| Portland 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 455 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] | 11:00 a.m. | 9:45 a.m. | |
| TBA | JV Baseball | Old Saybrook | Home - Portland HS [Directions] | 1:30 p.m. | ||
| TBA | JV Baseball | Westbrook | Away - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 4:00 p.m. | 2:25 p.m. | |
| TBA | JV Baseball | Westbrook | Home - Portland HS [Directions] | 4:00 p.m. | ||
| TBA | JV Boys Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | TBA | ||
| TBA | FR Boys Basketball | Haddam-Killingworth | Home - Portland HS [Directions] | Cancelled | ||
| TBA | JV Boys Soccer | Old Saybrook | Home - Portland HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| TBA | JV Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | TBA | 9:00 a.m. | |
| TBA | V Boys Swimming and Diving | CCC Swim Championships | Away | TBA | TBA | |
| TBA | JV Girls Basketball | Old Saybrook | Home - Portland HS [Directions] | TBA | ||
| TBA | JV Girls Soccer | East Hampton | Away - East Hampton HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| TBA | JV Girls Soccer | Old Lyme | Away - Old Lyme HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| TBA | JV Girls Soccer | Old Saybrook | Home - Portland HS [Directions] | 3:45 p.m. | ||
| TBA | JV Girls Soccer | Westbrook | Away - Westbrook HS Field #2 - Track/Soccer [Directions] | 3:45 p.m. | 2:25 p.m. | |
| TBA | JV Girls Soccer | Valley Regional | Away - VRHS [Directions] | 4:00 p.m. | 2:25 p.m. | |
| TBA | JV Girls Soccer | Cromwell | Away - Cromwell HS [Directions] | TBA | 2:25 p.m. | |
| Sat., 8/25 | V Football | jamboree | Home - Pierson Park, Cromwell [Directions] | 2:00 p.m. | 12:00 p.m. | Hartford Public, Foran, Killingly |
| Mon., 8/27 | V Boys Soccer | Middletown (Scrim.) | Away - Middletown HS [Directions] | 3:30 p.m. | 2:25 p.m. | |
| Thu., 8/30 | V Girls Soccer | Jonathan Law (Scrim.) | Home - Portland HS [Directions] | 4:30 p.m. | ||
| Fri., 8/31 | V Football | Berlin (Scrim.) | Away - Sage Park - Scalise Field [Directions] | 6:00 p.m. | 4:15 p.m. | |
| Fri., 8/31 | V Boys Soccer | Shepaug Valley (Scrim.) | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Mon., 9/3 | V Girls Soccer | Coventry (Scrim.) | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 9/4 | V Boys Cross Country | Glastonbury, RHAM, Hale Ray (Scrim.) | Away [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 9/4 | V Girls Cross Country | Glastonbury, RHAM, Hale Ray (Scrim.) | Away [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Wed., 9/5 | V Boys Soccer | East Granby (Scrim.) | Home [Directions] | 4:30 p.m. | ||
| Fri., 9/7 | V Boys Cross Country | Blue Dragon Invitational | Away | 3:45 p.m. | 2:25 p.m. | Vets Park |
| Fri., 9/7 | V Football | Rockville | Home - Pierson Park, Cromwell [Directions] | W 35-21 | 4:00 p.m. | |
| Fri., 9/7 | V Boys Soccer | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | L 1-4 | 2:25 p.m. | Non-League |
| Fri., 9/7 | V Girls Cross Country | Blue Dragon Invitational | Away | 3:45 p.m. | 2:25 p.m. | Vets Park |
| Sat., 9/8 | JV Football | Rockville | Away - RHS football field [Directions] | 10:30 a.m. | 8:30 a.m. | |
| Sat., 9/8 | JV Boys Soccer | Old Saybrook | Away - Old Saybrook HS [Directions] | 10:00 a.m. | 8:45 a.m. | |
| Tue., 9/11 | V Boys Cross Country | Highlander Invitational | Home - YMCA Camp Ingersoll [Directions] | 3:45 p.m. | Highlander Invitational | |
| Tue., 9/11 | V Girls Cross Country | Highlander Invitational | Home - YMCA Camp Ingersoll [Directions] | 3:45 p.m. | Highlander Invitational | |
| Wed., 9/12 | V Girls Swimming and Diving | Southington | Away - Southington YMCA [Directions] | L | 2:30pm | |
| Thu., 9/13 | V Boys Soccer | Cromwell | Away - Cromwell HS [Directions] | L 2-3 | 2:25 p.m. | |
| Thu., 9/13 | V Girls Soccer | Cromwell | Home - Portland HS [Directions] | W 1-0 | ||
| Fri., 9/14 | V Football | North Branford | Away - NBHS Colafati Field [Directions] | W 28-20 | 4:30 p.m. | |
| Fri., 9/14 | V Boys Soccer | Haddam-Killingworth | Home - Portland HS [Directions] | W 1-0 | ||
| Fri., 9/14 | V Girls Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | W 3-0 | 2:25 p.m. | |
| Mon., 9/17 | V Boys Soccer | North Branford | Away - North Branford HS [Directions] | W 6-0 | 2:25 p.m. | |
| Mon., 9/17 | JV Girls Soccer | Haddam-Killingworth | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Mon., 9/17 | V Girls Swimming and Diving | East Catholic | Home - Rocky Hill HS [Directions] | L | ||
| Thu., 9/20 | V Boys Cross Country | Run to the Sun Invitational | Away | 3:30 p.m. | 2:25 p.m. | Coginchaug |
| Thu., 9/20 | JV Boys Soccer | Old Lyme | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Thu., 9/20 | V Girls Cross Country | Run to the Sun Invitational | Away | 3:30 p.m. | 2:25 p.m. | Coginchaug |
| Fri., 9/21 | V Boys Cross Country | Sloper Relays | Away | Cancelled | 2:25 p.m. | Camp Farnam Southington |
| Fri., 9/21 | V Boys Soccer | Old Lyme | Away - Old Lyme HS [Directions] | L 0-2 | 2:25 p.m. | |
| Fri., 9/21 | V Girls Cross Country | Sloper Relays | Away | Cancelled | 2:25 p.m. | Camp Farnam Southington |
| Fri., 9/21 | JV Girls Soccer | North Branford/Hale Ray | Away - North Branford HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Sat., 9/22 | V Football | Lewis Mills | Away - Lewis Mills Track [Directions] | W 55-7 | 10:00 a.m. | |
| Sat., 9/22 | V Girls Soccer | Old Lyme | Home - Portland HS [Directions] | T 2-2 | ||
| Mon., 9/24 | JV Football | Lewis Mills | Home - Pierson Park, Cromwell [Directions] | 3:30 p.m. | 2:25 p.m. | |
| Mon., 9/24 | V Boys Soccer | Valley Regional | Home - Portland HS [Directions] | L 1-3 | ||
| Tue., 9/25 | V Girls Swimming and Diving | Plainville | Home - Rocky Hill HS [Directions] | L | ||
| Wed., 9/26 | V Boys Cross Country | League Meet 1-Small Schools | Away - Lyme Old Lyme | 3:30 p.m. | 2:25 p.m. | SLC League Meet 1- Small Schools |
| Wed., 9/26 | V Girls Cross Country | League Meet 1- Small Schools | Away - Lyme Old Lyme | 3:30 p.m. | 2:25 p.m. | |
