| Portland 2015-16 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 452 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Westbrook | Home - Portland HS [Directions] | Cancelled | Cancelled | |
| TBA | JV Baseball | Creed | Away - Bowen Field | Cancelled | Cancelled | |
| TBA | JV Baseball | Creed | Home - Portland HS [Directions] | TBA | ||
| TBA | JV Baseball | Morgan | Away - Indian River Complex [Directions] | TBA | ||
| TBA | JV Baseball | Old Lyme | Away - Old Lyme HS [Directions] | Cancelled | Cancelled | |
| TBA | JV Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | TBA | ||
| TBA | JV Baseball | Old Saybrook | Home - Portland HS [Directions] | TBA | ||
| TBA | FR Boys Basketball | Haddam-Killingworth | Home - Portland MS [Directions] | Cancelled | Cancelled | |
| TBA | FR Boys Basketball | Creed | Home - Portland HS [Directions] | TBA | ||
| TBA | FR Boys Basketball | Coginchaug | Away - Maynard Stender Gymnasium @ CRHS [Directions] | TBA | ||
| TBA | FR Boys Basketball | Morgan | Away - Morgan HS [Directions] | TBA | ||
| TBA | JV Football | North Branford | Away - Colafati Field - NBHS [Directions] | 10:30 a.m. | ||
| TBA | JV Football | Coginchaug/Hale Ray/East Hampton | Home - Pierson Park, Cromwell [Directions] | 3:45 p.m. | ||
| TBA | JV Boys Soccer | Westbrook | Home - Portland HS [Directions] | 3:45 p.m. | ||
| TBA | JV Boys Soccer | Coginchaug | Home - Portland HS [Directions] | TBA | ||
| TBA | JV Girls Soccer | East Hampton | Away - East Hampton HS [Directions] | TBA | ||
| TBA | JV Girls Soccer | Old Lyme | Away - Old Lyme HS [Directions] | TBA | ||
| TBA | JV Girls Soccer | North Branford/Hale Ray | Away - North Branford HS [Directions] | Cancelled | Cancelled | |
| Fri., 8/28 | V Boys Cross Country | Kettletown State Park Camping | Away | TBA | ||
| Fri., 8/28 | V Girls Cross Country | Kettletown State Park Camping | Away - Kettletown State Park | TBA | ||
| Sun., 8/30 | V Boys Soccer | Rye (NY) (Scrim.) | Home - Portland HS [Directions] | 4:00 p.m. | Boys & Girls | |
| Sun., 8/30 | V Girls Soccer | Rye (NY) (Scrim.) | Home - Portland HS [Directions] | 4:00 p.m. | Boys & Girls | |
| Mon., 8/31 | V Football | Sacred Heart (Scrim.) | Away - Sacred Heart HS | 3:30 p.m. | ||
| Mon., 8/31 | V Boys Soccer | Middletown (Scrim.) | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Tue., 9/1 | V Girls Soccer | Branford (Scrim.) | Away - Branford HS-Turf Field [Directions] | 6:00 p.m. | ||
| Thu., 9/3 | V Girls Soccer | SMSA (Scrim.) | Home - Portland HS [Directions] | 4:00 p.m. | JV scrimmage | |
| Fri., 9/4 | V Football | Granby/Canton (Scrim.) | Away - Granby Memorial HS [Directions] | 6:00 p.m. | ||
| Fri., 9/4 | JV Football | Granby/Canton (Scrim.) | Away - Granby Memorial HS [Directions] | 6:00 p.m. | ||
| Fri., 9/4 | V Boys Soccer | Goodwin Tech (Scrim.) | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 9/8 | V Boys Cross Country | Glastonbury (Scrim.) | Away - JB Williams Park [Directions] | 3:45 p.m. | ||
| Tue., 9/8 | V Boys Soccer | Windham (Scrim.) | Away [Directions] | 3:45 p.m. | ||
| Tue., 9/8 | V Girls Cross Country | Glastonbury (Scrim.) | Away - J B Williams Park [Directions] | 3:45 p.m. | ||
| Wed., 9/9 | V Girls Soccer | Windsor Locks (Scrim.) | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Fri., 9/11 | V Boys Cross Country | Blue Dragon Invitational | Away - Veteran's Park, Middletown | 3:30 p.m. | ||
| Fri., 9/11 | V Boys Soccer | Westbrook | Home - Portland HS [Directions] | 5:00 p.m. | W 4-1 | Non-Seeded |
| Fri., 9/11 | V Girls Cross Country | Blue Dragon Invitational | Away | 3:30 p.m. | ||
| Fri., 9/11 | V Girls Soccer | Westbrook | Home - Portland HS [Directions] | 7:00 p.m. | W 2-0 | |
| Sat., 9/12 | V Football | Coginchaug/Hale Ray/East Hampton | Away - CRHS Stadium Field & Track [Directions] | 1:00 p.m. | W 20-14 | |
| Mon., 9/14 | JV Boys Soccer | Westbrook | Away - Westbrook HS [Directions] | 3:45 p.m. | ||
| Tue., 9/15 | V Boys Cross Country | Highlander Invitational | Home - Camp Ingersoll [Directions] | 3:45 p.m. | ||
| Tue., 9/15 | V Girls Cross Country | Highlander Invitational | Home - Camp Ingersoll [Directions] | 3:45 p.m. | ||
| Tue., 9/15 | V Girls Swimming and Diving | Middletown | Away - Middletown HS [Directions] | 4:00 p.m. | L | |
| Wed., 9/16 | V Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | L 1-2 | |
| Wed., 9/16 | JV Girls Soccer | Coginchaug | Away - Field #2 - Middle Field @ CRHS [Directions] | 3:45 p.m. | ||
| Thu., 9/17 | V Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | T 1-1 | |
| Fri., 9/18 | V Football | Stafford/East Windsor/Somers | Home - Pierson Park, Cromwell [Directions] | 6:30 p.m. | W 39-7 | |
| Fri., 9/18 | V Boys Soccer | Hale Ray | Away - Hale-Ray HS, Nevers Field [Directions] | 7:00 p.m. | W 2-0 | |
| Fri., 9/18 | V Girls Soccer | Hale Ray | Away - Hale-Ray HS, Nevers Field [Directions] | 5:00 p.m. | W 4-0 | |
| Fri., 9/18 | JV Girls Soccer | Haddam-Killingworth | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Fri., 9/18 | V Girls Swimming and Diving | East Catholic | Home - Rocky Hill HS [Directions] | 3:45 p.m. | L | |
| Sat., 9/19 | JV Football | Stafford/East Windsor/Somers | Away - Stafford High, Lighted field behind school [Directions] | 10:30 a.m. | ||
| Sat., 9/19 | JV Boys Soccer | Hale Ray | Home - Portland HS [Directions] | 10:30 a.m. | ||
| Sat., 9/19 | V Girls Soccer | New Fairfield | Home - Portland HS [Directions] | 11:00 a.m. | L 1-2 | |
| Mon., 9/21 | V Boys Soccer | Ellis Tech | Away - Ellis Tech Athletic Field [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 9/22 | V Boys Cross Country | Run to the Sun Invitational | Away - Coginchaug HS | 3:30 p.m. | ||
| Tue., 9/22 | V Girls Cross Country | Run to the Sun Invitational | Away - Coginchaug HS | 3:30 p.m. | ||
| Tue., 9/22 | V Girls Soccer | Old Saybrook | Away - Old Saybrook HS [Directions] | 3:45 p.m. | T 2-2 | |
