| Portland 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 401 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 8/28 | V Football | Fitch, Foran, Killingly (Scrim.) | Home - Pierson Park, Cromwell [Directions] | 2:00 p.m. | ||
| Wed., 9/1 | JV Boys Soccer | Middletown (Scrim.) | Away - Middletown HS-MHS Stadium [Directions] | Canceled | Cancelled | |
| Wed., 9/1 | V Girls Soccer | Coventry (Scrim.) | Away - Coventry HS-Soccer field [Directions] | 3:30 p.m. | Cancelled | |
| Thu., 9/2 | V Boys Soccer | Middletown (Scrim.) | Away - Middletown HS-MHS Stadium [Directions] | 3:00 p.m. | Cancelled | |
| Fri., 9/3 | V Football | Berlin (Scrim.) | Away - Sage Park - Berlin-Scalise Field -Turf Field Sage Park Stadium [Directions] | 5:00 p.m. | ||
| Fri., 9/3 | V Boys Soccer | Manchester (Scrim.) | Away - Memorial Field @ MHS [Directions] | 3:45 p.m. | ||
| Sat., 9/4 | V Girls Soccer | Granby Memorial, Avon, Coventry, Enfield, Holy Cross, Notre Dame-Fairfield, Rocky Hill, Suffield, Wilton | Away - Granby Memorial HS-Stadium Field | 8:00 a.m. | ||
| Tue., 9/7 | V Boys Soccer | Lyman Memorial (Scrim.) | Away - Lyman Memorial HS-Soccer Field [Directions] | 5:15 p.m. | ||
| Tue., 9/7 | V Girls Soccer | RHAM (Scrim.) | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | ||
| Wed., 9/8 | V Boys Cross Country | Glastonbury, Hale Ray, RHAM (Scrim.) | Away - JB Williams Park [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Wed., 9/8 | V Girls Cross Country | Glastonbury, Hale Ray, RHAM (Scrim.) | Away - JB Williams Park [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Fri., 9/10 | V Boys Cross Country | Middletown | Away - Veterans Memorial Park, Middletown, CT [Directions] | 3:30 p.m. | ||
| Fri., 9/10 | V Football | MSW | Away - Peters Complex-Football Field [Directions] | 6:30 p.m. | W 36-8 | |
| Fri., 9/10 | V Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 5:00 p.m. | W 3-1 | |
| Sat., 9/11 | JV Football | MSW | Home - Pierson Park, Cromwell [Directions] | Canceled | Cancelled | |
| Mon., 9/13 | V Girls Swimming and Diving | Bristol Central/Eastern | Away - Dennis Malone Aquatic Center-Pool [Directions] | 3:45 p.m. | L | |
| Tue., 9/14 | V Boys Cross Country | Coginchaug, East Hampton, TBA, Hale Ray | Home - Camp Ingersoll [Directions] | 3:45 p.m. | ||
| Tue., 9/14 | V Boys Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:45 p.m. | W 7-1 | |
| Tue., 9/14 | V Girls Cross Country | Coginchaug, East Hampton, TBA, Hale Ray | Home - Camp Ingersoll [Directions] | 3:45 p.m. | ||
| Tue., 9/14 | V Girls Soccer | Old Lyme | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | T 2-2 | |
| Wed., 9/15 | JV Boys Soccer | Old Lyme | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 9/15 | JV Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Middle Field [Directions] | 3:45 p.m. | ||
| Thu., 9/16 | V Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 p.m. | W 2-1 | |
| Tue., 9/21 | V Boys Soccer | Hale Ray | Away - Nathan Hale Ray HS-Tom Nevers Field [Directions] | 5:00 p.m. | W 5-0 | |
| Tue., 9/21 | V Girls Soccer | Hale Ray | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | W 6-0 | |
| Tue., 9/21 | V Girls Swimming and Diving | East Hartford | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | W | |
| Fri., 9/24 | V Boys Cross Country | Sloper Invitational at Southington | Away - Not Listed | 3:45 p.m. | ||
| Fri., 9/24 | JV Boys Soccer | Valley Regional | Away - Valley Regional HS-JV Boys Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/24 | V Girls Cross Country | Sloper Invitational at Southington | Away - Not Listed | 3:45 p.m. | ||
| Fri., 9/24 | V Girls Soccer | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 9/24 | V Girls Swimming and Diving | Middletown | Away - Middletown HS-MHS Pool [Directions] | 3:45 p.m. | L | |
| Mon., 9/27 | V Boys Soccer | Morgan | Home - Portland HS-Varsity Soccer FIeld [Directions] | 5:00 p.m. | L 1-0 | need to move the game to 5pm we have an issue with our lights |
| Tue., 9/28 | V Boys Cross Country | LEAGUE MEET #1 Small Schools | Away - Old Saybrook HS-Old Saybrook Campus | 3:30 p.m. | ||
| Tue., 9/28 | V Girls Cross Country | LEAGUE MEET #1 Small Schools | Away - Old Saybrook HS-Old Saybrook Campus | 3:30 p.m. | ||
| Tue., 9/28 | V Girls Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 6:30 p.m. | T 2-2 | |
| Tue., 9/28 | JV Girls Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 9/28 | V Girls Swimming and Diving | Farmington | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Wed., 9/29 | V Boys Soccer | Valley Regional | Home - Portland HS-Varsity Soccer FIeld [Directions] | 5:30 p.m. | T 3-3 | |
| Thu., 9/30 | V Girls Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | W 6-0 | |
| Fri., 10/1 | V Boys Cross Country | Woods Trail Run Thetford, VT 10/1 - 10/2 | Away - Not Listed | 10:00 a.m. | ||
| Fri., 10/1 | V Football | Haddam-Killingworth | Home - Pierson Park, Cromwell [Directions] | 6:00 p.m. | W 41-3 | |
| Fri., 10/1 | V Boys Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | W 3-1 | |
| Fri., 10/1 | V Girls Cross Country | Woods Trail Run Thetford, VT 10/1 - 10/2 | Away - Not Listed | 10:00 a.m. | ||
| Fri., 10/1 | JV Girls Soccer | Westbrook | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/1 | V Girls Swimming and Diving | Wethersfield | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Sat., 10/2 | JV Football | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | 10:00 a.m. | ||
