| Portland 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 448 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 8/26 | V Football | Bloomfield, TBA (Scrim.) | Away - Bloomfield HS-Phil Rubin Stadium- Turf Field & Track [Directions] | 4:00 p.m. | ||
| Tue., 8/29 | V Boys Soccer | Windham (Scrim.) | Away - Windham HS-Ferrigno Field [Directions] | 6:30 p.m. | ||
| Tue., 8/29 | V Girls Soccer | Bristol Central (Scrim.) | Away - Bristol Central HS-BC Turf Field [Directions] | 3:45 p.m. | ||
| Wed., 8/30 | V Football | Lewis Mills (Scrim.) | Away - Lewis Mills HS-Lewis Mills Track [Directions] | 4:45 p.m. | ||
| Wed., 8/30 | V Boys Soccer | Manchester (Scrim.) | Away - Memorial Field @ MHS [Directions] | 3:45 p.m. | ||
| Wed., 8/30 | JV Boys Soccer | Manchester (Scrim.) | Away - Manchester HS-Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 8/30 | V Girls Soccer | Windham (Scrim.) | Away - Windham HS-Ferrigno Field [Directions] | 6:30 p.m. | ||
| Sat., 9/2 | V Boys Soccer | Lyme-Old Lyme Soccer Jamboree | Away - Lyme-Old Lyme HS-Track Field | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Tue., 9/5 | V Boys Soccer | St. Bernard (Scrim.) | Away - St. Bernard School-Delaporta Field [Directions] | 4:00 p.m. | ||
| Tue., 9/5 | V Girls Soccer | Plainfield (Scrim.) | Away - Plainfield HS Athletic Upper Complex-Varsity Soccer Field [Directions] | 4:00 p.m. | Cancelled | |
| Wed., 9/6 | V Boys Cross Country | TBA | Away - JB Williams Park | 3:45 p.m. | ||
| Wed., 9/6 | V Girls Cross Country | TBA | Away - JB Williams Park | 3:45 p.m. | ||
| Thu., 9/7 | V Girls Volleyball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 6:30 p.m. | L 0-3 | |
| Thu., 9/7 | JV Girls Volleyball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | Postponed | ||
| Fri., 9/8 | V Boys Soccer | Old Saybrook | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | T 0-0 | |
| Fri., 9/8 | V Girls Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 7:00 p.m. | T 0-0 | |
| Mon., 9/11 | JV Boys Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 4:00 p.m. | ||
| Mon., 9/11 | V Girls Volleyball | Old Lyme | Home - Portland HS-Portland HS [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 9/11 | JV Girls Volleyball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Boys Cross Country | Highlander Invitational | Home - Camp Ingersoll [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Boys Soccer | Haddam-Killingworth | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | T 0-0 | |
| Tue., 9/12 | V Girls Cross Country | Highlander Invitational | Home - Camp Ingersoll [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Girls Soccer | Rocky Hill | Away - Rocky Hill HS-Stadium [Directions] | 6:00 p.m. | W 2-0 | |
| Tue., 9/12 | V Girls Swimming and Diving | Bristol Central/Eastern | Away - Dennis Malone Aquatic Center-Pool [Directions] | 3:45 p.m. | L | |
| Wed., 9/13 | V Girls Volleyball | North Branford | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 9/13 | JV Girls Volleyball | North Branford | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Football | SMSA Coop | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 6:00 p.m. | W 22-20 | |
| Thu., 9/14 | V Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 p.m. | T 1-1 | |
| Thu., 9/14 | V Girls Volleyball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 9/14 | JV Girls Volleyball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/15 | V Boys Cross Country | Blue Dragon Invitational | Away - Veterans Park | 3:30 p.m. | ||
| Fri., 9/15 | V Boys Cross Country | Blue Dragon Invitational @ Middletown | Away - Veterans Memorial Park, Middletown, CT | 3:30 p.m. | ||
| Fri., 9/15 | JV Football | SMSA Coop | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 4:00 p.m. | ||
| Fri., 9/15 | V Boys Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 9/15 | V Girls Cross Country | Blue Dragon Invitational @ Middletown | Away - Veterans Memorial Park, Middletown, CT | 3:30 p.m. | ||
| Fri., 9/15 | V Girls Cross Country | Blue Dragon Invitational | Away - Veterans Park | 3:45 p.m. | ||
| Sat., 9/16 | V Girls Soccer | Coginchaug | Home - Country Club Field Road-Country Club Road [Directions] | 6:00 p.m. | W 3-1 | |
| Mon., 9/18 | V Boys Soccer | Northwest Catholic | Away - Northwest Catholic HS (Primary)-Neil J. Brewer Field [Directions] | 3:45 p.m. | T 0-0 | |
| Mon., 9/18 | V Girls Volleyball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 9/18 | JV Girls Volleyball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Girls Soccer | Bristol Eastern | Away - Bristol Eastern HS-Alumni Field-Turf [Directions] | 4:30 p.m. | W 1-0 | |
| Tue., 9/19 | V Girls Swimming and Diving | South Windsor | Home - Rocky Hill HS-Swimming Pool [Directions] | Postponed | ||
| Wed., 9/20 | V Boys Cross Country | 35th Annual - Going to the Sun Cross Country Invitational | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:30 p.m. | ||
| Wed., 9/20 | JV Boys Soccer | Morgan | Away - Morgan School-Soccer/Lax Field [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | V Girls Cross Country | 35th Annual - Going to the Sun Cross Country Invitational | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:30 p.m. | ||
| Wed., 9/20 | V Girls Volleyball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 9/20 | JV Girls Volleyball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/21 | V Boys Soccer | Valley Regional | Home - Portland HS-JV Soccer Field [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 9/21 | V Girls Soccer | Valley Regional | Away - Valley Regional HS-Richard B. Blythe - Turf Field [Directions] | 6:00 p.m. | L 0-1 | |
| Thu., 9/21 | V Girls Swimming and Diving | Middletown | Away - Middletown HS-MHS Pool [Directions] | 3:45 p.m. | L | |
| Fri., 9/22 | V Football | Valley Regional/Old Lyme | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 6:00 p.m. | W 55-7 | |