| Tue., 9/22 | V Girls Swimming and Diving | E.O. Smith/Tolland | Away - Mansfield Community Center Pool [Directions] | 4:00 p.m. | L | |
| Thu., 9/24 | V Boys Soccer | Old Saybrook | Away - Old Saybrook HS [Directions] | 3:45 p.m. | L 0-5 | |
| Fri., 9/25 | V Boys Cross Country | Bellringer Invitational | Away - East Hampton HS | 3:45 p.m. | ||
| Fri., 9/25 | JV Boys Soccer | Old Saybrook | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Fri., 9/25 | V Girls Cross Country | Bellringer Invitational | Away - East Hampton HS | 3:45 p.m. | ||
| Fri., 9/25 | V Girls Soccer | Morgan | Home - Portland HS [Directions] | 6:00 p.m. | L 1-4 | |
| Fri., 9/25 | V Girls Swimming and Diving | Manchester/Bacon/Bolton/Coventry/Rockville | Home - Rocky Hill HS [Directions] | 3:45 p.m. | W | |
| Sat., 9/26 | V Football | Ellington | Away - Ellington HS [Directions] | 1:00 p.m. | L 20-34 | |
| Sat., 9/26 | V Boys Soccer | Morgan | Home - Portland HS [Directions] | 10:00 a.m. | L 1-7 | |
| Sat., 9/26 | JV Girls Soccer | Morgan | Away - Morgan HS [Directions] | 10:30 a.m. | ||
| Mon., 9/28 | JV Football | Ellington | Home - Pierson Park, Cromwell [Directions] | 4:00 p.m. | ||
| Mon., 9/28 | JV Boys Soccer | Morgan | Away - Morgan HS [Directions] | Cancelled | Cancelled | |
| Mon., 9/28 | V Girls Soccer | Westbrook | Away - Westbrook HS [Directions] | 3:45 p.m. | W 7-1 | |
| Tue., 9/29 | V Boys Cross Country | Shoreline Conference Small Schools | Away - East Hampton HS | 3:45 p.m. | ||
| Tue., 9/29 | V Boys Soccer | Westbrook | Away - Westbrook HS [Directions] | 3:45 p.m. | T 0-0 | |
| Tue., 9/29 | V Girls Cross Country | Shoreline Conference Small Schools | Away - East Hampton HS | 3:45 p.m. | ||
| Tue., 9/29 | JV Girls Soccer | Westbrook | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Wed., 9/30 | V Girls Swimming and Diving | Southington | Away - Southington YMCA [Directions] | 3:45 p.m. | L | |
| Thu., 10/1 | V Girls Soccer | East Hampton | Home - Portland HS [Directions] | 6:00 p.m. | L 1-2 | |
| Fri., 10/2 | V Boys Cross Country | Woods Trail Run, Thetford, VT | Away - Thetford, VT | TBA | racing on 10/3/15 | |
| Fri., 10/2 | V Football | Coventry/Windham Tech/Bolton/Lyman | Away - Larry A. Pietrantonio Athletic Field Complex [Directions] | 7:00 p.m. | W Forfeit | |
| Fri., 10/2 | V Girls Cross Country | Woods Trail Run | Away - Thetford, VT | TBA | racing on 10/3/15 | |
| Fri., 10/2 | V Girls Swimming and Diving | East Hartford | Away - East Hartford HS [Directions] | 3:45 p.m. | L | |
| Sat., 10/3 | JV Football | Coventry/Windham Tech/Bolton/Lyman | Home - Pierson Park, Cromwell [Directions] | Cancelled | Cancelled | |
| Sat., 10/3 | JV Boys Soccer | East Hampton | Away - East Hampton HS [Directions] | Cancelled | Cancelled | |
| Mon., 10/5 | V Boys Soccer | Old Lyme | Home - Portland HS [Directions] | 3:45 p.m. | L 0-3 | |
| Tue., 10/6 | V Boys Soccer | Lyman Memorial | Home - Portland HS [Directions] | 5:00 p.m. | L 0-4 | |
| Tue., 10/6 | V Girls Soccer | Old Lyme | Home - Portland HS [Directions] | 7:00 p.m. | L 1-4 | |
| Tue., 10/6 | V Girls Swimming and Diving | Windsor | Home - Rocky Hill HS [Directions] | 3:45 p.m. | L | |
| Thu., 10/8 | V Boys Soccer | North Branford | Home - Portland HS [Directions] | 7:00 p.m. | W 5-0 | |
| Thu., 10/8 | V Girls Soccer | North Branford/Hale Ray | Home - Portland HS [Directions] | 5:00 p.m. | W 2-0 | |
| Sat., 10/10 | V Boys Cross Country | Wickham Invitational | Away | 9:00 a.m. | ||
| Sat., 10/10 | JV Boys Soccer | North Branford | Home - Portland HS [Directions] | 10:30 a.m. | ||
| Sat., 10/10 | V Girls Cross Country | Wickham Invitational | Away | 9:00 a.m. | ||
| Sat., 10/10 | JV Girls Soccer | Hale Ray | Away - Hale-Ray HS [Directions] | 11:00 a.m. | ||
| Mon., 10/12 | V Boys Soccer | Coginchaug | Away - CRHS Stadium Field & Track [Directions] | 3:45 p.m. | L 1-4 | |
| Mon., 10/12 | JV Girls Soccer | Old Saybrook | Home - Portland HS [Directions] | 10:30 a.m. | ||
| Tue., 10/13 | V Boys Cross Country | Shoreline Conference Mega Meet | Away - Morgan HS | 3:45 p.m. | ||
| Tue., 10/13 | V Girls Cross Country | Shoreline Conference Mega Meet | Away - Morgan HS | 3:45 p.m. | ||
| Tue., 10/13 | V Girls Soccer | Coginchaug | Away - CRHS Stadium Field & Track [Directions] | 3:45 p.m. | L 0-1 | |
| Wed., 10/14 | JV Girls Soccer | Coginchaug | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Thu., 10/15 | V Boys Soccer | Valley Regional | Away - VRHS Football Field [Directions] | 3:45 p.m. | L 1-5 | |
| Fri., 10/16 | V Football | North Branford | Home - Pierson Park, Cromwell [Directions] | 6:00 p.m. | W 14-7 | |
| Fri., 10/16 | JV Boys Soccer | Valley Regional | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Fri., 10/16 | V Girls Soccer | Valley Regional | Away - VRHS Football Field [Directions] | 3:45 p.m. | T 0-0 | |
| Fri., 10/16 | V Girls Swimming and Diving | EnricoFermi | Home - Rocky Hill HS [Directions] | 4:00 p.m. | W | |
| Sat., 10/17 | JV Football | Enfield | Away - Enfield HS [Directions] | 9:30 a.m. | ||
| Sat., 10/17 | V Boys Soccer | East Hampton | Home - Portland HS [Directions] | 7:00 p.m. | L 1-2 | |
| Sat., 10/17 | JV Girls Soccer | Valley Regional | Home - Portland HS [Directions] | 10:32 a.m. | ||
| Mon., 10/19 | V Boys Soccer | Cromwell | Home - Portland HS [Directions] | 5:00 p.m. | L 3-4 | |
| Mon., 10/19 | V Girls Soccer | Cromwell | Home - Portland HS [Directions] | 7:00 p.m. | T 1-1 | |
| Tue., 10/20 | V Girls Swimming and Diving | Bulkeley/HMTCA/Weaver | Away - Bulkeley HS Pool [Directions] | 4:00 p.m. | W | |
| Wed., 10/21 | JV Girls Soccer | Cromwell | Away - Cromwell HS [Directions] | 3:45 p.m. | ||
| Thu., 10/22 | V Boys Cross Country | Shoreline Conference Championship Meet | Away - Morgan HS | 2:30 p.m. | ||
| Thu., 10/22 | V Football | SMSA Coop | Home - Pierson Park, Cromwell [Directions] | 6:00 p.m. | W 48-13 | |