| Sat., 10/2 | V Boys Soccer | Haddam-Killingworth | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | W 3-1 | |
| Mon., 10/4 | JV Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 p.m. | ||
| Tue., 10/5 | V Boys Cross Country | Sheehan Invitational in Wallingford | Away - Not Listed | 3:30 p.m. | ||
| Tue., 10/5 | V Boys Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 4:30 p.m. | L 2-1 | |
| Tue., 10/5 | V Girls Cross Country | Sheehan Invitational in Wallingford | Away - Not Listed | 3:30 p.m. | ||
| Tue., 10/5 | V Girls Swimming and Diving | Enfield | Away - Annex (Old Fermi HS)-Annex Pool [Directions] | 4:00 p.m. | L | |
| Tue., 10/5 | JV Girls Volleyball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 4:45 p.m. | ||
| Wed., 10/6 | JV Boys Soccer | Morgan | Away - Morgan School-Soccer/Lax Field [Directions] | 3:45 p.m. | ||
| Wed., 10/6 | V Girls Soccer | Suffield | Home - Portland HS-Varsity Soccer FIeld [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 10/7 | V Boys Soccer | Suffield | Away - Suffield HS-Ted Beneski Turf Field [Directions] | 5:15 p.m. | L 2-0 | |
| Thu., 10/7 | V Girls Soccer | North Branford/Hale Ray | Away - North Branford HS-NBHS Front Field [Directions] | 3:45 p.m. | W 5-0 | |
| Thu., 10/7 | V Girls Swimming and Diving | Berlin | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Fri., 10/8 | V Boys Soccer | North Branford | Home - Portland HS-Varsity Soccer FIeld [Directions] | 4:15 p.m. | W 8-0 | |
| Sat., 10/9 | V Boys Cross Country | Wickham Invitational in Manchester CT | Away - Not Listed | 11:00 a.m. | ||
| Sat., 10/9 | V Football | Valley Regional/Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | 1:00 p.m. | W 21-6 | |
| Sat., 10/9 | V Girls Cross Country | Wickham Invitational in Manchester CT | Away - Not Listed | 11:00 a.m. | ||
| Mon., 10/11 | JV Football | Valley Regional/Old Lyme | Home - Pierson Park, Cromwell [Directions] | 10:00 a.m. | ||
| Tue., 10/12 | V Boys Soccer | Coginchaug | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | W 5-0 | |
| Tue., 10/12 | V Girls Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 4:30 p.m. | L 1-3 | |
| Tue., 10/12 | JV Girls Volleyball | East Hampton | Away - East Hampton HS-Gym [Directions] | 3:30 p.m. | ||
| Wed., 10/13 | JV Boys Soccer | Coginchaug | Away - Coginchaug Regional HS-Brookside Field [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:30 p.m. | ||||||
| Wed., 10/13 | JV Girls Soccer | Valley Regional | Away - Valley Regional HS-JV Girls Soccer Field [Directions] | 5:00 p.m. | ||
| Wed., 10/13 | V Girls Swimming and Diving | Bulkeley/HMTCA/Weaver | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | W | |
| Thu., 10/14 | V Boys Cross Country | SLC Mega Meet | Away - East Hampton HS-Cross Country Course | 2:30 p.m. | ||
| Thu., 10/14 | V Boys Soccer | Cromwell | Away - Cromwell HS-Main field [Directions] | 3:45 p.m. | W 3-1 | |
| Thu., 10/14 | V Girls Cross Country | Shoreline Conference Mega Meet | Away - East Hampton HS-Cross Country Course | 3:30 p.m. | ||
| Thu., 10/14 | V Girls Soccer | Cromwell | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | L 0-1 | |
| Thu., 10/14 | JV Girls Volleyball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 3:45 p.m. | ||
| Fri., 10/15 | JV Girls Soccer | Cromwell | Away - Cromwell HS-soccer field 1 [Directions] | 3:45 p.m. | ||
| Fri., 10/15 | V Girls Swimming and Diving | Windsor | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Sat., 10/16 | V Football | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | 2:00 p.m. | W 49-0 | |
| Sat., 10/16 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic HS-McPhee Field / Stadium Field [Directions] | 11:00 a.m. | W 1-0 | |
| Sat., 10/16 | JV Girls Volleyball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 11:00 a.m. | ||
| Mon., 10/18 | JV Football | North Branford | Home - Pierson Park, Cromwell [Directions] | Canceled | Cancelled | |
| Mon., 10/18 | V Girls Soccer | East Hampton | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | W 4-0 | |
| Mon., 10/18 | JV Girls Soccer | East Hampton | Home - Portland HS-JV Soccer Field [Directions] | 7:30 p.m. | ||
| Tue., 10/19 | V Boys Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 6:00 p.m. | T 0-0 | |
| Tue., 10/19 | JV Girls Volleyball | East Hampton | Away - East Hampton HS-Gym [Directions] | 3:30 p.m. | ||
| Wed., 10/20 | V Girls Soccer | Woodland | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/22 | V Football | Old Saybrook | Home - Pierson Park, Cromwell [Directions] | 6:00 p.m. | W 52-8 | |
| Fri., 10/22 | V Boys Soccer | Woodland | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | L 2-1 | |
| Fri., 10/22 | V Girls Swimming and Diving | Plainville | Home - Rocky Hill HS-Swimming Pool [Directions] | 4:00 p.m. | W | |
| Sat., 10/23 | V Boys Cross Country | Shoreline Cross Country Championship | Away - East Hampton HS-Cross Country Course | 10:45 a.m. | ||
| Sat., 10/23 | JV Football | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Back Field [Directions] | 11:00 a.m. | ||
| Sat., 10/23 | V Boys Soccer | St. Paul Catholic | Home - Portland HS-Varsity Soccer FIeld [Directions] | 4:00 p.m. | L 3-1 | |
| Sat., 10/23 | JV Boys Soccer | Cromwell | Home - Portland HS-JV Soccer Field [Directions] | 11:00 a.m. | ||