| Wed., 9/26 | V Girls Soccer | Innovation | Home - Portland HS [Directions] | W 9-1 | Non-League | |
| Thu., 9/27 | V Boys Soccer | Coginchaug | Home - Portland HS [Directions] | T 1-1 | ||
| Thu., 9/27 | JV Boys Soccer | Coginchaug | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Thu., 9/27 | V Girls Soccer | Coginchaug | Away - CRHS Stadium Field & Track [Directions] | W 3-0 | 2:25 p.m. | JV & V |
| Thu., 9/27 | JV Girls Soccer | Coginchaug | Away - CRHS Stadium Field & Track [Directions] | 5:30 p.m. | ||
| Fri., 9/28 | V Boys Cross Country | East Hampton | Away [Directions] | 3:45 p.m. | 2:25 p.m. | Bellringer Invitational |
| Fri., 9/28 | V Girls Cross Country | East Hampton | Away [Directions] | 3:45 p.m. | 2:25 p.m. | Bellringer Invitational |
| Fri., 9/28 | V Girls Swimming and Diving | East Hartford | Home - Rocky Hill HS [Directions] | L | ||
| Sat., 9/29 | V Football | Haddam-Killingworth | Home - Pierson Park, Cromwell [Directions] | W 47-19 | 4:00 p.m. | |
| Mon., 10/1 | JV Football | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | 8:30 a.m. | |
| Mon., 10/1 | V Boys Soccer | East Hampton | Away - East Hampton HS Main Field [Directions] | W 1-0 | 5:15 p.m. | |
| Mon., 10/1 | JV Boys Soccer | Valley Regional | Away - Valley Regional HS [Directions] | 3:30 p.m. | 2:25 p.m. | |
| Mon., 10/1 | V Girls Soccer | East Hampton | Home - Portland HS [Directions] | T 1-1 | ||
| Mon., 10/1 | JV Girls Soccer | East Hampton | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 10/2 | V Girls Swimming and Diving | Suffield | Home - Rocky Hill HS [Directions] | W | ||
| Tue., 10/2 | Unified Sports Soccer | Cromwell | Home - Portland HS [Directions] | Cancelled | ||
| Wed., 10/3 | V Boys Cross Country | Sheehan Invitational | Away | 3:45 p.m. | 2:25 p.m. | Wallingford |
| Wed., 10/3 | JV Boys Soccer | East Hampton | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Wed., 10/3 | V Girls Cross Country | Sheehan | Away [Directions] | 3:45 p.m. | 2:25 p.m. | Sheehan Invitational |
| Thu., 10/4 | V Boys Soccer | Hale Ray | Home - Portland HS [Directions] | L 0-1 | ||
| Thu., 10/4 | V Girls Soccer | Hale Ray | Away - Hale-Ray HS [Directions] | W 6-0 | 2:25 p.m. | |
| Sat., 10/6 | V Boys Cross Country | Woods Trail Run | Away | 10:00 a.m. | TBA | Thetford, VT 10/5 & 10/6 |
| Sat., 10/6 | V Football | Coginchaug/Hale Ray/East Hampton | Home - Pierson Park, Cromwell [Directions] | W 13-6 | 11:00 a.m. | |
| Sat., 10/6 | JV Boys Soccer | Hale Ray | Away - Hale-Ray HS [Directions] | 10:30 a.m. | 9:30 a.m. | |
| Sat., 10/6 | V Girls Cross Country | Woods Trail Run | Away | 10:00 a.m. | TBA | Thetford, VT 10/5 & 10/6 |
| Sat., 10/6 | V Girls Soccer | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | W 3-0 | 2:30 p.m. | Non-League |
| Tue., 10/9 | V Girls Soccer | Old Saybrook | Away - Old Saybrook HS [Directions] | W 1-0 | 2:25 p.m. | |
| Tue., 10/9 | V Girls Swimming and Diving | Berlin | Home - Rocky Hill HS [Directions] | L | ||
| Tue., 10/9 | Unified Sports Soccer | Middletown | Home - Portland HS [Directions] | 3:00 p.m. | ||
| Wed., 10/10 | V Boys Cross Country | League Meet 2 (Mega Meet) | Away - Hale Ray | 2:30 p.m. | 1:25 p.m. | |
| Wed., 10/10 | V Boys Soccer | Old Saybrook | Home - Portland HS [Directions] | L 2-6 | ||
| Wed., 10/10 | V Girls Cross Country | League Meet 2 (Mega Meet) | Away - Hale Ray | 2:30 p.m. | 1:25 p.m. | |
| Wed., 10/10 | V Girls Soccer | Morgan | Home - Portland HS [Directions] | L 0-2 | ||
| Wed., 10/10 | JV Girls Soccer | Morgan | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Thu., 10/11 | V Girls Swimming and Diving | Bulkeley/HMTCA/Weaver | Home - Rocky Hill HS [Directions] | W | ||
| Sat., 10/13 | V Girls Soccer | New Fairfield | Away - Rebel Turf [Directions] | W 3-2 | 12:00 p.m. | Non-League |
| Mon., 10/15 | JV Boys Soccer | Morgan | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Mon., 10/15 | V Girls Soccer | Westbrook | Home - Portland HS [Directions] | W 5-0 | ||
| Tue., 10/16 | V Boys Soccer | Westbrook | Away - Westbrook HS Field #2 - Track/Soccer [Directions] | W 4-1 | 2:25 p.m. | |
| Tue., 10/16 | V Girls Soccer | East Hampton | Home - Portland HS [Directions] | L 0-1 | 2:15 p.m. | Non-Seeding |
| Tue., 10/16 | V Girls Swimming and Diving | Windsor | Home - Rocky Hill HS [Directions] | L | ||
| Tue., 10/16 | Unified Sports Soccer | Cromwell | Away [Directions] | 3:00 p.m. | 2:15 p.m. | |
| Wed., 10/17 | JV Boys Soccer | Westbrook | Home - Portland HS [Directions] | Cancelled | ||
| Wed., 10/17 | V Girls Swimming and Diving | Enfield | Away - Fermi HS [Directions] | L | 2:30pm | |
| Thu., 10/18 | V Boys Soccer | Innovation | Home - Portland HS [Directions] | W 2-0 | Non-League | |
| Thu., 10/18 | V Girls Soccer | Valley Regional | Away - VRHS Football Field [Directions] | W 3-1 | 2:25 p.m. | |
| Fri., 10/19 | V Boys Cross Country | SLC Championship | Away - Hale Ray | 2:30 p.m. | 1:30 p.m. | SLC Championships |
| Fri., 10/19 | V Boys Soccer | East Hampton | Home - Portland HS [Directions] | L 0-2 | Non-League | |
| Fri., 10/19 | JV Boys Soccer | East Hampton | Home - Portland HS [Directions] | 3:30 p.m. | ||
| Fri., 10/19 | V Girls Cross Country | SLC Championship | Away - Hale Ray | 2:30 p.m. | 1:30 p.m. | SLC Championship |
| Fri., 10/19 | V Girls Swimming and Diving | Maloney/Platt | Away - Maloney HS [Directions] | W | 2:30pm | |
| Sat., 10/20 | V Football | Old Saybrook | Away - Old Saybrook HS Turf Field [Directions] | L 20-35 | 10:00 a.m. | |
| Sat., 10/20 | V Boys Soccer | Morgan | Away - Indian River Complex [Directions] | L 0-6 | 3:15 p.m. | |
| Sat., 10/20 | V Girls Soccer | North Branford/Hale Ray | Home - Portland HS [Directions] | L 0-4 | ||
| Mon., 10/22 | JV Football | Old Saybrook | Home - Pierson Park, Cromwell [Directions] | Cancelled | 2:25 p.m. | |
| Mon., 10/22 | V Boys Soccer | Aerospace | Home - Portland HS [Directions] | W 2-0 | Non-League - Senior Night | |