| Thu., 10/22 | V Boys Soccer | East Hampton | Away - East Hampton HS [Directions] | 6:00 p.m. | W 2-1 | Non-Seeded |
| Thu., 10/22 | V Girls Cross Country | Shoreline Conference Championship Meet | Away - Morgan HS | 2:30 p.m. | ||
| Fri., 10/23 | JV Boys Soccer | East Hampton | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Fri., 10/23 | V Girls Soccer | East Hampton | Away - East Hampton HS [Directions] | 7:30 p.m. | L 1-3 | |
| Fri., 10/23 | V Girls Swimming and Diving | Wethersfield | Away - Wethersfield HS [Directions] | 5:00 p.m. | L | |
| Sat., 10/24 | JV Football | SMSA Coop | Home - Pierson Park, Cromwell [Directions] | 10:30 a.m. | ||
| Sat., 10/24 | V Boys Soccer | Old Saybrook | Home - Portland HS [Directions] | 6:00 p.m. | W 3-2 | Non-Seeded |
| Sat., 10/24 | JV Girls Soccer | East Hampton | Home - Portland HS [Directions] | 10:30 a.m. | ||
| Mon., 10/26 | V Girls Soccer | Old Saybrook | Home - Portland HS [Directions] | 7:00 p.m. | W 3-0 | |
| Tue., 10/27 | V Boys Cross Country | JV Invitational | Away - Old Saybrook HS | 3:30 p.m. | ||
| Tue., 10/27 | JV Boys Soccer | Old Saybrook | Away - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Tue., 10/27 | V Girls Cross Country | JV Invitational | Away - Old Saybrook HS | 3:30 p.m. | ||
| Tue., 10/27 | JV Girls Soccer | Old Saybrook | Away - Old Saybrook HS [Directions] | 3:45 p.m. | ||
| Tue., 10/27 | V Girls Swimming and Diving | Maloney/Platt | Away - Platt HS [Directions] | 3:45 p.m. | W | |
| Thu., 10/29 | V Girls Soccer | St. Paul Catholic | Home - Portland HS [Directions] | 6:00 p.m. | L 3-4 | |
| Fri., 10/30 | V Girls Swimming and Diving | Plainville | Home - Rocky Hill HS [Directions] | 4:00 p.m. | T | |
| Sat., 10/31 | V Boys Cross Country | Class S State Championship | Away - Wickham Park | 9:15 a.m. | ||
| Sat., 10/31 | V Football | Gilbert/Northwestern/Housy | Away - Gilbert [Directions] | 1:00 p.m. | W 13-9 | |
| Sat., 10/31 | V Girls Cross Country | Class S State Championship | Away | 9:15 a.m. | ||
| Mon., 11/2 | V Boys Cross Country | Shoreline Freshman Championship Meet | Away - Valley Regional HS | 3:30 p.m. | ||
| Mon., 11/2 | JV Football | Gilbert/Northwestern/Housy | Home - Pierson Park, Cromwell [Directions] | 3:30 p.m. | ||
| Mon., 11/2 | V Girls Cross Country | Shoreline Freshman Championship Meet | Away - Valley Regional HS | 3:30 p.m. | ||
| Thu., 11/5 | V Girls Swimming and Diving | CCC East Diving Championships | Away - Windsor HS | 5:00 p.m. | ||
| Fri., 11/6 | V Boys Cross Country | State Open Championship | Away - Wickham Park | TBA | ||
| Fri., 11/6 | V Girls Cross Country | State Open Championship | Away - Wickham Park | TBA | ||
| Fri., 11/6 | V Girls Swimming and Diving | CCC East Swimming Championships | Away - Wethersfield HS | 4:30 p.m. | ||
| Sat., 11/7 | V Football | Windsor Locks/Suffield/East Granby | Away - Windsor Locks HS [Directions] | 2:00 p.m. | W 63-18 | |
| Mon., 11/9 | JV Football | Windsor Locks/Suffield/East Granby | Home - Pierson Park, Cromwell [Directions] | Cancelled | Cancelled | |
| Mon., 11/9 | V Girls Soccer | International/AAE | Away - MLC [Directions] | 2:00 p.m. | W 4-0 | |
| Tue., 11/10 | V Boys Soccer | Old Lyme | Away - Old Lyme HS [Directions] | 2:00 p.m. | ||
| Wed., 11/11 | V Girls Soccer | Parish Hill | Away [Directions] | 2:00 p.m. | W 3-0 | |
| Fri., 11/13 | V Boys Cross Country | New England Championship | Away | TBA | ||
| Fri., 11/13 | V Football | Creed | Home - Pierson Park, Cromwell [Directions] | 6:00 p.m. | W 33-12 | Senior Night |
| Fri., 11/13 | V Girls Cross Country | New England Championship | Away - TBA | TBA | ||
| Fri., 11/13 | V Girls Soccer | Notre Dame-Fairfield | Away - Veteran's Park - Bridgeport [Directions] | 2:00 p.m. | ||
| Sat., 11/14 | JV Football | Creed | Away - Wilbur Cross Athletic Complex | 12:30 p.m. | Senior Night | |
| Sat., 11/14 | V Girls Swimming and Diving | State Trials | Away - Plainville HS | 2:00 p.m. | ||
| Tue., 11/17 | V Girls Swimming and Diving | State Finals | Away - Wesleyan University | 7:00 p.m. | ||
| Sat., 11/21 | JV Football | Rocky Hill | Away - Rocky Hill HS [Directions] | Cancelled | Cancelled | |
| Thu., 11/26 | V Football | Rocky Hill | Away - Rocky Hill HS [Directions] | 10:00 a.m. | L 7-9 | Shunpike Showdown |
| Fri., 12/4 | V Girls Basketball | Choate Rosemary Hall (Scrim.) | Away | 7:00 p.m. | ||
| Sat., 12/5 | V Wrestling | Bacon Academy (Scrim.) | Away - Jack Jackter Intermediate School [Directions] | 9:00 a.m. | ||
| Wed., 12/9 | V Boys Basketball | Lyman Hall (Scrim.) | Home - Portland HS [Directions] | 5:00 p.m. | ||
| Sat., 12/12 | V Boys Basketball | Whitney Tech (Scrim.) | Home - Portland HS [Directions] | 9:00 a.m. | ||
| Sat., 12/12 | JV Boys Basketball | Whitney Tech (Scrim.) | Home - Portland HS [Directions] | 9:00 a.m. | ||
| Sat., 12/12 | V Wrestling | Bacon Academy, Middletown (Scrim.) | Away - Jack Jackter Intermediate School [Directions] | 9:00 a.m. | ||
| Tue., 12/15 | V Girls Basketball | Old Lyme | Home - Portland HS [Directions] | 7:00 p.m. | W 42-38 | |
| Tue., 12/15 | JV Girls Basketball | Old Lyme | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Wed., 12/16 | V Boys Basketball | Rocky Hill (Scrim.) | Away - Rocky Hill HS [Directions] | 3:00 p.m. | ||
| Wed., 12/16 | V Boys Indoor Track | SLC League Dev Meet | Away - Hillhouse | 4:30 p.m. | ||
| Wed., 12/16 | V Wrestling | Joel Barlow | Away - Upper Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/16 | V Girls Indoor Track | SLC League Dev Meet | Away - Hillhouse | 3:30 p.m. | ||
| Thu., 12/17 | V Boys Swimming and Diving | Wethersfield (Scrim.) | Away - Wethersfield HS [Directions] | 3:45 p.m. | ||
| Fri., 12/18 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | 7:00 p.m. | W 44-34 | |
| Fri., 12/18 | JV Girls Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Sat., 12/19 | V Wrestling | Pomperaug Tournament | Away - Pomperaug HS | 9:00 a.m. | ||