| Sat., 10/23 | V Girls Cross Country | Shoreline Cross Country Championship | Away - East Hampton HS-Cross Country Course | 10:00 a.m. | ||
| Mon., 10/25 | V Girls Soccer | Coventry | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | W 4-2 | |
| Tue., 10/26 | V Boys Cross Country | Frosh/Soph Invitational | Away - Old Saybrook HS-Old Saybrook Campus | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 10/27 | ||||||
| Tue., 10/26 | V Girls Cross Country | Frosh/Soph Invitational | Away - Old Saybrook HS-Old Saybrook Campus | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 10/27 | ||||||
| Wed., 10/27 | JV Boys Soccer | Old Lyme | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/27 | V Girls Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:45 p.m. | T 2-2 | |
| Thu., 10/28 | V Girls Swimming and Diving | Maloney/Platt | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | ||
| Fri., 10/29 | V Football | Granby/Canton | Home - Pierson Park, Cromwell [Directions] | 6:00 p.m. | W 45-6 | |
| Fri., 10/29 | V Boys Soccer | Haddam-Killingworth | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | W 1-0 | |
| Fri., 10/29 | V Girls Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 2:00 p.m. | W 2-1 | |
| Fri., 10/29 | JV Girls Volleyball | Coginchaug (Scrim.) | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 3:45 p.m. | ||
| Sat., 10/30 | JV Football | Granby/Canton | Away - Granby Memorial HS-Stadium Field [Directions] | 10:00 a.m. | ||
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class S Championship | Away - Wickham Park | 2:05 p.m. | ||
| Mon., 11/1 | V Boys Cross Country | Shoreline Freshman Championships at Valley Regional | Away - Not Listed | 3:30 p.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class S Championship | Away - Wickham Park | 2:35 p.m. | ||
| Mon., 11/1 | V Girls Cross Country | Shoreline Freshman Championships at Valley Regional | Away - Not Listed | 3:30 p.m. | ||
| Mon., 11/1 | V Girls Soccer | East Hartford | Away - East Hartford HS-Turf Field [Directions] | 3:45 p.m. | L Forfeit | |
| Tue., 11/2 | V Boys Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 3:00 p.m. | L 3-0 | |
| Tue., 11/2 | V Girls Soccer | Cromwell | Away - Cromwell HS-Main field [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | CREC Coop | Home - Pierson Park, Cromwell [Directions] | 6:30 p.m. | W 54-0 | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/5 | V Girls Soccer | Morgan | Away - East Hampton HS-Main Field [Directions] | 3:00 p.m. | L 1-2 | |
| Fri., 11/5 | V Girls Swimming and Diving | Wethersfield, Bulkeley/HMTCA/Weaver, Enfield, Windsor | Away - Wethersfield HS-Backman Pool [Directions] | 3:30 p.m. | ||
| Fri., 11/5 | V Girls Swimming and Diving | Wethersfield, Bulkeley/HMTCA/Weaver, Enfield, Windsor | Away - Wethersfield HS-Backman Pool [Directions] | 6:00 p.m. | ||
| Sat., 11/6 | JV Football | CREC Coop | Away - Civic Leadership HS-Civic Leadership Turf Field [Directions] | Canceled | Cancelled | |
| Mon., 11/8 | V Girls Soccer | Coventry | Home - Portland HS-Varsity Soccer FIeld [Directions] | 4:00 p.m. | L 1-2 [Detailed Results] | |
| Tue., 11/9 | V Boys Soccer | Thomaston | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:30 p.m. | W 3-1 | |
| Wed., 11/10 | V Girls Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Wed., 11/10 | V Girls Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Thu., 11/11 | V Boys Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | 2:00 p.m. | L 1-0 | |
| Sat., 11/13 | V Boys Cross Country | New England Championships in Thetford Vermont | Away - Not Listed | TBA | ||
| Sat., 11/13 | V Football | Coginchaug/Hale Ray/East Hampton | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 1:00 p.m. | W 49-6 | |
| Sat., 11/13 | V Girls Cross Country | New England Championships in Thetford Vermont | Away - Not Listed | TBA | ||
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cheshire Community Pool | 6:00 p.m. | ||
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cheshire Community Pool | 6:00 p.m. | ||
| Mon., 11/15 | JV Football | Coginchaug/Hale Ray/East Hampton | Home - Pierson Park, Cromwell [Directions] | Canceled | Cancelled | |
| Wed., 11/17 | V Girls Swimming and Diving | CIAC Class S Swimming Championships | Away - Cornerstone Pool | 6:00 p.m. | ||
| Wed., 11/17 | V Girls Swimming and Diving | CIAC Class S Swimming Championships | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 11/19 | V Football | Stafford/East Windsor/Somers | Home - Pierson Park, Cromwell [Directions] | 6:00 p.m. | W 14-6 | |
| Sat., 11/20 | JV Football | Stafford/East Windsor/Somers | Away - Stafford HS-Lighted Stadium Field (behind the school) [Directions] | Canceled | Cancelled | |
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Wed., 11/24 | V Football | Rocky Hill | Away - Rocky Hill HS-Stadium [Directions] | 6:00 p.m. | W 33-21 | |
| Tue., 11/30 | V Football | Notre Dame-Fairfield | Home - Pierson Park, Cromwell [Directions] | 6:30 p.m. | ||
| Sun., 12/5 | V Football | Ansonia | Home - Pierson Park, Cromwell [Directions] | 12:30 p.m. | ||
| Wed., 12/8 | V Boys Indoor Track | Shoreline Developmental Track Meet | Home - Hillhouse HS-Field House [Directions] | 5:00 p.m. | ||
| Wed., 12/8 | V Girls Indoor Track | Shoreline Developmental Track Meet | Home - Hillhouse HS-Field House [Directions] | 5:00 p.m. | ||
