry | Away - Coventry HS-Soccer field [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 10/25 | V Girls Swimming and Diving | Maloney/Platt | Away - Maloney HS-Pool [Directions] | 3:45 p.m. | L | |
| Wed., 10/26 | JV Boys Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/26 | JV Girls Soccer | Haddam-Killingworth | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/28 | V Football | Valley Regional/Old Lyme | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 6:30 p.m. | W 28-27 | senior night |
| Fri., 10/28 | V Boys Soccer | Windsor Locks | Away - Windsor Locks HS-Soccer Field 1 Upper [Directions] | 4:00 p.m. | ||
| Fri., 10/28 | V Girls Soccer | Suffield | Away - Suffield HS-Ted Beneski Turf Field [Directions] | 6:30 p.m. | L 0-4 | |
| Fri., 10/28 | JV Girls Soccer | Suffield | Away - Suffield HS-Ted Beneski Turf Field [Directions] | 5:00 p.m. | ||
| Sat., 10/29 | JV Football | Valley Regional/Old Lyme | Away - Valley Regional HS-Practice Football Field [Directions] | 10:00 a.m. | ||
| Fri., 11/4 | V Football | Coginchaug/Hale Ray/East Hampton | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 6:30 p.m. | W 55-0 | |
| Mon., 11/7 | JV Football | Coginchaug/Hale Ray/East Hampton | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | Canceled | Cancelled | |
| Thu., 11/10 | V Football | Rockville | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 6:00 p.m. | L 14-21 | |
| Mon., 11/14 | JV Football | Rockville | Away - Rockville HS (Varsity Field right side of school)-Football Field [Directions] | Postponed | ||
| Wed., 11/23 | V Football | Rocky Hill | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 6:00 p.m. | W 38-7 | |
| Wed., 12/14 | V Wrestling | Middletown | Away - Keigwin MS-Gym 1 [Directions] | 6:00 p.m. | ||
| Wed., 12/14 | V Girls Basketball | Stafford | Away - Stafford HS-Gymnasium [Directions] | 6:00 p.m. | L 47-19 | |
| Wed., 12/14 | JV Girls Basketball | Stafford | Away - Stafford HS-Gymnasium [Directions] | Canceled | Cancelled | |
| Thu., 12/15 | V | Basketball | Away - Valley Regional HS-Valley Regional High School Gym | 3:30 p.m. | ||
| Fri., 12/16 | V Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 7:00 p.m. | W 71-45 | |
| Fri., 12/16 | JV Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/16 | V Girls Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 6:00 p.m. | L 46-43 | |
| Fri., 12/16 | JV Girls Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | Canceled | Cancelled | |
| Sat., 12/17 | V Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 5:30 p.m. | L 57-62 | |
| Sat., 12/17 | JV Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/17 | FR Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 12/17 | V Wrestling | Pomperaug, Bacon Academy, New Canaan, Nonnewaug, Wethersfield | Away - Pomperaug HS-Auxiliary Gym | 9:00 a.m. | ||
| Tue., 12/20 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | W 73-30 | |
| Tue., 12/20 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Tue., 12/20 | V Girls Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 60-21 | |
| Tue., 12/20 | JV Girls Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/21 | V Wrestling | Granby Memorial | Away - Granby Memorial HS-Community Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/28 | V Boys Basketball | Valley Regional | Home - Middletown Holiday Tournament [Directions] | 4:00 p.m. | W 60-38 | |
| Wed., 12/28 | V Girls Basketball | Suffield | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 53-26 | |
| Wed., 12/28 | JV Girls Basketball | Suffield | Home - Portland HS-PHS Gym [Directions] | 5:00 p.m. | ||
| Thu., 12/29 | V Boys Basketball | Middletown | Away - Middletown HS-Main Gym [Directions] | 5:45 p.m. | L 52-67 | |
| Thu., 12/29 | V Boys Swimming and Diving | Middletown | Away - Middletown HS-MHS Pool [Directions] | 9:00 a.m. | L | |
| Fri., 12/30 | V Wrestling | Morgan, Bristol Eastern, Bunnell, Farmington, Haddam-Killingworth, Ellis Tech, TBA, Shelton | Away - Morgan School-Gym | 9:00 a.m. | ||
| Tue., 1/3 | V Boys Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 77-49 | |
| Tue., 1/3 | JV Boys Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | V Boys Swimming and Diving | Manchester/RHAM | Away - Manchester HS-Pool [Directions] | 3:45 p.m. | W | |
| Tue., 1/3 | V Girls Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 6:30 p.m. | L 52-31 | |
