| Portland 2019-20 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 417 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Sat., 8/31 | V Football | TBA | Home - Pierson Park, Cromwell [Directions] | 2:00 p.m. | ||
| Tue., 9/3 | V Boys Cross Country | Glastonbury, RHAM (Scrim.) | Away - JB Williams Park [Directions] | 4:00 p.m. | 2:25 PM | |
| Tue., 9/3 | V Girls Cross Country | Glastonbury, RHAM (Scrim.) | Away - JB Williams Park [Directions] | 4:00 p.m. | 2:25 PM | |
| Wed., 9/4 | V Boys Soccer | Middletown (Scrim.) | Away - Middletown HS-MHS Stadium [Directions] | 3:15 p.m. | 2:25 PM | |
| Wed., 9/4 | V Girls Soccer | RHAM (Scrim.) | Away - RHAM HS-Varsity Field [Directions] | 3:45 p.m. | 2:25 PM | |
| Fri., 9/6 | V Boys Cross Country | Middletown | Away - Veterans Memorial Park, Middletown, CT [Directions] | 3:30 p.m. | 2:25 PM | |
| Fri., 9/6 | V Football | Berlin (Scrim.) | Away - Sage Park Berlin-Scalise Field [Directions] | 6:00 p.m. | 4:00 PM | |
| Fri., 9/6 | V Boys Soccer | Shepaug Valley (Scrim.) | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | ||
| Fri., 9/6 | V Girls Cross Country | Middletown | Away - Veterans Memorial Park, Middletown, CT [Directions] | 3:45 p.m. | 2:25 PM | |
| Fri., 9/6 | V Girls Soccer | Mercy (Scrim.) | Away - Mercy HS-Soccer Field [Directions] | 3:45 p.m. | 2:25 PM | |
| Mon., 9/9 | V Boys Soccer | Lyman Memorial (Scrim.) | Away - Lyman Memorial HS-Soccer Field [Directions] | 4:00 p.m. | ||
| Mon., 9/9 | V Girls Soccer | Coventry (Scrim.) | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | ||
| Tue., 9/10 | V Boys Cross Country | Highlander Invitational | Home - Camp Ingersoll [Directions] | 3:45 p.m. | ||
| Tue., 9/10 | V Girls Cross Country | Highlander Invitational | Home - Camp Ingersoll [Directions] | 4:15 p.m. | ||
| Wed., 9/11 | V Girls Soccer | Middletown (Scrim.) | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | ||
| Thu., 9/12 | V Boys Soccer | Old Saybrook | Home - Portland HS-Varsity Soccer FIeld [Directions] | L 0-2 | ||
| Fri., 9/13 | V Football | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track Field [Directions] | W 3-0 | 4:30 PM | |
| Sat., 9/14 | JV Football | Haddam-Killingworth | Home - Pierson Park, Cromwell [Directions] | 10:30 a.m. | ||
| Sat., 9/14 | V Boys Soccer | Hale Ray | Home - Portland HS-Varsity Soccer FIeld [Directions] | W 3-1 | ||
| Sat., 9/14 | V Girls Soccer | Old Saybrook | Home - Portland HS-Varsity Soccer FIeld [Directions] | W 3-0 | ||
| Mon., 9/16 | JV Boys Soccer | Cromwell | Away - Cromwell HS-JV Field [Directions] | 3:45 p.m. | 2:25 PM, Return 4:45 PM | |
| Mon., 9/16 | V Girls Soccer | Cromwell | Away - Cromwell HS-Varsity field [Directions] | W 2-0 | 4:45 PM | |
| Tue., 9/17 | V Boys Soccer | Cromwell | Home - Portland HS-Varsity Soccer FIeld [Directions] | W 3-1 | ||
| Tue., 9/17 | V Boys Swimming and Diving | Bristol Boys Swim Team (Scrim.) | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | ||
| Tue., 9/17 | JV Girls Soccer | Cromwell | Away - Cromwell HS-JV field 2 [Directions] | 3:45 p.m. | 2:25 PM | |
| Thu., 9/19 | V Boys Cross Country | Going to the Sun Invite | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:45 p.m. | 2:25 PM | |
| Thu., 9/19 | V Boys Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | L 0-2 | 2:15 PM | |