| Sat., 9/23 | JV Football | Valley Regional/Old Lyme | Away - Valley Regional HS-Practice Football Field [Directions] | Postponed | ||
| Sat., 9/23 | V Boys Soccer | Cromwell | Home - Country Club Field Road-Country Club Road [Directions] | 6:00 p.m. | W 2-1 | |
| Tue., 9/26 | JV Boys Soccer | Cromwell | Away - Cromwell HS-soccer field 1 [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | JV Girls Soccer | Cromwell | Away - Cromwell HS-Soccer Field 2 [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | V Girls Swimming and Diving | Conard | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Tue., 9/26 | V Girls Volleyball | Morgan | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 9/26 | JV Girls Volleyball | Morgan | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Wed., 9/27 | V Boys Cross Country | Small Schools League Meet | Away - Lyme-Old Lyme HS-Cross Country Course | 3:45 p.m. | ||
| Wed., 9/27 | V Girls Cross Country | Small Schools League Meet | Away - Lyme-Old Lyme HS-Cross Country Course | 3:45 p.m. | ||
| Wed., 9/27 | V Girls Volleyball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 9/27 | JV Girls Volleyball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | V Boys Soccer | Old Lyme | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | W 2-1 | |
| Thu., 9/28 | V Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Turf Field [Directions] | 4:00 p.m. | L 0-2 | |
| Thu., 9/28 | V Girls Swimming and Diving | Plainville | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Thu., 9/28 | V Girls Volleyball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 9/28 | JV Girls Volleyball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 9/30 | JV Football | Old Saybrook, MSW | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Sat., 9/30 | V Boys Soccer | New Britain | Away - Osgood Park [Directions] | 11:00 a.m. | W 3-1 | |
| Sun., 10/1 | V Football | MSW | Home - Old Saybrook HS-Old Saybrook Campus [Directions] | 11:00 a.m. | W 35-6 | |
| Mon., 10/2 | V Boys Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | W 1-0 | |
| Mon., 10/2 | V Girls Volleyball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 10/2 | JV Girls Volleyball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 10/3 | V Girls Soccer | Westbrook | Home - Portland HS-JV Soccer Field [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/3 | V Girls Swimming and Diving | Haddam-Killingworth | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Wed., 10/4 | V Girls Soccer | St. Bernard | Away - St. Bernard School-Delaporta Field [Directions] | 3:45 p.m. | L 0-1 | |
| Wed., 10/4 | V Girls Volleyball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 10/4 | JV Girls Volleyball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | V Boys Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 6:00 p.m. | L 0-1 | |
| Fri., 10/6 | V Football | Rockville | Away - Rockville HS-Stadium Field [Directions] | 6:30 p.m. | L 20-36 | |
| Fri., 10/6 | V Girls Soccer | Morgan | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | L 1-2 | |
| Sat., 10/7 | JV Football | Rockville | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | Postponed | ||
| Tue., 10/10 | V Boys Soccer | E.O. Smith | Away - Farrell Field Park-Upper Field [Directions] | 3:45 p.m. | W 3-0 | |
| Tue., 10/10 | V Girls Soccer | East Granby | Away - East Granby HS-Lower Soccer Field [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 10/10 | V Girls Swimming and Diving | Wethersfield, Enfield | Away - Wethersfield HS-Backman Pool [Directions] | 5:00 p.m. | Wethersfield-L Enfield-W | |
| Wed., 10/11 | V Boys Cross Country | East Hampton | Away - East Hampton HS-Cross Country Course [Directions] | 3:45 p.m. | ||
| Wed., 10/11 | V Boys Soccer | Hale Ray | Away - Nathan Hale Ray HS-Hale-Ray MS [Directions] | 3:45 p.m. | W 5-1 | |
| Wed., 10/11 | V Girls Cross Country | East Hampton | Away - East Hampton HS-Cross Country Course [Directions] | 3:45 p.m. | ||
| Wed., 10/11 | V Girls Volleyball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Thu., 10/12 | JV Boys Soccer | Hale Ray | Away - Nathan Hale Ray HS-Hale-Ray MS [Directions] | 3:45 p.m. | ||
| Thu., 10/12 | JV Girls Soccer | Coginchaug | Away - Coginchaug Regional HS-Field #2 - Middle Field @ CRHS [Directions] | 3:45 p.m. | ||
| Fri., 10/13 | V Girls Swimming and Diving | Windsor | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Fri., 10/13 | V Girls Volleyball | East Hampton | Away - East Hampton HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/13 | JV Girls Volleyball | East Hampton | Away - East Hampton HS-Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/14 | V Girls Soccer | Cromwell | Away - Cromwell HS-Main field [Directions] | 9:00 a.m. | T 1-1 | |
| Mon., 10/16 | V Boys Soccer | North Branford | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | W 5-0 | |
| Mon., 10/16 | V Girls Soccer | Coventry | Away - Coventry HS-Soccer field [Directions] | 6:00 p.m. | W 1-0 | |
| Mon., 10/16 | V Girls Volleyball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 10/16 | JV Girls Volleyball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | JV Boys Soccer | Valley Regional | Away - Valley Regional HS-OxFord HS [Directions] | 3:45 p.m. | ||
| Tue., 10/17 | V Girls Soccer | North Branford/Hale Ray | Away - North Branford HS-NBHS Front Field [Directions] | 4:00 p.m. | W 8-1 | |
| Wed., 10/18 | V Boys Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 7:00 p.m. | L 3-2 | |
| Wed., 10/18 | JV Girls Soccer | Cromwell | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/18 | V Girls Swimming and Diving | Bulkeley/HMTCA/Weaver | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | W | |