| Tue., 1/3 | JV Girls Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/4 | V Boys Basketball | Guilford | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 36-56 | |
| Wed., 1/4 | JV Boys Basketball | Guilford | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/4 | FR Boys Basketball | Guilford | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/5 | V Boys Indoor Track | Shoreline League Meet 1 | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Thu., 1/5 | V Wrestling | Somers | Home - Portland HS-Portland HS [Directions] | 6:00 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 | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 56-51 | |
| Fri., 1/6 | JV Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | V Girls Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 40-22 | |
| Fri., 1/6 | JV Girls Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/7 | FR Boys Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 10:00 a.m. | ||
| Tue., 1/10 | V Boys Basketball | Cromwell | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 52-48 | |
| Tue., 1/10 | JV Boys Basketball | Cromwell | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | V Boys Swimming and Diving | Meriden Co-op | Away - Platt HS-Platt Pool [Directions] | 3:45 p.m. | L | |
| Tue., 1/10 | V Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 7:00 p.m. | L 72-22 | |
| Tue., 1/10 | JV Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/11 | V Wrestling | Stafford | Home - Portland HS-Portland HS [Directions] | 6:00 p.m. | ||
| Thu., 1/12 | V Boys Indoor Track | League Meet #2 | Away - Hillhouse HS-Floyd Little | 5:30 p.m. | ||
| Thu., 1/12 | V Girls Basketball | St. Bernard | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 46-37 | |
| Thu., 1/12 | JV Girls Basketball | St. Bernard | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/12 | V Girls Indoor Track | League Meet #2 | Away - Hillhouse HS-Floyd Little | 5:30 p.m. | ||
| Fri., 1/13 | V Boys Swimming and Diving | Bulkeley Cooperative Swim Team | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | W | |
| Sat., 1/14 | FR Boys Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/14 | V Girls Basketball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | 6:00 p.m. | L 88-24 | |
| Sat., 1/14 | JV Girls Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 4:30 p.m. | ||
| Sat., 1/14 | JV Girls Basketball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | Canceled | Cancelled | |
| Tue., 1/17 | V Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 7:00 p.m. | L 44-46 | |
| Tue., 1/17 | JV Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | V Boys Swimming and Diving | Simsbury | Home - Rocky Hill HS-Swimming Pool [Directions] | 4:00 p.m. | L | |
| Tue., 1/17 | V Girls Basketball | Morgan | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 65-21 | |
| Tue., 1/17 | JV Girls Basketball | Morgan | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/18 | V Wrestling | Canton | Home - Portland HS-Portland HS [Directions] | 6:00 p.m. | ||
| Fri., 1/20 | V Boys Basketball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 64-62(OT) | |
| Fri., 1/20 | JV Boys Basketball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | Farmington | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Fri., 1/20 | V Girls Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 7:00 p.m. | L 62-20 | |
| Fri., 1/20 | JV Girls Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/21 | FR Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/21 | V Wrestling | Bristol Eastern, Maloney, TBA, New Britain, Northwestern, Rocky Hill, South Windsor, New Haven Wrestling | Home - Portland HS-Portland HS [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 | North Branford | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 77-45 | |
| Tue., 1/24 | JV Boys Basketball | North Branford | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | V Boys Swimming and Diving | Avon | Away - Plainville HS-Pool [Directions] | 6:30 p.m. | L | |
| Thu., 1/26 | V Girls Basketball | Canton | Away - Canton HS-Gym [Directions] | 6:30 p.m. | L 49-23 | |
| Thu., 1/26 | JV Girls Basketball | Canton | Away - Canton HS-Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/27 | V Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 7:00 p.m. | W 79-41 | |