| Thu., 9/19 | V Girls Cross Country | Going to the Sun Invite | Away - Coginchaug Regional HS-Coginchaug Regional HS | 3:45 p.m. | 2:25 PM | |
| Thu., 9/19 | V Girls Soccer | Haddam-Killingworth | Home - Portland HS-Varsity Soccer FIeld [Directions] | W 2-1 | ||
| Fri., 9/20 | V Football | Valley Regional/Old Lyme | Home - Pierson Park, Cromwell [Directions] | L 0-21 | ||
| Fri., 9/20 | V Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | W 3-0 | 2:25 PM | |
| Fri., 9/20 | V Boys Swimming and Diving | East Catholic (Scrim.) | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | ||
| Sat., 9/21 | JV Football | Valley Regional/Old Lyme | Away - Valley Regional HS-Practice Football Field [Directions] | Cancelled | 8:30 AM | |
| Sat., 9/21 | JV Boys Soccer | Haddam-Killingworth | Home - Portland HS-JV Soccer Field [Directions] | 10:30 a.m. | ||
| Mon., 9/23 | V Boys Soccer | Morgan | Home - Portland HS-Varsity Soccer FIeld [Directions] | L 2-3 | ||
| Mon., 9/23 | V Girls Soccer | North Branford/Hale Ray | Away - North Branford HS-NBHS Front Field [Directions] | W 5-1 | 2:25 PM | |
| Tue., 9/24 | V Boys Cross Country | Old Lyme, TBA, Hale Ray, Old Saybrook | Home - Camp Ingersoll [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Boys Soccer | North Branford | Home - Portland HS-Varsity Soccer FIeld [Directions] | W 9-1 | ||
| Tue., 9/24 | V Girls Cross Country | East Hampton, Old Lyme, Hale Ray, Old Saybrook | Home - Camp Ingersoll [Directions] | 3:30 p.m. | ||
| Tue., 9/24 | JV Girls Soccer | North Branford/Hale Ray | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/24 | V Girls Swimming and Diving | East Hartford | Away - East Hartford HS-East Hartford Pool [Directions] | L | 2:40 PM | |
| Wed., 9/25 | JV Boys Soccer | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | 3:45 p.m. | 2:25 PM, Return 5:30 PM | |
| Thu., 9/26 | V Boys Soccer | Old Lyme | Home - Portland HS-Varsity Soccer FIeld [Directions] | W 3-1 | ||
| Thu., 9/26 | V Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | W 1-0 | 2:25 PM | |
| Fri., 9/27 | V Boys Cross Country | East Hampton | Away - East Hampton HS-Cross Country Course [Directions] | 3:45 p.m. | 2:25 PM | |
| Fri., 9/27 | V Girls Cross Country | East Hampton | Away - East Hampton HS-Cross Country Course [Directions] | 3:45 p.m. | 2:25 PM | |
| Fri., 9/27 | JV Girls Soccer | Old Lyme | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/27 | V Girls Swimming and Diving | Maloney/Platt | Home - Rocky Hill HS-Swimming Pool [Directions] | L | ||
| Sat., 9/28 | V Football | North Branford | Home - Pierson Park, Cromwell [Directions] | L 14-61 | ||
| Sat., 9/28 | JV Football | North Branford | Away - North Branford HS-NBHS Colafati Field [Directions] | Cancelled | 9:00 AM | |
| Tue., 10/1 | V Boys Swimming and Diving | Farmington (Scrim.) | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | ||
| Wed., 10/2 | V Boys Cross Country | NEUBAUER INVITATIONAL | Away - Sheehan HS-Sheehan HS Cross Country Course | 4:00 p.m. | 2:25 PM | |
| Wed., 10/2 | V Boys Soccer | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | L 0-1 | 2:25 PM | |
| Wed., 10/2 | V Girls Cross Country | NEUBAUER INVITATIONAL | Away - Sheehan HS-Sheehan HS Cross Country Course | 4:00 p.m. | 2:25 PM | |