| Wed., 10/18 | V Girls Volleyball | Morgan | Away - Morgan School-Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 10/18 | JV Girls Volleyball | Morgan | Away - Morgan School-Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | V Boys Cross Country | Shoreline Conference XC Championship | Away - Hammonasset Park | 1:30 p.m. | ||
| Thu., 10/19 | JV Boys Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Middle Field [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | V Girls Cross Country | Shoreline Conference XC Championship | Away - Hammonasset Park | 1:30 p.m. | ||
| Fri., 10/20 | V Football | Capital/Achievement | Away - Hartford Public HS-Turf field [Directions] | 7:00 p.m. | W 20-8 | |
| Fri., 10/20 | V Girls Soccer | East Hampton | Home - TD Bank Oakwood Soccer Park [Directions] | 7:00 p.m. | W 1-0 | |
| Fri., 10/20 | V Girls Swimming and Diving | East Hartford | Away - East Hartford MS-Pool [Directions] | 3:45 p.m. | W | |
| Sat., 10/21 | JV Football | Capital/Achievement | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 10:00 a.m. | ||
| Sat., 10/21 | JV Girls Soccer | Morgan | Away - Morgan School-Soccer/Lax Field [Directions] | Canceled | Cancelled | |
| Mon., 10/23 | V Boys Soccer | Windsor Locks | Home - TD Bank Oakwood Soccer Park [Directions] | 6:00 p.m. | W 2-1 | |
| Mon., 10/23 | V Girls Soccer | Suffield | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | L 1-6 | |
| Mon., 10/23 | V Girls Volleyball | Cromwell | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 10/23 | JV Girls Volleyball | Cromwell | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | V | Unified Fall Fest- Hale-Ray | Away - Nathan Hale Ray HS-HS Gym | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 3:30 p.m. | ||||||
| Tue., 10/24 | V Boys Cross Country | Freshmen/Sophmore Meet | Away - Old Saybrook HS-Old Saybrook Campus | 3:45 p.m. | ||
| Tue., 10/24 | JV Boys Soccer | Valley Regional | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/24 | V Girls Cross Country | Freshmen/Sophmore Meet | Away - Old Saybrook HS-Old Saybrook Campus | 3:45 p.m. | ||
| Wed., 10/25 | JV Boys Soccer | East Hampton | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/25 | V Girls Volleyball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 10/25 | JV Girls Volleyball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 4:15 p.m. | ||
| Thu., 10/26 | V Boys Soccer | Coventry | Away - Coventry HS-Soccer field [Directions] | 6:00 p.m. | T 0-0 | |
| Thu., 10/26 | V Girls Volleyball | North Branford | Away - East Haven HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 10/26 | JV Girls Volleyball | North Branford | Away - East Haven HS-Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/26 | V | Shoreline Conference Unified Soccer Tournament | Away - Valley Regional HS-Richard B. Blythe Field | 3:30 p.m. | ||
| Fri., 10/27 | V Football | Haddam-Killingworth | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 6:00 p.m. | W 48-12 | |
| Sat., 10/28 | V Boys Cross Country | CIAC Class S Championship | Away - Wickham Park | 9:35 a.m. | ||
| Sat., 10/28 | V Boys Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 6:00 p.m. | W 2-1 | |
| Sat., 10/28 | V Girls Cross Country | CIAC Class S Championship | Away - Wickham Park | 9:00 a.m. | ||
| Sat., 10/28 | V Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 11:00 a.m. | W 2-1 | |
| Mon., 10/30 | JV Football | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | Canceled | Cancelled | |
| Mon., 10/30 | V Boys Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 7:00 p.m. | L 0-2 | |
| Mon., 10/30 | V Girls Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 7:00 p.m. | L 1-2 | |
| Fri., 11/3 | V Football | Granby/Canton | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 6:30 p.m. | L 6-22 | |
| Fri., 11/3 | V Girls Swimming and Diving | Wethersfield, Enfield, Windsor | Away - Wethersfield HS-Backman Pool [Directions] | 3:30 p.m. | ||
| Fri., 11/3 | V Girls Swimming and Diving | Wethersfield, Enfield, Windsor | Away - Wethersfield HS-Backman Pool [Directions] | 5:45 p.m. | ||
| Sat., 11/4 | JV Football | Granby/Canton | Away - Granby Memorial HS-Stadium Field [Directions] | 10:00 a.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/6 | V Girls Soccer | Stafford | Home - Portland HS-Varsity Soccer FIeld [Directions] | 2:30 p.m. | L 2-3 | |
| Tue., 11/7 | V Boys Soccer | East Granby | Home - Portland HS-Varsity Soccer FIeld [Directions] | 2:30 p.m. | W 3-0 | |
| Wed., 11/8 | V Girls Swimming and Diving | CIAC Class S Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Wed., 11/8 | V Girls Swimming and Diving | CIAC Class S Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Thu., 11/9 | V Boys Soccer | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 11/11 | V Football | Coginchaug/Hale Ray/East Hampton | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | Suspended | ||
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cheshire Community Pool | 6:15 p.m. | ||
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cheshire Community Pool | 6:15 p.m. | ||
| Wed., 11/15 | V Girls Swimming and Diving | CIAC Class S Finals | Away - SCSU | 6:00 p.m. | ||
| Wed., 11/15 | V Girls Swimming and Diving | CIAC Class S Finals | Away - SCSU | 6:00 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/16 | V | Unified Shoreline Volleyball Tournament | Away - Haddam Killingworth HS (HK)-Gym 1 | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 11/21 | ||||||
| Fri., 11/17 | V Football | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 6:30 p.m. | W 52-18 | |
| Sat., 11/18 | JV Football | North Branford | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | Canceled | Cancelled | |
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Wed., 11/22 | V Football | Rocky Hill | Away - Rocky Hill HS-Stadium [Directions] | 6:00 p.m. | W 47-6 | |
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Tue., 11/28 | V Football | Griswold/Wheeler | Home - Pierson Park (Cromwell, CT)-Football Field [Directions] | 6:30 p.m. | W 26-18 | |