| Fri., 1/27 | JV Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | V Boys Swimming and Diving | Berlin | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Fri., 1/27 | V Girls Basketball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 63-28 | |
| Fri., 1/27 | JV Girls Basketball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/28 | V Wrestling | Avon, Bristol Eastern, Coventry, Daniel Hand, Griswold/Wheeler, Haddam-Killingworth, Old Lyme, Manchester, Morgan, TBA, New Britain, Nonnewaug, Plainville, Terryville/Thomaston | Home - . [Directions] | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Portland HS-PHS Gym | ||||||
| Mon., 1/30 | FR Boys Basketball | Cromwell | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | ||
| Mon., 1/30 | V Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 6:00 p.m. | W 56-36 | |
| Mon., 1/30 | JV Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | Canceled | Cancelled | |
| Tue., 1/31 | V Boys Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 54-40 | |
| Tue., 1/31 | JV Boys Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | V Boys Swimming and Diving | Wethersfield | Away - Wethersfield HS-Backman Pool [Directions] | 5:00 p.m. | L | |
| Wed., 2/1 | FR Boys Basketball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/1 | V Wrestling | Rockville | Away - Rockville HS-Main gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 2/1 | V Girls Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 6:30 p.m. | L 59-28 | |
| Wed., 2/1 | JV Girls Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 5:00 p.m. | ||
| Fri., 2/3 | V Boys Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 70-59 | |
| Fri., 2/3 | JV Boys Basketball | Coginchaug | Home - Portland HS-PHS 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 | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | L 55-20 | |
| Fri., 2/3 | JV Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Fri., 2/3 | V Girls Indoor Track | Shoreline Conference Indoor Track Championship | Away - Hillhouse HS-Field House | 5:30 p.m. | ||
| Sat., 2/4 | FR Boys Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/4 | V Wrestling | 2023 Bacon Academy Matt Bishel Bobcat Classic | Away - Bacon Academy | 9:00 a.m. | ||
| Tue., 2/7 | V Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 64-46 | |
| Tue., 2/7 | JV Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | V Boys Swimming and Diving | Hartford Public | Away - Hartford Public HS-Pool [Directions] | 4:00 p.m. | W | |
| Tue., 2/7 | V Wrestling | Suffield Windsor Locks Wrestling Co Op | Away - Suffield HS [Directions] | 6:00 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 36-26 | |
| Tue., 2/7 | JV Girls Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | Postponed | ||
| Wed., 2/8 | V Wrestling | Coventry | Home - Portland HS-Portland HS [Directions] | 6:00 p.m. | ||
| Fri., 2/10 | V Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 84-52 | |
| Fri., 2/10 | JV Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/10 | V Boys Swimming and Diving | Plainville Boys Swimming | Home - Rocky Hill HS-Swimming Pool [Directions] | 4:00 p.m. | L | |
| Fri., 2/10 | V Girls Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 51-26 | |
| Fri., 2/10 | JV Girls Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 6:00 p.m. | ||
| Sat., 2/11 | FR Boys Basketball | Morgan | Home - Portland HS-PHS Gym [Directions] | 9:00 a.m. | ||
| Tue., 2/14 | V Boys Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 58-46 | |
| Tue., 2/14 | JV Boys Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/14 | V Boys Swimming and Diving | Newington | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Tue., 2/14 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 54-25 | |
| Tue., 2/14 | JV Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 2/16 | V Boys Basketball | Ellington | Away - Ellington HS-Gym [Directions] | 7:00 p.m. | L 50-58(OT) | |
| Thu., 2/16 | JV Boys Basketball | Ellington | Away - Ellington HS-Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/16 | FR Boys Basketball | Ellington | Away - Ellington HS-Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/17 | V Girls Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 6:00 p.m. | L 40-19 | |
