| Portland 2017-18 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 380 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Cromwell | Away - Fran Monnes Baseball Field @ Cromwell HS [Directions] | 3:30 p.m. | 2:25 p.m. | |
| TBA | JV Baseball | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | 2:25 pm. | |
| TBA | JV Baseball | Creed | Home - Portland HS [Directions] | 4:00 p.m. | ||
| TBA | JV Baseball | ValleyReg/Westbrook | Home - Portland HS [Directions] | 4:00 p.m. | ||
| TBA | JV Baseball | Old Saybrook | Home - Portland HS [Directions] | TBA | ||
| TBA | JV Baseball | Morgan | Away - Morgan HS [Directions] | TBA | 2:25 pm. | |
| TBA | JV Baseball | Coginchaug | Away - Field #1 - Brookside Field @ CRHS [Directions] | Cancelled | 1:30 p.m. | |
| TBA | JV Baseball | Old Saybrook | Home - Portland HS [Directions] | TBA | ||
| TBA | JV Baseball | Westbrook | Home - Portland HS [Directions] | TBA | ||
| TBA | JV Boys Basketball | Valley Regional | Away - Valley Regional HS [Directions] | TBA | 4:20 p.m. | |
| TBA | FR Boys Basketball | Morgan | Away - Morgan HS [Directions] | TBA | 2:30 p.m. | |
| TBA | FR Boys Basketball | Valley Regional | Away - Valley Regional HS [Directions] | TBA | 9:30 a.m. | |
| TBA | FR Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | TBA | 8:45 a.m. | |
| TBA | V Boys Golf | Glastonbury, Simsbury | Away - Glastonbury Hills Country Club [Directions] | 3:00 p.m. | 2:00 p.m. | Non- League |
| TBA | JV Boys Golf | Xavier | Away - Portland Golf Club [Directions] | TBA | ||
| TBA | JV Boys Soccer | Hale Ray | Away - Hale-Ray HS, Nevers Field [Directions] | TBA | 2:25 p.m. | |
| TBA | V Boys Swimming and Diving | Suffield | Home - Rocky Hill HS [Directions] | 3:45 p.m. | ||
| TBA | JV Girls Basketball | North Branford | Away - North Branford HS [Directions] | TBA | ||
| Fri., 9/8 | V Boys Cross Country | Blue Dragon Invitational | Away | 3:30 p.m. | 2:25 p.m. | Blue Dragon Invitational |
| Fri., 9/8 | V Football | Rockville | Away - RHS football field [Directions] | W 54-20 | 4:00 p.m. | |
| Fri., 9/8 | V Girls Cross Country | Blue Dragon Invitational | Away | 3:30 p.m. | 2:25 p.m. | Blue Dragon Invitational |
| Fri., 9/8 | V Girls Soccer | Old Saybrook | Home - Portland HS [Directions] | L 1-2 | Non-League | |
| Sat., 9/9 | JV Football | Rockville | Home - Pierson Park, Cromwell [Directions] | 10:30 a.m. | 9:00 a.m. | |
| Mon., 9/11 | V Boys Soccer | Hale Ray | Away - Hale-Ray HS, Nevers Field [Directions] | T 1-1 | 5:00 p.m. | |
| Mon., 9/11 | V Girls Soccer | St. Paul Catholic | Home - Portland HS [Directions] | L 2-3 | Non-League | |
| Mon., 9/11 | JV Girls Soccer | Old Saybrook | Home - Portland [Directions] | 3:45 p.m. | Non-League | |
| Tue., 9/12 | V Boys Cross Country | Highlander Invitational | Home - YMCA Camp Ingersoll [Directions] | 3:45 p.m. | Highlander Invitational | |
| Tue., 9/12 | JV Boys Soccer | Hale Ray | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Girls Cross Country | Highlander Invitational | Home - YMCA Camp Ingersoll [Directions] | 3:45 p.m. | Highlander Invitational | |
| Tue., 9/12 | V Girls Swimming and Diving | Southington | Home - Rocky Hill HS [Directions] | L | ||
| Thu., 9/14 | V Boys Soccer | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | L 0-6 | 2:25 p.m. | |
| Fri., 9/15 | V Football | North Branford | Home - Pierson Park, Cromwell [Directions] | W 44-0 | 4:00 p.m. | |
| Fri., 9/15 | JV Boys Soccer | Old Saybrook | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Fri., 9/15 | V Girls Soccer | Old Saybrook | Home - Portland HS [Directions] | W 2-0 | ||
| Sat., 9/16 | JV Football | North Branford | Away - Colafati Field - NBHS [Directions] | 10:30 a.m. | 8:30 a.m. | |
| Sat., 9/16 | JV Girls Soccer | Old Saybrook | Away - Old Saybrook HS [Directions] | 11:00 a.m. | 9:30 a.m. | |
| Mon., 9/18 | V Boys Soccer | Morgan | Home - Portland HS [Directions] | L 0-4 | ||
| Tue., 9/19 | JV Boys Soccer | Morgan | Away - Morgan HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 9/19 | V Girls Swimming and Diving | East Catholic | Home - Rocky Hill HS [Directions] | L | ||
| Thu., 9/21 | V Boys Cross Country | Going to the Sun Invitational | Away | 3:45 p.m. | 2:25 p.m. | Going to the Sun Invitational |
| Thu., 9/21 | V Boys Soccer | International | Home - Portland HS [Directions] | W 8-0 | Non-League | |
| Thu., 9/21 | V Girls Cross Country | Going to the Sun Invitational | Away | 3:45 p.m. | 2:25 p.m. | Going to the Sun Invitational |
| Thu., 9/21 | V Girls Soccer | Morgan | Home - Portland HS [Directions] | L 1-3 | ||
| Thu., 9/21 | JV Girls Soccer | Morgan | Home - Portland HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Fri., 9/22 | V Football | Lewis Mills | Home - Pierson Park, Cromwell [Directions] | W 44-20 | 4:30 p.m. | |
| Fri., 9/22 | V Boys Soccer | Westbrook | Home - Portland HS [Directions] | W 3-0 | ||
| Fri., 9/22 | V Girls Soccer | Westbrook | Home - Portland HS [Directions] | T 0-0 | ||
