| Portland 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 452 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Old Saybrook | Away - Old Saybrook High School [Directions] | 10:30 a.m. | 9:15 a.m. | |
| TBA | JV Baseball | Morgan | Away - Indian River Complex [Directions] | TBA | 12:45 p.m. | |
| TBA | JV Baseball | North Branford | Home - Portland High School [Directions] | TBA | ||
| TBA | JV Baseball | Hale Ray | Home - Portland High School [Directions] | TBA | ||
| TBA | JV Baseball | Westbrook | Home - Portland High School [Directions] | TBA | ||
| TBA | JV Baseball | East Hampton | Away - East Hampton High School [Directions] | TBA | 9:30 a.m. | |
| TBA | JV Baseball | Old Lyme | Home - Portland High School [Directions] | TBA | ||
| TBA | V Boys Basketball | North Haven (Scrim.) | Home - Portland High School [Directions] | Cancelled | ||
| TBA | JV Boys Basketball | East Hampton | Home - Portland High School [Directions] | TBA | ||
| TBA | FR Boys Basketball | Old Saybrook | Home - Portland High School [Directions] | 10:30 a.m. | ||
| TBA | FR Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 7:00 p.m. | 6:30 p.m | |
| TBA | FR Boys Basketball | East Hampton | Away - East Hampton High School [Directions] | TBA | 6:00 p.m. | |
| TBA | FR Boys Basketball | Valley Regional | Home - Portland High School [Directions] | TBA | ||
| TBA | JV Boys Soccer | Morgan | Away - Morgan HS [Directions] | 10:30 a.m. | 9:00 a.m. | |
| TBA | JV Boys Soccer | Valley Regional | Away - Valley Regional High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| TBA | JV Boys Soccer | Westbrook | Home - Portland High School [Directions] | 3:45 p.m. | ||
| TBA | JV Girls Basketball | East Hampton | Home - Portland High School [Directions] | 5:30 p.m. | ||
| TBA | V Softball | Vinal Tech (Scrim.) | Home - Nolan Field @ Brownstone Park [Directions] | Cancelled | ||
| TBA | JV Softball | Cromwell | Away - Cromwell High School [Directions] | Cancelled | 2:25 | |
| TBA | JV Softball | Westbrook/Old Saybrook | Home - Brownstone Park Nolan Field [Directions] | 3:45 p.m. | ||
| TBA | JV Softball | Westbrook/Old Saybrook | Away - Westbrook H.S. [Directions] | TBA | 2:25pm | |
| TBA | JV Softball | North Branford | Home - Brownstone Park Nolan Field [Directions] | TBA | ||
| Sat., 8/24 | V Boys Cross Country | Pre-season training weekend | Away - Kettletown State Park (Oxford, CT) | 8:00 a.m. | TBA | XC Training & Camping Trip |
| Sat., 8/24 | V Girls Cross Country | Pre-season training weekend | Away - Kettletown State Park (Oxford, CT) | 8:00 a.m. | TBA | |
| Wed., 8/28 | V Boys Soccer | Middletown (Scrim.) | Away - Middletown High School [Directions] | 4:00 p.m. | 2:25 p.m. | |
| Wed., 8/28 | JV Boys Soccer | Middletown (Scrim.) | Away - 395 Country Club Rd [Directions] | 4:00 p.m. | 2:25 p.m. | |
| Wed., 8/28 | V Girls Soccer | Branford (Scrim.) | Away - Branford High School-Turf Field [Directions] | 6:00 p.m. | 4:30 p.m. | |
| Sat., 8/31 | V Football | Oxford vs. Hillhouse vs. Fairfield Ward | Away - Oxford High School | 10:00 a.m. | Hillhouse vs. Fairfield WArd | |
| Sat., 8/31 | V Girls Soccer | Coventry (Scrim.) | Away - Coventry High School [Directions] | 10:00 a.m.m. | 8:30 a.m. | |
| Tue., 9/3 | V Football | Platt (Scrim.) | Home - Pierson Park, Cromwell [Directions] | 3:30 p.m. | ||
| Tue., 9/3 | V Girls Soccer | Valley Regional (Scrim.) | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Wed., 9/4 | V Boys Cross Country | Glastonbury (Scrim.) | Away - JB William Park [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Wed., 9/4 | V Boys Soccer | Lyman Memorial (Scrim.) | Home - Portland High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Wed., 9/4 | V Girls Cross Country | Glastonbury (Scrim.) | Away - JB William Park [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Fri., 9/6 | V Football | Berlin (Scrim.) | Away - Scalise Field - Sage Park [Directions] | 6:00 p.m. | ||
| Fri., 9/6 | JV Boys Soccer | Cromwell (Scrim.) | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Sat., 9/7 | V Boys Soccer | Goodwin Tech (Scrim.) | Home - Portland High School [Directions] | 11:00 a.m. | ||
| Sat., 9/7 | V Girls Soccer | Windsor Locks (Scrim.) | Away - Windsor Locks High School [Directions] | 11:00 a.m. | 9:15 a.m. | |
| Mon., 9/9 | V Girls Swimming and Diving | CCC East Relays | Away - Windsor High School | 4:00 p.m. | 2:30pm | |
| Tue., 9/10 | V Boys Cross Country | Highlander Invitational | Home - YMCA Camp Ingersoll [Directions] | 3:45 p.m. | ||
| Tue., 9/10 | V Girls Cross Country | Highlander Invitational | Home - YMCA Camp Ingersoll [Directions] | 3:45 p.m. | ||
| Tue., 9/10 | V Girls Soccer | Old Saybrook | Away - Old Saybrook High School [Directions] | W 3-0 | 2:25 p.m. | non-seeding game |
| Wed., 9/11 | V Boys Soccer | Old Saybrook | Away - Old Saybrook High School [Directions] | L 3-5 | 2:25 p.m. | non-seeding game |
| Thu., 9/12 | V Football | Gilbert/Northwestern/Housy | Home - Pierson Park, Cromwell [Directions] | L 27-34 | 0-1 | |
| Thu., 9/12 | JV Boys Soccer | Old Saybrook | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Fri., 9/13 | V Boys Cross Country | Blue Dragon Invitational | Away - Veteran's Park (Middletown, CT) | 3:30 p.m. | 2:25 p.m. | |
| Fri., 9/13 | JV Boys Soccer | Hale Ray | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Fri., 9/13 | V Girls Cross Country | Blue Dragon Invitational | Away - Veteran's Park (Middletown, CT) | 3:30 p.m. | 2:25 p.m. | |
| Fri., 9/13 | V Girls Soccer | Hale Ray | Away - Hale-Ray HS, Nevers Field [Directions] | W 3-0 | 4:30 p.m. | |
| Sat., 9/14 | V Girls Soccer | Griswold | Away - Griswold [Directions] | W 6-0 | 9:15 p.m. | |
| Mon., 9/16 | JV Football | Gilbert/Northwestern/Housy | Away - Gilbert [Directions] | 3:45 p.m. | ||
| Mon., 9/16 | V Girls Soccer | Westbrook | Away - Westbrook High School [Directions] | W 6-1 | 2:25p.m. | |
| Tue., 9/17 | V Boys Soccer | Westbrook | Away - Westbrook High School [Directions] | W 3-2 | 2:25 p.m. | |
| Tue., 9/17 | JV Girls Soccer | Valley Regional | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Tue., 9/17 | V Girls Swimming and Diving | Conard | Home - Rocky Hill High School [Directions] | L | ||
| Thu., 9/19 | V Boys Cross Country | Run to the Sun Invitational | Away - Coginchaug High School | 3:30 p.m. | 2:25 p.m. | |