| Sat., 2/18 | V Boys Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 2:00 p.m. | W 67-40 | |
| Sat., 2/18 | JV Boys Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 12:30 p.m. | ||
| Sat., 2/18 | FR Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 10:00 a.m. | ||
| Fri., 2/24 | V Boys Swimming and Diving | E.O. Smith - Tolland Hammerheads | Away - Mansfield Community Center-Pool [Directions] | 3:30 p.m. | L | |
| Sat., 2/25 | FR Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 10:00 a.m. | ||
| Tue., 2/28 | V Boys Swimming and Diving | CCC North Boys Diving Championships | Home - Rocky Hill HS-Swimming Pool [Directions] | 6:00 p.m. | ||
| Fri., 3/3 | V Boys Swimming and Diving | Newington, Avon, E.O. Smith/Tolland, Hartford Public, Wethersfield | Away - Newington HS-Pool | 4:30 p.m. | ||
| Sat., 4/1 | V Boys Outdoor Track | East Hampton | Away - East Hampton HS-Track [Directions] | 9:00 a.m. | ||
| Sat., 4/1 | V Girls Outdoor Track | East Hampton | Away - East Hampton HS-Track [Directions] | 9:00 a.m. | ||
| Mon., 4/3 | V Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | L 8-5 | |
| Mon., 4/3 | V Boys Tennis | Morgan | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Mon., 4/3 | V Softball | Hale Ray | Home - Portland HS-MS Softball Field [Directions] | 4:00 p.m. | L 29 - 0 | |
| Mon., 4/3 | V Girls Tennis | Morgan | Home - Portland HS-Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Tue., 4/4 | JV Baseball | Hale Ray | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | V Boys Golf | Cromwell | Away - TPC River Highlands [Directions] | 2:40 p.m. | ||
| Wed., 4/5 | V Baseball | Old Saybrook | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | W 8-4 | |
| Wed., 4/5 | V Boys Tennis | Valley Regional | Home - Valley Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Wed., 4/5 | V Girls Tennis | Valley Regional | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 4/6 | V Boys Golf | Coventry | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Thu., 4/6 | V Softball | Coginchaug | Away - Coginchaug Regional HS-Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 4:00 p.m. | L 0-20 | |
| Fri., 4/7 | V Baseball | Coginchaug | Home - Portland HS-Portland HS [Directions] | 11:00 a.m. | L 9-3 | |
| Fri., 4/7 | V Boys Tennis | East Hampton | Away - East Hampton HS-Tennis Courts [Directions] | 1:00 p.m. | W 3-2 | |
| Fri., 4/7 | V Girls Tennis | East Hampton | Away - East Hampton HS-Tennis Courts [Directions] | 1:00 p.m. | W 5-2 | |
| Mon., 4/10 | V Baseball | Westbrook | Home - Portland HS-Portland HS [Directions] | 11:00 a.m. | L 12-11 | |
| Mon., 4/10 | V Boys Tennis | Cromwell | Away - Watrous park [Directions] | 1:00 p.m. | L 0-5 | |
| Mon., 4/10 | V Girls Tennis | Cromwell | Away - Watrous park [Directions] | 1:00 p.m. | L 2-3 | |
| Wed., 4/12 | V Girls Tennis | North Branford | Home - Portland HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 4/13 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Gloria Maddocks Field [Directions] | 4:00 p.m. | L 13-10 | |
| Fri., 4/14 | V Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 4:00 p.m. | L 16-4 | |
| Sat., 4/15 | JV Baseball | North Branford | Home - Portland HS-Portland HS [Directions] | 11:00 a.m. | ||
| Mon., 4/17 | V Softball | North Branford | Home - Portland HS-PHS Softball Field [Directions] | 4:00 p.m. | L 18-0 | |
| Tue., 4/18 | V Baseball | Haddam-Killingworth | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | L 10-4 | |
| Tue., 4/18 | V Boys Golf | Old Saybrook | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Tue., 4/18 | V Boys Tennis | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | W 4-1 | |
| Tue., 4/18 | V Girls Outdoor Track | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track [Directions] | 3:45 p.m. | ||
| Tue., 4/18 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Varsity Softball Field [Directions] | 3:45 p.m. | L 29-0 | |
| Tue., 4/18 | V Girls Tennis | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Wed., 4/19 | JV Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 4/19 | V Boys Tennis | Coginchaug | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Wed., 4/19 | V Girls Tennis | Coginchaug | Home - Portland HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Thu., 4/20 | V Baseball | East Hampton | Away - East Hamprton HS [Directions] | 4:00 p.m. | L 9-2 | |