| Sun., 12/3 | V Football | Ansonia | Away - Derby HS-Ryan Field [Directions] | 12:00 p.m. | W 28-0 | |
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Wed., 12/6 | V Boys Basketball | Branford (Scrim.) | Home - Portland HS-PHS Gym [Directions] | 6:00 p.m. | ||
| Fri., 12/8 | V Girls Basketball | East Windsor (Scrim.) | Away - East Windsor Senior HS-Gym [Directions] | 5:00 p.m. | ||
| Sat., 12/9 | V Boys Basketball | Newtown (Scrim.) | Away - Newtown HS-Gym [Directions] | 11:00 a.m. | ||
| Sat., 12/9 | V Football | Bloomfield | Away - Rentschler Field [Directions] | 10:30 a.m. | L 20-42 | |
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Sat., 12/9 | V Girls Basketball | Granby Memorial (Scrim.) | Away - Granby Memorial HS-K.L. King Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 12/11 | V Boys Indoor Track | Wesleyan Developmental Meet | Away - Wesleyan University-Freeman Athletic Center | 5:00 p.m. | ||
| Mon., 12/11 | V Girls Indoor Track | Wesleyan Developmental Meet | Away - Wesleyan University-Freeman Athletic Center | 5:00 p.m. | ||
| Tue., 12/12 | V Girls Basketball | Plainville | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 39-25 | |
| Tue., 12/12 | JV Girls Basketball | Plainville | Home - Portland HS-PHS Gym [Directions] | Canceled | Cancelled | |
| Wed., 12/13 | V Boys Indoor Track | Shoreline Developmental Meet | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Wed., 12/13 | V Wrestling | Haddam-Killingworth | Home - Portland HS-Portland HS [Directions] | 6:00 p.m. | ||
| Wed., 12/13 | V Girls Indoor Track | Shoreline Developmental Meet | Away - Hillhouse HS-Floyd Little | 5:00 p.m. | ||
| Thu., 12/14 | V Boys Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 36-38 | |
| Thu., 12/14 | JV Boys Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/14 | V Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | L 37-33 | |
| Thu., 12/14 | JV Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 7:00 p.m. | ||
| Thu., 12/14 | V | Shoreline Conference Unified Basketball Tournament | Away - Valley Regional HS-Valley Regional High School Gym | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:00 p.m. | ||||||
| Fri., 12/15 | V Girls Basketball | East Granby | Away - East Granby HS-Gym [Directions] | 6:45 p.m. | L 43-16 | |
| Fri., 12/15 | JV Girls Basketball | East Granby | Away - East Granby HS-Gym [Directions] | 5:15 p.m. | ||
| Sat., 12/16 | V Boys Basketball | Guilford | Home - Portland HS-PHS Gym [Directions] | 1:30 p.m. | L 52-65 | |
| Sat., 12/16 | JV Boys Basketball | Guilford | Home - Portland HS-PHS Gym [Directions] | 12:00 p.m. | ||
| Sat., 12/16 | V Wrestling | Plainville Invitational | Away - Plainville HS-Wood Gymnasium | 9:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Tue., 12/19 | V Boys Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 62-71 (OT) | |
| Tue., 12/19 | JV Boys Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/19 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 6:00 p.m. | L 60-31 | |
| Tue., 12/19 | JV Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | Canceled | Cancelled | |
| Thu., 12/21 | V Wrestling | Somers | Away - Somers HS-Somers High School Gymnasium [Directions] | 6:00 p.m. | ||
| Fri., 12/22 | V Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 5:00 p.m. | L 40-52 | |
| Fri., 12/22 | JV Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 3:30 p.m. | ||
| Fri., 12/22 | V Girls Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 3:30 p.m. | L 52-24 | |
| Fri., 12/22 | JV Girls Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 5:00 p.m. | ||
| Sat., 12/23 | V Wrestling | Rockville, Bacon Academy, Canton, Maloney, Notre Dame-West Haven, Platt, Plainville, Rocky Hill | Away - Rockville HS-Main gymnasium | 10:00 a.m. | ||
| Thu., 12/28 | FR Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 11:15 a.m. | ||
| Thu., 12/28 | V Wrestling | Terryville-Thomaston, Thomaston | Home - Portland HS-Portland HS [Directions] | 10:00 a.m. | ||
| Fri., 12/29 | V Boys Swimming and Diving | Middletown | Home - Rocky Hill HS-Swimming Pool [Directions] | 9:00 a.m. | L | |
| Sat., 12/30 | V Boys Basketball | Ellington | Home - Portland HS-PHS Gym [Directions] | 1:00 p.m. | L 44-46 (OT) | |
| Sat., 12/30 | JV Boys Basketball | Ellington | Home - Portland HS-PHS Gym [Directions] | 11:30 a.m. | ||
| Sat., 12/30 | V Wrestling | Morgan Duals | Away - Morgan School-Gym | 9:00 a.m. | ||
| Wed., 1/3 | V Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 73-35 | |
| Wed., 1/3 | JV Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | V Girls Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 40-25 | |
| Thu., 1/4 | V Boys Indoor Track | Shoreline League Meet | Away - Hillhouse HS-Floyd Little | 5:00 p.m. | ||
| Thu., 1/4 | V Wrestling | Stafford | Away - Stafford HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/4 | V Girls Indoor Track | Shoreline League Meet | Away - Hillhouse HS-Floyd Little | 5:00 p.m. | ||
| Fri., 1/5 | V Boys Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 48-34 | |
| Fri., 1/5 | JV Boys Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/5 | V Boys Swimming and Diving | East Hartford | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | W | |
| Sat., 1/6 | FR Boys Basketball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/6 | V Wrestling | The Casey Yates Memorial Wrestling Tournament | Away - Lyman Memorial HS-Gym | 10:00 a.m. | ||
| Tue., 1/9 | V Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 7:00 p.m. | L 47-63 | |
| Tue., 1/9 | JV Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/9 | V Boys Swimming and Diving | Simsbury | Away - Westminster School-Pool [Directions] | 8:00 p.m. | L | |
| Tue., 1/9 | V Girls Basketball | Cromwell | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 46-16 | |