| Fri., 9/22 | V Girls Swimming and Diving | Maloney/Platt | Home - Rocky Hill HS [Directions] | W | ||
| Fri., 9/22 | Unified Sports Soccer | Middletown | Home - Portland HS [Directions] | 2:30 p.m. | ||
| Sat., 9/23 | JV Football | Lewis Mills | Home - Pierson Park, Cromwell [Directions] | 10:30 a.m. | 9:00 a.m. | |
| Sat., 9/23 | JV Boys Soccer | Westbrook | Away - Westbrook HS Field #2 - Track/Soccer [Directions] | Cancelled | 9:15 a.m. | |
| Mon., 9/25 | V Boys Soccer | East Hampton | Away - East Hampton HS [Directions] | W 1-0 | 5:15 p.m. | |
| Mon., 9/25 | JV Girls Soccer | Westbrook | Away - Westbrook HS Field #5 - Softball [Directions] | Cancelled | 2:25 p.m. | |
| Tue., 9/26 | V Boys Cross Country | East Hampton | Away [Directions] | 3:45 p.m. | 2:25 p.m. | League Meet #1 SLC Small Schools |
| Tue., 9/26 | JV Boys Soccer | East Hampton | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Girls Cross Country | East Hampton | Away [Directions] | 3:45 p.m. | 2:25 p.m. | League Meet #1 SLC Small Schools |
| Tue., 9/26 | V Girls Soccer | East Hampton | Away - East Hampton HS [Directions] | L 0-2 | 5:15 p.m. | |
| Tue., 9/26 | V Girls Swimming and Diving | Plainville | Away - Plainville HS [Directions] | W | 3:15pm | |
| Wed., 9/27 | V Boys Soccer | Old Lyme | Home - Portland HS [Directions] | W 2-1 | ||
| Wed., 9/27 | JV Girls Soccer | East Hampton | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Thu., 9/28 | V Football | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | W 43-7 | 4:30 p.m. | |
| Thu., 9/28 | JV Boys Soccer | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Thu., 9/28 | V Girls Soccer | Old Lyme | Home - Portland HS [Directions] | L 0-3 | ||
| Fri., 9/29 | V Boys Cross Country | East Hampton | Away [Directions] | 3:45 p.m. | 2:25 p.m. | East Hampton Invitational |
| Fri., 9/29 | JV Football | Haddam-Killingworth | Away - Haddam-Killingworth HS [Directions] | 4:00 p.m. | 2:25 p.m. | |
| Fri., 9/29 | V Boys Soccer | East Hampton | Home - Portland HS [Directions] | L 1-4 | Non-League | |
| Fri., 9/29 | V Girls Cross Country | East Hampton Invitational | Away | 3:45 p.m. | 2:25 p.m. | |
| Fri., 9/29 | V Girls Soccer | Hale Ray | Home - Portland HS [Directions] | W 5-1 | Non-League | |
| Fri., 9/29 | JV Girls Soccer | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Fri., 9/29 | V Girls Swimming and Diving | Manchester/Bacon/Bolton/Coventry/Rockville | Home - Rocky Hill HS [Directions] | W | ||
| Mon., 10/2 | V Boys Soccer | Ellis Tech | Away - Ellis Tech Track/Soccer Field [Directions] | W 6-2 | 2:25 p.m. | Non-League |
| Mon., 10/2 | V Girls Soccer | North Branford/Hale Ray | Away - Colafati Field - NBHS [Directions] | L 0-1 | 5:00 p.m. | |
| Tue., 10/3 | V Boys Cross Country | Sheehan Invitational | Away | 3:45 p.m. | 2:25 p.m. | |
| Tue., 10/3 | V Boys Soccer | North Branford | Home - Portland HS [Directions] | W 2-1 | ||
| Tue., 10/3 | V Girls Cross Country | Sheehan Invitational | Away | 3:45 p.m. | 2:25 p.m. | |
| Tue., 10/3 | V Girls Swimming and Diving | Windsor Locks/Ellington/E.Granby/E.Windsor | Home - Rocky Hill HS [Directions] | L | ||
| Wed., 10/4 | JV Boys Soccer | North Branford | Away - North Branford HS [Directions] | Cancelled | 2:25 p.m. | |
| Wed., 10/4 | JV Girls Soccer | North Branford/Hale Ray | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Thu., 10/5 | V Girls Soccer | Coginchaug | Away - CRHS Stadium Field & Track [Directions] | W 3-2 | 2:25 p.m. | |
| Thu., 10/5 | JV Girls Soccer | Coginchaug | Away - CRHS Stadium Field & Track [Directions] | 5:30 p.m. | 2:25pm | |
| Thu., 10/5 | Unified Sports Soccer | Cromwell | Home - Portland HS [Directions] | 3:15 p.m. | ||
| Fri., 10/6 | V Boys Soccer | Coginchaug | Away - CRHS Stadium Field & Track [Directions] | L 0-3 | 2:00 p.m. | |
| Fri., 10/6 | V Girls Swimming and Diving | Enfield | Home - Rocky Hill HS [Directions] | W | ||
| Sat., 10/7 | V Boys Cross Country | Woods Trail Run | Away | 10:00 a.m. | TBA | Thetford, VT |
| Sat., 10/7 | V Football | Coginchaug/Hale Ray/East Hampton | Away - CRHS Stadium Field & Track [Directions] | W 50-6 | 11:15 a.m. | |
| Sat., 10/7 | JV Boys Soccer | Coginchaug | Home - Portland HS [Directions] | 11:00 a.m. | ||
| Sat., 10/7 | V Girls Cross Country | Woods Trail Run | Away | 10:00 a.m. | TBA | Thetford, VT |
| Mon., 10/9 | JV Football | Coginchaug/Hale Ray/East Hampton | Home - Pierson Park, Cromwell [Directions] | Cancelled | 9:00 a.m. | |
| Tue., 10/10 | V Boys Soccer | Valley Regional | Away - VRHS Football Field [Directions] | L 0-4 | 2:25 p.m. | |
| Tue., 10/10 | V Girls Soccer | Valley Regional | Away - VRHS Football Field [Directions] | T 0-0 | 5:00 p.m. | |
| Tue., 10/10 | JV Girls Soccer | Valley Regional | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Wed., 10/11 | JV Boys Soccer | Valley Regional | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Wed., 10/11 | V Girls Swimming and Diving | Haddam-Killingworth | Home - Rocky Hill HS [Directions] | W | ||