| Thu., 9/19 | V Girls Cross Country | Run to the Sun Invitational | Away - Coginchaug High School | 3:30 p.m. | 2:25 p.m. | |
| Thu., 9/19 | V Girls Soccer | Coginchaug | Home [Directions] | L 1-2 | ||
| Fri., 9/20 | V Football | Coventry/Windham Tech/Bolton/Lyman | Away - Coventry High School [Directions] | W 20-14 | 1-1 (1-0) | |
| Fri., 9/20 | V Boys Soccer | Coginchaug | Home - Portland High School [Directions] | L 2-3 | ||
| Fri., 9/20 | JV Girls Soccer | Coginchaug | Away - Coginchaug Regional High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Fri., 9/20 | V Girls Swimming and Diving | East Catholic | Home - Rocky Hill High School [Directions] | L | ||
| Sat., 9/21 | JV Football | Coventry/Windham Tech/Bolton/Lyman | Away - Coventry High School [Directions] | 10:30 a.m. | ||
| Mon., 9/23 | V Girls Soccer | Cromwell | Home - Portland High School [Directions] | W 5-1 | ||
| Tue., 9/24 | V Boys Cross Country | Shoreline Conference Small School Division | Away | 3:45 p.m. | 2:25 p.m. | |
| Tue., 9/24 | V Boys Soccer | Cromwell | Home - Portland High School [Directions] | L 0-4 | ||
| Tue., 9/24 | V Girls Cross Country | Shoreline Conference Small School Division | Away - Old Lyme High School | 3:45 p.m. | 2:25 p.m. | |
| Tue., 9/24 | JV Girls Soccer | Cromwell | Away - Cromwell High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 9/24 | V Girls Swimming and Diving | Plainville | Home - Rocky Hill High School [Directions] | L | ||
| Wed., 9/25 | JV Boys Soccer | Cromwell | Away - Cromwell High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Thu., 9/26 | JV Boys Soccer | Coginchaug | Away - Coginchaug Regional High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Thu., 9/26 | V Girls Soccer | Morgan | Home - Portland High School [Directions] | W 1-0 | ||
| Fri., 9/27 | V Boys Cross Country | Bellringer Invitational | Away - East Hampton High School | 3:45 p.m. | 2:25 p.m. | |
| Fri., 9/27 | V Boys Soccer | Morgan | Home - Portland High School [Directions] | L 0-2 | ||
| Fri., 9/27 | V Girls Cross Country | Bellringer Invitational | Away - East Hampton High School | 3:45 p.m. | 2:25 p.m. | |
| Fri., 9/27 | JV Girls Soccer | Morgan | Away - Morgan HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Fri., 9/27 | V Girls Swimming and Diving | E.O. Smith/Tolland | Away - Mansfield Community Center Pool [Directions] | L | 2:30pm | |
| Sat., 9/28 | V Football | Ellington | Away - Ellington High School [Directions] | W 20-8 | 2-1 (2-0) | |
| Mon., 9/30 | JV Football | Ellington | Home - Pierson Park, Cromwell [Directions] | 3:35 p.m. | ||
| Mon., 9/30 | V Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | L 1-2 | 2:25 p.m. | |
| Tue., 10/1 | V Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | L 0-3 | 2:25 p.m. | |
| Tue., 10/1 | JV Girls Soccer | Haddam-Killingworth | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Tue., 10/1 | V Girls Swimming and Diving | Haddam-Killingworth | Home - Rocky Hill High School [Directions] | L | ||
| Wed., 10/2 | JV Boys Soccer | Haddam-Killingworth | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Thu., 10/3 | V Girls Soccer | Old Saybrook | Home - Portland High School [Directions] | W 1-0 | ||
| Fri., 10/4 | V Boys Cross Country | Woods Trail Run | Away - Thetford (VT) Academy | 10:00 a.m. | TBA | overnight in Thetford, VT; racing on Saturday |
| Fri., 10/4 | V Boys Soccer | Old Saybrook | Home - Portland High School [Directions] | L 0-6 | ||
| Fri., 10/4 | V Girls Cross Country | Woods Trail Run | Away - Thetford (VT) Academy | 10:00 a.m. | TBA | overnight in Thetford, VT; races are on Saturday |
| Fri., 10/4 | JV Girls Soccer | Old Saybrook | Away - Old Saybrook High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Fri., 10/4 | V Girls Swimming and Diving | Newington | Away - NHS Pool [Directions] | L | 2:30pm | |
| Fri., 10/4 | V Girls Swimming and Diving | Newington | Away - NHS Pool [Directions] | L | 2:30pm | |
| Sat., 10/5 | V Football | Stafford/East Windsor/Somers | Home - Pierson Park, Cromwell [Directions] | W 37-0 | 3-1 (3-0) | |
| Sat., 10/5 | JV Boys Soccer | Old Saybrook | Away - Old Saybrook High School [Directions] | 10:30 a.m. | 9:15 a.m. | |
| Sat., 10/5 | V Girls Soccer | St. Paul Catholic | Home - Portland High School [Directions] | W 2-0 | ||
| Mon., 10/7 | JV Football | Stafford/East Windsor/Somers | Away - Stafford High, Lighted field behind school [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Boys Soccer | East Hampton | Home - Portland High School [Directions] | L 0-1 | ||
| Mon., 10/7 | JV Girls Soccer | Morgan | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Tue., 10/8 | V Boys Cross Country | Shoreline Conference Mega Meet | Away - Haddam Killingworth High School | 3:45 p.m. | 2:25 p.m. | |
| Tue., 10/8 | JV Boys Soccer | East Hampton | Away - East Hampton High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 10/8 | V Girls Cross Country | Shoreline Conference Mega Meet | Away - Haddam Killingworth High School | 3:45 p.m. | 2:25 p.m. | |
| Tue., 10/8 | V Girls Swimming and Diving | EnricoFermi | Home - Rocky Hill High School [Directions] | L | ||
| Wed., 10/9 | JV Girls Soccer | East Hampton | Away - East Hampton High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Thu., 10/10 | V Boys Soccer | Valley Regional | Home - Portland High School [Directions] | L 3-4 | ||
| Thu., 10/10 | V Girls Soccer | Valley Regional | Home - Portland High School [Directions] | L 1-2 | ||
| Fri., 10/11 | V Girls Swimming and Diving | East Hartford | Away - East Hartford High School [Directions] | L | 2:30PM | |
| Sat., 10/12 | V Boys Cross Country | Wickham Park XC Invitational | Away - Wickham Park | 9:00 a.m. | 8:00 a.m. | |
| Sat., 10/12 | V Boys Soccer | Griswold | Away - Griswold [Directions] | W 4-3 | 9:00 a.m. | |
| Sat., 10/12 | V Girls Cross Country | Wickham Park XC Invitational | Away - Nonnewaug High School | 9:00 a.m. | 8:00 a.m. | |
| Sat., 10/12 | V Girls Soccer | East Hampton | Home - Portland High School [Directions] | W 1-0 | ||
| Sat., 10/12 | JV Girls Soccer | Valley Regional | Away - Valley Regional High School [Directions] | 10:30 a.m. | 9:00 a.m. | |
| Mon., 10/14 | V Boys Soccer | North Branford | Away - North Branford High School [Directions] | W 2-0 | 9:30 a.m. | |