| Sat., 12/11 | V Football | Bloomfield | Away - Trumbull HS-McDougall Stadium [Directions] | 11:00 a.m. | ||
| Sat., 12/11 | V Wrestling | Suffield/Windsor Locks, Canton, Coventry, Darien, Granby Memorial, Rockville | Away - Suffield HS | 9:00 a.m. | ||
| Tue., 12/14 | V Girls Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 43-35 | |
| Tue., 12/14 | JV Girls Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/16 | V Boys Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 65-58 | |
| Thu., 12/16 | JV Boys Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/16 | V Girls Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | L 36-48 | |
| Sat., 12/18 | FR Boys Basketball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/18 | V Wrestling | Pomperaug Quads | Away - Pomperaug HS-Auxiliary Gym | 10:00 a.m. | ||
| Mon., 12/20 | V Boys Basketball | Ellington | Away - Ellington HS-Gym [Directions] | 6:45 p.m. | L 66-44 | |
| Mon., 12/20 | JV Boys Basketball | Ellington | Away - Ellington HS-Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/21 | V Wrestling | Coventry | Away - Coventry HS-Gym [Directions] | Postponed | ||
| Wed., 12/22 | V Boys Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 56-67 | |
| Wed., 12/22 | JV Boys Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/22 | V Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 7:00 p.m. | L 34-51 | |
| Wed., 12/22 | JV Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/23 | V Wrestling | Rockville Duals- Bacon, Canton, Portland, Rocky Hill, St. Paul, Platt | Away - Rockville HS-Main gymnasium | 1:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:00 p.m. | ||||||
| Mon., 12/27 | V Wrestling | Morgan Duals | Away - Morgan School-Gym | 11:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Thu., 12/30 | V Boys Swimming and Diving | Middletown | Home - Rocky Hill HS-Swimming Pool [Directions] | 9:00 a.m. | L | |
| Tue., 1/4 | V Boys Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 62-43 | |
| Tue., 1/4 | JV Boys Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/4 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | L 56-44 | |
| Tue., 1/4 | JV Girls Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Wed., 1/5 | V Boys Indoor Track | Shoreline League Meet #1 | Home - Hillhouse HS-Field House [Directions] | 5:00 p.m. | ||
| Wed., 1/5 | V Wrestling | Granby Memorial | Home - Portland HS-Portland HS [Directions] | 6:00 p.m. | ||
| Wed., 1/5 | V Girls Indoor Track | Shoreline League Meet #1 | Home - Hillhouse HS-Field House [Directions] | 5:00 p.m. | ||
| Fri., 1/7 | JV Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | Canceled | Cancelled | |
| Sat., 1/8 | V Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 4:00 p.m. | W 63-43 | |
| Sat., 1/8 | FR Boys Basketball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | Postponed | ||
| Sat., 1/8 | V Wrestling | Casey Yates Memorial Wrestling Tournament | Away - Lyman Memorial HS-Gym | 10:00 a.m. | ||
| Mon., 1/10 | V Boys Basketball | North Branford | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 56-53 | |
| Mon., 1/10 | JV Boys Basketball | North Branford | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Mon., 1/10 | V Boys Indoor Track | HK Invite | Away - New Haven Athletic Center/Hillhouse HS | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:45 p.m. | ||||||
| Mon., 1/10 | V Girls Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 7:00 p.m. | L 34-52 | |
| Mon., 1/10 | JV Girls Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 5:30 p.m. | ||
| Mon., 1/10 | V Girls Indoor Track | HK Invite | Away - Floyd Little Athletic Center-Field House | 4:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Hillhouse HS-Field House | ||||||
| Tue., 1/11 | V Boys Swimming and Diving | Meriden Co-op | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Wed., 1/12 | V Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | L 54-62 | |
| Wed., 1/12 | JV Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | Canceled | Cancelled | |
| Wed., 1/12 | V Wrestling | Somers | Away - Somers HS-Somers High School Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 1/13 | V Boys Indoor Track | Shoreline League Meet #2 | Away - TBA-connell memorial rink | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Hillhouse HS-Field House | ||||||
| Thu., 1/13 | V Girls Basketball | Suffield | Away - Suffield HS [Directions] | 6:30 p.m. | L 37-44 | |
| Thu., 1/13 | JV Girls Basketball | Suffield | Away - Suffield HS [Directions] | 5:00 p.m. | ||
| Thu., 1/13 | V Girls Indoor Track | Shoreline League Meet #2 | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Fri., 1/14 | V Boys Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 7:00 p.m. | W 56-37 | |
| Fri., 1/14 | JV Boys Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/14 | V Girls Basketball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | 6:00 p.m. | L 54-26 | |
| Sat., 1/15 | FR Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | Postponed | ||
| Sat., 1/15 | V Wrestling | Berlin, Avon, Bethel, Branford, Pomperaug, Terryville/Thomaston | Away - Berlin HS-Jim Day Gymnasium | 10:00 a.m. | ||
| Tue., 1/18 | V Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 7:00 p.m. | L 51-55 | |
| Tue., 1/18 | JV Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/18 | V Boys Swimming and Diving | Simsbury | Away - Westminster School-Pool [Directions] | 8:00 p.m. | ||