| Thu., 10/12 | V Boys Cross Country | Old Lyme | Away [Directions] | 3:45 p.m. | 2:45 p.m. | |
| Thu., 10/12 | V Boys Soccer | Cromwell | Home - Portland HS [Directions] | L 1-4 | ||
| Thu., 10/12 | JV Boys Soccer | Cromwell | Home - Portland HS [Directions] | 3:30 p.m. | ||
| Thu., 10/12 | V Girls Cross Country | Old Lyme | Away [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Thu., 10/12 | V Girls Soccer | Cromwell | Home - Portland HS [Directions] | L 1-2 | ||
| Fri., 10/13 | JV Girls Soccer | Cromwell | Away - Cromwell HS [Directions] | 3:15 p.m. | 2:15 p.m. | |
| Fri., 10/13 | V Girls Swimming and Diving | Bulkeley/HMTCA/Weaver | Away - Bulkeley HS Pool [Directions] | W | 2:45pm | |
| Sat., 10/14 | JV Boys Soccer | Cromwell | Away - Cromwell HS [Directions] | 11:00 a.m. | 9:45 a.m. | |
| Sat., 10/14 | V Girls Soccer | New Fairfield | Home - Portland HS [Directions] | W 2-0 | ||
| Mon., 10/16 | JV Boys Soccer | Old Lyme | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Mon., 10/16 | V Girls Soccer | Haddam-Killingworth | Home - Portland HS [Directions] | W 1-0 | ||
| Tue., 10/17 | V Boys Soccer | Haddam-Killingworth | Home - Portland HS [Directions] | L 1-3 | ||
| Tue., 10/17 | JV Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 10/17 | V Girls Swimming and Diving | Windsor | Away - Windsor H.S. [Directions] | L | 2:30pm | |
| Wed., 10/18 | JV Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Thu., 10/19 | V Girls Soccer | Morgan | Away - Indian River Complex [Directions] | L 0-1 | 5:00 p.m. | Non-League |
| Thu., 10/19 | JV Girls Soccer | Morgan | Away - Indian River Complex #3 [Directions] | Cancelled | 2:25pm | Non-League |
| Fri., 10/20 | V Boys Cross Country | SLC Championship | Away | 2:30 p.m. | 1:15 p.m. | Old Lyme |
| Fri., 10/20 | V Football | Old Saybrook | Home - Pierson Park, Cromwell [Directions] | W 12-6 | 4:00 p.m. | |
| Fri., 10/20 | V Girls Cross Country | SLC Championship | Away | 2:30 p.m. | 1:15 p.m. | Old Lyme |
| Fri., 10/20 | V Girls Swimming and Diving | Wethersfield | Away - Wethersfield HS [Directions] | L | 3:30pm | |
| Sat., 10/21 | JV Football | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | Cancelled | 8:30 a.m. | |
| Sat., 10/21 | V Boys Soccer | Lyman Memorial | Home - Portland HS [Directions] | L 0-3 | Non-League | |
| Mon., 10/23 | V Girls Soccer | East Hampton | Home - Portland HS [Directions] | L 0-3 | Non-League Senior Night | |
| Tue., 10/24 | V Boys Cross Country | Old Saybrook | Away [Directions] | Cancelled | 2:25 p.m. | Frosh Invitational (JV G & B) |
| Tue., 10/24 | V Girls Cross Country | Old Saybrook | Away [Directions] | Cancelled | 2:25 p.m. | Frosh Invitational (JV G & B) |
| Wed., 10/25 | V Boys Cross Country | Old Saybrook Frosh/JV Invitational | Away | 4:15 p.m. | 2:25 p.m. | OS Frosh/JV Invitational |
| Wed., 10/25 | V Girls Cross Country | Old Saybrook Frosh/JV Invitational | Away | 4:15 p.m. | 2:25 p.m. | OS Frosh/ JV Invitational |
| Thu., 10/26 | JV Girls Soccer | East Hampton | Away - East Hampton HS [Directions] | Cancelled | 2:25 p.m. | Non-League |
| Fri., 10/27 | V Football | Valley Regional/Old Lyme | Home - Pierson Park, Cromwell [Directions] | L 28-34 (OT) | 4:00 p.m. | |
| Sat., 10/28 | JV Football | Valley Regional/Old Lyme | Away - Valley Regional HS [Directions] | 10:30 a.m. | 8:30 a.m. | |
| Mon., 10/30 | V Boys Cross Country | Valley Regional | Away [Directions] | Cancelled | 2:25 p.m. | Fresh Invitational (Fr. G & B) |
| Tue., 10/31 | V Boys Cross Country | Valley Regional | Away [Directions] | 3:30 p.m. | 2:25 p.m. | Fresh Invitational (Fr. G & B) |
| Wed., 11/1 | V Boys Soccer | Innovation | Home - Portland HS [Directions] | W 3-0 | Non-League Senior Day | |
| Thu., 11/2 | Unified Sports Soccer | Conard | Away [Directions] | 3:15 p.m. | 2:15 p.m. | CIAC Soccer Tournament |
| Fri., 11/3 | V Football | MSW | Away - Peters Complex [Directions] | W 33-8 | 4:00 p.m. | |
| Sat., 11/4 | JV Football | MSW | Home - Pierson Park, Cromwell [Directions] | Cancelled | 9:00 a.m. | |
| Sat., 11/11 | V Football | Nonnewaug | Away - Nonnewaug HS Football Field [Directions] | W 56-14 | 9:30 a.m. | |
| Mon., 11/13 | JV Football | Nonnewaug | Home - Pierson Park, Cromwell [Directions] | Cancelled | 2:25 p.m. | |
| Wed., 11/22 | V Football | Rocky Hill | Away - Rocky Hill HS [Directions] | L 7-35 | 8:15 a.m. | |
| Mon., 12/11 | V Girls Basketball | Goodwin Tech | Home - Portland HS [Directions] | W 66-13 | Non-League | |
| Mon., 12/11 | JV Girls Basketball | Goodwin Tech | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Wed., 12/13 | V Wrestling | Notre Dame-West Haven | Away - Notre Dame HS [Directions] | 7:00 p.m. | 5:00 p.m. | |
| Wed., 12/13 | Unified Sports Basketball | Callahans in Newington- Bowling | Away | 3:15 p.m. | 2:15 p.m. | Callahans in Newington- Bowling |
| Thu., 12/14 | V Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | W 38-33 | 4:20 p.m. | |
| Thu., 12/14 | JV Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | 5:30 p.m. | 4:20 p.m. | |