| Mon., 12/21 | V Boys Basketball | Creed | Away - Fair Haven School | 7:30 p.m. | L 61-47 | |
| Mon., 12/21 | JV Boys Basketball | Creed | Away - Fair Haven School | 6:00 p.m. | ||
| Mon., 12/21 | V Girls Basketball | Creed | Home - Portland HS [Directions] | 7:00 p.m. | W 55-46 | |
| Mon., 12/21 | JV Girls Basketball | Creed | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Wed., 12/23 | V Boys Basketball | East Hampton | Home - Portland HS [Directions] | 7:00 p.m. | L 51-73 | |
| Wed., 12/23 | JV Boys Basketball | East Hampton | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Wed., 12/23 | V Wrestling | Ellis Tech | Away - Ellis Tech Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 12/23 | V Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | 7:00 p.m. | L 21-72 | |
| Wed., 12/23 | JV Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | 5:30 p.m. | ||
| Mon., 12/28 | V Wrestling | Danbury Tournament | Away - Danbury HS | 10:00 a.m. | ||
| Tue., 12/29 | FR Boys Basketball | Morgan | Home - Portland HS [Directions] | 10:30 a.m. | ||
| Wed., 12/30 | V Boys Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | 7:00 p.m. | L 48-66 | |
| Wed., 12/30 | JV Boys Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Wed., 12/30 | V Boys Swimming and Diving | Middletown | Away - Middletown HS [Directions] | 9:00 a.m. | L | |
| Wed., 12/30 | V Girls Basketball | Old Saybrook | Home - Portland HS [Directions] | 7:00 p.m. | W 55-30 | |
| Wed., 12/30 | JV Girls Basketball | Old Saybrook | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Sat., 1/2 | V Boys Basketball | Morgan | Home - Portland HS [Directions] | 1:30 p.m. | W 58-52 | |
| Sat., 1/2 | JV Boys Basketball | Morgan | Home - Portland HS [Directions] | 12:00 p.m. | ||
| Sat., 1/2 | V Boys Indoor Track | SLC Coaches Invitational | Away - Hillhouse | 10:00 a.m. | ||
| Sat., 1/2 | V Wrestling | South Windsor Duals | Away - South Windsor HS | 9:00 a.m. | ||
| Sat., 1/2 | V Girls Basketball | Morgan | Away - Morgan HS [Directions] | 1:15 p.m. | L 21-78 | |
| Sat., 1/2 | JV Girls Basketball | Morgan | Away - Morgan HS [Directions] | 12:00 p.m. | ||
| Sat., 1/2 | V Girls Indoor Track | SLC Coaches Invitational | Away - Hillhouse | 10:00 a.m. | ||
| Mon., 1/4 | FR Boys Basketball | Westbrook | Home - Portland HS [Directions] | 7:00 p.m. | ||
| Tue., 1/5 | V Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 7:00 p.m. | L 70-72 | |
| Tue., 1/5 | JV Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Tue., 1/5 | V Boys Swimming and Diving | East Hartford | Away - East Hartford HS [Directions] | 3:45 p.m. | L | |
| Tue., 1/5 | V Girls Basketball | Haddam-Killingworth | Home - Portland HS [Directions] | 7:00 p.m. | W 40-39 | |
| Tue., 1/5 | JV Girls Basketball | Haddam-Killingworth | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Wed., 1/6 | FR Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Wed., 1/6 | V Wrestling | New Canaan | Home - Portland HS [Directions] | 6:00 p.m. | ||
| Fri., 1/8 | V Boys Basketball | Valley Regional | Away - Valley Regional HS [Directions] | 7:00 p.m. | L 52-55 | |
| Fri., 1/8 | JV Boys Basketball | Valley Regional | Away - Valley Regional HS [Directions] | 5:30 p.m. | ||
| Fri., 1/8 | V Boys Swimming and Diving | East Catholic/Platt tri-meet | Home - Rocky Hill HS [Directions] | 3:45 p.m. | W | |
| Fri., 1/8 | V Girls Basketball | Valley Regional | Home - Portland HS [Directions] | 7:00 p.m. | L 40-42 | |
| Fri., 1/8 | JV Girls Basketball | Valley Regional | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Sat., 1/9 | FR Boys Basketball | North Branford | Home - Portland HS [Directions] | 10:30 a.m. | ||
| Sat., 1/9 | V Wrestling | GHO Tournament | Away | 9:00 a.m. | ||
| Tue., 1/12 | V Boys Indoor Track | SLC Meet #1 | Away - Hillhouse | 4:30 p.m. | ||
| Tue., 1/12 | V Girls Indoor Track | SLC Meet #1 | Away - Hillhouse | 3:30 p.m. | ||
| Wed., 1/13 | V Wrestling | Platt Tech | Home - Portland HS [Directions] | 5:00 p.m. | ||
| Fri., 1/15 | V Boys Basketball | Old Lyme | Home - Portland HS [Directions] | 7:00 p.m. | L 43-59 | |
| Fri., 1/15 | JV Boys Basketball | Old Lyme | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Fri., 1/15 | V Boys Swimming and Diving | Plainville Boys Swimming | Home - Rocky Hill HS [Directions] | 4:00 p.m. | W | |
| Fri., 1/15 | V Girls Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 7:00 p.m. | L 50-56 | |
| Fri., 1/15 | JV Girls Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Sat., 1/16 | FR Boys Basketball | Valley Regional | Away - Valley Regional HS [Directions] | 10:30 a.m. | ||
| Sat., 1/16 | V Boys Indoor Track | H-K Inv. | Away - Hillhouse | 10:00 a.m. | ||
| Sat., 1/16 | V Wrestling | Casey Yates Tournament | Away - Lyman Memorial HS | 9:00 a.m. | ||
| Sat., 1/16 | V Girls Indoor Track | H-K Inv. | Away - Hillhouse | 10:00 a.m. | ||
| Tue., 1/19 | V Boys Basketball | North Branford | Away - North Branford HS [Directions] | 5:30 p.m. | L 52-61 | |
| Tue., 1/19 | JV Boys Basketball | North Branford | Away - North Branford HS [Directions] | 4:00 p.m. | ||
| Tue., 1/19 | V Boys Swimming and Diving | Bulkeley Cooperative Swim Team | Away - Bulkeley HS Pool [Directions] | 4:00 p.m. | W | |
| Tue., 1/19 | V Girls Basketball | North Branford | Home - Portland HS [Directions] | 5:30 p.m. | W 46-33 | |
| Tue., 1/19 | JV Girls Basketball | North Branford | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Wed., 1/20 | FR Boys Basketball | East Hampton | Home - Portland HS [Directions] | 7:00 p.m. | ||
| Wed., 1/20 | V Wrestling | East Catholic | Away - Rev. Robert Saunders Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/20 | V Wrestling | East Catholic | Away [Directions] | 6:00 p.m. | ||
| Thu., 1/21 | V Boys Basketball | Westbrook | Away - Westbrook HS [Directions] | 7:00 p.m. | L 60-71 | |
| Thu., 1/21 | JV Boys Basketball | Westbrook | Away - Westbrook HS [Directions] | 5:30 p.m. | ||