| Tue., 10/15 | V Girls Soccer | North Branford/Hale Ray | Away - North Branford High School [Directions] | W 6-1 | 2:25 p.m. | |
| Tue., 10/15 | V Girls Swimming and Diving | Bulkeley/HMTCA/Weaver | Away - Bulkeley High School Pool [Directions] | W | 3:00pm | |
| Wed., 10/16 | JV Girls Soccer | North Branford/Hale Ray | Home - Portland High School [Directions] | Cancelled | ||
| Thu., 10/17 | V Boys Cross Country | Shoreline Championship Meet | Away - Haddam Killingworth High School | 2:30 p.m. | 1:30 p.m. | |
| Thu., 10/17 | V Boys Soccer | Old Lyme | Away - Old Lyme High School [Directions] | L 0-2 | 2:25 p.m. | |
| Thu., 10/17 | V Girls Cross Country | Shoreline Championship Meet | Away - Haddam Killingworth High School | 2:30 p.m. | 1:30 p.m. | |
| Thu., 10/17 | V Girls Swimming and Diving | Wethersfield | Away - WHS [Directions] | L | 3:45pm | |
| Fri., 10/18 | JV Boys Soccer | Old Lyme | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Fri., 10/18 | V Girls Soccer | Old Lyme | Away - Old Lyme High School [Directions] | W 1-0 | 2:25 p.m. | |
| Sat., 10/19 | V Football | Windsor Locks/Suffield/East Granby | Home - Pierson Park, Cromwell [Directions] | W 27-13 | 4-1 (4-0) | |
| Sat., 10/19 | V Boys Soccer | Hale Ray | Away - Hale-Ray HS, Nevers Field [Directions] | L 0-4 | 5:45 p.m. | |
| Sat., 10/19 | JV Girls Soccer | Old Lyme | Home - Portland High School [Directions] | 10:30 a.m. | ||
| Mon., 10/21 | JV Football | Windsor Locks/Suffield/East Granby | Away - Windsor Locks High School [Directions] | 3:45 p.m. | ||
| Mon., 10/21 | JV Girls Soccer | Hale Ray | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Tue., 10/22 | V Boys Cross Country | Freshmen/Sophomore Invitational | Away - Old Saybrook High School | 3:45 p.m. | 2:25 p.m. | |
| Tue., 10/22 | V Boys Soccer | East Hampton | Away - East Hampton High School [Directions] | L 0-3 | 6:30 p.m. | non-seeding game |
| Tue., 10/22 | V Girls Cross Country | Freshman/Sophomore Invitational | Away - Old Saybrook High School | 3:45 p.m. | 2:25 p.m. | |
| Tue., 10/22 | V Girls Soccer | East Hampton | Away - East Hampton High School [Directions] | W 2-0 | 4:30 p.m. | non-seeding game |
| Tue., 10/22 | V Girls Swimming and Diving | Windsor | Away - Windsor H.S. [Directions] | L | 2:30pm | |
| Wed., 10/23 | JV Boys Soccer | East Hampton | Home - Portland High School [Directions] | 5:00 p.m. | ||
| Wed., 10/23 | JV Girls Soccer | East Hampton | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Thu., 10/24 | V Boys Soccer | Old Lyme | Home - Portland High School [Directions] | W 1-0 | non-seeding game/Senior night | |
| Fri., 10/25 | JV Boys Soccer | Old Lyme | Away - Old Lyme High School [Directions] | Cancelled | 2:25 p.m. | |
| Fri., 10/25 | V Girls Soccer | Old Lyme | Home - Portland HS [Directions] | L 0-2 | non-seeding game | |
| Fri., 10/25 | JV Girls Soccer | Old Saybrook | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Fri., 10/25 | V Girls Swimming and Diving | Maloney/Platt | Home - Rocky Hill High School [Directions] | 3:45 p.m. | ||
| Sat., 10/26 | V Boys Cross Country | Class S State Championship | Away - Wickham Park | 11:25 a.m. | 10:00 a.m. | |
| Sat., 10/26 | V Football | SMSA Coop | Away - Dillon Stadium [Directions] | L 19-36 | 4-2 (4-1) | |
| Sat., 10/26 | V Girls Cross Country | CIAC Class S Championship | Away - Wickham Park - East Hartford [Directions] | 9:15 a.m. | TBA | |
| Sat., 10/26 | JV Girls Soccer | Old Lyme | Away - Old Lyme High School [Directions] | 11:00 a.m. | 9:30 a.m. | |
| Mon., 10/28 | V Boys Cross Country | Freshman Championships | Away - Valley Regional High School | 3:30 p.m. | 2:00 p.m. | |
| Mon., 10/28 | JV Football | SMSA Coop | Home - Pierson Park, Cromwell [Directions] | Cancelled | ||
| Mon., 10/28 | V Girls Cross Country | Freshman Championships | Away - Valley Regional High School | 3:30 p.m. | 2:00 p.m. | |
| Wed., 10/30 | V Girls Soccer | Haddam-Killingworth | Home - Portland High School [Directions] | W 2-0 | ||
| Fri., 11/1 | V Boys Cross Country | State Open Championship | Away - Wickham Park | 2:00 p.m. | 12:30 p.m. | |
| Fri., 11/1 | V Football | Enfield | Away - Enfield High Turf Field [Directions] | L 7-20 | 4-3 (4-2) | |
| Fri., 11/1 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | 12:30 p.m. | |
| Fri., 11/1 | V Girls Soccer | Old Lyme | Away - Indian River, Clinton [Directions] | L 1-0 | 5:30 p.m. | |
| Fri., 11/1 | V Girls Swimming and Diving | CCC East Swimming and Diving Championships | Away - Bulkeley High School | 4:00 p.m. | 2:30pm | |
| Sat., 11/2 | JV Football | Enfield | Home - Pierson Park, Cromwell [Directions] | 10:30 a.m. | ||
| Wed., 11/6 | V Girls Soccer | Wheeler | Home - Portland High School [Directions] | W 4-0 | 2nd round state tournament | |
| Fri., 11/8 | V Football | Valley Regional/Old Lyme | Home - Pierson Park, Cromwell [Directions] | L 2-49 | 4-4 (4-2) | |
| Fri., 11/8 | V Girls Soccer | Bolton | Away - Bolton High School [Directions] | W 1-0 | 12:00pm | Quarter final round |
| Sat., 11/9 | V Boys Cross Country | New England Championships | Away - Cumberland, ME | TBA | TBA | |
| Sat., 11/9 | JV Football | Valley Regional/Old Lyme | Away - Valley Regional High School [Directions] | Cancelled | ||
| Sat., 11/9 | V Girls Cross Country | New England Championship | Away - Site TBA [Directions] | TBA | TBA | Cumberland, ME |
| Sat., 11/9 | V Girls Swimming and Diving | State Trials | Away - Plainville H.S. | 12:30 p.m. | 11:00am | |
| Mon., 11/11 | V Girls Soccer | Coventry | Away - Middletown High School [Directions] | W 2-1 | semi-final | |
| Wed., 11/13 | V Girls Swimming and Diving | State Finals | Away - Wesleyan | 5:00 p.m. | 3:00pm | |
| Sat., 11/16 | V Football | Avon | Away - Avon High School [Directions] | L 14-44 | ||
| Sat., 11/16 | V Girls Soccer | Old Saybrook | Away - Middletown High School [Directions] | Cancelled | 2:00pm | State Champion! |
| Sat., 11/16 | V Girls Soccer | Old Saybrook | Away - Middletown High School [Directions] | T 0-0 | 2:00 p.m. | Class S State Championship |
| Mon., 11/18 | JV Football | Avon | Home - Pierson Park, Cromwell [Directions] | 3:00 p.m. | ||
| Fri., 11/22 | V Football | North Branford | Away - Colafati Field - NBHS [Directions] | L 6-24 | ||
| Sat., 11/23 | JV Football | North Branford | Home - Pierson Park, Cromwell [Directions] | 10:30 a.m. | ||