| Sat., 12/16 | V Boys Basketball | Creed | Home - Portland HS [Directions] | L 39-47 | ||
| Sat., 12/16 | JV Boys Basketball | Creed | Home - Portland HS [Directions] | 12:00 p.m. | ||
| Sat., 12/16 | FR Boys Basketball | Cromwell | Home - Portland HS [Directions] | 10:30 a.m. | ||
| Sat., 12/16 | V Wrestling | Pomperaug Tournament | Away | 9:00 a.m. | 7:00 a.m. | |
| Sat., 12/16 | V Girls Basketball | Creed | Away - Truman School | W 33-32 | 9:00 a.m. | |
| Sat., 12/16 | JV Girls Basketball | Creed | Away - Truman School | 10:30 a.m. | ||
| Mon., 12/18 | V Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | L 48-76 | 4:30 p.m. | |
| Mon., 12/18 | JV Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 5:30 p.m. | 4:30 p.m. | |
| Tue., 12/19 | V Boys Swimming and Diving | East Catholic | Home - Rocky Hill HS [Directions] | W 97-77 | ||
| Tue., 12/19 | V Girls Basketball | East Hampton | Home - Portland HS [Directions] | W 36-24 | ||
| Tue., 12/19 | JV Girls Basketball | East Hampton | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Thu., 12/21 | V Boys Basketball | Morgan | Home - Portland HS [Directions] | W 57-49 | ||
| Thu., 12/21 | JV Boys Basketball | Morgan | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Thu., 12/21 | V Boys Indoor Track | Old Saybrook Qualifier | Away - Floyd Little Athletic Center | 5:00 p.m. | 3:40 p.m. | |
| Thu., 12/21 | V Girls Indoor Track | Old Saybrook Qualifier | Away - Floyd Little Athletic Center | 5:00 p.m. | 3:40 p.m. | |
| Sat., 12/23 | V Wrestling | Berlin | Away [Directions] | 9:00 a.m. | 8:00 a.m. | |
| Wed., 12/27 | V Wrestling | Plainville | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Wed., 12/27 | V Girls Basketball | Griswold | Away - GHS Gym [Directions] | W 50-36 | 4:00 p.m. | Non-League |
| Wed., 12/27 | JV Girls Basketball | Griswold | Away - GHS Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/28 | V Boys Basketball | Old Saybrook | Home - Portland HS [Directions] | L 55-68 | ||
| Thu., 12/28 | JV Boys Basketball | Old Saybrook | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Thu., 12/28 | FR Boys Basketball | Old Saybrook | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Fri., 12/29 | FR Boys Basketball | Creed | Away - Fair Haven School | 12:00 p.m. | 10:30 a.m. | |
| Fri., 12/29 | V Boys Swimming and Diving | Middletown | Home - Rocky Hill HS [Directions] | L | ||
| Fri., 12/29 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | L 50-54 | 4:15 p.m. | |
| Fri., 12/29 | JV Girls Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | 5:30 p.m. | ||
| Sat., 12/30 | V Wrestling | Killingly Duals | Away | 9:00 a.m. | 7:00 a.m. | |
| Tue., 1/2 | V Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | W 65-49 | 4:20 p.m. | |
| Tue., 1/2 | JV Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:30 p.m. | 4:20 p.m. | |
| Tue., 1/2 | V Girls Basketball | Haddam-Killingworth | Home - Portland HS [Directions] | L 50-40 | ||
| Tue., 1/2 | JV Girls Basketball | Haddam-Killingworth | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | FR Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 7:00 p.m. | 5:45 p.m. | |
| Wed., 1/3 | V Boys Indoor Track | SLC League Meet #1 | Away - Floyd Little Athletic Center | 5:00 p.m. | 3:40 p.m. | |
| Wed., 1/3 | V Wrestling | Ellis Tech | Away - Ellis Tech Gymnasium [Directions] | 5:00 p.m. | 3:30 p.m. | |
| Wed., 1/3 | V Girls Indoor Track | SLC League Meet #1 | Away - Floyd Little Athletic Center | 5:00 p.m. | 3:40 p.m. | |
| Sat., 1/6 | V Wrestling | Nonnewaug Tournament | Away | Cancelled | 7:00 a.m. | |
| Tue., 1/9 | V Boys Basketball | Westbrook | Home - Portland HS [Directions] | W 80-49 | ||
| Tue., 1/9 | JV Boys Basketball | Westbrook | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Tue., 1/9 | FR Boys Basketball | Westbrook | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Tue., 1/9 | V Boys Swimming and Diving | Simsbury | Home - Rocky Hill HS [Directions] | W 102-82 | ||
| Tue., 1/9 | V Girls Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | L 44-39 | 5:30 p.m. | |
| Wed., 1/10 | V Wrestling | Morgan | Home - Portland HS [Directions] | 6:30 p.m. | ||
| Thu., 1/11 | V Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | L 56-64 | 4:15 p.m. | |
| Thu., 1/11 | JV Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Fri., 1/12 | V Boys Swimming and Diving | Manchester/RHAM | Away - MHS POOL [Directions] | W 95-63 | 2:30pm | |
| Fri., 1/12 | V Girls Basketball | Old Lyme | Home - Portland HS [Directions] | L 49-28 | ||
| Fri., 1/12 | JV Girls Basketball | Old Lyme | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Sat., 1/13 | V Boys Basketball | Valley Regional | Away - Valley Regional HS [Directions] | L 54-66 | 9:15 a.m. | |
| Sat., 1/13 | V Wrestling | Hall Tournament | Away | 9:00 a.m. | 7:30 a.m. | |
| Tue., 1/16 | V Boys Basketball | North Branford | Home - Portland HS [Directions] | L 38-60 | ||