| Thu., 1/21 | V Girls Basketball | Windsor Locks | Away - Windsor Locks HS [Directions] | 7:00 p.m. | L 20-29 | |
| Thu., 1/21 | JV Girls Basketball | Windsor Locks | Away - Windsor Locks HS [Directions] | 5:30 p.m. | ||
| Fri., 1/22 | V Boys Indoor Track | SLC Meet #2 | Away - Hillhouse | 4:30 p.m. | ||
| Fri., 1/22 | V Boys Swimming and Diving | Suffield | Home - Rocky Hill HS [Directions] | 4:00 p.m. | W | |
| Fri., 1/22 | V Girls Indoor Track | SLC Meet #2 | Away - Hillhouse | 3:30 p.m. | ||
| Sat., 1/23 | V Wrestling | New Milford Tournament | Away - New Milford HS | 9:00 a.m. | ||
| Tue., 1/26 | V Boys Basketball | Cromwell | Home - Portland HS [Directions] | 7:00 p.m. | L 37-61 | |
| Tue., 1/26 | JV Boys Basketball | Cromwell | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Tue., 1/26 | V Boys Swimming and Diving | Avon | Away - CCSU [Directions] | 3:45 p.m. | L | |
| Tue., 1/26 | V Girls Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 7:00 p.m. | L 17-66 | |
| Tue., 1/26 | JV Girls Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 5:30 p.m. | ||
| Wed., 1/27 | V Wrestling | RHAM | Home - Portland HS [Directions] | 6:00 p.m. | ||
| Fri., 1/29 | V Boys Basketball | Coginchaug | Home - Portland HS [Directions] | 7:00 p.m. | L 50-62 | |
| Fri., 1/29 | JV Boys Basketball | Coginchaug | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Fri., 1/29 | FR Boys Basketball | Coginchaug | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Fri., 1/29 | V Boys Swimming and Diving | Manchester/RHAM | Away - MHS POOL [Directions] | 3:45 p.m. | W | |
| Fri., 1/29 | V Girls Basketball | Coginchaug | Away - Maynard Stender Gymnasium @ CRHS [Directions] | 7:00 p.m. | L 34-45 | |
| Fri., 1/29 | JV Girls Basketball | Coginchaug | Away - Maynard Stender Gymnasium @ CRHS [Directions] | 5:30 p.m. | ||
| Sat., 1/30 | FR Boys Basketball | Creed | Away - Fair Haven School | 12:00 p.m. | ||
| Sat., 1/30 | V Wrestling | Portland Highlander Invitational | Home - Portland HS [Directions] | 9:00 a.m. | ||
| Mon., 2/1 | V Girls Basketball | Westbrook | Home - Portland HS [Directions] | 7:00 p.m. | L 36-46 | |
| Mon., 2/1 | JV Girls Basketball | Westbrook | Home - Portland HS [Directions] | Cancelled | Cancelled | |
| Tue., 2/2 | V Boys Basketball | Hale Ray | Home - Portland HS [Directions] | 7:00 p.m. | W 54-49 | |
| Tue., 2/2 | JV Boys Basketball | Hale Ray | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Tue., 2/2 | V Boys Swimming and Diving | Wethersfield | Away - Wethersfield HS [Directions] | 5:00 p.m. | L | |
| Tue., 2/2 | V Girls Basketball | Hale Ray | Home - Portland HS [Directions] | 5:30 p.m. | W 43-29 | |
| Wed., 2/3 | FR Boys Basketball | Valley Regional | Home - Portland HS [Directions] | 7:00 p.m. | ||
| Thu., 2/4 | V Wrestling | Morgan | Away - Morgan HS [Directions] | 6:00 p.m. | ||
| Fri., 2/5 | JV Girls Basketball | Westbrook | Away - Westbrook HS [Directions] | 5:30 p.m. | ||
| Sat., 2/6 | FR Boys Basketball | North Branford | Away - North Branford HS [Directions] | 3:00 p.m. | ||
| Sat., 2/6 | V Boys Indoor Track | SLC Conference Champs | Away - Hillhouse | 10:00 a.m. | ||
| Sat., 2/6 | V Wrestling | Bacon Academy | Away [Directions] | 9:00 a.m. | ||
| Sat., 2/6 | V Girls Basketball | Westbrook | Away - Westbrook HS [Directions] | 5:00 p.m. | L 31-43 | |
| Sat., 2/6 | V Girls Indoor Track | SLC Conference Champs | Away - Hillhouse | 10:00 a.m. | ||
| Mon., 2/8 | JV Boys Basketball | Creed | Home - Portland HS [Directions] | Cancelled | Cancelled | |
| Tue., 2/9 | V Boys Swimming and Diving | Hartford Public | Away - Hartford Public HS [Directions] | 4:00 p.m. | W | |
| Wed., 2/10 | V Boys Basketball | Westbrook | Home - Portland HS [Directions] | 7:00 p.m. | L 51-70 | |
| Wed., 2/10 | JV Boys Basketball | Westbrook | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Wed., 2/10 | V Wrestling | Haddam-Killingworth | Away - Haddam Killingworth MS in Killingworth [Directions] | 6:00 p.m. | ||
| Thu., 2/11 | V Boys Basketball | Creed | Home - Portland HS [Directions] | 5:30 p.m. | L 47-63 | |
| Thu., 2/11 | V Boys Swimming and Diving | Newington | Home - Rocky Hill HS [Directions] | 3:45 p.m. | L | |
| Thu., 2/11 | V Girls Basketball | Windsor Locks | Home - Portland HS [Directions] | 7:00 p.m. | L 26-45 | |
| Thu., 2/11 | JV Girls Basketball | Windsor Locks | Home - Portland HS [Directions] | Cancelled | Cancelled | |
| Fri., 2/12 | V Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 5:30 p.m. | W 57-38 | |
| Fri., 2/12 | V Boys Indoor Track | Class S State Meet | Away - Hillhouse | 4:00 p.m. | ||
| Fri., 2/12 | V Girls Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 7:00 p.m. | W 38-20 | |
| Fri., 2/12 | JV Girls Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 4:00 p.m. | ||
| Fri., 2/12 | V Girls Indoor Track | Class S State Meet | Away - Hillhouse | 4:00 p.m. | ||
| Sat., 2/13 | FR Boys Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | 10:30 a.m. | ||
| Tue., 2/16 | FR Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 3:00 p.m. | ||
| Tue., 2/16 | V Girls Basketball | Creed | Away - Truman School | 6:30 p.m. | W 46-26 | |
| Tue., 2/16 | JV Girls Basketball | Creed | Away - Truman School | 5:00 p.m. | ||
| Wed., 2/17 | V Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 7:00 p.m. | L 49-79 | |
| Wed., 2/17 | JV Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 5:30 p.m. | ||
| Wed., 2/17 | V Boys Swimming and Diving | Simsbury | Home - Rocky Hill HS [Directions] | 4:00 p.m. | W | |
| Wed., 2/17 | V Girls Basketball | East Hampton | Home - Portland HS [Directions] | 7:00 p.m. | L 24-34 | |
| Wed., 2/17 | JV Girls Basketball | East Hampton | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Fri., 2/19 | V Boys Basketball | Whitney Tech | Home - Portland HS [Directions] | 7:00 p.m. | W 74-70 | |