| Wed., 10/2 | V Girls Soccer | Valley Regional | Home - Portland HS-Varsity Soccer FIeld [Directions] | T 3-3 | ||
| Thu., 10/3 | V Boys Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | T 0-0 | 5:15 PM, Return 8:10 PM | |
| Thu., 10/3 | JV Boys Soccer | Valley Regional | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/3 | V Girls Soccer | Coginchaug | Home - Portland HS-Varsity Soccer FIeld [Directions] | W 8-0 | ||
| Thu., 10/3 | JV Girls Soccer | Coginchaug | Home - Portland HS-JV Soccer Field [Directions] | Postponed | JV Game will be played right after V game and will have shortened half depending on time. | |
| Fri., 10/4 | V Boys Swimming and Diving | Middletown (Scrim.) | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | ||
| Sat., 10/5 | V Boys Cross Country | Woods Trail Run (Thetford, VT) | Away - Camp Ingersoll | 10:00 a.m. | TBA | |
| Sat., 10/5 | V Football | Coventry/Windham Tech/Bolton/Lyman | Home - Pierson Park, Cromwell [Directions] | L 20-40 | ||
| Sat., 10/5 | JV Boys Soccer | Coginchaug | Home - Portland HS-JV Soccer Field [Directions] | 10:30 a.m. | ||
| Sat., 10/5 | V Girls Cross Country | Woods Trail Run (Thetford, VT) | Away - Camp Ingersoll | 3:45 p.m. | TBA | |
| Sat., 10/5 | V Girls Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | L 1-3 | 11:30 AM, Return 12:00 PM | |
| Mon., 10/7 | JV Football | Coventry/Windham Tech/Bolton/Lyman | Away - Coventry HS-Football Field [Directions] | 3:45 p.m. | 8:00 AM | |
| Mon., 10/7 | V Boys Soccer | East Hampton | Home - Portland HS-Varsity Soccer FIeld [Directions] | T 1-1 | ||
| Mon., 10/7 | V Boys Swimming and Diving | Enfield/Ellington/Suffield (Scrim.) | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | ||
| Mon., 10/7 | JV Girls Soccer | Valley Regional | Away - Valley Regional HS-JV Girls Soccer Field [Directions] | 3:45 p.m. | 2:25 PM | |
| Tue., 10/8 | JV Boys Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 3:45 p.m. | 2:25 PM, Return 5:30 PM | |
| Thu., 10/10 | V Boys Cross Country | League Meet 2(Mega Meet) | Away - Cromwell HS-Cross Country Course | Cancelled | 2:25 PM | |
| Thu., 10/10 | JV Boys Soccer | Woodland | Home - Portland HS-JV Soccer Field [Directions] | Cancelled | ||
| Thu., 10/10 | V Girls Cross Country | League Meet 2(Mega Meet) | Away - Cromwell HS-Cross Country Course | Cancelled | 2:25 PM | |
| Thu., 10/10 | V Girls Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | W 2-1 | 2:25 PM | |
| Thu., 10/10 | JV Girls Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | Cancelled | 4:00 PM | |
| Thu., 10/10 | V Girls Swimming and Diving | Manchester/Bacon/Bolton/Coventry/Rockville | Away - Manchester HS-Pool [Directions] | L | 2:40 PM | |
| Fri., 10/11 | V Football | Stafford/East Windsor/Somers | Home - Pierson Park, Cromwell [Directions] | L 7-44 | ||
| Fri., 10/11 | V Boys Soccer | Hale Ray | Away - Nathan Hale Ray HS-Tom Nevers Field [Directions] | W 2-1 | 4:45 PM, Return 8:00 PM | |
| Sat., 10/12 | V Boys Cross Country | Wickham Invitational (Wickham Park- Manchester, CT) | Away - Camp Ingersoll | 10:00 a.m. | 8:00 AM | |
| Sat., 10/12 | JV Football | Stafford/East Windsor/Somers | Away - Stafford HS-Lighted Field behind the High School [Directions] | 10:00 a.m. | ||