| Tue., 1/16 | JV Boys Basketball | North Branford | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Tue., 1/16 | V Boys Swimming and Diving | Plainville Boys Swimming | Home - Rocky Hill HS [Directions] | W 94-87 | ||
| Tue., 1/16 | V Girls Basketball | North Branford | Away - North Branford HS [Directions] | L 43-47 | 4:15 p.m. | |
| Thu., 1/18 | V Wrestling | Nonnewaug | Home - Portland HS [Directions] | 6:30 p.m. | ||
| Fri., 1/19 | V Boys Swimming and Diving | Berlin | Home - Rocky Hill HS [Directions] | L 76-99 | ||
| Sat., 1/20 | V Boys Basketball | Coginchaug | Home - Portland HS [Directions] | W 58-42 | Non-League | |
| Sat., 1/20 | JV Boys Basketball | Coginchaug | Home - Portland HS [Directions] | 12:00 p.m. | Non-League | |
| Sat., 1/20 | FR Boys Basketball | Coginchaug | Home - Portland HS [Directions] | 10:30 a.m. | ||
| Sat., 1/20 | V Boys Indoor Track | SLC Coaches Invitational | Away - Floyd Little Athletic Center | 10:00 a.m. | 8:00 a.m. | |
| Sat., 1/20 | V Wrestling | New Milford Tournament | Away | 9:00 a.m. | 7:00 a.m. | |
| Sat., 1/20 | V Girls Indoor Track | SLC Coaches Invitational | Away - Floyd Little Athletic Center | 10:00 a.m. | 8:00 a.m. | |
| Mon., 1/22 | V Girls Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | L 58-32 | 4:20 p.m. | |
| Mon., 1/22 | JV Girls Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | V Boys Basketball | Cromwell | Home - Portland HS [Directions] | L 50-59 | ||
| Tue., 1/23 | JV Boys Basketball | Cromwell | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | V Boys Swimming and Diving | Wethersfield | Away - Wethersfield HS [Directions] | L 103-74 | 3:45pm | |
| Wed., 1/24 | V Wrestling | Terryville-Thomaston | Away [Directions] | 6:30 p.m. | 4:30 p.m. | |
| Thu., 1/25 | V Girls Basketball | Coginchaug | Home - Portland HS [Directions] | L 52-31 | ||
| Thu., 1/25 | JV Girls Basketball | Coginchaug | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Fri., 1/26 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | W 46-35 | 4:30 p.m. | |
| Fri., 1/26 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | 5:30 p.m. | 4:30 p.m. | |
| Fri., 1/26 | V Boys Indoor Track | SLC League Meet #2 | Away - Floyd Little Athletic Center | 4:30 p.m. | 3:40 p.m. | |
| Fri., 1/26 | V Boys Swimming and Diving | Meriden Co-op | Home - Rocky Hill HS [Directions] | W 91-90 | ||
| Fri., 1/26 | V Girls Indoor Track | SLC League Meet #2 | Away - Floyd Little Athletic Center | 4:30 p.m. | 3:40 p.m. | |
| Sat., 1/27 | FR Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 9:00 a.m. | 8:00 a.m. | |
| Sat., 1/27 | V Wrestling | Highlander Invitational | Home - Portland HS [Directions] | 9:00 a.m. | ||
| Sat., 1/27 | V Girls Basketball | Morgan | Away - Morgan HS [Directions] | L 53-29 | 4:00 p.m. | |
| Sat., 1/27 | JV Girls Basketball | Morgan | Away - Morgan HS [Directions] | Cancelled | ||
| Mon., 1/29 | V Girls Basketball | Hale Ray | Home - Portland HS [Directions] | W 67-46 | ||
| Mon., 1/29 | JV Girls Basketball | Hale Ray | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Mon., 1/29 | Unified Sports Basketball | Middletown | Away [Directions] | 3:30 p.m. | 2:15 p.m. | |
| Tue., 1/30 | V Boys Swimming and Diving | Hartford Public | Home - Rocky Hill high School [Directions] | W 97-67 | ||
| Wed., 1/31 | V Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | L 52-53 | 2:25 p.m. | |
| Wed., 1/31 | JV Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 4:00 p.m. | 2:25 p.m. | |
| Wed., 1/31 | FR Boys Basketball | Haddam-Killingworth | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Thu., 2/1 | V Wrestling | Brookfield/Shepaug | Home - Portland HS [Directions] | 5:30 p.m. | Senior Night | |
| Fri., 2/2 | V Boys Basketball | Old Lyme | Home - Portland HS [Directions] | L 61-63 | ||
| Fri., 2/2 | JV Boys Basketball | Old Lyme | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Fri., 2/2 | V Boys Swimming and Diving | Windsor | Home - Rocky Hill HS [Directions] | W 91-81 | ||
| Fri., 2/2 | V Girls Basketball | Old Lyme | Away - Old Lyme HS [Directions] | L 67-48 | 4:15 p.m. | |
| Fri., 2/2 | JV Girls Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Sat., 2/3 | FR Boys Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | 12:00 p.m. | 10:45 p.m. | |
| Sat., 2/3 | V Boys Indoor Track | SLC Championship Meet | Away - Floyd Little Athletic Center | 10:00 a.m. | 8:00 a.m. | |
| Sat., 2/3 | V Wrestling | Bacon Academy | Away [Directions] | 9:00 a.m. | 7:30 a.m. | |
| Sat., 2/3 | V Girls Indoor Track | SLC Championship Meet | Away - Floyd Little Athletic Center | 10:00 a.m. | 8:00 a.m. | |
| Mon., 2/5 | V Girls Basketball | Old Saybrook | Home - Portland HS [Directions] | W 59-46 | ||
| Mon., 2/5 | JV Girls Basketball | Old Saybrook | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | V Boys Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | L 54-66 | 4:15 p.m. | |
| Tue., 2/6 | JV Boys Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Tue., 2/6 | V Boys Swimming and Diving | Newington | Home - Rocky Hill HS [Directions] | W 98-88 | ||