| Tue., 1/9 | JV Girls Basketball | Cromwell | Home - Portland HS-PHS Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/10 | V Boys Indoor Track | Old Saybrook Qualifier | Away - Hillhouse HS-Floyd Little | 5:00 p.m. | ||
| Wed., 1/10 | V Girls Indoor Track | Old Saybrook Qualifier | Away - Hillhouse HS-Floyd Little | 5:00 p.m. | ||
| Thu., 1/11 | V Boys Basketball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 60-54 | |
| Thu., 1/11 | JV Boys Basketball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/11 | V Wrestling | Canton | Away - Canton HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/11 | V Girls Basketball | Montville | Away - Montville HS-Gym [Directions] | 6:00 p.m. | L 54-37 | |
| Thu., 1/11 | JV Girls Basketball | Montville | Away - Montville HS-Gym [Directions] | Canceled | Cancelled | |
| Fri., 1/12 | V Boys Swimming and Diving | Berlin | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Sat., 1/13 | V Boys Basketball | Middletown | Home - Portland HS-PHS Gym [Directions] | 3:30 p.m. | L 58-81 | |
| Sat., 1/13 | JV Boys Basketball | Middletown | Home - Portland HS-PHS Gym [Directions] | 2:00 p.m. | ||
| Sat., 1/13 | FR Boys Basketball | Cromwell | Home - Portland HS-PHS Gym [Directions] | 12:00 p.m. | ||
| Tue., 1/16 | JV Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/17 | V Wrestling | Suffield Windsor Locks Wrestling Co Op | Home - Portland HS-Portland HS [Directions] | 6:00 p.m. | ||
| Wed., 1/17 | V Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | 4:00 p.m. | L 61-9 | |
| Thu., 1/18 | V Boys Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 5:00 p.m. | L 61-65 | |
| Thu., 1/18 | JV Boys Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 3:30 p.m. | ||
| Thu., 1/18 | V Girls Basketball | Cheney Tech | Home - Portland HS-PHS Gym [Directions] | 6:00 p.m. | W 42-17 | |
| Thu., 1/18 | JV Girls Basketball | Cheney Tech | Home - Portland HS-PHS Gym [Directions] | Canceled | Cancelled | |
| Fri., 1/19 | V Girls Basketball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 3:30 p.m. | L 72-22 | |
| Fri., 1/19 | JV Girls Basketball | East Hampton | Home - Portland HS-PHS Gym [Directions] | Canceled | Cancelled | |
| Sat., 1/20 | FR Boys Basketball | North Branford | Away - JEROME HARRISON SCHOOL-Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/20 | V Wrestling | Arrigoni Classic | Home - Portland HS-Portland HS [Directions] | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Mon., 1/22 | V Boys Indoor Track | Joe Sincrope Invite | Away - Hillhouse HS-Floyd Little | 5:00 p.m. | ||
| Mon., 1/22 | V Girls Indoor Track | Joe Sincrope Invite | Away - Hillhouse HS-Floyd Little | 5:00 p.m. | ||
| Wed., 1/24 | V Boys Basketball | North Branford | Away - JEROME HARRISON SCHOOL-Gym [Directions] | 7:00 p.m. | W 51-49 (OT) | |
| Wed., 1/24 | JV Boys Basketball | North Branford | Away - JEROME HARRISON SCHOOL-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/24 | V Boys Swimming and Diving | Avon | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Wed., 1/24 | V Wrestling | Rockville | Home - Portland HS-Portland HS [Directions] | 6:00 p.m. | ||
| Thu., 1/25 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | L 56-28 | |
| Thu., 1/25 | JV Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 1/26 | V Boys Basketball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 55-58 | |
| Fri., 1/26 | JV Boys Basketball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | V Boys Swimming and Diving | Bulkeley Cooperative Swim Team | Away - HMTCA-Pool [Directions] | 3:45 p.m. | W | |
| Fri., 1/26 | V Girls Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 7:00 p.m. | L 64-26 | |
| Fri., 1/26 | JV Girls Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | Canceled | Cancelled | |
| Sat., 1/27 | FR Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 10:00 a.m. | ||
| Sat., 1/27 | V Wrestling | Highlander Invitational | Home - Portland HS-Portland HS [Directions] | 9:00 a.m. | ||
| Mon., 1/29 | V Boys Basketball | Morgan | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 33-46 | |
| Mon., 1/29 | JV Boys Basketball | Morgan | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | V Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 7:00 p.m. | L 41-69 | |
| Tue., 1/30 | JV Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | V Boys Swimming and Diving | Wethersfield | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Tue., 1/30 | V Wrestling | Coventry | Away - Coventry HS-Gym [Directions] | 6:00 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 6:00 p.m. | L 45-38 | |
| Tue., 1/30 | JV Girls Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | Canceled | Cancelled | |
| Fri., 2/2 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | L 53-63 | |
| Fri., 2/2 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Fri., 2/2 | V Boys Indoor Track | Shoreline Championship | Away - Hillhouse HS-Floyd Little | 5:00 p.m. | ||
| Fri., 2/2 | V Boys Swimming and Diving | Northwest Catholic | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | W | |
| Fri., 2/2 | V Girls Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 62-24 | |
| Fri., 2/2 | JV Girls Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | ||
| Fri., 2/2 | V Girls Indoor Track | Shoreline Championship | Away - Hillhouse HS-Floyd Little | 5:00 p.m. | ||
| Sat., 2/3 | V Wrestling | 2024 Bobcat Classic | Away - Bacon Academy | 9:00 a.m. | ||
| Sat., 2/3 | V Girls Basketball | North Branford | Home - Portland HS-PHS Gym [Directions] | 12:00 p.m. | L 63-29 | |
| Sat., 2/3 | JV Girls Basketball | North Branford | Home - Portland HS-PHS Gym [Directions] | 1:30 p.m. | ||
| Mon., 2/5 | V Boys Indoor Track | "Last Chance" Qualifier | Away - Hillhouse HS-Floyd Little | 4:30 p.m. | ||
| Mon., 2/5 | V Girls Indoor Track | "Last Chance" Qualifier | Away - Hillhouse HS-Floyd Little | 4:30 p.m. | ||