| Thu., 11/28 | V Football | Coginchaug/Hale Ray/East Hampton | Home - Pierson Park, Cromwell [Directions] | L 6-35 | ||
| Wed., 12/4 | V Girls Basketball | Cheshire (Scrim.) | Away - Cheshire High East Gym [Directions] | 3:30 p.m. | 2:25 p.m. | |
| Fri., 12/6 | V Girls Basketball | Choate Rosemary Hall (Scrim.) | Away | 4:00 p.m. | 2:25 p.m. | |
| Wed., 12/11 | V Boys Basketball | Whitney Tech (Scrim.) | Home - Portland High School [Directions] | 3:30 p.m. | ||
| Wed., 12/11 | V Boys Indoor Track | Shoreline Developmental Meet | Away - New Haven Athletic Center | 4:00 p.m. | 2:25 p.m. | |
| Wed., 12/11 | V Girls Basketball | Creed | Away - Truman School | L 34-50 | 4:30 p.m. | |
| Wed., 12/11 | V Girls Indoor Track | Shoreline Developmental Meet | Away - New Haven Athletic Center | 4:00 p.m. | 2:25 p.m. | |
| Mon., 12/16 | V Girls Basketball | Old Saybrook | Home - Portland High School [Directions] | L 33-64 | ||
| Mon., 12/16 | JV Girls Basketball | Old Saybrook | Home - Portland High School [Directions] | 5:30 p.m. | ||
| Wed., 12/18 | V Boys Basketball | Old Saybrook | Home - Portland High School [Directions] | L 40-55 | ||
| Wed., 12/18 | JV Boys Basketball | Old Saybrook | Home - Portland High School [Directions] | 5:30 p.m. | ||
| Thu., 12/19 | V Boys Swimming and Diving | Middletown | Away - Middletown High School [Directions] | L | 2:30pm | |
| Thu., 12/19 | V Wrestling | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | 6:30 p.m. | 4:30pm | |
| Fri., 12/20 | V Girls Basketball | Morgan | Home - Portland High School [Directions] | L 30-83 | ||
| Fri., 12/20 | JV Girls Basketball | Morgan | Home - Portland High School [Directions] | 5:30 p.m. | ||
| Sat., 12/21 | V Boys Basketball | Morgan | Home - Portland High School [Directions] | W 51-37 | ||
| Sat., 12/21 | JV Boys Basketball | Morgan | Home - Portland High School [Directions] | 3:30 p.m. | ||
| Sat., 12/21 | FR Boys Basketball | Old Saybrook | Away - Old Saybrook Gymnasium [Directions] | 10:00 a.m. | 9:00 a.m. | |
| Sat., 12/21 | V Wrestling | Pomperaug Coop | Away [Directions] | 9:00 a.m. | 7:00am | |
| Mon., 12/23 | V Wrestling | RHAM | Home - Portland High School [Directions] | 9:00 a.m. | ||
| Mon., 12/23 | V Girls Basketball | Windsor Locks | Home - Portland High School [Directions] | L 39-52 | ||
| Mon., 12/23 | JV Girls Basketball | Windsor Locks | Home - Portland High School [Directions] | 3:30 p.m. | ||
| Fri., 12/27 | V Girls Basketball | Coventry | Home - Portland High School [Directions] | W 50-36 | ||
| Fri., 12/27 | JV Girls Basketball | Coventry | Home - Portland High School [Directions] | 3:30 p.m. | ||
| Sat., 12/28 | FR Boys Basketball | Morgan | Away - Morgan HS [Directions] | 9:00 a.m. | 8:00 a.m. | |
| Sat., 12/28 | V Wrestling | RHAM Tournament | Away - RHAM High School | 9:00 a.m. | 7:00 a.m. | |
| Mon., 12/30 | V Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | L 28-64 | 4:30 p.m. | |
| Mon., 12/30 | JV Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Mon., 12/30 | V Wrestling | Coventry (Scrim.) | Home - Portland High School [Directions] | 10:00 a.m. | ||
| Mon., 12/30 | V Girls Basketball | East Hampton | Away - East Hampton High School [Directions] | L 25-46 | 5:00 p.m. | |
| Mon., 12/30 | JV Girls Basketball | East Hampton | Away - East Hampton High School [Directions] | 11:30 a.m. | 5:00 p.m. | |
| Sat., 1/4 | FR Boys Basketball | Westbrook | Home - Portland High School [Directions] | 10:30 a.m. | ||
| Sat., 1/4 | V Boys Indoor Track | Shoreline Coaches Invitational | Away - New Haven Athletic Center | 10:00 a.m. | 8:00 a.m. | |
| Sat., 1/4 | V Wrestling | South Windsor | Away - South Windsor High School [Directions] | TBA | New Years Classic Duals | |
| Sat., 1/4 | V Girls Basketball | Valley Regional | Away - Valley Regional High School [Directions] | L 41-54 | 4:15 p.m. | |
| Sat., 1/4 | JV Girls Basketball | Valley Regional | Away - Valley Regional High School [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Sat., 1/4 | V Girls Indoor Track | Shoreline Coaches Invitational | Away - New Haven Athletic Center | 10:00 a.m. | 8:00 a.m. | |
| Mon., 1/6 | V Boys Basketball | Westbrook | Home - Portland High School [Directions] | L 49-51 | ||
| Mon., 1/6 | JV Boys Basketball | Westbrook | Home - Portland High School [Directions] | 5:30 p.m. | ||
| Tue., 1/7 | V Boys Swimming and Diving | East Hartford | Away - East Hartford High School [Directions] | L | 2:30pm | |
| Tue., 1/7 | V Girls Basketball | Westbrook | Home - Portland High School [Directions] | L 44-50 | ||
| Tue., 1/7 | JV Girls Basketball | Westbrook | Home - Portland High School [Directions] | 5:30 p.m. | ||
| Wed., 1/8 | V Wrestling | Seymour | Away - Seymour High School [Directions] | 7:00 p.m. | 5:00pm | |
| Wed., 1/8 | V Girls Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | L 31-58 | 4:30 p.m. | |
| Wed., 1/8 | JV Girls Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Thu., 1/9 | V Boys Basketball | Old Lyme | Home - Portland High School [Directions] | W 46-42 | ||
| Thu., 1/9 | JV Boys Basketball | Old Lyme | Home - Portland High School [Directions] | 5:30 p.m. | ||
| Fri., 1/10 | V Boys Swimming and Diving | East Catholic | Home - Rocky Hill High School [Directions] | L | ||
| Fri., 1/10 | V Girls Basketball | Old Lyme | Home - Portland High School [Directions] | L 26-59 | ||
| Fri., 1/10 | JV Girls Basketball | Old Lyme | Home - Portland High School [Directions] | 5:30 p.m. | ||
| Sat., 1/11 | V Boys Basketball | Valley Regional | Away - Valley Regional High School [Directions] | L 45-61 | 12:01 p.m. | |
| Sat., 1/11 | JV Boys Basketball | Valley Regional | Away - Valley Regional High School [Directions] | 1:00 p.m. | 12:01 p.m. | |
| Sat., 1/11 | FR Boys Basketball | North Branford | Home - Portland High School [Directions] | 10:30 a.m. | ||
| Sat., 1/11 | V Wrestling | Lawless Invitational | Away - Nonnewaug High School | TBA | 7:30am | |
| Mon., 1/13 | V Boys Basketball | North Branford | Away - North Branford High School [Directions] | L 72-85 | 4:15 p.m. | |
| Mon., 1/13 | JV Boys Basketball | North Branford | Away - North Branford High School [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Tue., 1/14 | FR Boys Basketball | Coginchaug | Home - Portland High School [Directions] | 6:30 p.m. | 5:30 p.m. | |
| Tue., 1/14 | V Boys Indoor Track | Shoreline One | Away - New Haven Athletic Center | 4:00 p.m. | 2:25 p.m. | |