| Thu., 4/20 | V Boys Tennis | Old Lyme | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 4/20 | V Girls Tennis | Old Lyme | Home - Portland HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Fri., 4/21 | JV Baseball | East Hampton | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | ||
| Fri., 4/21 | V Boys Outdoor Track | Xavier | Away - Xavier HS-Track [Directions] | 5:00 p.m. | ||
| Fri., 4/21 | V Girls Outdoor Track | Xavier | Away - Xavier HS [Directions] | 5:00 p.m. | ||
| Fri., 4/21 | V Girls Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 4/22 | V Baseball | Ellington | Home - Portland HS-Portland HS [Directions] | 12:00 p.m. | L 14-3 | |
| Mon., 4/24 | V Baseball | ValleyReg/Westbrook | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | L 14-1 | |
| Mon., 4/24 | V Boys Outdoor Track | Cromwell, Old Lyme | Away - Cromwell HS-Don Luke Track [Directions] | 3:30 p.m. | ||
| Mon., 4/24 | V Girls Outdoor Track | Cromwell, Old Lyme | Away - Cromwell HS-Don Luke Track [Directions] | 3:30 p.m. | ||
| Mon., 4/24 | V Softball | Valley Regional | Away - Valley Regional HS-Joseph Camarota Memorial Field [Directions] | 4:00 p.m. | L Forfeit | |
| Mon., 4/24 | V Girls Tennis | Ellington | Away - Ellington HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Tue., 4/25 | JV Baseball | ValleyReg/Westbrook | Away - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Boys Golf | Coginchaug | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Tue., 4/25 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 4/25 | V Girls Golf | Coginchaug | Home - Portland West [Directions] | 3:45 p.m. | ||
| Tue., 4/25 | V Girls Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Wed., 4/26 | V Boys Golf | Morgan | Away - Clinton Country Club [Directions] | 2:45 p.m. | ||
| Wed., 4/26 | JV Boys Golf | Coventry, Xavier | Home - Portland West [Directions] | 2:45 p.m. | ||
| Wed., 4/26 | V Softball | Morgan | Home - Portland HS-PHS Softball Field [Directions] | 4:00 p.m. | L Forfeit | |
| Thu., 4/27 | V Boys Golf | Tolland, Enfield | Away - Twin Hills Country Club [Directions] | 3:00 p.m. | ||
| Thu., 4/27 | V Softball | Westbrook/Old Saybrook | Away - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | 4:00 p.m. | L Forfeit | |
| Fri., 4/28 | V Baseball | Cromwell | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | L 6-5 | |
| Fri., 4/28 | V Softball | Cromwell | Away - Cromwell HS-Softball Diamond [Directions] | 4:00 p.m. | L Forfeit | |
| Fri., 4/28 | V Girls Tennis | Westbrook | Home - Portland HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| 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 | Hale Ray | Home - Portland HS-Portland HS [Directions] | 3:45 p.m. | W 8-1 | |
| Mon., 5/1 | V Boys Golf | North Branford | Away - Indian Springs Golf Course-Indian Springs CC [Directions] | 3:00 p.m. | ||
| Mon., 5/1 | V Boys Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Mon., 5/1 | V Softball | Hale Ray | Away - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 4:00 p.m. | L Forfeit | |
| Mon., 5/1 | V Girls Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 5/2 | V Boys Golf | Valley Regional | Away - Black Hall Golf Club [Directions] | 3:00 p.m. | ||
| Tue., 5/2 | V Boys Outdoor Track | Morgan, Coginchaug | Away - Peters Complex-Track [Directions] | 3:45 p.m. | ||
| Tue., 5/2 | V Girls Golf | Valley Regional | Away - Black Hall Golf Club [Directions] | 3:00 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | Morgan, Coginchaug | Away - Peters Complex-Track [Directions] | 3:45 p.m. | ||
| Wed., 5/3 | V Baseball | Old Saybrook | Away - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | L 9-1 | |
| Wed., 5/3 | V Boys Tennis | Cromwell | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-5 | |
| Wed., 5/3 | V Girls Tennis | Cromwell | Home - Portland HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Thu., 5/4 | V Boys Golf | Cromwell | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Fri., 5/5 | V Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 4:00 p.m. | W 7-5 | |
| Fri., 5/5 | V Softball | Coginchaug | Home - Portland HS-MS Softball Field [Directions] | 4:00 p.m. | L Forfeit | |