| Tue., 2/6 | V Boys Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 55-48 | |
| Tue., 2/6 | JV Boys Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | V Boys Swimming and Diving | Hartford Public | Home - Rocky Hill HS-Swimming Pool [Directions] | 4:00 p.m. | W | |
| Tue., 2/6 | V Girls Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | L 41-23 | |
| Tue., 2/6 | JV Girls Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/7 | V Wrestling | Granby Memorial | Home - Portland HS-Portland HS [Directions] | 6:00 p.m. | ||
| Fri., 2/9 | V Boys Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 57-42 | |
| Fri., 2/9 | JV Boys Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | V Boys Indoor Track | CIAC S Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/9 | V Boys Swimming and Diving | South Windsor | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Fri., 2/9 | V Girls Indoor Track | CIAC S Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Sat., 2/10 | FR Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 3:00 p.m. | ||
| Sat., 2/10 | V Wrestling | NCCC Wrestling Championships | Away - Stafford HS-Gym | 10:00 a.m. | ||
| Sat., 2/10 | V Girls Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 5:00 p.m. | W 44-36 | |
| Mon., 2/12 | V Boys Swimming and Diving | Newington | Away - Newington HS-Pool [Directions] | 4:00 p.m. | L | |
| Tue., 2/13 | V Girls Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | Canceled | Cancelled | |
| Tue., 2/13 | JV Girls Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | Canceled | Cancelled | |
| Wed., 2/14 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | L 63-35 | |
| Thu., 2/15 | V Boys Basketball | Conard | Away - Conard HS-Main Gym [Directions] | 5:15 p.m. | L 40-80 | |
| Thu., 2/15 | JV Boys Basketball | Conard | Away - Conard HS-Main Gym [Directions] | Canceled | Cancelled | |
| Thu., 2/15 | V Girls Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 5:30 p.m. | L 63-17 | |
| Thu., 2/15 | JV Girls Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | Canceled | Cancelled | |
| Thu., 2/15 | V | Shoreline Unified Cornhole Tournament | Away - Lyme-Old Lyme HS | 3:00 p.m. | ||
| Fri., 2/16 | V Wrestling | CIAC M Divisional Championship | Away - Guilford | TBA | ||
| Sat., 2/17 | V Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 12:00 p.m. | W 53-45 | |
| Sat., 2/17 | FR Boys Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Wed., 2/21 | V Boys Swimming and Diving | E.O. Smith - Tolland Hammerheads | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Fri., 2/23 | V Boys Swimming and Diving | Plainville Boys Swimming | Away - Plainville HS-Pool [Directions] | 3:45 p.m. | L | |
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 2/24 | V Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 3:00 p.m. | ||
| Sat., 2/24 | V Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:00 p.m. | L 28-54 | |
| Sat., 2/24 | FR Boys Basketball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | 9:00 a.m. | ||
| Wed., 2/28 | V Boys Swimming and Diving | Avon, E.O. Smith - Tolland Hammerheads, Hartford Public, Newington, Wethersfield | Home - Rocky Hill HS-Swimming Pool [Directions] | 6:00 p.m. | ||
| Fri., 3/1 | V Boys Swimming and Diving | Newington, Avon, E.O. Smith - Tolland Hammerheads, Hartford Public, Wethersfield | Away - Newington HS-Pool | 4:30 p.m. | ||
| Wed., 3/6 | V Boys Swimming and Diving | CIAC Class S Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Fri., 3/8 | V Boys Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cornerstone Pool | 5:15 p.m. | ||
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Mon., 3/25 | V Softball | Hale Ray (Scrim.) | Away - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | V Baseball | Haddam-Killingworth (Scrim.) | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 3/28 | V Baseball | Putnam (Scrim.) | Home - Portland HS-Portland HS [Directions] | Canceled | Cancelled | |
| Thu., 3/28 | V Girls Tennis | RHAM (Scrim.) | Away - RHAM HS-Tennis Courts [Directions] | 3:45 p.m. | Cancelled | |
| Sat., 3/30 | V Softball | Old Lyme | Home - Portland HS-PHS Softball Field [Directions] | 11:00 a.m. | L 18-0 | |
| Mon., 4/1 | V Baseball | Hale Ray | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | W 10-2 | |
| Mon., 4/1 | V Softball | Hale Ray | Home - Portland HS-PHS Softball Field [Directions] | 4:00 p.m. | L 30-0 | |
| Mon., 4/1 | V Girls Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/2 | JV Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | Postponed | ||
| Wed., 4/3 | V | Unified Track Meet | Away - Nathan Hale Ray HS-Martin Ryczek Track | 3:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 5/1 | ||||||
| Fri., 4/5 | V Girls Tennis | East Hampton | Away - East Hampton HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Sat., 4/6 | V Baseball | Coginchaug | Home - Portland HS-Portland HS [Directions] | 1:00 p.m. | ||
| Sat., 4/6 | JV Baseball | Coginchaug | Home - Portland HS-Portland HS [Directions] | Postponed | ||
| Sat., 4/6 | V Boys Outdoor Track | East Hampton | Away - East Hampton HS-Track [Directions] | 9:00 a.m. | ||
| Sat., 4/6 | V Girls Outdoor Track | East Hampton | Away - East Hampton HS-Track [Directions] | 9:00 a.m. | ||
| Sat., 4/6 | V Softball | Coginchaug | Home - Portland HS-PHS Softball Field [Directions] | 1:00 p.m. | L 23-3 | |
| Mon., 4/8 | V Girls Tennis | Cromwell | Away - Watrous park [Directions] | 10:00 a.m. | W 6-1 | |
| Tue., 4/9 | V Baseball | Old Lyme | Home - Portland HS-Portland HS [Directions] | 12:00 p.m. | ||
| Tue., 4/9 | V Softball | North Branford | Home - Portland HS-PHS Softball Field [Directions] | 11:00 a.m. | L 22 - 0 | |
| Wed., 4/10 | JV Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Gloria Maddocks Field [Directions] | 3:45 p.m. | ||
| Thu., 4/11 | V Boys Golf | Coventry | Home - Portland Golf Course [Directions] | 2:30 p.m. | ||