| Fri., 2/19 | JV Boys Basketball | Whitney Tech | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Fri., 2/19 | V Boys Swimming and Diving | E.O. Smith - Tolland Hammerheads | Home - Rocky Hill HS [Directions] | 3:45 p.m. | L | |
| Fri., 2/19 | V Wrestling | State Tournament | Away - Plainville HS | 3:00 p.m. | ||
| Sat., 2/20 | FR Boys Basketball | Westbrook | Away - Westbrook HS [Directions] | 9:00 a.m. | ||
| Sat., 2/20 | V Boys Indoor Track | CT. State Open Meet | Away - Hillhouse | 12:00 p.m. | ||
| Sat., 2/20 | V Wrestling | Plainville HS | Away - Plainville HS | 9:00 a.m. | ||
| Sat., 2/20 | V Girls Indoor Track | CT. State Open Meet | Away - Hillhouse | 12:00 p.m. | ||
| Mon., 2/22 | V Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 7:00 p.m. | L 42-81 | |
| Mon., 2/22 | JV Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Wed., 2/24 | V Boys Basketball | Old Saybrook | Home - Portland HS [Directions] | 7:00 p.m. | L 70-46 | |
| Wed., 2/24 | JV Boys Basketball | Old Saybrook | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Wed., 2/24 | FR Boys Basketball | Old Saybrook | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Thu., 2/25 | V Boys Swimming and Diving | Northwest Catholic | Home - Rocky Hill HS [Directions] | 4:00 p.m.. | W | |
| Fri., 2/26 | V Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 7:00 p.m. | L 64-65 | |
| Fri., 2/26 | JV Boys Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 5:30 p.m. | ||
| Fri., 2/26 | V Boys Indoor Track | New England Meet | Away - Boston | Cancelled | Cancelled | |
| Fri., 2/26 | V Wrestling | States | Away - Hill House New haven | 2:00 p.m. | ||
| Fri., 2/26 | V Girls Indoor Track | New England Meet | Away - Boston | Cancelled | Cancelled | |
| Sat., 2/27 | V Wrestling | States | Away | 8:00 a.m. | ||
| Mon., 2/29 | V Girls Basketball | Windham Tech | Away - Windham Tech Main Gym [Directions] | 5:30 p.m. | W 62-42 | |
| Thu., 3/3 | V Boys Swimming and Diving | CCC East Diving Championships | Home - Rocky Hill HS [Directions] | 6:00 p.m. | ||
| Fri., 3/4 | V Boys Swimming and Diving | CCC East Swimming Championships | Away - Wethersfield HS | 4:30 p.m. | ||
| Fri., 3/4 | V Girls Basketball | Windsor Locks | Away [Directions] | 7:00 p.m. | L 58-25 | |
| Sat., 3/12 | V Boys Swimming and Diving | Class S State Trials | Away - Plainville HS | 3:30 p.m. | ||
| Tue., 3/15 | V Boys Swimming and Diving | Class S State Finals | Away - Wesleyan University | 6:00 p.m. | ||
| Sat., 3/26 | V Baseball | Old Lyme (Scrim.) | Away - Old Lyme HS [Directions] | 11:00 a.m. | doubleheader: games at 11:00 and 1:00 p.m. | |
| Tue., 3/29 | V Baseball | Haddam-Killingworth (Scrim.) | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | ||
| Wed., 3/30 | V Boys Golf | South Windsor (Scrim.) | Away - Top Stone Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 3/30 | V Softball | Valley Regional (Scrim.) | Home - Nolan Field Maple Ave. off Airline Ave [Directions] | 3:45 p.m. | ||
| Thu., 3/31 | V Baseball | East Windsor/International (Scrim.) | Away - East Windsor HS [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Boys Outdoor Track | Morgan, Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | Cancelled | Cancelled | |
| Tue., 4/5 | V Girls Outdoor Track | Haddam-Killingworth | Away - HK [Directions] | Cancelled | Cancelled | |
| Wed., 4/6 | V Boys Outdoor Track | Haddam-Killingworth | Away - HK [Directions] | 3:30 p.m. | ||
| Wed., 4/6 | V Boys Tennis | Morgan | Away - Morgan HS [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 4/6 | V Girls Outdoor Track | Haddam-Killingworth | Away - HK [Directions] | 3:30 p.m. | ||
| Wed., 4/6 | V Girls Tennis | Morgan | Home - Portland HS [Directions] | 3:45 p.m. | L 2-5 | |
| Fri., 4/8 | V Baseball | Old Saybrook | Home - Portland HS [Directions] | 3:45 p.m. | W 11-5 | |
| Fri., 4/8 | V Boys Tennis | Westbrook | Home - Portland HS [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 4/8 | V Softball | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | W 24-3 | |
| Fri., 4/8 | V Girls Tennis | Westbrook | Away - Westbrook HS [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 4/9 | JV Baseball | Old Saybrook | Away - Old Saybrook HS [Directions] | 11:00 a.m. | ||
| Sat., 4/9 | V Boys Outdoor Track | East Hampton | Away [Directions] | 9:30 a.m. | ||
| Sat., 4/9 | V Girls Outdoor Track | East Hampton | Away [Directions] | 9:30 a.m. | ||
| Sun., 4/10 | V Baseball | East Hampton | Away - East Hampton HS [Directions] | 3:00 p.m. | W 6-5 (9 inn) | |
| Mon., 4/11 | V Baseball | Morgan | Home - Portland HS [Directions] | 3:45 p.m. | L 2-15 | |
| Mon., 4/11 | V Boys Golf | North Branford | Home - PGC [Directions] | 2:45 p.m. | Portland: 158 North Branford: 210 (non-league) | Non-League |
| Mon., 4/11 | V Softball | Hale Ray | Home - Nolan Field Maple Ave. off Airline Ave [Directions] | 4:00 p.m. | L 0-16(5) | |
| Mon., 4/11 | V Girls Tennis | Cromwell | Home - Portland HS [Directions] | 3:45 p.m. | L 3-4 | |
| Tue., 4/12 | V Boys Golf | Morgan | Away - CCC [Directions] | 3:00 p.m. | Portland: 175 Morgan: 173 (non-league) | Non-League |
| Wed., 4/13 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | L 10-0 | |
| Wed., 4/13 | V Boys Outdoor Track | Hale Ray, Valley Regional, North Branford | Away - North Branford HS [Directions] | 3:45 p.m. | ||
| Wed., 4/13 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | W 5-0 | |
| Wed., 4/13 | V Girls Outdoor Track | North Branford, Valley Regional, Hale Ray | Away - North Branford HS [Directions] | 3:45 p.m. | ||
| Wed., 4/13 | V Softball | Old Saybrook | Away - Old Saybrook HS [Directions] | 3:45 p.m. | L 9-10 | |
| Wed., 4/13 | V Girls Tennis | Haddam-Killingworth | Home - Portland HS [Directions] | 3:45 p.m. | L 3-4 | |
| Thu., 4/14 | JV Baseball | Haddam-Killingworth | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Thu., 4/14 | V Boys Tennis | East Hampton | Home - Portland HS [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 4/14 | V Girls Tennis | East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | L 3-4 | |