| Mon., 10/22 | V Girls Soccer | Comp Sci | Home - Portland HS [Directions] | W 6-0 | Non-League - Senior Night | |
| Tue., 10/23 | JV Boys Soccer | Cromwell | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 10/23 | V Girls Swimming and Diving | Wethersfield | Home - Rocky Hill HS [Directions] | L | ||
| Wed., 10/24 | V Boys Cross Country | Frosh Invitational (JV G&B) | Away - Old Saybrook | 3:30 p.m. | 2:30 p.m. | Frosh Invitational (JV G&B) |
| Wed., 10/24 | V Boys Soccer | Ellis Tech | Home - Portland HS [Directions] | W 6-3 | Non-League | |
| Wed., 10/24 | V Girls Cross Country | Frosh Invitational (JV B&G) | Away - Old Saybrook | 3:30 p.m. | Frosh Invitational (JV B&G) | |
| Wed., 10/24 | Unified Sports Soccer | SLC Unified Soccer Tournament | Away - Westbrook HS | 3:00 p.m. | 2:15 p.m. | |
| Fri., 10/26 | V Boys Cross Country | CIAC Class S Championship | Away - Wickham Park | TBA | 8:30 a.m. | CIAC Class S Championship |
| Fri., 10/26 | V Football | Valley Regional/Old Lyme | Away - VRHS Football Field [Directions] | W 21-14 (OT) | 4:30 p.m. | |
| Fri., 10/26 | V Girls Cross Country | Class S Championship | Away - Wickham Park | TBA | 8:30 a.m. | Class S Championships |
| Fri., 10/26 | V Girls Swimming and Diving | Bristol Central/Eastern | Home - Rocky Hill HS [Directions] | W | ||
| Sat., 10/27 | V Boys Soccer | SLC Quarterfinals | Away | TBA | SLC Quarterfinals | |
| Mon., 10/29 | V Boys Cross Country | Fresh Invitational (Fr. G&B) | Away - John Winthrop | 3:30 p.m. | 2:25 p.m. | |
| Mon., 10/29 | JV Football | Valley Regional/Old Lyme | Home - Pierson Park, Cromwell [Directions] | 3:45 p.m. | 9:30 a.m. | |
| Mon., 10/29 | V Girls Cross Country | Fresh Invitational (FR. G&B) | Away - John Winthrop | 3:30 p.m. | 2:25 p.m. | |
| Tue., 10/30 | V Girls Soccer | East Hampton | Home - Portland HS [Directions] | L 4-3 PKs | SLC Quarterfinals | |
| Tue., 10/30 | V Girls Swimming and Diving | Bristol Eastern | Home - Rocky Hill HS [Directions] | W | ||
| Thu., 11/1 | V Boys Cross Country | CIAC State Open | Away | TBA | TBA | CIAC Class S Open |
| Thu., 11/1 | V Football | MSW | Home - Pierson Park, Cromwell [Directions] | W 48-18 | 5:00 p.m. | |
| Thu., 11/1 | V Boys Soccer | SLC Semifinals | Away | TBA | SLC Semifinals | |
| Thu., 11/1 | V Girls Cross Country | CIAC State Open | Away | TBA | TBA | CIAC State Open |
| Thu., 11/1 | V Girls Soccer | SLC Semifinals | Away | TBA | SLC Semifinals | |
| Fri., 11/2 | V Boys Soccer | SLC Championship | Away | TBA | SLC Championship | |
| Fri., 11/2 | V Girls Soccer | SLC Championships | Away | TBA | SLC Championships | |
| Fri., 11/2 | V Girls Swimming and Diving | CCC Championships | Away - Wethersfield HS | 3:45 p.m. | 2:30pm | |
| Sat., 11/3 | JV Football | MSW | Away - Peters Complex [Directions] | Cancelled | 9:30 a.m. | |
| Mon., 11/5 | JV Football | Coginchaug/Hale Ray/East Hampton | Away - Coginchaug HS [Directions] | Cancelled | ||
| Mon., 11/5 | JV Football | Coginchaug/Hale Ray/East Hampton | Away - CRHS Stadium Field & Track [Directions] | 3:45 p.m. | 8:30 a.m. | |
| Tue., 11/6 | V Boys Soccer | Wheeler | Away - Waterford soccer field [Directions] | L 3-1 | 10:15 a.m. | 1st Round CIAC States |
| Wed., 11/7 | V Girls Soccer | Canton | Home - Portland HS [Directions] | W 5-2 | 2nd Round CIAC States | |
| Thu., 11/8 | V Girls Swimming and Diving | State Diving Meet | Away - Bulkeley HS | Cancelled | 3:30pm | |
| Fri., 11/9 | V Girls Soccer | Old Lyme | Away - Old Saybrook HS (Turf Field) [Directions] | 2:00 p.m. | 12:15 p.m. | Quarterfinal CIAC States |
| Sat., 11/10 | V Football | Woodstock Academy | Away [Directions] | W 41-0 | ||
| Sat., 11/10 | V Girls Swimming and Diving | State Swimming Trials | Away - Cheshire Community Pool | 10:00 a.m. | 7:15am | |
| Wed., 11/14 | V Girls Swimming and Diving | State Swimming Finals | Away - Wesleyan University | 7:00 p.m. | 4:00pm | |
| Sat., 11/17 | JV Football | Xavier | Away - Larry McHugh Field (Xavier H.S.) [Directions] | Cancelled | ||
| Sat., 11/17 | FR Football | Xavier | Away - Larry McHugh Field (Xavier H.S.) [Directions] | 1:00 p.m. | ||
| Wed., 11/21 | V Football | Rocky Hill | Away - Rocky Hill HS [Directions] | W 30-0 | 4:00 p.m. | |
| Tue., 11/27 | V Football | Stafford/East Windsor/Somers | Away - Enfield HS [Directions] | 6:30 p.m. | ||
| Fri., 11/30 | V Girls Basketball | Lyman Hall (Scrim.) | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Sat., 12/1 | V Wrestling | Bacon Academy (Scrim.) | Away [Directions] | 9:30 a.m. | 8:30 a.m. | |
| Wed., 12/5 | V Boys Basketball | Lyman Hall (Scrim.) | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Thu., 12/6 | V Girls Basketball | Windsor Locks (Scrim.) | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Sat., 12/8 | V Wrestling | Bacon Academy (Scrim.) | Away [Directions] | 9:30 a.m. | 8:30 a.m. | |
| Mon., 12/10 | V Boys Basketball | Innovation (Scrim.) | Away - Academy of Science and Innovation [Directions] | 4:00 p.m. | 2:25 p.m. | |
| Tue., 12/11 | V Girls Basketball | Hale Ray | Home - Portland HS [Directions] | W 53-6 | ||
| Tue., 12/11 | JV Girls Basketball | Hale Ray | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Wed., 12/12 | V Boys Indoor Track | Shoreline Developmental Track Meet | Away - Floyd Little Athletic Center | 5:30 p.m. | 4:00 p.m. | |
| Wed., 12/12 | V Wrestling | Notre Dame-West Haven | Home - Portland HS [Directions] | 6:30 p.m. | ||
| Wed., 12/12 | V Girls Indoor Track | Shoreline Developmental Track Meet | Away - Floyd Little Athletic Center | 5:30 p.m. | 4:00 p.m. | |
| Thu., 12/13 | V Boys Basketball | Haddam-Killingworth | Home - Portland HS [Directions] | W 65-48 | ||
| Thu., 12/13 | JV Boys Basketball | Haddam-Killingworth | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Thu., 12/13 | V Girls Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | W 75-33 | 4:30 p.m. | |
| Thu., 12/13 | JV Girls Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:30 p.m. | ||
| Sat., 12/15 | V Wrestling | Pomperaug Tournament | Away | 10:00 a.m. | 7:30 a.m. | Pomperaug Tournament |