| Sat., 10/12 | JV Boys Soccer | Hale Ray | Home - Portland HS-JV Soccer Field [Directions] | 10:30 a.m. | ||
| Sat., 10/12 | V Girls Cross Country | Wickham Invitational | Away - Camp Ingersoll | 10:00 a.m. | 8:00 AM | |
| Sat., 10/12 | V Girls Soccer | Hale Ray | Home - Portland HS-Varsity Soccer FIeld [Directions] | W 4-0 | ||
| Sat., 10/12 | JV Girls Soccer | Hale Ray | Home - Portland HS-JV Soccer Field [Directions] | 12:30 p.m. | ||
| Mon., 10/14 | V Boys Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | L 0-3 | 9:30 AM | |
| Mon., 10/14 | V Girls Soccer | Bacon Academy | Home - Portland HS-Varsity Soccer FIeld [Directions] | L 1-3 | ||
| Tue., 10/15 | JV Boys Soccer | Old Saybrook | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/15 | Unified Sports Soccer | Old Lyme | Home - Portland HS-JV Soccer Field 2 (Baseball Outfield) [Directions] | 3:15 p.m. | ||
| Wed., 10/16 | V Girls Soccer | St. Paul Catholic | Home - Portland HS-Portland HS [Directions] | W 4-0 | ||
| Wed., 10/16 | V Girls Swimming and Diving | Bulkeley/HMTCA/Weaver | Away - Bulkeley HS-Pool [Directions] | W | 2:40 PM | |
| Thu., 10/17 | V Boys Soccer | St. Paul Catholic | Home - Portland HS-Portland HS [Directions] | L 1-3 | ||
| Fri., 10/18 | V Boys Cross Country | Shoreline Championship | Away - Cromwell HS-Cross Country Course | 3:00 p.m. | ||
| Fri., 10/18 | JV Boys Soccer | Morgan | Away - Morgan School-Soccer/Lax Field [Directions] | 3:45 p.m. | 2:25 PM, Return 4:45 PM | |
| Fri., 10/18 | V Girls Cross Country | Shoreline Championship | Away - Cromwell HS-Cross Country Course | 2:30 p.m. | 2:25 PM | |
| Fri., 10/18 | V Girls Soccer | Morgan | Away - Indian River Complex -Turf Field [Directions] | T 0-0 | 2:25 PM, Return 4:45 PM | |
| Fri., 10/18 | V Girls Swimming and Diving | Windsor | Away - Windsor HS-Indoor Pool [Directions] | L | 2:40 PM | |
| Mon., 10/21 | V Boys Soccer | Westbrook | Home - Portland HS-Varsity Soccer FIeld [Directions] | W 5-1 | Senior Night | |
| Tue., 10/22 | V Boys Cross Country | Froshmore Invitational | Away - Old Saybrook HS-Old Saybrook Campus | 3:45 p.m. | 2:25 PM | |
| Tue., 10/22 | JV Boys Soccer | Westbrook | Home - Portland HS-JV Soccer Field [Directions] | 3:30 p.m. | ||
| Tue., 10/22 | V Girls Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | W 4-0 | 2:25 PM | |
| Wed., 10/23 | JV Girls Soccer | Westbrook | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/24 | V Boys Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | T 2-2 | 2:25 PM | |
| Thu., 10/24 | V Boys Swimming and Diving | Plainville Boys Swimming (Scrim.) | Away - Plainville HS-Pool [Directions] | 4:00 p.m. | 2:40 PM | |
| Thu., 10/24 | V Girls Soccer | Cromwell | Home - Portland HS-Varsity Soccer FIeld [Directions] | W 2-1 | Senior Night | |
| Fri., 10/25 | JV Boys Soccer | East Hampton | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/25 | V Girls Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | W 1-0 | 2:25 PM | Non-League |
| Sat., 10/26 | V Boys Cross Country | CIAC Boys Class S Divisional Championship | Away - Wickham Park | 9:50 a.m. | ||
| Sat., 10/26 | V Football | MSW | Away - Peters Complex-Football Field [Directions] | L 15-33 | 11:15 AM | |