| Fri., 4/15 | V Baseball | ValleyReg/Westbrook | Away - Valley Regional HS [Directions] | 4:00 p.m. | W 2-0 (8 innings) | |
| Fri., 4/15 | V Softball | Westbrook/Old Saybrook | Home - Nolan Field Maple Ave. off Airline Ave [Directions] | 4:00 p.m. | L 3-4 | |
| Fri., 4/15 | V Girls Tennis | North Branford | Home - Portland HS [Directions] | 3:45 p.m. | L 3-4 | |
| Sat., 4/16 | JV Baseball | ValleyReg/Westbrook | Home - Portland HS [Directions] | 11:00 a.m. | ||
| Tue., 4/19 | JV Baseball | Westbrook | Away - Westbrook HS [Directions] | 2:00 p.m. | ||
| Thu., 4/21 | V Baseball | Old Lyme | Home - Portland HS [Directions] | 4:00 p.m. | L 16-11 | |
| Thu., 4/21 | V Boys Tennis | Valley Regional | Away - Valley Regional HS [Directions] | 2:30 p.m. | L 0-7 | |
| Fri., 4/22 | V Baseball | North Branford | Away - North Branford HS [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 4/22 | V Boys Golf | Cromwell, Haddam-Killingworth | Home - PGC [Directions] | 3:00 p.m. | Portland: 161 Cromwell: 177 (league) HK: 179 (non-league) | |
| Fri., 4/22 | V Softball | North Branford | Away - Totoket Park [Directions] | 3:45 p.m. | L 0-9 | |
| Sat., 4/23 | V Baseball | Westbrook | Home - Portland HS [Directions] | 12:00 p.m. | W 4-0 | |
| Sat., 4/23 | JV Baseball | North Branford | Home - Portland HS [Directions] | 3:00 p.m. | ||
| Mon., 4/25 | V Boys Golf | Morgan | Home - PGC [Directions] | 2:45 p.m. | Portland: 155 Morgan: 165 (league) | |
| Mon., 4/25 | V Boys Tennis | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | L 0-7 | |
| Mon., 4/25 | V Softball | Haddam-Killingworth | Home - Nolan Field Maple Ave. off Airline Ave [Directions] | 3:45 p.m. | L 1-12 | |
| Mon., 4/25 | V Girls Tennis | Old Lyme | Home - Portland HS [Directions] | 3:45 p.m. | L 3-4 | |
| Wed., 4/27 | V Baseball | Cromwell | Home - Portland HS [Directions] | 4:00 p.m. | L 13-0 | |
| Wed., 4/27 | V Boys Golf | Haddam-Killingworth | Away - Black Birch [Directions] | 3:00 p.m. | Portland: 160 HK: 189 (league) | |
| Wed., 4/27 | V Boys Outdoor Track | Coginchaug, Creed | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Wed., 4/27 | V Boys Tennis | East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | L 1-6 | |
| Wed., 4/27 | V Girls Outdoor Track | Coginchaug, Creed | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Wed., 4/27 | V Softball | Coginchaug | Away - Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | 3:45 p.m. | L 9-0 | |
| Wed., 4/27 | V Girls Tennis | East Hampton | Home - Portland HS [Directions] | 3:45 p.m. | W 5-2 | |
| Thu., 4/28 | JV Baseball | Cromwell | Away - Cromwell HS [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Boys Golf | Valley Regional | Home - PGC [Directions] | 2:45 p.m. | Portland: 155 Valley: 226 (league) | |
| Thu., 4/28 | V Boys Tennis | Old Saybrook | Away - Old Saybrook HS [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 4/28 | V Softball | East Hampton | Away - East Hampton HS [Directions] | 4:00 p.m. | L 6-8 | |
| Thu., 4/28 | V Girls Tennis | Old Saybrook | Home - Portland HS [Directions] | 3:45 p.m. | L 2-5 | |
| Fri., 4/29 | V Baseball | Coginchaug | Home - Portland HS [Directions] | 3:45 p.m. | L 3-1 | |
| Fri., 4/29 | V Boys Outdoor Track | Stafford | Away [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Boys Tennis | Old Saybrook | Home - Portland HS [Directions] | 3:45 p.m. | L 1-6 | |
| Fri., 4/29 | V Girls Outdoor Track | Stafford | Away [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Softball | Cromwell | Away - Cromwell HS [Directions] | 3:45 p.m. | L 2-15 | |
| Sat., 4/30 | V Baseball | Creed | Away - East Shore Athletic Complex | 2:00 p.m. | W 20-4 | |
| Sat., 4/30 | JV Baseball | Coginchaug | Away - Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 10:30 a.m. | ||
| Mon., 5/2 | V Girls Tennis | Morgan | Away - Morgan HS [Directions] | 3:45 p.m. | L 2-5 | |
| Tue., 5/3 | V Boys Outdoor Track | East Hampton, Old Lyme | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 5/3 | V Girls Outdoor Track | East Hampton, Old Lyme | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Thu., 5/5 | JV Baseball | Old Lyme | Home - Portland HS [Directions] | Cancelled | Cancelled | |
| Thu., 5/5 | V Boys Golf | East Hampton | Home - PGC [Directions] | 2:45 p.m. | Portland: 164 EH: 220 (league) Cromwell: 176(non-league) | |
| Thu., 5/5 | V Boys Tennis | Morgan | Home - Portland HS [Directions] | 3:45 p.m. | L 0-7 | |
| Thu., 5/5 | V Softball | Hale Ray | Away - Hale-Ray HS, Lou Milardo Field [Directions] | 4:30 p.m. | L 2-14 | |
| Thu., 5/5 | V Girls Tennis | Coginchaug | Away - Tennis Courts @ CRHS [Directions] | 3:45 p.m. | L 2-5 | |
| Fri., 5/6 | V Boys Golf | Coginchaug, Morgan | Away - Lyman Orchards [Directions] | 3:00 p.m. | Portland: 173 Coginchaug: 195 (league) Morgan: 177 (non-league) | |
| Sat., 5/7 | V Baseball | Old Lyme | Away - Old Lyme HS [Directions] | 1:00 p.m. | L 5-0 | |
| Sat., 5/7 | V Boys Outdoor Track | Coginchaug | Away [Directions] | 1:30 p.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Coginchaug | Away [Directions] | 1:30 p.m. | ||
| Mon., 5/9 | V Baseball | Westbrook | Away - Westbrook HS [Directions] | 4:00 p.m. | W 11-3 | |
| Mon., 5/9 | V Boys Golf | Hale Ray | Home - PGC [Directions] | 3:00 p.m. | Portland: 167 Hale Ray: DQ (3 players)(league) | |
| Mon., 5/9 | V Boys Tennis | Haddam-Killingworth | Home - Portland HS [Directions] | 3:45 p.m. | W 3-1 | |
| Mon., 5/9 | V Softball | Old Lyme | Home - Nolan Field Maple Ave. off Airline Ave [Directions] | 3:45 p.m. | W 13-1 | |
| Mon., 5/9 | V Girls Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | L 3-4 | |
| Tue., 5/10 | V Boys Golf | Old Lyme | Away - Black Hall Club Old Lyme [Directions] | 3:00 p.m. | Portland: 162 Old Lyme: 165 (league) | |