| Tue., 1/18 | V Girls Basketball | Cromwell | Home - Portland HS-PHS Gym [Directions] | 6:00 p.m. | L 19-57 | |
| Tue., 1/18 | JV Girls Basketball | Cromwell | Home - Portland HS-PHS Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/19 | V Boys Basketball | Simsbury | Home - Portland HS-PHS Gym [Directions] | 6:45 p.m. | W 54-50 | |
| Wed., 1/19 | JV Boys Basketball | Simsbury | Home - Portland HS-PHS Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/19 | V Wrestling | Stafford | Away - Stafford HS-Gym [Directions] | 6:00 p.m. | ||
| Fri., 1/21 | V Boys Basketball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 66-56 | |
| Fri., 1/21 | JV Boys Basketball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/21 | V Girls Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 6:00 p.m. | L 24-70 | |
| Fri., 1/21 | JV Girls Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 4:30 p.m. | ||
| Sat., 1/22 | FR Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 10:30 a.m. | ||
| Sat., 1/22 | V Wrestling | Lyman Memorial/Windham Tech, TBA, Northwestern, Putnam, South Windsor, Stafford | Home - Portland HS-Portland HS [Directions] | 10:00 a.m. | Hello ADs. Portland is allowing spectators at the meet on 1/22/22. All mask guidelines must be followed. We will have concessions in our cafeteria. No food/beverages will be allowed in the gym. | |
| Mon., 1/24 | V Wrestling | Old Lyme | Home - Portland HS-Portland HS [Directions] | 7:00 p.m. | ||
| Tue., 1/25 | V Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:30 p.m. | W 62-56 | |
| Tue., 1/25 | JV Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | Canceled | Cancelled | |
| Tue., 1/25 | V Boys Swimming and Diving | Avon | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Tue., 1/25 | V Girls Basketball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | 5:45 p.m. | W 44-34 | |
| Tue., 1/25 | JV Girls Basketball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | 4:15 p.m. | ||
| Wed., 1/26 | V Wrestling | Canton | Away - Canton HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/27 | V Boys Swimming and Diving | Manchester/RHAM | Away - Manchester HS-Pool [Directions] | 3:45 p.m. | W | |
| Thu., 1/27 | V Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | 7:00 p.m. | L 32-47 | |
| Thu., 1/27 | JV Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/28 | V Boys Basketball | Morgan | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 51-50 | |
| Fri., 1/28 | JV Boys Basketball | Morgan | Home - Portland HS-PHS Gym [Directions] | Canceled | Cancelled | |
| Fri., 1/28 | V Boys Indoor Track | Shoreline Coaches Invite | Home - Hillhouse HS-Field House [Directions] | 5:00 p.m. | ||
| Fri., 1/28 | V Girls Indoor Track | Shoreline Coaches Invite | Home - Hillhouse HS-Field House [Directions] | 5:00 p.m. | ||
| Sat., 1/29 | V Wrestling | Avon, Cheshire, Coventry, Daniel Hand, East Haven, Gilbert, Glastonbury, Griswold/Wheeler, Morgan, TBA, TBA, New Britain, Nonnewaug, Plainville, Somers, St. Paul Catholic, Terryville/Thomaston, Thomaston, New Haven Wrestling | Home - Portland HS-Portland HS [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Tue., 2/1 | V Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 7:00 p.m. | W 60-42 | |
| Tue., 2/1 | JV Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/1 | V Boys Swimming and Diving | Wethersfield | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Tue., 2/1 | V Girls Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 6:00 p.m. | W 39-34 | |
| Wed., 2/2 | V Wrestling | Suffield Windsor Locks Wrestling Co Op | Home - Portland HS-Portland HS [Directions] | 6:00 p.m. | ||
| Thu., 2/3 | V Boys Basketball | Conard | Home - Portland HS-PHS Gym [Directions] | 6:00 p.m. | L 64-41 | |
| Sat., 2/5 | FR Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/5 | V Boys Indoor Track | Shoreline Conference Indoor Track Championship | Away - Hillhouse HS-Field House | 10:00 a.m. | ||
| Sat., 2/5 | V Wrestling | 2022 Bacon Academy Matt Bishel Bobcat Classic | Away - Bacon Academy-Gym | 9:00 a.m. | ||
| Sat., 2/5 | V Girls Indoor Track | Shoreline Conference Indoor Track Championship | Away - Coginchaug Regional HS-Floyd Little Athletic Center - Hillhouse HS | 10:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Hillhouse HS-Field House | ||||||
| Mon., 2/7 | FR Boys Basketball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/7 | V Girls Basketball | Stafford | Home - Portland HS-PHS Gym [Directions] | 7:15 p.m. | L 51-36 | |
| Mon., 2/7 | JV Girls Basketball | Stafford | Home - Portland HS-PHS Gym [Directions] | 5:45 p.m. | ||
| Tue., 2/8 | V Boys Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 55-43 | |
| Tue., 2/8 | JV Boys Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/8 | V Boys Swimming and Diving | Hartford Public | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | W | |
| Tue., 2/8 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 7:00 p.m. | W 52-31 | |
| Tue., 2/8 | JV Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/9 | V Wrestling | Rockville | Home - Portland HS-Portland HS [Directions] | 6:00 p.m. | ||
| Thu., 2/10 | V Boys Swimming and Diving | Simsbury, Windsor | Away - Westminster School-Pool [Directions] | 8:00 p.m. | L | |
| Fri., 2/11 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | W 49-36 | |
| Fri., 2/11 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Fri., 2/11 | V Girls Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 62-36 | |