| Tue., 2/6 | V Girls Basketball | Westbrook | Home - Portland HS [Directions] | W 50-37 | ||
| Tue., 2/6 | Unified Sports Basketball | Cromwell | Home - Portland HS [Directions] | 3:30 p.m. | ||
| Thu., 2/8 | V Wrestling | Haddam-Killingworth | Away - Haddam Killingworth MS in Killingworth [Directions] | 6:00 p.m. | 4:30 p.m. | |
| Fri., 2/9 | V Boys Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | L 56-69 | 4:15 p.m. | |
| Fri., 2/9 | JV Boys Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | 5:30 p.m. | 4:15 p.m. | |
| Fri., 2/9 | V Boys Swimming and Diving | Bulkeley Cooperative Swim Team | Home - Rocky Hill HS [Directions] | W 84-56 | ||
| Fri., 2/9 | V Girls Basketball | Valley Regional | Home - Portland HS [Directions] | W 44-31 | ||
| Fri., 2/9 | JV Girls Basketball | Valley Regional | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Sat., 2/10 | FR Boys Basketball | Valley Regional | Home - Portland HS [Directions] | 10:30 a.m. | ||
| Sat., 2/10 | V Competitive Cheerleading | SLC Competition | Away - Westbrook | 1:00 p.m. | 11:30 a.m. | SLC Competition |
| Mon., 2/12 | V Girls Basketball | Creed | Home - Portland HS [Directions] | W 48-25 | Senior Night | |
| Mon., 2/12 | JV Girls Basketball | Creed | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Tue., 2/13 | V Boys Basketball | Creed | Away - Fair Haven School | L 55-59 | 4:10 p.m. | |
| Tue., 2/13 | JV Boys Basketball | Creed | Away - Fair Haven School | 6:00 p.m. | 4:10 p.m. | |
| Tue., 2/13 | V Boys Swimming and Diving | Avon | Away - CCSU [Directions] | L 98-82 | 3:15pm | |
| Wed., 2/14 | V Girls Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | W 47-39 | 4:20 p.m. | |
| Wed., 2/14 | JV Girls Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 5:30 p.m. | ||
| Thu., 2/15 | Unified Sports Basketball | Middletown | Home - Portland HS [Directions] | 3:00 p.m. | ||
| Fri., 2/16 | V Boys Basketball | Hale Ray | Home - Portland HS [Directions] | W 66-38 | ||
| Fri., 2/16 | JV Boys Basketball | Hale Ray | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Fri., 2/16 | FR Boys Basketball | Hale Ray | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Sat., 2/17 | FR Boys Basketball | East Hampton | Home - Portland HS [Directions] | 10:30 a.m. | ||
| Mon., 2/19 | V Boys Basketball | Whitney Tech | Home - Portland HS [Directions] | W 92-77 | Non-League | |
| Mon., 2/19 | JV Boys Basketball | Whitney Tech | Home - Portland HS [Directions] | 5:30 p.m. | Non-League | |
| Mon., 2/19 | FR Boys Basketball | Whitney Tech | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Wed., 2/21 | V Boys Basketball | East Hampton | Home - Portland HS [Directions] | L 55-67 | Senior Night | |
| Wed., 2/21 | JV Boys Basketball | East Hampton | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Wed., 2/21 | V Boys Swimming and Diving | E.O. Smith - Tolland Hammerheads | Home - Rocky Hill HS [Directions] | L 92-79 | ||
| Sat., 2/24 | V Competitive Cheerleading | NECA Competition | Away - East Haven HS | TBA | TBA | |
| Fri., 3/2 | V Competitive Cheerleading | CIAC Class S Competition | Away - Floyd Little Athletic Center | 5:00 p.m. | 3:40 p.m. | |
| Tue., 3/13 | Unified Sports Basketball | New Britain | Away [Directions] | 3:00 p.m. | 2:15 p.m. | |
| Tue., 4/3 | V Boys Outdoor Track | Haddam-Killingworth, North Branford | Away - Haddam Killingworth HS [Directions] | 3:30 p.m. | 2:25 p.m. | |
| Tue., 4/3 | V Girls Outdoor Track | Haddam-Killingworth, North Branford | Away - Haddam Killingworth HS [Directions] | 3:30 p.m. | 2:25 p.m. | |
| Thu., 4/5 | V Boys Golf | Old Saybrook | Home - PGC [Directions] | Portland: 183 Old Saybrook: 186 (non-league) | Non-League | |
| Thu., 4/5 | V Softball | Old Saybrook | Away - Old Saybrook HS [Directions] | L 2-20 | 2:25 p.m. | |
| Thu., 4/5 | V Girls Tennis | Westbrook | Home - Portland HS [Directions] | L 0-7 | ||
| Sat., 4/7 | V Boys Outdoor Track | East Hampton | Away [Directions] | 10:00 a.m. | 9:00 a.m. | Bellringer Invitational |
| Sat., 4/7 | V Girls Outdoor Track | East Hampton | Away [Directions] | 10:00 a.m. | 9:00 a.m. | Bellringer Invitational |
| Sat., 4/7 | V Softball | Hale Ray | Away - Hale-Ray HS, Lou Milardo Field [Directions] | L 0-13 | 12:30 p.m. | |
| Sat., 4/7 | V Girls Tennis | East Hampton | Home - Portland HS [Directions] | W 5-2 | ||
| Mon., 4/9 | V Baseball | Morgan | Home - Portland HS [Directions] | L 8-5 | ||
| Mon., 4/9 | JV Boys Golf | Xavier | Home - PGC [Directions] | 2:45 p.m. | ||
| Mon., 4/9 | V Softball | Innovation | Away - Osgood Park [Directions] | W 9-8 | 2:25 p.m. | Non-League |
| Mon., 4/9 | V Girls Tennis | Old Lyme | Home - Portland HS [Directions] | L 1-6 | ||
| Tue., 4/10 | V Boys Golf | Cromwell | Away - TPC [Directions] | Portland: 186 Cromwell: 192 (league) | 1:40 p.m. | |