| Mon., 12/17 | V Boys Basketball | Morgan | Away - Morgan HS [Directions] | L 40-64 | 4:20 p.m. | |
| Mon., 12/17 | JV Boys Basketball | Morgan | Away - Morgan HS [Directions] | 5:30 p.m. | ||
| Mon., 12/17 | V Girls Basketball | Morgan | Home - Portland HS [Directions] | L 51-50 | ||
| Mon., 12/17 | JV Girls Basketball | Morgan | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Tue., 12/18 | V Boys Basketball | Whitney Tech | Away - Whitney Tech School Gymnasium [Directions] | W 66-65 | 2:25 p.m. | Non-League |
| Tue., 12/18 | JV Boys Basketball | Whitney Tech | Away - Whitney Tech School Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 12/18 | V Boys Swimming and Diving | East Catholic | Home - Rocky Hill HS [Directions] | W | ||
| Wed., 12/19 | V Wrestling | Ellis Tech | Home - Portland HS [Directions] | 6:30 p.m. | ||
| Wed., 12/19 | V Girls Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | L 31-64 | 4:30 p.m. | Non-League |
| Wed., 12/19 | JV Girls Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 5:30 p.m. | Non-League | |
| Thu., 12/20 | V Boys Basketball | Coginchaug | Home - Portland HS [Directions] | L 44-46 | ||
| Thu., 12/20 | JV Boys Basketball | Coginchaug | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Fri., 12/21 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | L 52-38 | 4:30 p.m. | |
| Fri., 12/21 | JV Girls Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | 5:30 p.m. | ||
| Sat., 12/22 | V Wrestling | Rockville Duals | Away | 10:00 a.m. | 8:00 a.m. | |
| Thu., 12/27 | FR Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 5:30 p.m. | 4:30 p.m. | |
| Thu., 12/27 | V Wrestling | Plainville | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Fri., 12/28 | V Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | L 41-79 | 4:20 p.m. | |
| Fri., 12/28 | JV Boys Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Fri., 12/28 | V Boys Swimming and Diving | Middletown | Away - Middletown HS [Directions] | L | 7:30am | |
| Fri., 12/28 | V Girls Basketball | Old Lyme | Home - Portland HS [Directions] | L 38-42 | ||
| Fri., 12/28 | JV Girls Basketball | Old Lyme | Home - Portland HS [Directions] | 3:30 p.m. | ||
| Sat., 12/29 | FR Boys Basketball | Valley Regional | Home - Portland HS [Directions] | 10:00 a.m. | ||
| Sat., 12/29 | V Wrestling | Killingly Duals | Away | 9:00 a.m. | 7:00 a.m. | Killingly Duals |
| Wed., 1/2 | V Boys Basketball | Cromwell | Home - Portland HS [Directions] | L 34-67 | Non-League | |
| Wed., 1/2 | FR Boys Basketball | Cromwell | Home - Portland HS [Directions] | 3:30 p.m. | ||
| Wed., 1/2 | V Girls Basketball | Cromwell | Home - Portland HS [Directions] | L 33-61 | ||
| Thu., 1/3 | V Boys Indoor Track | Shoreline League Meet #1 | Away | 5:30 p.m. | 4:00 p.m. | |
| Thu., 1/3 | V Wrestling | Morgan | Away - Morgan HS [Directions] | 7:00 p.m. | 4:45 p.m. | |
| Thu., 1/3 | V Girls Indoor Track | Shoreline League Meet #1 | Away | 5:30 p.m. | 4:00 a.m. | |
| Fri., 1/4 | V Boys Basketball | Westbrook | Home - Portland HS [Directions] | W 53-38 | ||
| Fri., 1/4 | JV Boys Basketball | Westbrook | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Fri., 1/4 | V Boys Swimming and Diving | Manchester/RHAM | Home - Rocky Hill HS [Directions] | W | ||
| Fri., 1/4 | V Girls Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | W 49-31 | 4:20 p.m. | |
| Fri., 1/4 | JV Girls Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | 5:45 p.m. | ||
| Sat., 1/5 | V Wrestling | Nonnewaug Tournament | Away | 9:30 a.m. | 7:00 a.m. | Nonnewaug Tournament |
| Mon., 1/7 | V Boys Basketball | North Branford | Away - North Branford HS [Directions] | W 62-54 | 4;20 p.m. | |
| Mon., 1/7 | JV Boys Basketball | North Branford | Away - North Branford HS [Directions] | 5:30 p.m. | ||
| Tue., 1/8 | V Boys Swimming and Diving | Simsbury | Away - Westminster School [Directions] | L | 5:30pm | |
| Tue., 1/8 | V Girls Basketball | North Branford | Home - Portland HS [Directions] | W 42-35 | ||
| Tue., 1/8 | JV Girls Basketball | North Branford | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Wed., 1/9 | V Wrestling | Haddam-Killingworth | Home - Portland HS [Directions] | 6:30 p.m. | ||
| Thu., 1/10 | V Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | L 48-53 | 4:30 p.m. | |
| Thu., 1/10 | JV Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 5:30 p.m. | ||
| Fri., 1/11 | V Girls Basketball | East Hampton | Home - Portland HS [Directions] | L 30-39 | ||
| Fri., 1/11 | JV Girls Basketball | East Hampton | Home - Portland HS [Directions] | 5:45 p.m. | ||
| Sat., 1/12 | V Boys Indoor Track | Shoreline Coaches Track Meet | Away - Floyd Little Athletic Center | Cancelled | 8:00 a.m. | |
| Sat., 1/12 | V Wrestling | Lyman Memorial Tournament | Away | 9:00 a.m. | 7:30 a.m. | Lyman Memorial Tournament |
| Sat., 1/12 | V Girls Indoor Track | Shoreline Coaches Track Meet | Away - Floyd Little Athletic Center | Cancelled | 8:00 a.m. | |
| Mon., 1/14 | V Boys Basketball | Valley Regional | Home - Portland HS [Directions] | L 53-72 | ||
| Mon., 1/14 | JV Boys Basketball | Valley Regional | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Tue., 1/15 | V Boys Swimming and Diving | Plainville Boys Swimming | Away - Plainville HS Pool [Directions] | L | 2:30pm | |
| Tue., 1/15 | V Girls Basketball | Valley Regional | Away - Valley Regional HS [Directions] | L 45-31 | 4:30 p.m. | |
| Tue., 1/15 | JV Girls Basketball | Valley Regional | Away - Valley Regional HS [Directions] | 5:30 p.m. | ||
| Tue., 1/15 | Unified Sports Basketball | Old Saybrook | Home - Portland HS [Directions] | 3:00 p.m. | ||
| Wed., 1/16 | FR Boys Basketball | Coginchaug | Home - Portland HS [Directions] | 7:00 p.m. | ||
| Wed., 1/16 | V Wrestling | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 6:30 p.m. | 4:25 p.m. | |
| Thu., 1/17 | V Boys Basketball | Amistad | Home - Portland HS [Directions] | L 53-56 | Non-League | |
| Thu., 1/17 | JV Boys Basketball | Amistad | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Thu., 1/17 | V Boys Indoor Track | Wesleyan Developmental Meet | Away | Cancelled | 2:25 p.m. | |