| Thu., 4/11 | JV Boys Golf | Coventry | Home - Portland West [Directions] | 2:30 p.m. | ||
| Sat., 4/13 | JV Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 3:00 p.m. | ||
| Mon., 4/15 | V Baseball | Putnam | Away - Putnam Complex, Murphy Park [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | V Boys Golf | East Hampton | Away - Quarry Ridge Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 4/15 | V Girls Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 4/16 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 4/16 | V Boys Golf | Old Saybrook | Away - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 4/16 | V Boys Outdoor Track | Haddam-Killingworth, Hale Ray | Away - Haddam Killingworth HS (HK)-HKHS Track [Directions] | 3:30 p.m. | ||
| Tue., 4/16 | V Girls Outdoor Track | Haddam-Killingworth, Hale Ray | Away - Haddam Killingworth HS (HK)-HKHS Track [Directions] | 3:30 p.m. | ||
| Tue., 4/16 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Varsity Softball Field [Directions] | 3:45 p.m. | L 12 - 0 | |
| Wed., 4/17 | JV Baseball | Haddam-Killingworth | Home - Portland HS-Portland HS [Directions] | 3:45 p.m. | ||
| Wed., 4/17 | V Softball | East Hampton | Home - Portland HS-PHS Softball Field [Directions] | 4:00 p.m. | L 25-7 | |
| Wed., 4/17 | V Girls Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 4:00 p.m. | L 2-5 | |
| Thu., 4/18 | V Boys Golf | Cheshire, Branford | Away - Farms Country club [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Fri., 4/19 | V Baseball | Cromwell | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | JV Baseball | East Hampton | Away - East Hampton HS-Baseball Field [Directions] | Postponed | ||
| Fri., 4/19 | V Boys Outdoor Track | Distance Classic-Hall High School West Hartford CT | Away - Hall HS | 3:45 p.m. | ||
| Fri., 4/19 | V Girls Outdoor Track | Distance Classic-Hall High School West Hartford CT | Away - Hall HS | 3:45 p.m. | ||
| Fri., 4/19 | V Softball | Westbrook/Old Saybrook | Away - Old Saybrook HS-Old Saybrook Softball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | V Girls Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 4/20 | JV Baseball | Old Saybrook | Away - Old Saybrook HS-OSHS Baseball Field [Directions] | Postponed | ||
| Mon., 4/22 | V Baseball | ValleyReg/Westbrook | Away - Valley Regional HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Mon., 4/22 | V Boys Golf | Norwich Tech, Valley Regional | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Mon., 4/22 | V Softball | Valley Regional | Away - Valley Regional HS-Joseph Camarota Memorial Field [Directions] | 3:45 p.m. | ||
| Mon., 4/22 | V Girls Tennis | Sheehan | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Tue., 4/23 | V Boys Golf | Coginchaug | Away - Coginchaug Regional HS-Lyman Orchards Golf course [Directions] | 3:00 p.m. | ||
| Tue., 4/23 | JV Boys Golf | Xavier | Away - Portland Golf Course [Directions] | 2:30 p.m. | ||
| Tue., 4/23 | V Boys Outdoor Track | Cromwell, Old Lyme | Home - Portland HS-HS Track [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Cromwell, Old Lyme | Home - Portland HS-HS Track [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Softball | Vinal Tech | Away - Vinal Tech-Softball Diamond [Directions] | 3:45 p.m. | ||
| Wed., 4/24 | V Baseball | Morgan | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Softball | Morgan | Home - Portland HS-PHS Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Girls Tennis | Haddam-Killingworth | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Thu., 4/25 | JV Baseball | Morgan | Away - Morgan School-Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 4/25 | V Boys Golf | Morgan | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Thu., 4/25 | V Girls Tennis | Valley Regional | Away - Valley Regional HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 4/26 | V Baseball | Cromwell | Away - Cromwell HS-Fran Monnes Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Softball | Cromwell | Away - Cromwell HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Sat., 4/27 | V Baseball | Old Saybrook | Home - Portland HS-Portland HS [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | JV Baseball | Cromwell | Home - Portland HS-Portland HS [Directions] | 1:30 p.m. | ||
| Sat., 4/27 | V Boys Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Sat., 4/27 | V Girls Outdoor Track | Ellington Invitational | Away - Ellington HS-Track | 9:00 a.m. | ||
| Mon., 4/29 | V Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Boys Golf | East Catholic | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Mon., 4/29 | JV Boys Golf | East Catholic | Home - Portland West [Directions] | 2:50 p.m. | ||
| Mon., 4/29 | V Softball | Hale Ray | Away - Nathan Hale Ray HS-Lou Milardo Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Girls Tennis | Morgan | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 4/30 | JV Baseball | Hale Ray | Home - Portland HS-Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Boys Golf | Tolland, E.O. Smith | Away - Twin Hills Country Club [Directions] | 3:00 p.m. | ||
| Tue., 4/30 | V Boys Outdoor Track | Coginchaug, Morgan | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | V Girls Outdoor Track | Coginchaug, Morgan | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | V Baseball | Old Saybrook | Away - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Boys Golf | North Branford | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Wed., 5/1 | V Girls Tennis | Cromwell | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Wed., 5/1 | V | Hale Ray unified | Away - Not Listed | 3:00 p.m. | ||
| Thu., 5/2 | V Boys Golf | Cromwell | Away - TPC River Highlands [Directions] | 2:40 p.m. | ||