| Tue., 4/10 | V Boys Outdoor Track | Creed, Cromwell | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 4/10 | V Girls Outdoor Track | Creed, Cromwell | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 4/10 | V Softball | Westbrook/Old Saybrook | Home - Nolan Field [Directions] | L 7-15 | ||
| Wed., 4/11 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | L 2-3 (8 innings) | 2:25 p.m. | |
| Wed., 4/11 | JV Baseball | Haddam-Killingworth | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Wed., 4/11 | V Boys Golf | Hale Ray | Home - PGC [Directions] | Portland: 171 Hale Ray: 219 (league) | ||
| Wed., 4/11 | V Softball | East Hampton | Away - East Hampton HS [Directions] | L 5-17 | 2:25 p.m. | |
| Wed., 4/11 | V Girls Tennis | North Branford | Away [Directions] | L 0-7 | 2:25 p.m. | |
| Tue., 4/17 | V Baseball | Westbrook | Home - Portland HS [Directions] | L 6-5 (8 innings) | ||
| Tue., 4/17 | V Softball | Old Lyme | Home - Nolan Field [Directions] | L 0-19 | ||
| Tue., 4/17 | V Girls Tennis | Valley Regional | Home - Portland HS [Directions] | L 0-7 | ||
| Wed., 4/18 | V Baseball | Old Lyme | Home - Portland HS [Directions] | L 14-4 | ||
| Wed., 4/18 | V Softball | North Branford | Home - Nolan Field [Directions] | L 0-19 | ||
| Thu., 4/19 | JV Boys Golf | Glastonbury | Away - Minnechaug [Directions] | 3:00 p.m. | ||
| Fri., 4/20 | V Baseball | North Branford | Away - North Branford HS [Directions] | W 15-6 | 2:25 p.m. | |
| Fri., 4/20 | V Softball | Coginchaug | Away - Nolan Field - Portland [Directions] | L 1-22 | 2:25 p.m. | |
| Fri., 4/20 | V Girls Tennis | Morgan | Away - Morgan HS [Directions] | L 3-4 | 2:25 p.m. | |
| Sat., 4/21 | V Baseball | Ellington | Home - Portland HS [Directions] | W 14-4 (6 inn) | Non-League | |
| Sat., 4/21 | JV Baseball | Ellington | Home - Rose Hill Park [Directions] | 11:00 a.m. | ||
| Sat., 4/21 | JV Baseball | North Branford | Home - Portland HS [Directions] | 2:00 p.m. | ||
| Mon., 4/23 | V Softball | Valley Regional | Away - Valley Regional HS [Directions] | L 0-16 | 2:25 p.m. | |
| Mon., 4/23 | V Girls Tennis | Coginchaug | Home - Portland HS [Directions] | L 1-6 | ||
| Tue., 4/24 | V Baseball | Creed | Away - West Rock Park | W 12-1 | 2:25 p.m. | |
| Tue., 4/24 | V Boys Golf | Coginchaug | Home - PGC [Directions] | Portland: 175 Coginchaug: 169 (league) | ||
| Tue., 4/24 | V Boys Outdoor Track | Coginchaug, Valley Regional, Hale Ray | Away - CRHS Stadium Field & Track [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 4/24 | V Girls Outdoor Track | Coginchaug, Valley Regional, Hale Ray | Away - CRHS Stadium Field & Track [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 4/24 | V Softball | Morgan | Away - Morgan HS [Directions] | L 0-18 | 2:25 p.m. | |
| Tue., 4/24 | Unified Sports Track | Cromwell | Away [Directions] | 3:00 p.m. | 2:25 p.m. | |
| Thu., 4/26 | V Boys Golf | East Hampton | Away - Black Birch Country Club [Directions] | Portland:169 East Hampton: 224 (league) | 2:25 p.m. | |
| Sat., 4/28 | V Baseball | East Hampton | Home - Portland HS [Directions] | W 16-7 | ||
| Sat., 4/28 | V Boys Outdoor Track | Stafford | Away [Directions] | 4:00 p.m. | 2:00 p.m. | Stafford Invitational |
| Sat., 4/28 | V Girls Outdoor Track | Stafford | Away [Directions] | 4:00 p.m. | 2:00 p.m. | Stafford Invitational |
| Sat., 4/28 | V Softball | Haddam-Killingworth | Home - Nolan Field [Directions] | L 2-20 | ||
| Mon., 4/30 | V Baseball | Hale Ray | Home - Portland HS [Directions] | W 8-3 | ||
| Mon., 4/30 | V Softball | Old Saybrook | Home - Nolan Field [Directions] | L 9-24 | ||
| Tue., 5/1 | V Baseball | Cromwell | Home - Portland HS [Directions] | L 11-7 | ||
| Tue., 5/1 | V Boys Golf | Old Lyme | Home - PGC [Directions] | Portland: 168 Old Lyme: 176 (league) | ||
| Tue., 5/1 | V Boys Outdoor Track | Morgan, Cromwell | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 5/1 | V Girls Outdoor Track | Morgan, Cromwell | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 5/1 | V Softball | Cromwell | Home - Nolan Field [Directions] | L 1-14 | ||
| Tue., 5/1 | V Girls Tennis | Old Saybrook | Away - Old Saybrook HS [Directions] | L 1-6 | 2:25 p.m. | |
| Wed., 5/2 | V Baseball | Old Lyme | Away - Old Lyme HS [Directions] | W 8-6 | 2:25 p.m. | |
| Wed., 5/2 | V Boys Golf | Morgan | Away - Clinton Country Club [Directions] | Portland: 187 Morgan: 199 (non-league) | 2:15 p.m. | |
| Wed., 5/2 | V Softball | Westbrook/Old Saybrook | Away - Westbrook HS Field #5 - Softball [Directions] | L 8-10 | 2:25 p.m. | |
| Wed., 5/2 | V Girls Tennis | Haddam-Killingworth | Home - Portland HS [Directions] | L 0-7 | ||
| Wed., 5/2 | V Girls Tennis | Haddam-Killingworth | Home - Portland HS [Directions] | L 0-7 | ||
| Wed., 5/2 | Unified Sports Track | Cromwell | Home - Portland HS [Directions] | 2:45 p.m. | ||
| Thu., 5/3 | JV Baseball | Old Lyme | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Thu., 5/3 | V Boys Golf | North Branford | Home - PGC [Directions] | Portland: 161 North Branford: 199 (league) | ||
| Thu., 5/3 | V Girls Tennis | Westbrook | Away - Westbrook HS/MS Tennis Courts [Directions] | L 0-7 | 2:25 p.m. | |