| Thu., 1/17 | V Girls Basketball | Whitney Tech | Away - Whitney Tech School Gymnasium [Directions] | W 67-35 | 3:15 p.m. | Non-League |
| Thu., 1/17 | V Girls Indoor Track | Wesleyan Developmental Meet | Away - Wesleyan University | Cancelled | 2:25 p.m. | |
| Fri., 1/18 | V Boys Indoor Track | HK Invitational | Away - Floyd Little Athletic Center (N. Haven) | 4:30 p.m. | 2:25 p.m. | |
| Fri., 1/18 | V Boys Swimming and Diving | Meriden Co-op | Away - Platt high school [Directions] | L | 2:30pm | |
| Fri., 1/18 | V Girls Indoor Track | HK Invitational | Away - Floyd Little Athletic Center (N. Haven) | 4:30 p.m. | 2:25 p.m. | |
| Sat., 1/19 | V Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | L 30-57 | 1:30 p.m. | |
| Sat., 1/19 | JV Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 2:30 p.m. | ||
| Sat., 1/19 | FR Boys Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | 9:00 a.m. | 7:30 a.m. | |
| Sat., 1/19 | V Wrestling | Granby Duals | Away | 9:00 a.m. | 7:00 a.m. | |
| Tue., 1/22 | V Boys Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | L 44-60 | 2:25 p.m. | |
| Tue., 1/22 | V Boys Swimming and Diving | Wethersfield | Home - Rocky Hill HS [Directions] | L | ||
| Tue., 1/22 | V Girls Basketball | Old Saybrook | Home - Portland HS [Directions] | W 64-31 | ||
| Wed., 1/23 | V Wrestling | Terryville-Thomaston | Home - Portland HS [Directions] | 4:30 p.m. | Senior Night | |
| Thu., 1/24 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | L 39-56 | 3:30 p.m. | Non-League |
| Thu., 1/24 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | 4:30 p.m. | ||
| Fri., 1/25 | V Boys Indoor Track | Shoreline League Meet #2 | Away - Floyd Little Athletic Center | 5:00 p.m. | 4:00 p.m. | |
| Fri., 1/25 | V Boys Swimming and Diving | Bulkeley Cooperative Swim Team | Away - Bulkeley HS Pool [Directions] | W | 2:30pm | |
| Fri., 1/25 | V Girls Indoor Track | Shoreline League Meet #2 | Away - Floyd Little Athletic Center | 5:00 p.m. | 4:00 p.m. | |
| Sat., 1/26 | FR Boys Basketball | East Hampton | Away - East Hampton HS [Directions] | 9:00 a.m. | 7:45 a.m. | |
| Sat., 1/26 | V Wrestling | Highlander Invitational | Home - Portland HS [Directions] | 9:00 a.m. | Highlander Invitational | |
| Mon., 1/28 | V Girls Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | W 61-11 | 4:30 p.m. | |
| Mon., 1/28 | JV Girls Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | Cancelled | ||
| Mon., 1/28 | Unified Sports Basketball | Westbrook | Away [Directions] | 3:00 p.m. | 2:15 p.m. | |
| Thu., 1/31 | V Boys Basketball | Hale Ray | Home - Portland HS [Directions] | W 50-43 | ||
| Thu., 1/31 | JV Boys Basketball | Hale Ray | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Thu., 1/31 | V Boys Swimming and Diving | Hartford Public | Home - Rocky Hill HS [Directions] | W | ||
| Thu., 1/31 | V Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | L 48-33 | 4:30 p.m. | |
| Thu., 1/31 | JV Girls Basketball | East Hampton | Away - East Hampton HS [Directions] | 5:45 p.m. | ||
| Fri., 2/1 | V Boys Basketball | East Hampton | Home - Portland HS [Directions] | L 46-53 | ||
| Fri., 2/1 | JV Boys Basketball | East Hampton | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Fri., 2/1 | FR Boys Basketball | East Hampton | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Fri., 2/1 | V Boys Swimming and Diving | Windsor | Away - Windsor HS [Directions] | L | 2:30pm | |
| Fri., 2/1 | V Girls Basketball | St. Bernard | Away - St. Bernard Gymnasium [Directions] | W 45-30 | 4:15 p.m. | Non-League |
| Fri., 2/1 | JV Girls Basketball | St. Bernard | Away - St. Bernard Gymnasium [Directions] | 5:30 p.m. | Non-League | |
| Sat., 2/2 | FR Boys Basketball | Valley Regional | Away - Valley Regional HS [Directions] | 11:00 a.m. | 9:30 a.m. | |
| Sat., 2/2 | V Boys Indoor Track | SLC Indoor Track Championships | Away - Floyd Little Athletic Center- New Haven | 10:00 a.m. | 8:30 a.m. | |
| Sat., 2/2 | V Wrestling | Bacon Tourney | Away | 9:30 a.m. | 7:45 a.m. | |
| Sat., 2/2 | V Girls Indoor Track | SLC Indoor Track Championships | Away - Floyd Little Athletic Center- New Haven | 10:00 a.m. | 8:00 a.m. | |
| Mon., 2/4 | V Wrestling | Thomaston | Away - Thomaston H.S. Gymnasium [Directions] | 6:00 p.m. | 4:00 p.m. | |
| Mon., 2/4 | V Girls Basketball | Westbrook | Home - Portland HS [Directions] | W 53-39 | ||
| Mon., 2/4 | JV Girls Basketball | Westbrook | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Tue., 2/5 | V Boys Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | W 52-45 | 4:20 p.m. | |
| Tue., 2/5 | JV Boys Basketball | Westbrook | Away - Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/5 | V Boys Swimming and Diving | Newington | Away - NHS Pool [Directions] | L | 3:30pm | |
| Wed., 2/6 | FR Boys Basketball | Cromwell | Away - Jake Salafia Gymnasium @ Cromwell HS [Directions] | 7:00 p.m. | 5:30 p.m. | |
| Wed., 2/6 | V Wrestling | Gilbert/Torrington | Away [Directions] | 6:30 p.m. | 4:30 p.m. | |
| Thu., 2/7 | V Boys Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Thu., 2/7 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | W 47-29 | 3:30 p.m. | |
| Thu., 2/7 | JV Girls Basketball | Old Saybrook | Away - Old Saybrook HS [Directions] | 4:45 p.m. | ||
| Thu., 2/7 | V Girls Indoor Track | CIAC Class S Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | V Boys Basketball | Old Saybrook | Home - Portland HS [Directions] | L 59-47 | ||
| Fri., 2/8 | JV Boys Basketball | Old Saybrook | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Fri., 2/8 | FR Boys Basketball | Old Saybrook | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Sat., 2/9 | FR Boys Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | 12:00 p.m. | 10:45 a.m. | |
| Sat., 2/9 | V Competitive Cheerleading | SLC Cheerleading Championship | Away - Westbrook HS | 4:00 p.m. | 2:15pm | |
| Mon., 2/11 | V Girls Basketball | Cheney Tech | Home - Portland HS [Directions] | W 68-22 | Non-League- Senior Night | |