| Tue., 5/10 | V Boys Outdoor Track | Hale Ray, Cromwell, Old Saybrook | Away - Old Saybrook [Directions] | 3:45 p.m. | ||
| Tue., 5/10 | V Boys Tennis | Westbrook | Away - Portland HS [Directions] | 3:45 p.m. | L 1-6 | |
| Tue., 5/10 | V Girls Outdoor Track | Old Saybrook | Away [Directions] | 3:45 p.m. | ||
| Tue., 5/10 | V Softball | Westbrook/Old Saybrook | Away - Westbrook HS [Directions] | 4:00 p.m. | L 4-5 | |
| Tue., 5/10 | V Girls Tennis | Westbrook | Home - Portland HS [Directions] | 3:45 p.m. | L 2-5 | |
| Wed., 5/11 | V Baseball | Creed | Home - Portland HS [Directions] | 3:45 p.m. | W 21-0 | |
| Wed., 5/11 | V Softball | East Hampton | Home - Nolan Field Maple Ave. off Airline Ave [Directions] | 3:45 p.m. | W 15-14 | |
| Wed., 5/11 | V Girls Tennis | North Branford | Home - Portland HS [Directions] | 3:45 p.m. | L 3-4 | |
| Thu., 5/12 | V Baseball | Norwich Tech | Home - Portland HS [Directions] | 3:30 p.m. | W 4-1 | |
| Thu., 5/12 | JV Baseball | Norwich Tech | Home - Rose Hill [Directions] | 3:30 p.m. | ||
| Thu., 5/12 | V Boys Tennis | Old Lyme | Home - Portland HS [Directions] | 3:45 p.m. | L 0-6 | |
| Thu., 5/12 | V Softball | Old Saybrook | Home - Nolan Field Maple Ave. off Airline Ave [Directions] | 3:30 p.m. | W 7-6 | |
| Thu., 5/12 | V Girls Tennis | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 5/13 | V Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | 3:30 p.m. | W 13-4 | |
| Sat., 5/14 | JV Baseball | Hale Ray | Home - Portland HS [Directions] | 11:00 a.m. | ||
| Sun., 5/15 | V Baseball | Old Saybrook | Away - Old Saybrook HS [Directions] | 1:00 p.m. | L 5-9 | |
| Mon., 5/16 | V Boys Golf | Norwich Free Academy | Away - Mohegan Sun GC [Directions] | 9:00 a.m. | Portland: 169 (front) 336 total. 1st place Wildcat Invitational | |
| Mon., 5/16 | V Boys Tennis | Valley Regional | Home - Portland HS [Directions] | 3:45 p.m. | L 1-6 | |
| Mon., 5/16 | V Softball | Cromwell | Home - Nolan Field [Directions] | 7:00 p.m. | W 6-2 | |
| Mon., 5/16 | V Girls Tennis | Valley Regional | Away [Directions] | 3:45 p.m. | L 0-7 | |
| Mon., 5/16 | V Girls Tennis | Valley Regional | Away - Valley Regional HS [Directions] | 5:30 p.m. | L 1-6 | |
| Tue., 5/17 | V Baseball | Ellington | Home - Portland HS [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 5/17 | JV Baseball | Ellington | Home - Rose Hill [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Boys Golf | Old Saybrook | Away - Fenwick [Directions] | 3:00 p.m. | Portland: 159 Old Saybrook: 178 (league) | |
| Tue., 5/17 | V Boys Outdoor Track | Westbrook, East Hampton | Away - East Hampton [Directions] | 3:45 p.m. | ||
| Tue., 5/17 | V Boys Tennis | Coginchaug | Home - Portland HS [Directions] | 3:45 p.m. | L 3-4 | |
| Tue., 5/17 | V Girls Outdoor Track | East Hampton | Away [Directions] | 3:45 p.m. | ||
| Tue., 5/17 | V Softball | St. Bernard | Home - Nolan Field Maple Ave. off Airline Ave [Directions] | 4:00 p.m. | W 15-2 | |
| Wed., 5/18 | V Baseball | East Hampton | Home - Portland HS [Directions] | 3:45 p.m. | L 8-2 | |
| Wed., 5/18 | V Boys Tennis | Coginchaug | Away [Directions] | 3:45 p.m. | L 0-7 | |
| Wed., 5/18 | V Softball | Morgan | Away - Peters Complex [Directions] | 6:30 p.m. | L 6-16 | |
| Wed., 5/18 | V Girls Tennis | Coginchaug | Home - Portland HS [Directions] | 3:45 p.m. | L 3-4 | |
| Thu., 5/19 | V Baseball | Hale Ray | Home - Portland HS [Directions] | 4:00 p.m. | W 9-2 | |
| Thu., 5/19 | V Boys Golf | Conard | Away - Rockledge Golf Course [Directions] | 3:15 p.m. | Portland: 156 Conard: 161 | |
| Thu., 5/19 | V Boys Tennis | Cromwell | Home - Portland HS [Directions] | 3:45 p.m. | L 1-6 | |
| Thu., 5/19 | V Boys Tennis | Cromwell | Home - Portland HS [Directions] | 4:30 p.m. | L 2-5 | |
| Thu., 5/19 | V Girls Outdoor Track | Valley Regional | Away [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Softball | Valley Regional | Home - Nolan Field Maple Ave. off Airline Ave [Directions] | 3:30 p.m. | L 5-6 | |
| Thu., 5/19 | V Girls Tennis | Old Saybrook | Away - Old Saybrook HS [Directions] | 3:45 p.m. | L 1-6 | |
| Fri., 5/20 | JV Baseball | East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | ||
| Sat., 5/21 | JV Baseball | East Hampton | Home - Portland HS [Directions] | 11:00 a.m. | ||
| Mon., 5/23 | V Baseball | Morgan | Away - Indian River Complex [Directions] | 5:00 p.m. | L 5-4 | SLC Quarterfinals |
| Mon., 5/23 | V Boys Golf | North Branford | Away - Indian Springs [Directions] | 3:00 p.m. | Portland: 159 N. Branford: 199 (league) | |
| Mon., 5/23 | V Softball | Windsor Locks | Away - Veteran's Memorial Park [Directions] | 7:00 p.m. | L 5-3 | |
| Mon., 5/23 | JV Softball | Windsor Locks | Away - Windsor Locks HS [Directions] | Cancelled | Cancelled | |
| Mon., 5/23 | V Girls Tennis | Cromwell | Away - Cromwell HS [Directions] | 3:45 p.m. | L 2-5 | |
| Wed., 5/25 | V Boys Golf | Valley Regional | Away - Fox Hopyard CC [Directions] | 3:00 p.m. | Portland: 162 Valley: 203 (non-league) | Non-League |
| Wed., 5/25 | V Boys Outdoor Track | SLC Championship | Away - Hyde/ Hillhouse | 2:00 p.m. | ||
| Wed., 5/25 | V Girls Outdoor Track | Shoreline Tournament | Away - New Haven Athletic Facility | 2:00 p.m. | ||
| Wed., 5/25 | V Softball | Goodwin Tech | Home - Nolan Field Maple Ave. off Airline Ave [Directions] | 3:45 p.m. | W 13-0 | |
| Thu., 5/26 | V Boys Golf | Shoreline Championship | Away - Stanley GC | 9:00 a.m. | ||
| Tue., 5/31 | V Baseball | WCA | Home - Portland HS [Directions] | 3:30 p.m. | W 10-0 | CIAC 1st Round State Tournament |
| Tue., 5/31 | V Boys Golf | Coginchaug | Home - PGC [Directions] | 2:45 p.m. | Portland: 169 Coginchaug: 179 (non-league) | Non-League |
| Wed., 6/1 | V Baseball | Immaculate | Home - Portland HS [Directions] | 2:00 p.m. | W 4-3 | CIAC 2nd Round State Tournament |
| Sat., 6/4 | V Baseball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:30 p.m. | CIAC Quarterfinal Round State Tournament | |