| Fri., 5/5 | V Girls Tennis | North Branford | Away - North Branford HS-NBHS Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Sat., 5/6 | JV Baseball | Coginchaug | Home - Portland HS-Portland HS [Directions] | 11:00 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. | ||
| Mon., 5/8 | V Boys Golf | Wildcat Invite | Away - Norwich Golf Course | 12:30 p.m. | ||
| Mon., 5/8 | JV Boys Golf | Xavier | Away - Portland Golf Course [Directions] | 2:30 p.m. | ||
| Mon., 5/8 | V Boys Outdoor Track | North Branford, Old Saybrook | Away - North Branford HS-NBHS Track [Directions] | 4:15 p.m. | ||
| Mon., 5/8 | V Boys Tennis | Valley Regional | Away - Valley Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Mon., 5/8 | V Girls Outdoor Track | North Branford, Old Saybrook | Away - North Branford HS-NBHS Track [Directions] | 4:15 p.m. | ||
| Mon., 5/8 | V Softball | Westbrook/Old Saybrook | Home - Portland HS-PHS Softball Field [Directions] | 4:00 p.m. | L Forfeit | |
| Mon., 5/8 | V Girls Tennis | Valley Regional | Away - Valley Regional HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 5/9 | JV Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | ||
| Tue., 5/9 | JV Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 4:00 p.m. | L Forfeit | |
| Wed., 5/10 | V Baseball | Old Lyme | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | L 11-4 | |
| Wed., 5/10 | V Boys Golf | East Hampton | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Wed., 5/10 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 6:00 p.m. | L Forfeit | |
| Wed., 5/10 | V Girls Tennis | Haddam-Killingworth | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Thu., 5/11 | V Baseball | Morgan | Away - Morgan School-Baseball Field [Directions] | 4:00 p.m. | L 12-6 | |
| Thu., 5/11 | JV Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Gloria Maddocks Field [Directions] | Canceled | Cancelled | |
| Sat., 5/13 | V Baseball | Westbrook | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:00 p.m. | W 10-9 (8 inn) | |
| Mon., 5/15 | V Baseball | Morgan | Away - Indian River Complex-Baseball Field [Directions] | 6:00 p.m. | L 8-7 (14 inn) | |
| Mon., 5/15 | V Boys Golf | East Catholic | Away - Tallwood Country Club [Directions] | 2:30 p.m. | ||
| Tue., 5/16 | JV Baseball | Morgan | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Boys Golf | Hale Ray | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Tue., 5/16 | V Boys Outdoor Track | Valley Regional, Westbrook | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:30 p.m. | ||
| Tue., 5/16 | V Boys Tennis | East Hampton | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-0 | |
| Tue., 5/16 | V Girls Outdoor Track | Valley Regional, Westbrook | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:30 p.m. | ||
| Tue., 5/16 | V Girls Tennis | East Hampton | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Wed., 5/17 | V Baseball | East Hampton | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | W 13-3 | |
| Wed., 5/17 | V Boys Golf | Haddam-Killingworth | Away - Black Birch Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/17 | V Boys Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 5/17 | V Softball | East Hampton | Home - Portland HS-PHS Softball Field [Directions] | 3:45 p.m. | L Forfeit | |
| Thu., 5/18 | V Boys Golf | Old Lyme | Away - Black Hall Golf Club [Directions] | 3:00 p.m. | ||
| Thu., 5/18 | JV Boys Golf | Xavier | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Thu., 5/18 | V Boys Outdoor Track | Haddam-Killingworth, Morgan | Away - Haddam Killingworth HS (HK)-HKHS Track [Directions] | 3:45 p.m. | ||
| Thu., 5/18 | JV Girls Golf | Wethersfield | Away - Goodwin Park Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/18 | V Girls Outdoor Track | Haddam-Killingworth, Morgan | Away - Haddam Killingworth HS (HK)-HKHS Track [Directions] | 3:45 p.m. | ||
| Fri., 5/19 | V Baseball | Middletown | Away - Palmer Field-Baseball Diamond [Directions] | 6:00 p.m. | L 10-3 | |
| Sat., 5/20 | JV Baseball | Cromwell | Home - Portland HS-Portland HS [Directions] | Postponed | ||
| Tue., 5/23 | JV Boys Golf | Coventry | Home - Portland West [Directions] | 2:45 p.m. | ||
| Wed., 5/24 | JV Baseball | Putnam | Away - Putnam HS-Baseball Diamond [Directions] | 4:00 p.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. | ||
| Wed., 5/31 | V Boys Golf | Daniel Hand | Away - Madison Country Club [Directions] | 2:30 p.m. | ||