| Mon., 2/11 | JV Girls Basketball | Cheney Tech | Home - Portland HS [Directions] | 5:30 p.m. | Non-League | |
| Mon., 2/11 | Unified Sports Basketball | Westbrook | Away [Directions] | 3:30 p.m. | 2:15 p.m. | |
| Wed., 2/13 | FR Boys Basketball | Morgan | Home - Portland HS [Directions] | 6:00 p.m. | ||
| Wed., 2/13 | V Girls Basketball | Old Lyme | Away - Old Lyme HS [Directions] | L 44-35 | 4:20 p.m. | |
| Wed., 2/13 | JV Girls Basketball | Old Lyme | Away - Old Lyme HS [Directions] | 5:30 p.m. | ||
| Fri., 2/15 | V Boys Basketball | Old Lyme | Home - Portland HS [Directions] | L 39-54 | Senior Night | |
| Fri., 2/15 | JV Boys Basketball | Old Lyme | Home - Portland HS [Directions] | 5:30 p.m. | ||
| Fri., 2/15 | FR Boys Basketball | Old Lyme | Home - Portland HS [Directions] | 4:00 p.m. | ||
| Fri., 2/15 | V Boys Swimming and Diving | E.O. Smith - Tolland Hammerheads | Away - Mansfield Community Center Pool [Directions] | L | 2:30pm | |
| Fri., 2/15 | V Wrestling | CIAC Class S Championships | Away - Windham [Directions] | 4:45 p.m. | ||
| Fri., 2/15 | V Wrestling | CIAC Class S Tournament | Away | TBA | 1:30 p.m. | CIAC Class S Tournament |
| Sat., 2/16 | FR Boys Basketball | Old Saybrook | Home - Portland HS [Directions] | 10:00 a.m. | ||
| Sat., 2/16 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/16 | V Wrestling | CIAC Class S Championships | Away - Windham [Directions] | 9:00 a.m. | ||
| Sat., 2/16 | V Wrestling | CIAC Class S Tournament | Away | TBA | 7:00 a.m. | CIAC Class S Tournament |
| Sat., 2/16 | V Girls Basketball | Morgan | Away [Directions] | L 50-38 | 3:30 p.m. | SLC Quarterfinals |
| Sat., 2/16 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Thu., 2/21 | V Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | W 45-43 | 3:30 p.m. | |
| Thu., 2/21 | JV Boys Basketball | Hale Ray | Away - Hale-Ray HS [Directions] | 4:45 p.m. | ||
| Thu., 2/21 | V Boys Swimming and Diving | Avon | Home - Rocky Hill HS [Directions] | L | ||
| Fri., 2/22 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 3:00 p.m. | 11:00 a.m. | |
| Fri., 2/22 | V Wrestling | State Opens | Away | TBA | TBA | State Opens |
| Sat., 2/23 | V Boys Basketball | Old Lyme | Away [Directions] | L 54-37 | 4:15 p.m. | SLC Quarterfinal |
| Sat., 2/23 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | 7:45 a.m. | |
| Sat., 2/23 | V Wrestling | State Opens | Away | TBA | TBA | State Opens |
| Sat., 2/23 | V Competitive Cheerleading | NECA | Away - East Haven HS | 1:00 p.m. | 11:00 a.m. | |
| Mon., 2/25 | V Girls Basketball | Coginchaug | Away - Coginchaug Regional HS [Directions] | L 55-36 | 4:30 p.m. | |
| Wed., 2/27 | V Boys Swimming and Diving | CCC Dive Championships | Home - Rocky Hill HS [Directions] | 5:00 p.m. | ||
| Thu., 2/28 | V Girls Basketball | CIAC Tourney 2nd Round | Away - Higher Seed | TBA | ||
| Fri., 3/1 | V Boys Swimming and Diving | CCC Swim Championships | Away - Wethersfield HS | 4:30 p.m. | 2:30pm | |
| Sat., 3/2 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sat., 3/2 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sun., 3/3 | V Competitive Cheerleading | States | Away - F. Little New Haven | 3:00 p.m. | 1:00 p.m. | |
| Mon., 3/4 | V Girls Basketball | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Tue., 3/5 | V Boys Basketball | CIAC Tourney 1st Round | Away - Higher Seed | TBA | ||
| Wed., 3/6 | Unified Sports Basketball | Middletown | Away [Directions] | 3:00 p.m. | 2:15 p.m. | |
| Thu., 3/7 | V Boys Basketball | CIAC Tourney 2nd Round | Away - Higher Seed | TBA | ||
| Fri., 3/8 | V Girls Basketball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Sat., 3/9 | V Boys Swimming and Diving | State Trials | Away - Cheshire Community Pool | 3:00 p.m. | 12:00pm | |
| Mon., 3/11 | V Boys Basketball | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Mon., 3/11 | V Boys Swimming and Diving | State Finals | Away - Wesleyan University | 6:00 p.m. | 4:15pm | |
| Wed., 3/13 | V Boys Basketball | CIAC Tourney Semifinals | Away - Site TBA | TBA | ||
| Sat., 3/16 | V Boys Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | ||
| Sat., 3/16 | V Girls Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | ||
| Sun., 3/17 | V Boys Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | ||
| Sun., 3/17 | V Girls Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | TBA | ||
| Tue., 3/19 | Unified Sports Basketball | Portland Unified Basketball Tournament | Home - Portland HS [Directions] | 3:00 p.m. | 4 Team Tournament- Crom, Midd, Port, West | |
| Tue., 3/26 | V Baseball | Haddam-Killingworth (Scrim.) | Away - Haddam Killingworth HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Wed., 3/27 | V Baseball | ValleyReg/Westbrook (Scrim.) | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Sat., 3/30 | V Girls Tennis | Valley Regional | Home - Portland HS [Directions] | L 1-6 | ||
| Mon., 4/1 | V Baseball | ValleyReg/Westbrook | Away - Valley Regional HS [Directions] | W 1-0 | 2:25 p.m. | |
| Mon., 4/1 | V Softball | Valley Regional | Away - Valley Regional HS [Directions] | L 0-21 | 2:25 p.m. | |
| Mon., 4/1 | V Girls Tennis | North Branford | Away - North Branford HS [Directions] | L 0-7 | 2:25 p.m. | |
| Tue., 4/2 | JV Baseball | ValleyReg/Westbrook | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 4/2 | V Boys Golf | Old Saybrook | Away - Fenwick [Directions] | Portland:172 Old Saybrook: 173 (non-league) | 2:00 p.m. | Non-League |
| Wed., 4/3 | V Baseball | Westbrook | Home - Portland HS [Directions] | W 13-6 | ||
| Wed., 4/3 | V Softball | Westbrook/Old Saybrook | Home - Nolan Field [Directions] | W 25-13 | ||
| Wed., 4/3 | V Girls Tennis | Morgan | Home - Portland HS [Directions] | W 4-3 | ||
| Thu., 4/4 | V Baseball | North Branford | Away - North Branford HS [Directions] | L 11-1 | 2:25 p.m. | |
| Thu., 4/4 | V Softball | North Branford | Away - North Branford HS [Directions] | L 0-18 | 2:25 p.m. | |
| Thu., 4/4 | V Girls Tennis | Coginchaug | Away - Tennis Courts @ CRHS [Directions] | L 1-6 | 2:25 p.m. | |