| Tue., 1/14 | V Girls Basketball | North Branford | Away - North Branford High School [Directions] | L 63-64 | 4:15 p.m. | |
| Tue., 1/14 | JV Girls Basketball | North Branford | Away - North Branford High School [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Tue., 1/14 | V Girls Indoor Track | Shoreline One | Away - New Haven Athletic Center | 4:00 p.m. | 2:25 p.m. | |
| Wed., 1/15 | V Boys Basketball | Somers | Home - Portland High School [Directions] | L 48-59 | ||
| Wed., 1/15 | JV Boys Basketball | Somers | Home - Portland High School [Directions] | 5:30 p.m. | ||
| Wed., 1/15 | V Boys Swimming and Diving | Southington | Away - Southington YMCA [Directions] | L | 2:30pm | |
| Fri., 1/17 | V Boys Indoor Track | HK Invitational | Away - New Haven Athletic Center | 4:00 p.m. | 2:00 p.m. | |
| Fri., 1/17 | V Boys Swimming and Diving | Bulkeley Cooperative Swim Team | Away - Bulkeley High School Pool [Directions] | W | 3:00pm | |
| Fri., 1/17 | V Girls Indoor Track | HK Invitational | Away - New Haven Athletic Center | 4:00 p.m. | 2:00 p.m. | |
| Sat., 1/18 | FR Boys Basketball | Valley Regional | Away - Valley Regional High School [Directions] | 10:30 a.m. | 9:15 a.m. | |
| Sat., 1/18 | V Wrestling | Lyman Memorial/Windham Tech | Away - Lyman Memorial High School [Directions] | TBA | 7:30 | Casey Yates Invitational 10:00 am Start |
| Mon., 1/20 | V Girls Basketball | Cromwell | Home - Portland High School [Directions] | L 65-31 | ||
| Mon., 1/20 | JV Girls Basketball | Cromwell | Home - Portland High School [Directions] | 12:00 p.m. | ||
| Wed., 1/22 | FR Boys Basketball | East Hampton | Home - Portland High School [Directions] | 7:00 p.m. | ||
| Thu., 1/23 | V Boys Swimming and Diving | Meriden Co-op | Home - Rocky Hill High School [Directions] | L | ||
| Thu., 1/23 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional High School [Directions] | L 26-55 | 2:25 p.m. | |
| Thu., 1/23 | JV Girls Basketball | Coginchaug | Away - Coginchaug Regional High School [Directions] | 3:30 p.m. | 2:25 p.m. | |
| Fri., 1/24 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional High School [Directions] | L 36-45 | 5:00 p.m. | |
| Fri., 1/24 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional High School [Directions] | 6:00 p.m. | 5:00 p.m. | |
| Fri., 1/24 | V Boys Indoor Track | Shoreline Two | Away - New Haven Athletic Center | 4:00 p.m. | 2:25 p.m. | |
| Fri., 1/24 | V Boys Swimming and Diving | Plainville Boys Swimming | Home - Rocky Hill High School [Directions] | W | ||
| Fri., 1/24 | V Girls Indoor Track | Shoreline Two | Away - New Haven Athletic Center | 4:00 p.m. | 2:25 p.m. | |
| Sat., 1/25 | FR Boys Basketball | Creed | Away - Fair Haven School | 12:00 p.m. | 10:45 a.m. | |
| Sat., 1/25 | V Wrestling | Highlander Invitational | Home - Portland High School [Directions] | 9:00 a.m. | ||
| Tue., 1/28 | V Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | W 50-38 | 6:00 p.m. | |
| Tue., 1/28 | V Boys Swimming and Diving | Newington | Home - Rocky Hill High School [Directions] | L | ||
| Tue., 1/28 | V Girls Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | L 44-52 | 3:30 p.m. | |
| Tue., 1/28 | JV Girls Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 4:00 p.m. | 3:30 p.m. | |
| Wed., 1/29 | V Boys Basketball | Cromwell | Home - Portland High School [Directions] | L 44-69 | ||
| Wed., 1/29 | JV Boys Basketball | Cromwell | Home - Portland High School [Directions] | 5:30 p.m. | ||
| Wed., 1/29 | V Wrestling | Haddam-Killingworth | Away - Haddam Killingworth Middle School [Directions] | 6:00 p.m. | 4:30 p.m. | |
| Thu., 1/30 | V Girls Basketball | Westbrook | Away - Wesrbrook H.S. [Directions] | L 32-52 | 4:45 p.m. | |
| Thu., 1/30 | JV Girls Basketball | Westbrook | Away - Wesrbrook H.S. [Directions] | 6:00 p.m. | 5:00 p.m. | |
| Fri., 1/31 | V Boys Basketball | Westbrook | Away - Wesrbrook H.S. [Directions] | L 55-59 | 4:45 p.m. | |
| Fri., 1/31 | JV Boys Basketball | Westbrook | Away - Wesrbrook H.S. [Directions] | 6:00 p.m. | 4:45 p.m. | |
| Fri., 1/31 | V Boys Swimming and Diving | Windsor | Home - Rocky Hill High School [Directions] | L | ||
| Sat., 2/1 | FR Boys Basketball | Creed | Home - Portland High School [Directions] | 10:30 a.m. | ||
| Sat., 2/1 | V Boys Indoor Track | Shoreline Championships | Away - New Haven Athletic Center | 10:00 a.m. | 8:00 a.m. | |
| Sat., 2/1 | V Wrestling | South Windsor | Away - South Windsor High School [Directions] | TBA | Groundhog Duals | |
| Sat., 2/1 | V Girls Indoor Track | Shoreline Championships | Away - New Haven Athletic Center | 10:00 a.m. | 8:00 a.m. | |
| Tue., 2/4 | V Boys Basketball | East Hampton | Home - Portland High School [Directions] | L 43-61 | ||
| Tue., 2/4 | V Girls Basketball | East Hampton | Home - Portland High School [Directions] | L 34-44 | ||
| Thu., 2/6 | V Wrestling | Morgan | Away - Morgan HS [Directions] | 6:00 p.m. | 4:30pm | |
| Thu., 2/6 | V Girls Basketball | Hale Ray | Home - Portland High School [Directions] | L 43-51 | Senior Night | |
| Thu., 2/6 | JV Girls Basketball | Hale Ray | Home - Portland High School [Directions] | 5:30 p.m. | ||
| Fri., 2/7 | V Boys Basketball | Hale Ray | Home - Portland High School [Directions] | L 42-45 | Senior Night | |
| Sat., 2/8 | FR Boys Basketball | North Branford | Away - North Branford High School [Directions] | 10:00 a.m. | 8:45 a.m. | |
| Sat., 2/8 | V Boys Indoor Track | Class S State Meet | Away - New Haven Athletic Center | 4:30 p.m. | 2:30 p.m. | |
| Sat., 2/8 | V Wrestling | NFA Duals | Away - NFA | 9:30 a.m. | 7:30 a.m. | |
| Sat., 2/8 | V Girls Indoor Track | Class S State Meet | Away | 4:30 p.m. | 2:30 p.m. | |
| Mon., 2/10 | V Boys Basketball | Creed | Home - Portland High School [Directions] | L 44-54 | ||
| Mon., 2/10 | JV Boys Basketball | Creed | Home - Portland High School [Directions] | 5:30 p.m. | ||
| Mon., 2/10 | V Wrestling | Housatonic Regional | Home - Portland High School [Directions] | 6:00 p.m. | ||
| Mon., 2/10 | V Girls Basketball | Creed | Home - Portland High School [Directions] | L 37-65 | ||
| Tue., 2/11 | V Boys Swimming and Diving | Wethersfield | Away - Wethersfield High School [Directions] | L | 3:45pm | |
| Wed., 2/12 | FR Boys Basketball | Coginchaug | Away - Coginchaug Regional High School [Directions] | 6:30 p.m. | 5:15 p.m. | |