| Fri., 2/11 | JV Girls Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Sat., 2/12 | FR Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 11:00 a.m. | ||
| Sat., 2/12 | V Boys Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/12 | V Wrestling | NCCC Wrestling Championships | Away - Rockville HS-Main gymnasium | 10:30 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Sat., 2/12 | V Girls Indoor Track | Class S Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Mon., 2/14 | V Boys Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | L 57-49 | |
| Mon., 2/14 | JV Boys Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/15 | V Boys Swimming and Diving | Newington | Away - Newington HS-Pool [Directions] | 4:00 p.m. | L | |
| Tue., 2/15 | V Girls Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 7:00 p.m. | W 50-44 | |
| Tue., 2/15 | JV Girls Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/16 | JV Boys Basketball | Hale Ray | Home - Portland HS-MS Gym [Directions] | Canceled | Cancelled | |
| Wed., 2/16 | V Girls Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 51-33 | |
| Wed., 2/16 | JV Girls Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/17 | V Boys Basketball | Ellington | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | W 50-41 | |
| Thu., 2/17 | JV Boys Basketball | Ellington | Home - Portland HS-MS Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/17 | V Girls Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 5:00 p.m. | L 37-52 | |
| Thu., 2/17 | JV Girls Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/18 | V Wrestling | Class S Championship - Day 1 | Away - Killingly | 3:00 p.m. | ||
| Sat., 2/19 | FR Boys Basketball | North Branford | Home - Portland HS-PHS Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class S Championship - Day 2 | Away - Killingly | 9:00 a.m. | ||
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Tue., 2/22 | V Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 7:00 p.m. | W 70-46 | |
| Tue., 2/22 | JV Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/23 | V Boys Swimming and Diving | E.O. Smith - Tolland Hammerheads | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Sat., 2/26 | V Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | W 49-41 | |
| Sat., 2/26 | FR Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Tue., 3/1 | V Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 6:00 p.m. | L 65-38 | |
| Tue., 3/1 | V Girls Basketball | Parish Hill | Away - Parish Hill HS-Gym [Directions] | 6:00 p.m. | ||
| Fri., 3/4 | V Boys Swimming and Diving | Newington, Avon, E.O. Smith - Tolland Hammerheads, Wethersfield | Away - Newington HS-Pool [Directions] | 4:30 p.m. | ||
| Tue., 3/8 | V Boys Basketball | Coventry | Home - Portland HS-PHS Gym [Directions] | 6:30 p.m. | W 58-38 | |
| Thu., 3/10 | V Boys Basketball | Terryville | Away - Terryville HS-Gym [Directions] | 6:30 p.m. | W 57-52 | |
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 4:00 p.m. | ||
| Fri., 3/11 | V Boys Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cornerstone Pool | 1:00 p.m. | ||
| Mon., 3/14 | V Boys Basketball | Windham | Away - Windham HS-Callahan Gymnasium [Directions] | 7:00 p.m. | ||
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class S Swimming Championships | Away - Cornerstone Pool | 6:30 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Sat., 3/26 | V Baseball | Woodland (Scrim.) | Home - Portland HS-Portland HS [Directions] | 1:00 p.m. | Cancelled | Infield not playable |
| Wed., 3/30 | V Baseball | Haddam-Killingworth (Scrim.) | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/1 | V Girls Tennis | RHAM (Scrim.) | Home - Portland HS-Tennis Courts [Directions] | 3:00 p.m. | ||
| Sat., 4/2 | V Baseball | Coginchaug | Home - Portland HS-Portland HS [Directions] | 11:00 a.m. | L 9-1 | |
| Mon., 4/4 | V Baseball | Hale Ray | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | L 6-4 (10 inn) | |
| Mon., 4/4 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 3:45 p.m. | L 0-4 | |
| Mon., 4/4 | V Girls Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 3:30 p.m. | W 5-2 | |
| Tue., 4/5 | V Boys Golf | Coventry | Home - Portland Golf Course [Directions] | 2:45 p.m. | Portland: 169 Coventry: 197 (non-league) | |
| Tue., 4/5 | V Boys Outdoor Track | Valley Regional, East Hampton | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Boys Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 4:45 p.m. | L 0-7 | |
| Tue., 4/5 | V Girls Outdoor Track | Valley Regional, East Hampton | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Girls Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Fri., 4/8 | V Boys Tennis | Coginchaug | Away - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 3-2 | |
| Fri., 4/8 | V Girls Tennis | Coginchaug | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 4/12 | V Boys Outdoor Track | Westbrook, East Hampton | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | ||
| Tue., 4/12 | V Girls Outdoor Track | Westbrook, East Hampton | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | ||
| Wed., 4/13 | V Baseball | North Branford | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | L 5-1 | |
| Wed., 4/13 | V Boys Tennis | Westbrook | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 4/13 | V Girls Tennis | Westbrook | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 4/14 | V Baseball | Old Lyme | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | L 4-7 | |