| Sat., 4/6 | V Boys Outdoor Track | Bellringer Invitational | Away - East Hampton HS | 10:00 a.m. | 8:00 a.m. | |
| Sat., 4/6 | V Girls Outdoor Track | Bellringer Invitational | Away - East Hampton HS | 10:00 a.m. | 8:00 a.m. | |
| Mon., 4/8 | JV Boys Golf | Xavier | Home - PGC [Directions] | 3:00 p.m. | ||
| Tue., 4/9 | V Baseball | Old Lyme | Home - Portland HS [Directions] | W 10-1 | ||
| Tue., 4/9 | V Boys Golf | Old Lyme | Away - Black Hall Club Old Lyme [Directions] | Portland: 176 Old Lyme: 179 (league) | 2:15 p.m. | |
| Tue., 4/9 | V Softball | Old Lyme | Home - Nolan Field [Directions] | L 0-20 | ||
| Wed., 4/10 | V Baseball | Morgan | Home - Portland HS [Directions] | W 10-0 | ||
| Wed., 4/10 | V Softball | Morgan | Home - Nolan Field [Directions] | L 2-26 | ||
| Wed., 4/10 | V Girls Tennis | Old Lyme | Home - Portland HS [Directions] | L 1-6 | ||
| Thu., 4/11 | JV Baseball | Morgan | Away - Morgan HS [Directions] | 4:00 p.m. | 2:25 p.m. | |
| Thu., 4/11 | V Girls Tennis | East Hampton | Home - Portland HS [Directions] | W 4-3 | ||
| Fri., 4/12 | V Baseball | Old Saybrook | Away - Old Saybrook HS [Directions] | W 3-2 | 2:25 p.m. | |
| Fri., 4/12 | V Softball | Old Saybrook | Away - Old Saybrook HS [Directions] | L 4-16 | 2:25 p.m. | |
| Fri., 4/12 | V Girls Tennis | Old Saybrook | Away - Old Saybrook HS [Directions] | W 4-3 | 2:25 p.m. | |
| Tue., 4/16 | V Baseball | Haddam-Killingworth | Home - Portland HS [Directions] | W 3-2 | ||
| Wed., 4/17 | V Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | W 3-2 | 2:25 p.m. | |
| Wed., 4/17 | V Boys Golf | Cromwell | Away - TPC River Highlands [Directions] | Portland:176 Cromwell: 174 (non-league) | 1:45 p.m. | |
| Wed., 4/17 | V Girls Tennis | Westbrook | Away - Westbrook HS/MS Tennis Courts [Directions] | L 0-7 | 8:45 a.m. | |
| Thu., 4/18 | JV Baseball | Hale Ray | Home - Portland HS [Directions] | 11:00 a.m. | ||
| Fri., 4/19 | V Baseball | Ellington | Away - Ellington HS [Directions] | W 11-1 | 2:25 p.m. | Non-League |
| Tue., 4/23 | V Boys Golf | Cromwell | Home - PGC [Directions] | Portland:166 Cromwell: 184 (league) | ||
| Tue., 4/23 | V Boys Outdoor Track | Hale Ray, Cromwell | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Hale Ray, Cromwell | Home - Portland HS [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Softball | Haddam-Killingworth | Home - Nolan Field [Directions] | L 0-3 | ||
| Tue., 4/23 | V Girls Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | L 3-4 | 2:25 p.m. | |
| Wed., 4/24 | V Baseball | East Hampton | Home - Portland HS [Directions] | W 11-0 | ||
| Wed., 4/24 | V Boys Golf | Old Saybrook | Home - PGC [Directions] | Portland:170 Old Saybrook:180 (league) | ||
| Wed., 4/24 | V Softball | East Hampton | Home - Nolan Field [Directions] | L 1-8 | ||
| Wed., 4/24 | V Girls Tennis | Valley Regional | Away - Valley Regional HS [Directions] | L 1-6 | 2:25 p.m. | |
| Thu., 4/25 | JV Baseball | East Hampton | Home - Portland HS [Directions] | 4:00 p.m. | 2:25 p.m. | |
| Thu., 4/25 | V Boys Golf | North Branford | Away - Indian Springs Golf Club [Directions] | Portland: 168 North Branford: 232 (league) | 1:45 p.m. | |
| Thu., 4/25 | V Girls Tennis | North Branford | Home - Portland HS [Directions] | L 0-7 | ||
| Sat., 4/27 | V Baseball | Cromwell | Home - Portland HS [Directions] | W 3-2 | ||
| Sat., 4/27 | V Boys Outdoor Track | Stafford Invitational | Away - Stafford HS | 10:00 a.m. | 8:00 a.m. | |
| Sat., 4/27 | V Girls Outdoor Track | Stafford Invitational | Away - Stafford HS | 10:00 a.m. | 8:00 a.m. | |
| Mon., 4/29 | V Baseball | Westbrook | Away - Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | W 8-0 | 2:25 p.m. | |
| Mon., 4/29 | V Boys Golf | Conard | Home - PGC [Directions] | Portland:170 Conard: 173 | ||
| Mon., 4/29 | JV Boys Golf | Conard | Home - PGC [Directions] | 2:30 p.m. | ||
| Mon., 4/29 | V Softball | Westbrook/Old Saybrook | Away - Westbrook HS Field #5 - Softball [Directions] | W 13-11 | 2:25 p.m. | |
| Mon., 4/29 | V Girls Tennis | Morgan | Away - Morgan HS [Directions] | L 3-4 | 3:45 p.m. | |
| Tue., 4/30 | V Boys Outdoor Track | East Hampton, Westbrook | Away - East Hampton HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 4/30 | V Girls Outdoor Track | East Hampton, Westbrook | Away - East Hampton HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 4/30 | V Softball | Cromwell | Home - Nolan Field [Directions] | L 1-18 | ||
| Wed., 5/1 | V Baseball | Old Lyme | Away - Old Lyme HS [Directions] | L 7-4 | 2:25 p.m. | |
| Wed., 5/1 | V Boys Golf | Morgan | Away - Clinton CC [Directions] | Portland: 162 Morgan: 193 (league) | 2:00 p.m. | |
| Wed., 5/1 | V Softball | Old Lyme | Away - Old Lyme HS [Directions] | L 2-12 | 2:25 p.m. | |
| Wed., 5/1 | V Girls Tennis | Coginchaug | Home - Portland HS [Directions] | L 3-4 | ||
| Thu., 5/2 | JV Baseball | Old Lyme | Away - Old Lyme HS [Directions] | 4:00 p.m. | 2:25 p.m. | |
| Thu., 5/2 | V Boys Golf | Glastonbury | Away - Glastonbury Hills Country Club [Directions] | Portland: 177 Glastonbury: 164 | 2:15 p.m. | |
| Thu., 5/2 | JV Boys Golf | Glastonbury | Away - Minnechaug Golf Course [Directions] | 3:00 p.m. | With V Bus | |
| Thu., 5/2 | V Softball | Coginchaug | Away - Ed Parmelee Memorial Varsity Softball Field @ CRHS [Directions] | L 0-17 | 2:25 p.m. | |
| Sat., 5/4 | V Boys Outdoor Track | Coginchaug | Away - Coginchaug HS [Directions] | 10:00 a.m. | 8:30 a.m. | |
| Sat., 5/4 | V Girls Outdoor Track | Coginchaug | Away - Coginchaug HS [Directions] | 10:00 a.m. | 8:30 a.m. | Coginchaug Invitational |
| Mon., 5/6 | V Baseball | Hale Ray | Home - Palmer Field- Middletown [Directions] | W 7-0 | 4:30 p.m. | |
| Mon., 5/6 | V Boys Golf | Wildcat Invitational | Away | 170 front nine. 334 total. (4th place) | 11:00 a.m. | |
| Mon., 5/6 | V Softball | Hale Ray | Away - Hale Ray [Directions] | L 2-15 | 2:25 p.m. | |
| Mon., 5/6 | V Softball | Hale Ray | Away - Hale-Ray HS, Lou Milardo Field [Directions] | L 0-21 | 2:25 p.m. | |