| Fri., 5/3 | V Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | V Softball | Coginchaug | Away - Coginchaug Regional HS-Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | V Girls Tennis | North Branford | Away - North Branford HS-NBHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Sat., 5/4 | V Baseball | North Branford | Home - Portland HS-Portland HS [Directions] | 3:00 p.m. | ||
| Sat., 5/4 | V Boys Outdoor Track | Marty Roberts invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Sat., 5/4 | V Girls Outdoor Track | Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 9:30 a.m. | ||
| Mon., 5/6 | V Boys Golf | Wildcat Invite | Away - Norwich Golf Course | 12:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 12:00 p.m. | ||||||
| Mon., 5/6 | JV Boys Golf | Coventry | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Mon., 5/6 | V Girls Tennis | Valley Regional | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 5/7 | JV Baseball | Coginchaug | Away - Coginchaug Regional HS-Field #1 - Brookside Field @ CRHS [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | North Branford, Old Saybrook | Home - Portland HS-HS Track [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | North Branford, Old Saybrook | Home - Portland HS-HS Track [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Softball | Westbrook/Old Saybrook | Home - Portland HS-PHS Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Boys Golf | Cromwell, Haddam-Killingworth | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Wed., 5/8 | V Girls Tennis | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Thu., 5/9 | V Baseball | Middletown | Away - Palmer Field-Baseball Diamond [Directions] | 6:00 p.m. | ||
| Thu., 5/9 | V Girls Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Fri., 5/10 | V Baseball | East Hampton | Home - Legion Field - Moodus-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Fri., 5/10 | V Baseball | East Hampton | Away - Legion Field - Moodus-Baseball Diamond [Directions] | 6:30 p.m. | ||
| Fri., 5/10 | V Boys Outdoor Track | Running Rams Invitational | Away - Old Saybrook HS-Old Saybrook Track (HS) | 2:00 p.m. | ||
| Fri., 5/10 | V Girls Outdoor Track | Running Rams Invitational | Away - Old Saybrook HS-Old Saybrook Track (HS) | 2:00 p.m. | ||
| Fri., 5/10 | V Girls Tennis | North Branford | Home - Portland HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Sat., 5/11 | JV Baseball | East Hampton | Home - Portland HS-Portland HS [Directions] | 11:00 a.m. | ||
| Tue., 5/14 | V Baseball | Ellington | Away - Ellington HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Tue., 5/14 | V Boys Golf | Hale Ray | Away - Nathan Hale Ray HS-Tallwood GC [Directions] | 3:15 p.m. | ||
| Tue., 5/14 | V Boys Outdoor Track | East Hampton, TBA, Westbrook | Away - East Hampton HS-Track [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Tue., 5/14 | V Girls Outdoor Track | East Hampton, TBA, Westbrook | Away - East Hampton HS-Track [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Tue., 5/14 | V Girls Tennis | East Hampton | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Thu., 5/16 | V Boys Golf | Old Lyme | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Thu., 5/16 | JV Girls Golf | Glastonbury | Home - Portland West [Directions] | 2:50 p.m. | ||
| Fri., 5/17 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Gloria Maddocks Field [Directions] | 4:00 p.m. | ||
| Fri., 5/17 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 5/17 | V Girls Tennis | Sheehan | Away - Sheehan HS-Sheehan HS Tennis Courts [Directions] | 3:45 p.m. | ||
| Sun., 5/19 | V Baseball | Morgan | Away - Morgan School-Baseball Field [Directions] | 2:00 p.m. | ||
| Mon., 5/20 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/20 | V Boys Tennis | Shoreline Conference Boys Individual Tennis Tournament | Away - Not Listed | 9:00 a.m. | ||
| Mon., 5/20 | V Girls Tennis | Shoreline Conference Girls Individual Tennis Tournament | Away - Not Listed | 9:00 a.m. | ||
| Tue., 5/21 | V Boys Golf | Shoreline Conference Championship | Away - Stanley Golf Course | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to TBA | ||||||
| Tue., 5/21 | JV Boys Golf | Xavier | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Tue., 5/21 | V Boys Tennis | Shoreline Conference Boys Individual Tennis Tournament | Away - Morgan School-Tennis Courts | 4:00 p.m. | ||
| Tue., 5/21 | V Girls Tennis | Shoreline Conference Girls Individual Tennis Tournament | Away - Lyme-Old Lyme HS-Tennis Courts | 12:00 p.m. | ||
| Wed., 5/22 | V Boys Outdoor Track | Cromwell, Coginchaug, East Hampton, Haddam-Killingworth, Old Lyme, Morgan, Hale Ray, North Branford, Old Saybrook, Valley Regional, Westbrook | Away - Portland HS-Default Facility | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:00 p.m. | ||||||
| Wed., 5/22 | V Girls Golf | Coventry | Home - Portland West [Directions] | 2:30 p.m. | ||
| Wed., 5/22 | V Girls Outdoor Track | Shoreline Track and FIeld Championship | Away - TBA | TBA | ||
| Pending changes awaiting acceptance by one or more parties involved: Time to 2:00 p.m., Facility to Portland HS-Default Facility | ||||||
| Thu., 5/23 | JV Baseball | Morgan | Home - Portland HS-Portland HS [Directions] | 3:45 p.m. | ||
| Thu., 5/23 | V Boys Golf | Daniel Hand | Away - Madison Country Club [Directions] | 2:30 p.m. | ||
| Thu., 5/23 | V | Shoreline Conference Unified Track Meet - Senior Celebration | Away - Valley Regional HS-Valley Regional High School Gym | 3:30 p.m. | ||
| Fri., 5/24 | JV Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 3:45 p.m. | ||
| Fri., 5/24 | V Girls Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:00 p.m. | ||
| Tue., 5/28 | V Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 5/29 | V Boys Golf | Cheshire | Away - Southington Country Club [Directions] | 2:30 p.m. | ||
| Wed., 5/29 | V | , , , , , , , , , | Away - Lyme-Old Lyme HS | 3:00 p.m. | ||
| Thu., 5/30 | JV Boys Golf | Coventry | Home - Portland West [Directions] | 2:45 p.m. | ||