| Thu., 4/14 | V Boys Golf | North Branford | Home - Portland Golf Course [Directions] | 2:45 p.m. | Portland: 167 North Branford: 196 (league) | |
| Sat., 4/16 | V Girls Tennis | Cromwell vs East Hampton at Portland Tennis Courts Place Holder Boys and girls match | Home - Portland HS-Tennis Courts [Directions] | 1:00 p.m. | ||
| Mon., 4/18 | V Baseball | Cromwell | Away - Cromwell HS-Fran Monnes Baseball Field [Directions] | 4:00 p.m. | L 14-2 | |
| Mon., 4/18 | V Boys Tennis | Cromwell | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-5 | |
| Mon., 4/18 | V Girls Tennis | Cromwell | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Wed., 4/20 | V Baseball | East Hampton | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | L 14-0 | |
| Wed., 4/20 | V Boys Golf | East Catholic | Home - Portland Golf Course [Directions] | 2:45 p.m. | Portland: 161 East Catholic: 177 (non-league) | |
| Wed., 4/20 | JV Boys Golf | East Catholic | Home - Portland West [Directions] | 3:00 p.m. | ||
| Wed., 4/20 | V Boys Tennis | East Hampton | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-5 | |
| Wed., 4/20 | V Girls Tennis | East Hampton | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Fri., 4/22 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | 4:00 p.m. | L 12-2 | |
| Fri., 4/22 | V Boys Outdoor Track | CT Distance Festival at Hall High School | Away - Hall HS | 4:30 p.m. | ||
| Fri., 4/22 | V Boys Tennis | Old Lyme | Home - Portland HS-Tennis Courts [Directions] | 4:30 p.m. | L 1-4 | |
| Fri., 4/22 | V Girls Outdoor Track | CT Distance Festival at Hall High School | Away - Hall HS | 4:30 p.m. | ||
| Fri., 4/22 | V Girls Tennis | Old Lyme | Home - Portland HS-Tennis Courts [Directions] | 2:45 p.m. | L 0-7 | |
| Mon., 4/25 | V Baseball | Morgan | Home - Portland HS-Portland HS [Directions] | 5:00 p.m. | L 9-5 | |
| Tue., 4/26 | V Boys Golf | Cromwell | Away - TPC River Highlands [Directions] | 3:00 p.m. | Portland: 163 Cromwell: 177 (league) | |
| Tue., 4/26 | JV Boys Golf | Xavier | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Wed., 4/27 | V Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 4:00 p.m. | L 11-1 | |
| Wed., 4/27 | V Boys Outdoor Track | Valley Regional, Old Saybrook | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Valley Regional | Home - Portland HS-Tennis Courts [Directions] | 5:15 p.m. | L 0-7 | |
| Wed., 4/27 | V Girls Outdoor Track | Valley Regional, Old Saybrook | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Girls Tennis | Valley Regional | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 4/28 | V Boys Golf | Valley Regional | Away - Black Hall Golf Club [Directions] | 3:30 p.m. | Portland: 164 Valley: 218 (league) | |
| Thu., 4/28 | JV Girls Golf | Girls will play vs Valley | Away - Not Listed | 2:30 p.m. | ||
| Sat., 4/30 | V Baseball | Westbrook | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 11:00 a.m. | W 12-1 | |
| Sat., 4/30 | V Boys Indoor Track | Track and Field Stafford Invitational in Ellington | Away - Not Listed | 10:30 a.m. | ||
| Sat., 4/30 | V Girls Outdoor Track | Track and Field Stafford Invitational in Ellington | Away - Not Listed | 10:30 a.m. | ||
| Mon., 5/2 | V Boys Golf | Old Lyme | Home - Portland Golf Course [Directions] | 2:45 p.m. | Portland: 165 Old Lyme: 202 (league) | |
| Tue., 5/3 | V Baseball | Westbrook | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | W 5-2 | |
| Wed., 5/4 | V Boys Golf | Haddam-Killingworth | Home - Portland Golf Course [Directions] | 2:45 p.m. | Portland: 163 HK: 182 (league) | |
| Wed., 5/4 | V Boys Outdoor Track | Cromwell, Morgan | Away - Cromwell HS-Don Luke Track [Directions] | 3:45 p.m. | ||
| Wed., 5/4 | V Girls Outdoor Track | Cromwell, Morgan | Away - Cromwell HS-Don Luke Track [Directions] | 3:45 p.m. | ||
| Thu., 5/5 | V Baseball | Old Saybrook | Home - Portland HS-Portland HS [Directions] | 4:30 p.m. | L 15-7 | |
| Thu., 5/5 | V Boys Golf | Daniel Hand | Away - Madison Country Club [Directions] | 2:30 p.m. | Portland: 151 Hand: 177 (non-league) | |
| Thu., 5/5 | V Boys Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 3:45 p.m. | L 2-3 | |
| Thu., 5/5 | V Girls Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 3:45 p.m. | L 1-6 | |
| Fri., 5/6 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Baseball Diamond [Directions] | 3:00 p.m. | L 0-10 | |
| Fri., 5/6 | V Boys Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 5/6 | V Girls Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Sat., 5/7 | V Boys Outdoor Track | Coginchaug - Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 10:00 a.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Coginchaug - Marty Roberts Invitational | Away - Coginchaug Regional HS-CRHS Stadium Field & Track | 10:00 a.m. | ||
| Mon., 5/9 | V Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | L 9-5 | |
| Mon., 5/9 | V Boys Golf | Wildcat Invite - Shotgun Start | Away - Norwich Golf Course | 12:30 p.m. | Front 9:171 | |
| Mon., 5/9 | V Boys Tennis | Old Saybrook | Home - Portland HS-Tennis Courts [Directions] | 4:15 p.m. | L 2-3 | |
| Mon., 5/9 | V Girls Tennis | Old Saybrook | Home - Portland HS-Tennis Courts [Directions] | 4:15 p.m. | W 4-3 | |