| Wed., 2/12 | V Wrestling | Terryville-Thomaston | Home - Portland High School [Directions] | 6:30 p.m. | ||
| Mon., 2/17 | V Boys Basketball | Old Lyme | Away - Old Lyme High School [Directions] | L 30-50 | 6:45 p.m. | |
| Mon., 2/17 | JV Boys Basketball | Old Lyme | Away - Old Lyme High School [Directions] | 1:30 p.m. | 12:30 p.m. | |
| Mon., 2/17 | JV Boys Basketball | Old Lyme | Away - Old Lyme High School [Directions] | Cancelled | 9:45 a.m. | |
| Mon., 2/17 | V Girls Basketball | Coventry | Away - Matthew J. Hurlock Gymnasium [Directions] | L 49-53 | 4:00 p.m. | |
| Mon., 2/17 | JV Girls Basketball | Coventry | Away - Matthew J. Hurlock Gymnasium [Directions] | 5:30 p.m. | 4:00 a.m. | |
| Tue., 2/18 | JV Girls Basketball | Old Lyme | Away - Old Lyme High School [Directions] | Cancelled | 4:30 p.m. | |
| Wed., 2/19 | FR Boys Basketball | Morgan | Home - Portland High School [Directions] | Cancelled | ||
| Thu., 2/20 | V Girls Basketball | Old Lyme | Away - Old Lyme High School [Directions] | L 31-61 | 4:15 p.m. | |
| Thu., 2/20 | JV Girls Basketball | Old Lyme | Away - Old Lyme High School [Directions] | Cancelled | 4:15 p.m. | |
| Thu., 2/20 | JV Girls Basketball | Old Lyme | Away - Old Lyme High School [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Fri., 2/21 | V Boys Basketball | Creed | Away - Fair Haven School | L 51-61 | 4:30 p.m. | |
| Fri., 2/21 | JV Boys Basketball | Creed | Away - Fair Haven School | 6:00 p.m. | 4:30 p.m. | |
| Fri., 2/21 | V Boys Swimming and Diving | E.O. Smith - Tolland Hammerheads | Home - Rocky Hill High School [Directions] | L | ||
| Fri., 2/21 | V Wrestling | Class S Championship | Away - Windham High School | 4:00 p.m. | 1:00 p.m. | |
| Sat., 2/22 | FR Boys Basketball | Westbrook | Away - Westbrook H.S. [Directions] | 9:00 a.m. | 8:00 a.m. | |
| Sat., 2/22 | V Wrestling | Class S Championship | Away - Windham High School | 9:00 a.m. | 7:00 a.m. | |
| Mon., 2/24 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | L 43-54 | 4:15 p.m. | |
| Mon., 2/24 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Wed., 2/26 | V Boys Basketball | East Hampton | Away - East Hampton High School [Directions] | W 55-50 | 5:00 p.m. | |
| Wed., 2/26 | JV Boys Basketball | East Hampton | Away - East Hampton High School [Directions] | 6:00 p.m. | 5:00 p.m. | |
| Wed., 2/26 | V Boys Swimming and Diving | HK-Valley | Home - Rocky Hill High School [Directions] | W | ||
| Thu., 2/27 | FR Boys Basketball | Haddam-Killingworth | Home - Portland High School [Directions] | 7:00 p.m. | ||
| Thu., 2/27 | V Boys Swimming and Diving | Hartford Public | Away - Hartford Public High School [Directions] | W | 2:45pm | |
| Fri., 2/28 | V Boys Basketball | Amistad | Home - Portland High School [Directions] | W 60-40 | ||
| Fri., 2/28 | JV Boys Basketball | Amistad | Home - Portland High School [Directions] | Cancelled | ||
| Wed., 3/5 | V Boys Swimming and Diving | CCC East Diving Championships | Away - Newington H.S. | 6:00 p.m. | ||
| Thu., 3/6 | V Boys Swimming and Diving | CCC East Swim Champs | Away - Hartford Public High School | 5:00 p.m. | 3:00pm | |
| Sat., 3/15 | V Boys Swimming and Diving | Class S State Trials | Away - Plainville H.S. | 2:00 p.m. | 12:00pm | |
| Tue., 3/18 | V Boys Swimming and Diving | Class S State Finals | Away - Wesleyan University | 5:30 p.m. | 4:00pm | |
| Tue., 4/1 | V Baseball | Haddam-Killingworth (Scrim.) | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Wed., 4/2 | V Boys Golf | South Windsor (Scrim.) | Away - Top Stone Golf Course [Directions] | 3:00 p.m. | 2:15 p.m. | |
| Fri., 4/4 | V Baseball | East Windsor/International (Scrim.) | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Mon., 4/7 | V Baseball | Cheney Tech (Scrim.) | Away - Cheney Tech [Directions] | 3:30 p.m. | 2:25 p.m. | |
| Tue., 4/8 | V Boys Golf | South Windsor (Scrim.) | Home - PGC [Directions] | 2:45 p.m. | ||
| Wed., 4/9 | V Baseball | East Hampton | Home - Portland High School [Directions] | W 3-0 | 2:25 p.m. | |
| Wed., 4/9 | V Boys Tennis | East Hampton | Away - East Hampton High School [Directions] | L 3-4 | 2:25 p.m. | |
| Wed., 4/16 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | L 4-3 | 2:25 p.m. | |
| Wed., 4/16 | V Boys Tennis | Cromwell | Home - Portland High School [Directions] | L 2-5 | ||
| Thu., 4/17 | JV Baseball | Haddam-Killingworth | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Thu., 4/17 | V Boys Golf | Haddam-Killingworth | Home [Directions] | Portland: 170 Haddam-Killingworth: 191 (non-league) | ||
| Thu., 4/17 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | L 1-16 | 11:00 a.m. | |
| Thu., 4/17 | JV Softball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 2:00 p.m. | ||
| Sat., 4/19 | V Baseball | ValleyReg/Westbrook | Away - Valley Regional High School [Directions] | W 4-0 | 9:30 a.m. | |
| Sat., 4/19 | JV Baseball | ValleyReg/Westbrook | Away - Valley Regional High School [Directions] | 1:00 p.m. | 9:30 a.m. | |
| Sat., 4/19 | V Softball | Valley Regional | Away - Valley Regional High School [Directions] | L 1-8 | 9:30 a.m. | |
| Mon., 4/21 | V Baseball | Westbrook | Home - Portland High School [Directions] | W 11-4 | ||
| Mon., 4/21 | V Boys Golf | North Branford | Away - Tradition Golf Course - Wallingford [Directions] | Portland: 174 North Branford: 209 (league) | 1:30 p.m. | |
| Mon., 4/21 | V Boys Tennis | North Branford | Away - North Branford High School [Directions] | L 1-6 | 2:25 p.m. | |
| Mon., 4/21 | V Softball | Westbrook/Old Saybrook | Home - Portland High School [Directions] | L 4-17(6) | ||
| Tue., 4/22 | JV Baseball | Westbrook | Away - Westbrook H.S. [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 4/22 | V Boys Golf | Old Saybrook, Canton | Home - PGC [Directions] | Portland: 166 Canton: 168 Old Saybrook: 209 (non-league) | ||
| Tue., 4/22 | V Boys Outdoor Track | East Hampton, Hale Ray | Away - East Hampton High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 4/22 | V Boys Tennis | Old Saybrook | Away - Old Saybrook High School [Directions] | L 1-6 | 2:25 p.m. | |
| Tue., 4/22 | V Girls Outdoor Track | East Hampton, Hale Ray | Away - East Hampton High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Wed., 4/23 | V Boys Golf | Morgan, Daniel Hand | Away - Clinton CC [Directions] | Portland: 190 Morgan:184 Hand: 162 (non-league) | 1:40 p.m. | |