| Mon., 5/6 | V Girls Tennis | Old Lyme | Away - Old Lyme HS [Directions] | L 1-6 | 2:25 p.m. | |
| Tue., 5/7 | JV Baseball | Hale Ray | Away - Hale-Ray HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 5/7 | V Boys Outdoor Track | Coginchaug, Old Saybrook | Away - Coginchaug HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 5/7 | V Girls Outdoor Track | Coginchaug, Old Saybrook | Away - Coginchaug HS [Directions] | 3:45 p.m. | 2:25 p.m. | |
| Tue., 5/7 | Unified Sports Track | Middletown | Home - Portland HS [Directions] | 3:00 p.m. | ||
| Wed., 5/8 | V Boys Golf | East Hampton | Away [Directions] | Portland: 158 East Hampton: 206 (league) | 2:15 p.m. | |
| Wed., 5/8 | V Softball | East Hampton | Away - East Hampton HS [Directions] | L 5-15 | 2;25 p.m. | |
| Thu., 5/9 | V Baseball | Old Saybrook | Home - Palmer Field- Middletown [Directions] | W 12-5 | 4:30 p.m. | Senior Night |
| Thu., 5/9 | V Boys Golf | Hale Ray | Away [Directions] | Portland: 173 Hale Ray: 185 (league) | 2:15 p.m. | |
| Thu., 5/9 | V Softball | Goodwin Tech | Away - Goodwin Tech HS Field [Directions] | W 19-6 | 2:25 p.m. | Non-League |
| Thu., 5/9 | V Girls Tennis | Cromwell | Home - Portland HS [Directions] | L 2-5 | ||
| Fri., 5/10 | V Baseball | Coginchaug | Away - Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | W 5-4 | 2:25 p.m. | |
| Fri., 5/10 | V Boys Outdoor Track | Old Saybrook | Away [Directions] | 3:30 p.m. | 2:15 p.m. | |
| Fri., 5/10 | V Girls Outdoor Track | Old Saybrook | Away - Old Saybrook HS [Directions] | 3:30 p.m. | 2:15 p.m. | Old Saybrook Invitational |
| Sat., 5/11 | JV Baseball | East Hampton | Home - Portland HS [Directions] | 12:00 p.m. | ||
| Tue., 5/14 | V Baseball | Morgan | Away - Indian River Complex [Directions] | L 6-4 | 5:00 p.m. | Non-League |
| Tue., 5/14 | V Boys Golf | Valley Regional | Home - PGC [Directions] | Portland: 166 Valley: 212 (league) | ||
| Tue., 5/14 | V Softball | Old Saybrook | Home - Nolan Field [Directions] | L 3-16 | ||
| Tue., 5/14 | V Girls Tennis | East Hampton | Away - East Hampton HS [Directions] | L 1-6 | 2:25 p.m. | |
| Tue., 5/14 | Unified Sports Track | Old Lyme | Home - Portland HS [Directions] | 3:00 p.m. | ||
| Wed., 5/15 | V Baseball | East Hampton | Away - Portland HS [Directions] | W 10-3 | 2:25 p.m. | |
| Wed., 5/15 | V Boys Golf | Haddam-Killingworth, Coventry | Home - PGC [Directions] | Portland: 157 H-K: 200 (league) Coventry:175 | ||
| Wed., 5/15 | V Boys Outdoor Track | Freshman Invitational | Away - HK HS | 3:45 p.m. | 2:25 p.m. | Freshman Invitational |
| Wed., 5/15 | V Girls Outdoor Track | Tournament Game - Opponent Not Known | Away - HK HS | 3:45 p.m. | 2:25 p.m. | Freshman Invitational |
| Wed., 5/15 | V Girls Tennis | Cromwell | Home - Portland HS [Directions] | L 1-6 | ||
| Wed., 5/15 | V Girls Tennis | Westbrook | Home - Portland HS [Directions] | L 0-7 | ||
| Thu., 5/16 | V Baseball | Middletown | Away - Palmer Field [Directions] | W 4-2 | 4:45 p.m. | Non-League |
| Thu., 5/16 | V Boys Golf | Coginchaug | Home - PGC [Directions] | Portland: 171 Coginchaug: 151 (league) | Senior Day | |
| Thu., 5/16 | V Girls Tennis | Haddam-Killingworth | Home - Portland HS [Directions] | L 2-5 | Senior Day | |
| Sat., 5/18 | V Baseball | St. Bernard | Away - Dodd Stadium [Directions] | W 10-1 | 3:00 p.m. | Non-League |
| Sat., 5/18 | V Girls Tennis | Old Saybrook | Home - Portland HS [Directions] | W 5-2 | ||
| Mon., 5/20 | V Baseball | Hale Ray | Home - PHS Varsity Baseball Field [Directions] | W 7-4 | SLC Quarterfinals | |
| Mon., 5/20 | JV Boys Golf | Xavier | Home - PGC [Directions] | Cancelled | ||
| Mon., 5/20 | V Softball | Comp Sci | Home - Nolan Field [Directions] | W 10-7 | Non-League | |
| Mon., 5/20 | V Softball | Comp Sci | Home - Nolan Field [Directions] | L 9-12 | Non-League | |
| Mon., 5/20 | V Girls Tennis | SLC Championships | Away - Morgan/OS/Westbrook | 9:00 a.m. | 7:45 a.m. | SLC Championships |
| Tue., 5/21 | JV Boys Golf | Xavier | Home - PGC [Directions] | 2:45 p.m. | ||
| Tue., 5/21 | V Softball | Innovation | Home - Nolan Field [Directions] | W 12-11 | Senior Night Non-League | |
| Wed., 5/22 | V Baseball | Coginchaug | Home - PHS Varsity Baseball Field [Directions] | W 1-0 | SLC Semifinals | |
| Wed., 5/22 | V Boys Golf | SLC Championships | Away - Stanley GC | 9:00 a.m. | 7:30 a.m. | |
| Wed., 5/22 | V Boys Outdoor Track | SLC Championships | Away | TBA | TBA | SLC Championships |
| Wed., 5/22 | V Girls Outdoor Track | SLC Championships | Away - TBA | TBA | TBA | SLC Championships |
| Thu., 5/23 | JV Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS [Directions] | 4:00 p.m. | 2:25 p.m. | |
| Fri., 5/24 | V Baseball | Haddam-Killingworth | Home - Palmer Field- Middletown [Directions] | W 2-1 | 4:15 p.m. | SLC Championship Game |
| Wed., 5/29 | V Baseball | Westbrook | Home - PHS Varsity Baseball Field [Directions] | W 5-0 | CIAC State Tournament 1st Round | |
| Wed., 5/29 | V Boys Golf | Coginchaug | Away - Lyman Orchards [Directions] | Portland:172 Coginchaug: 165 (non-league) | 2:15 p.m. | Non-League |
| Wed., 5/29 | JV Boys Golf | Glastonbury | Home - PGC [Directions] | 2:45 p.m. | ||
| Thu., 5/30 | V Baseball | East Windsor/International | Home - PHS Varsity Baseball Field [Directions] | W 5-2 | CIAC State Tournament 2nd Round | |
| Thu., 5/30 | V Boys Outdoor Track | Class S State Championships | Away - New Britain | 3:00 p.m. | TBA | |
| Thu., 5/30 | V Girls Outdoor Track | Class S State Championships | Away - New Britain | 3:00 p.m. | TBA | |
| Sat., 6/1 | V Baseball | St. Paul Catholic | Home - PHS Varsity Baseball Field [Directions] | L 3-2 | CIAC State Tournament Quarterfinals | |
| Mon., 6/3 | V Boys Golf | CIAC DIV IV State Championships | Away - Tallwood CC, Hebron | 8:00 a.m. | TBA | CIAC DIV IV State Championship |
| Mon., 6/3 | V Boys Outdoor Track | State Open Championships | Away - New Britain | 2:00 p.m. | TBA | |
| Mon., 6/3 | V Girls Outdoor Track | State Open Championships | Away - New Britain | TBA | TBA | |