| Fri., 5/4 | V Baseball | Old Saybrook | Away - Old Saybrook HS [Directions] | L 5-2 | ||
| Fri., 5/4 | V Softball | Hale Ray | Home - Nolan Field [Directions] | L 1-13 | ||
| Fri., 5/4 | V Girls Tennis | Old Lyme | Away - Old Lyme HS [Directions] | L 0-7 | 2:25 p.m. | |
| Sat., 5/5 | V Boys Outdoor Track | Coginchaug | Away [Directions] | 10:00 a.m. | 9:00 a.m. | |
| Sat., 5/5 | V Girls Outdoor Track | Coginchaug | Away [Directions] | 10:00 a.m. | 9:00 a.m. | |
| Mon., 5/7 | V Baseball | Westbrook | Away - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | W 3-2 | 2:25 p.m. | |
| Mon., 5/7 | V Boys Golf | Wildcat Invitational | Away - Norwich GC | Portland: 171 7th place | 10:00 a.m. | Wildcat Invitational |
| Mon., 5/7 | V Softball | East Hampton | Home - Nolan Field [Directions] | L 5-13 | ||
| Mon., 5/7 | Unified Sports Track | Middletown | Home - Portland HS [Directions] | 2:45 p.m. | ||
| Tue., 5/8 | V Baseball | Coginchaug | Home - Portland HS [Directions] | W 5-3 | ||
| Tue., 5/8 | V Boys Golf | Conard | Away - Rockledge Golf Course [Directions] | Portland: 188 Conard:150 | 2:00 p.m. | Non-League JV as well |
| Tue., 5/8 | JV Boys Golf | Conard | Away - Rockledge GC [Directions] | 3:00 p.m. | ||
| Tue., 5/8 | V Boys Outdoor Track | East Hampton, Old Saybrook | Away - East Hampton HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 5/8 | V Girls Outdoor Track | East Hampton, Old Saybrook | Away - East Hampton HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 5/8 | V Girls Tennis | East Hampton | Away - East Hampton HS [Directions] | W 5-2 | 2:25 p.m. | |
| Wed., 5/9 | V Baseball | Creed | Home - Portland HS [Directions] | W 14-6 | Senior Day | |
| Wed., 5/9 | V Softball | Old Lyme | Away - Old Lyme HS [Directions] | L 1-18 | 2:25 p.m. | |
| Wed., 5/9 | V Girls Tennis | Cromwell | Home - Portland HS [Directions] | L 1-6 | ||
| Wed., 5/9 | V Girls Tennis | Cromwell | Home - Portland HS [Directions] | L 1-6 | 2:25 p.m. | |
| Thu., 5/10 | JV Baseball | Hale Ray | Home - Portland HS [Directions] | 3:45 p.m. | 2:25 a.m. | |
| Thu., 5/10 | V Girls Tennis | North Branford | Home - Portland HS [Directions] | L 1-6 | ||
| Fri., 5/11 | V Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | W 11-1 | 2:25 p.m. | |
| Fri., 5/11 | V Boys Golf | Valley Regional | Away - Fox Hopyard CC [Directions] | Portland: 171 Valley: 232 (league) | 2:25 p.m. | |
| Fri., 5/11 | V Girls Tennis | Valley Regional | Away - Valley Regional HS [Directions] | L 1-6 | 2:25 p.m. | |
| Mon., 5/14 | V Baseball | ValleyReg/Westbrook | Away - Valley Regional HS [Directions] | W 14-4 | 2:25 p.m. | |
| Tue., 5/15 | V Boys Golf | Haddam-Killingworth | Away - Black Birch [Directions] | Portland: 166 H-K: 197 (league) | 2:25 p.m. | |
| Wed., 5/16 | V Baseball | East Hampton | Away - East Hampton HS [Directions] | W 8-3 | 2:25 p.m. | |
| Wed., 5/16 | V Boys Golf | Morgan | Home - PGC [Directions] | Portland: 161 Morgan:191 (league) | ||
| Wed., 5/16 | V Boys Outdoor Track | Old Lyme, Hale Ray, Westbrook | Home - Portland HS [Directions] | 3:45 p.m. | Senior Day | |
| Wed., 5/16 | V Girls Outdoor Track | Old Lyme, Hale Ray, Westbrook | Home - Portland HS [Directions] | 3:45 p.m. | Senior Day | |
| Wed., 5/16 | V Softball | Goodwin Tech | Home - Nolan Field [Directions] | L 8-9 | Non-League | |
| Thu., 5/17 | V Baseball | Old Saybrook | Home - Portland HS [Directions] | L 1-9 | ||
| Thu., 5/17 | V Baseball | Middletown | Away - Palmer Field [Directions] | L 5-1 | 5:45 p.m. | Non-League |
| Thu., 5/17 | V Boys Outdoor Track | SLC Freshman Invitational | Away | 3:45 p.m. | 2:25 p.m. | SLC Freshman Invitational- HK HS |
| Thu., 5/17 | V Girls Outdoor Track | SLC Freshman Invitational | Away | 3:45 p.m. | 2:25 p.m. | SLC Freshman Invitational- HK HS |
| Thu., 5/17 | V Girls Tennis | Coginchaug | Away - Tennis Courts @ CRHS [Directions] | L 1-6 | 2;25 p.m. | |
| Mon., 5/21 | V Boys Golf | Old Saybrook | Away - Fenwick [Directions] | Portland: 161 Old Saybrook: 168 (league) | 2:25 p.m. | |
| Mon., 5/21 | V Softball | Comp Sci | Home - Portland HS [Directions] | W 15-4 | 2:25 p.m. | Non-League |
| Mon., 5/21 | V Softball | Comp Sci | Home - Nolan Field [Directions] | W 5-3 | Non-League (Senior Night) | |
| Mon., 5/21 | V Girls Tennis | Old Saybrook | Home - Portland HS [Directions] | L 0-7 | Senior Day | |
| Tue., 5/22 | V Boys Golf | Haddam-Killingworth | Home - PGC [Directions] | Portland: 160 H-K: 197 (non-league) | Non-League/ Senior Day | |
| Wed., 5/23 | JV Boys Golf | Glastonbury | Home - PGC [Directions] | 2:45 p.m. | ||
| Wed., 5/23 | V Girls Tennis | Morgan | Home - Portland HS [Directions] | W 5-2 | ||
| Thu., 5/24 | JV Baseball | Hale Ray | Away - Hale Ray [Directions] | 4:10 p.m. | ||
| Wed., 5/30 | V Boys Golf | Glastonbury | Away - Glastonbury CC [Directions] | Portland: 179 Glastonbury: 164 East Hartford: 239 | 2:00 p.m. | |
| Wed., 5/30 | JV Boys Golf | Glastonbury | Away - Minnechaug [Directions] | 3:00 p.m. | ||