| Thu., 4/24 | V Baseball | Old Lyme | Home - Portland High School [Directions] | W 9-8 | ||
| Thu., 4/24 | JV Baseball | Old Lyme | Away - Old Lyme High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Thu., 4/24 | V Boys Golf | Haddam-Killingworth | Away - Banner [Directions] | Portland: 186 Haddam-Killingworth: 180 (league) | 2:00 p.m. | |
| Thu., 4/24 | V Boys Tennis | Morgan | Home - Portland High School [Directions] | L 0-7 | ||
| Thu., 4/24 | JV Softball | Innovation | Home - Brownstone Park [Directions] | 4:15 p.m. | ||
| Fri., 4/25 | V Baseball | North Branford | Away - North Branford High School [Directions] | W 1-0 | 2:25 p.m. | |
| Fri., 4/25 | V Boys Outdoor Track | Stafford Invitational | Away | 4:00 p.m. | 2:25 p.m. | |
| Fri., 4/25 | V Boys Tennis | Valley Regional | Home - Portland High School [Directions] | L 2-5 | ||
| Fri., 4/25 | V Girls Outdoor Track | Stafford Invitational | Away - Stafford High School | 4:00 p.m. | 2:25 p.m. | |
| Fri., 4/25 | V Softball | North Branford | Away - Totoket Park [Directions] | L 0-12(5) | 2:25 p.m. | |
| Mon., 4/28 | V Baseball | Ellington | Home - Portland High School [Directions] | L 2-0 | ||
| Mon., 4/28 | JV Baseball | Ellington | Home - Rose Hill [Directions] | 4:00 p.m. | Rose Hill Field | |
| Mon., 4/28 | V Boys Golf | Coginchaug | Home - PGC [Directions] | Portland: 177 Coginchaug: 206 (non-league) | ||
| Mon., 4/28 | V Boys Tennis | Coginchaug | Away - Coginchaug Regional High School [Directions] | L 2-5 | 2:25 p.m. | |
| Mon., 4/28 | V Softball | Old Saybrook | Away - Old Saybrook High School [Directions] | L 0-16 | 2:25 p.m. | |
| Tue., 4/29 | V Boys Outdoor Track | Coginchaug, Hale Ray | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Tue., 4/29 | V Boys Tennis | Westbrook | Away - Wesrbrook H.S. [Directions] | L 2-4 | 9:45 a.m. | |
| Tue., 4/29 | V Girls Outdoor Track | Coginchaug, Hale Ray | Home - Portland High School [Directions] | 3:45 p.m. | ||
| Tue., 4/29 | JV Softball | Old Saybrook | Home - Brownstone Park Nolan Field [Directions] | 3:45 p.m. | ||
| Thu., 5/1 | V Boys Golf | Cromwell | Away - TPC [Directions] | Portland: 169 Cromwell: 157 (non-league) | 1:40 p.m. | |
| Fri., 5/2 | V Baseball | Coginchaug | Away - Coginchaug Regional High School [Directions] | L 3-4(9) | 2:25 p.m. | |
| Fri., 5/2 | V Boys Tennis | Coginchaug | Home - Portland High School [Directions] | L 1-6 | ||
| Fri., 5/2 | V Softball | Coginchaug | Home - Portland High School [Directions] | L 0-12 | ||
| Sat., 5/3 | V Baseball | Cromwell | Home - Portland High School [Directions] | W 3-2 | ||
| Sat., 5/3 | JV Baseball | Coginchaug | Away - Coginchaug Regional High School [Directions] | 10:30 a.m. | ||
| Sat., 5/3 | V Boys Outdoor Track | Coginchaug Invitational | Away - Coginchaug High School | 2:00 p.m. | 12:30 p.m. | |
| Sat., 5/3 | V Girls Outdoor Track | Coginchaug Invitational | Away - Coginchaug High School | 2:00 p.m. | 12:30 p.m. | |
| Sat., 5/3 | JV Softball | Coginchaug | Away - Coginchaug Regional High School [Directions] | Cancelled | 9:30 a.m. | |
| Mon., 5/5 | V Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | L 3-1 | 2:25 p.m. | |
| Mon., 5/5 | V Boys Tennis | Valley Regional | Away - Valley Regional High School [Directions] | L 1-6 | 2:25 p.m. | |
| Mon., 5/5 | V Softball | Hale Ray | Away - Hale-Ray HS, Lou Milardo Field [Directions] | L 1-13 | TBA | |
| Mon., 5/5 | JV Softball | Hale Ray | Away - Hale-Ray HS [Directions] | 4:15 p.m. | 2:25 p.m. | |
| Tue., 5/6 | JV Baseball | Cromwell | Home - Portland High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 5/6 | V Boys Golf | Valley Regional | Home - PGC [Directions] | Portland: 163 Valley: 182 (league) | ||
| Tue., 5/6 | V Boys Outdoor Track | Cromwell, Old Lyme | Away - Cromwell High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 5/6 | V Girls Outdoor Track | Cromwell, Old Lyme | Away [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 5/6 | V Softball | Old Saybrook | Home - Portland High School [Directions] | L 1-13 | ||
| Tue., 5/6 | JV Softball | Old Saybrook | Home - Portland High School [Directions] | Cancelled | ||
| Wed., 5/7 | V Baseball | Westbrook | Away - Westbrook H.S. [Directions] | L 0-4 | 2:25 p.m. | |
| Wed., 5/7 | V Boys Golf | Morgan | Home - PGC [Directions] | Portland: 175 Morgan: 168 (league) | ||
| Wed., 5/7 | V Boys Tennis | Westbrook | Home - Portland High School [Directions] | L 3-4 | ||
| Wed., 5/7 | V Softball | Westbrook/Old Saybrook | Away - Wesrbrook H.S. [Directions] | L 3-16(5) | ||
| Thu., 5/8 | V Boys Golf | Coginchaug | Away - Lyman Orchards [Directions] | Portland: 173 Coginchaug: 194 (league) | 2:00 p.m. | |
| Thu., 5/8 | V Softball | East Hampton | Home - Portland High School [Directions] | L 6-10(9) | ||
| Mon., 5/12 | V Baseball | Hale Ray | Home - Portland High School [Directions] | W 4-2 | ||
| Mon., 5/12 | V Boys Golf | East Hampton | Home - PGC [Directions] | Portland: 169 East Hampton: 190 (league) | ||
| Mon., 5/12 | V Boys Tennis | Morgan | Away - Morgan HS [Directions] | L 1-6 | 2:25 p.m. | |
| Mon., 5/12 | V Softball | Hale Ray | Home - Portland High School [Directions] | L 4-16 | ||
| Mon., 5/12 | JV Softball | Hale Ray | Home - Portland High School [Directions] | 4:15 p.m. | ||
| Tue., 5/13 | JV Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 5/13 | V Boys Golf | Old Lyme | Away - Black Hall Club Old Lyme [Directions] | Portland: 185 Old Lyme: 194 (league) | 1:45 p.m. | |
| Tue., 5/13 | V Boys Outdoor Track | Valley Regional, Westbrook | Home - Westbrook High School [Directions] | 3:45 p.m. | 1:45 p.m. | |
| Tue., 5/13 | V Girls Outdoor Track | Valley Regional, Westbrook | Home - Westbrook High School [Directions] | 3:45 p.m. | 1:45 p.m. | |
| Tue., 5/13 | V Softball | Cromwell | Home - Portland High School [Directions] | L 7-5 | ||
| Wed., 5/14 | V Baseball | Creed | Home - Portland High School [Directions] | W 15-4 | ||
| Wed., 5/14 | V Boys Tennis | Old Saybrook | Home - Portland High School [Directions] | L 1-6 | ||
| Wed., 5/14 | JV Softball | Morgan | Away - Peters Complex [Directions] | Cancelled | 2:25 p.m. | |
| Thu., 5/15 | V Baseball | Morgan | Home - Portland High School [Directions] | L 2-3 | ||
| Thu., 5/15 | JV Baseball | Creed | Away - Bowen Field | 3:45 p.m. | 2:25 p.m. | |