| Tue., 5/10 | V Boys Golf | Morgan | Away - Clinton Country Club [Directions] | 3:00 p.m. | Portland: 170 Morgan: 182 (league) | |
| Tue., 5/10 | JV Girls Golf | Girls will go to Morgan with the Boys | Away - Not Listed | Canceled | Cancelled | |
| Wed., 5/11 | V Baseball | Morgan | Away - Indian River Complex-Baseball Field [Directions] | 6:30 p.m. | L 4-3 | |
| Thu., 5/12 | V Boys Golf | Hale Ray | Away - Nathan Hale Ray HS-Tallwood GC [Directions] | 3:00 p.m. | Portland: 170 Hale Ray: 188 (league) | |
| Thu., 5/12 | V Boys Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Thu., 5/12 | V Girls Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 3:00 p.m. | L 0-7 | |
| Thu., 5/12 | Miscellaneous Events | East Hampton High School using Portland Tennis courts | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | Shaun Russel at East Hampton is using our tennis courts | |
| Fri., 5/13 | V Baseball | Coventry | Home - Portland HS-Portland HS [Directions] | 3:45 p.m. | L 15-2 | |
| Fri., 5/13 | V Boys Outdoor Track | Running Rams Invitational | Away - Old Saybrook HS-Old Saybrook Track (HS) | 3:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Fri., 5/13 | V Girls Outdoor Track | Running Rams Invitational | Away - Old Saybrook HS-Old Saybrook Track (HS) | 3:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Fri., 5/13 | V Girls Tennis | North Branford | Away - North Branford HS-NBHS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Sat., 5/14 | V Baseball | Old Saybrook | Away - Old Saybrook HS-OSHS Baseball Field [Directions] | 12:00 p.m. | L 5-1 | |
| Mon., 5/16 | V Boys Golf | East Hampton | Home - Portland Golf Course [Directions] | 2:45 p.m. | Portland: 153 East Hampton: 279 (league) | |
| Tue., 5/17 | V Baseball | East Hampton | Away - Dunkin Donuts Park [Directions] | 6:30 p.m. | W 2-0 | |
| Tue., 5/17 | V Boys Golf | Coginchaug | Home - Portland Golf Course [Directions] | 2:45 p.m. | Portland: 160 Coginchaug: 192 | |
| Tue., 5/17 | V Boys Outdoor Track | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track [Directions] | 3:30 p.m. | ||
| Tue., 5/17 | V Boys Tennis | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | L 2-3 | |
| Tue., 5/17 | JV Girls Golf | Girls will play Coginchaug at PGC same time as boys | Home - Portland West [Directions] | 2:00 p.m. | ||
| Tue., 5/17 | V Girls Outdoor Track | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track [Directions] | 3:30 p.m. | ||
| Tue., 5/17 | V Girls Tennis | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Wed., 5/18 | V Boys Tennis | Cromwell | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | non league |
| Thu., 5/19 | V Boys Golf | Old Saybrook | Away - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:45 p.m. | Portland: 156 Old Saybrook: 178 (league) | |
| Thu., 5/19 | JV Boys Golf | Coventry | Home - Portland West [Directions] | 3:00 p.m. | ||
| Thu., 5/19 | V Boys Outdoor Track | SLC Novice Meet | Away - Haddam Killingworth HS (HK)-HKHS Track | 3:30 p.m. | ||
| Thu., 5/19 | V Girls Outdoor Track | SLC Novice Meet | Away - Haddam Killingworth HS (HK)-HKHS Track | 3:30 p.m. | ||
| Thu., 5/19 | Miscellaneous Events | cromwell vs east hampton tennis | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | cromwell and east hampton will be using portland courts | |
| Sat., 5/21 | V Baseball | ValleyReg/Westbrook | Away - Valley Regional HS-Baseball Diamond [Directions] | 4:00 p.m. | L 13-0 | |
| Mon., 5/23 | V Baseball | Ellington | Away - Ellington HS-Baseball Diamond [Directions] | 4:00 p.m. | L 5-0 | |
| Mon., 5/23 | V Boys Tennis | Shoreline Conference Tennis Tournament - First Round | Away - Westbrook HS-Westbrook HS / MS Tennis Courts | 9:00 a.m. | ||
| Mon., 5/23 | V Girls Tennis | Shoreline Conference Tennis Tournament - First Round | Away - Old Saybrook HS | 9:00 a.m. | ||
| Tue., 5/24 | V Boys Golf | Shoreline Conference Golf Championship | Away - TPC River Highlands | 9:00 a.m. | ||
| Tue., 5/24 | JV Boys Golf | Xavier | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Wed., 5/25 | V Boys Outdoor Track | Shoreline Conference Championship | Away - Old Saybrook HS-Old Saybrook Track (HS) | 2:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:30 p.m. | ||||||
| Wed., 5/25 | JV Girls Golf | Girls Golf Highlander Invitational | Home - Portland West [Directions] | 2:00 p.m. | ||
| Wed., 5/25 | V Girls Outdoor Track | Shoreline Conference Championship | Away - Old Saybrook HS-Old Saybrook Track (HS) | 2:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:30 p.m. | ||||||
| Thu., 5/26 | V Boys Golf | Tolland, E.O. Smith | Away - Twin Hills Country Club [Directions] | 3:00 p.m. | Portland: 158 Tolland: 159 EO Smith: 171 | |
| Tue., 5/31 | V Boys Golf | Old Saybrook | Home - Portland Golf Course [Directions] | 2:30 p.m. | Portland: 150 Old Saybrook: 171 (non-league) | |
| Tue., 5/31 | V Boys Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/31 | V Girls Outdoor Track | CIAC Class S Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/1 | Miscellaneous Events | Girls golf to Lyman Orchards Apple 9 | Home - TBA [Directions] | 1:30 p.m. | ||
| Thu., 6/2 | JV Boys Golf | Coventry | Home - Portland West [Directions] | 3:00 p.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Tue., 6/7 | V Boys Golf | CIAC Division III Spring Championship | Away - Fairview Farms | 8:00 a.m. | ||
| Sat., 6/11 | V Boys Golf | CIAC State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||