| Thu., 5/15 | V Boys Tennis | Old Lyme | Home - Portland High School [Directions] | L 0-7 | ||
| Thu., 5/15 | V Softball | Morgan | Home - Portland High School [Directions] | L 1-9 | ||
| Fri., 5/16 | V Baseball | Old Lyme | Away - Old Lyme High School [Directions] | W 4-1 | 2:25 p.m. | |
| Fri., 5/16 | V Boys Tennis | Old Lyme | Away - Old Lyme High School [Directions] | L 0-7 | 2:25 p.m. | |
| Fri., 5/16 | V Softball | Old Lyme | Away - Old Lyme High School [Directions] | L 8-12 | 2:25 p.m. | |
| Fri., 5/16 | V Softball | Old Lyme | Away - Old Lyme High School [Directions] | W 16-15 | ||
| Mon., 5/19 | V Baseball | Creed | Away - Bowen Field | W 12-6 | 2:25 p.m. | |
| Mon., 5/19 | V Boys Tennis | North Branford | Home - Portland High School [Directions] | L 2-5 | ||
| Mon., 5/19 | V Softball | Whitney Tech | Away - Pine Rock Park [Directions] | W 18-1(5) | 2:25 p.m. | |
| Tue., 5/20 | V Baseball | Norwich Tech | Away - NTHS Outdoor Athletic Complex [Directions] | W 3-2 | 2:25 p.m. | |
| Tue., 5/20 | JV Baseball | Norwich Tech | Home - Portland High School [Directions] | 4:00 p.m. | ||
| Tue., 5/20 | JV Baseball | Creed | Home - Portland High School [Directions] | Cancelled | ||
| Tue., 5/20 | V Boys Golf | Hale Ray | Home - PGC [Directions] | Portland: 171 Hale Ray: 182 (league) | ||
| Tue., 5/20 | V Boys Outdoor Track | North Branford | Away - North Branford High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 5/20 | V Girls Outdoor Track | North Branford | Away - North Branford High School [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 5/20 | JV Softball | TwoRiversMagnet | Home - Brownstone Park [Directions] | 4:15 p.m. | ||
| Wed., 5/21 | V Baseball | East Hampton | Away - East Hampton High School [Directions] | L 2-0 | ||
| Wed., 5/21 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | W 7-0 | 2:25 p.m. | |
| Wed., 5/21 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | W 5-2 | ||
| Wed., 5/21 | V Softball | Goodwin Tech | Away - Goodwin Tech HS Field [Directions] | W 12-5 | 2:25 p.m. | |
| Thu., 5/22 | V Boys Outdoor Track | Valley Freshman Invitational | Away - Valley Regional High School | 4:00 p.m. | 2:25 p.m. | |
| Thu., 5/22 | V Girls Outdoor Track | Valley Freshman Invitational | Away - Valley Regional High School | 4:00 p.m. | 2:25 p.m. | |
| Fri., 5/23 | JV Baseball | Coginchaug | Home - Portland High School [Directions] | 3:45 p.m. | 2:25 p.m. | non-seeding game |
| Fri., 5/23 | V Boys Tennis | Cromwell | Away - Cromwell High School [Directions] | L 0-7 | 2:25 p.m. | |
| Sat., 5/24 | V Baseball | Old Saybrook | Home - Portland High School [Directions] | L 2-0 | ||
| Mon., 5/26 | V Baseball | Coginchaug | Home - Portland High School [Directions] | L 6-8 | non-seeding game | |
| Tue., 5/27 | V Baseball | Westbrook | Home - Portland High School [Directions] | L 1-0 | First Round SLC Playoffs | |
| Tue., 5/27 | V Boys Golf | Valley Regional | Away - Fox Hopyard CC [Directions] | Portland: 174 Valley: 178 Hale Ray: 198 (non-league) | 2:10 p.m. | |
| Tue., 5/27 | V Boys Tennis | East Hampton | Home - Portland High School [Directions] | L 2-5 | ||
| Tue., 5/27 | V Softball | East Hampton | Away - East Hampton High School [Directions] | L 3-5 | 2:25 p.m. | |
| Wed., 5/28 | JV Baseball | East Hampton | Home - Portland High School [Directions] | 4:15 p.m. | ||
| Wed., 5/28 | V Boys Outdoor Track | SLC Championship Meet | Away - Westbrook High School | 2:00 p.m. | 12:30 p.m. | |
| Wed., 5/28 | V Girls Outdoor Track | SLC Championship Meet | Away - Westbrook High School | 2:00 p.m. | 12:30 p.m. | |
| Wed., 5/28 | V Softball | Windsor Locks | Away - Veteran's Memorial Park [Directions] | L 6-7(8) | 5:00 p.m. | |
| Thu., 5/29 | V Softball | Bolton | Home - Portland High School [Directions] | W 3-1 | Senior Night | |
| Fri., 5/30 | JV Baseball | Hale Ray | Away - Hale Ray High School [Directions] | 4:00 p.m. | 2:25 p.m. | |
| Fri., 5/30 | V Boys Golf | Old Saybrook | Away - Fenwick [Directions] | Portland: 167 Old Saybrook: 182 (league) | 2:00 p.m. | |
| Sat., 5/31 | JV Baseball | East Hampton | Away - East Hampton High School [Directions] | 11:00 a.m. | 9:45 a.m. | |
| Mon., 6/2 | V Baseball | Coventry | Away - Coventry High School [Directions] | W 5-0 | 1:45 p.m. | First Round - State Tournament |
| Mon., 6/2 | V Boys Golf | Cromwell | Home - PGC [Directions] | Portland: 173 Cromwell: 163 (league) | ||
| Tue., 6/3 | V Baseball | East Hampton | Away - East Hampton High School [Directions] | W 4-1 | 2:00 p.m. | Class S Tourney - Round of 16 |
| Wed., 6/4 | V Boys Golf | Shoreline Conference Championship | Away - Alling Memorial GC, New haven | TBA | TBA | |
| Wed., 6/4 | V Boys Outdoor Track | CIAC Class S Championship | Away - Danbury HS [Directions] | 2:30 p.m. | TBA | |
| Wed., 6/4 | V Girls Outdoor Track | CIAC Class S Championship | Away - Danbury HS [Directions] | 2:30 p.m. | ||
| Fri., 6/6 | V Baseball | Old Lyme | Home [Directions] | W 3-1 | Class S Quarter Final game | |
| Mon., 6/9 | V Boys Outdoor Track | CIAC Open Championship | Away - Middletown [Directions] | 1:30 p.m. | TBA | |
| Mon., 6/9 | V Girls Outdoor Track | CIAC Open Championship | Away - Middletown [Directions] | 1:30 p.m. | ||
| Tue., 6/10 | V Baseball | Trinity Catholic | Away - Sage Park Berlin, CT | W 4-0 | 1:45 p.m. | Neutral site - Class S Semi-Final |
| Wed., 6/11 | V Boys Golf | Division IV State Tournament | Away - Timberlin GC, Berlin | TBA | TBA | |
| Sat., 6/14 | V Baseball | Thomaston | Away - Palmer Field Middletown [Directions] | W 8-0 | 10:30am | Class S State Championship |
| Sat., 6/14 | V Baseball | Thomaston | Away - Palmer Field, Middletown, CT [Directions] | Cancelled | 10:45 a.m. | Class S State Final |
| Sat., 6/14 | V Boys Outdoor Track | New England Championship | Away - Norwell (MA) HS | TBA | ||
| Sat., 6/14 | V Girls Outdoor Track | New England Championship | Away - Norwell (MA) HS | TBA | ||
| Tue., 6/17 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - USCG Academy [Directions] | 11:00 a.m. | ||
| Tue., 6/17 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - USCG Academy | 11:30 a.m. | ||
| Wed., 6/18 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Willowbrook Park - New Britain [Directions] | 11:00 a.m. | ||
| Wed., 6/18 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - USCG Academy [Directions] | 11:00 a.m. | ||