| Sat., 10/26 | V Girls Cross Country | CIAC Girls Class S Divisional Championship | Away - Wickham Park | 9:15 a.m. | ||
| Sat., 10/26 | JV Girls Soccer | Old Saybrook | Home - Portland HS-JV Soccer Field [Directions] | Cancelled | ||
| Mon., 10/28 | V Boys Cross Country | Freshman Invitational | Away - John Winthrop MS | 3:30 p.m. | 2:25 PM | |
| Mon., 10/28 | V Boys Cross Country | Freshmen Invitational | Away - John Winthrop MS | 4:00 p.m. | ||
| Mon., 10/28 | JV Football | MSW | Home - Pierson Park, Cromwell [Directions] | Cancelled | ||
| Mon., 10/28 | V Girls Cross Country | Freshmen Invitational | Away - TBA | 3:30 p.m. | 2:25 PM | |
| Tue., 10/29 | V | Cromwell, LymeOldLyme, OldSaybrook | Away - Cromwell HS-JV Field [Directions] | 3:15 p.m. | 2:25 PM | |
| Tue., 10/29 | V Girls Swimming and Diving | Wethersfield | Away - Wethersfield HS-Backman Pool [Directions] | L | 3:30 PM | |
| Fri., 11/1 | V Boys Cross Country | CIAC Boys State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/1 | V Boys Swimming and Diving | HK-Valley (Scrim.) | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | ||
| Fri., 11/1 | V Girls Cross Country | CIAC Girls State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Sat., 11/2 | V Football | Old Saybrook | Away - Old Saybrook HS-Old Saybrook HS Turf [Directions] | L 8-35 | 12:00 PM | |
| Sat., 11/2 | V Boys Soccer | Hale Ray | Home - Portland HS-Varsity Soccer FIeld [Directions] | W 0-0 4-2 PKs | ||
| Mon., 11/4 | JV Football | Old Saybrook | Home - Pierson Park, Cromwell [Directions] | 4:00 p.m. | ||
| Tue., 11/5 | V Boys Soccer | Morgan | Away - Indian River Complex -Turf Field [Directions] | 6:30 p.m. | 4:45 PM | |
| Tue., 11/5 | V Girls Soccer | Valley Regional | Home - Portland HS-Varsity Soccer FIeld [Directions] | 5:00 p.m. | ||
| Thu., 11/7 | V Girls Swimming and Diving | Wethersfield, Bulkeley/HMTCA/Weaver, Enfield, Windsor | Away - Windsor HS-Pool [Directions] | 4:00 p.m. | ||
| Thu., 11/7 | V Girls Swimming and Diving | Windsor | Away - Windsor HS-Pool [Directions] | Cancelled | 2:30 PM | |
| Fri., 11/8 | V Football | SMSA Coop | Home - Pierson Park, Cromwell [Directions] | L 0-36 | ||
| Fri., 11/8 | V Girls Swimming and Diving | CCC Girls Swimming Championships at Wethersfield HS | Away - TBA | 4:15 p.m. | 2:30 PM | |
| Fri., 11/8 | V Girls Swimming and Diving | Wethersfield, Bulkeley/HMTCA/Weaver, Enfield, Windsor | Away - Wethersfield HS-Backman Pool [Directions] | 4:15 p.m. | ||
| Mon., 11/11 | JV Football | SMSA Coop | Home - Pierson Park, Cromwell [Directions] | 3:45 p.m. | ||
| Mon., 11/11 | V Boys Soccer | Somers | Away - Somers HS [Directions] | 2:00 p.m. | 12:00 PM | |
| Wed., 11/13 | V Boys Soccer | Lyman Memorial | Away - Lyman Memorial HS-Soccer Field [Directions] | 2:00 p.m. | 12:30 PM | |
| Thu., 11/14 | V Girls Soccer | Northwest Catholic | Home - Portland HS-Varsity Soccer FIeld [Directions] | 4:00 p.m. | ||
| Thu., 11/14 | V Girls Swimming and Diving | CIAC Girls Class S Diving Championship | Away - Plainville HS-Pool | 5:30 p.m. | ||
| Sat., 11/16 | V Football | Coginchaug/Hale Ray/East Hampton | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | L 14-32 | 11:00 AM | |
| Sat., 11/16 | V Girls Swimming and Diving | CIAC Girls Class S Trials | Away - Cheshire Community Pool | 5:15 p.m. | ||
| Mon., 11/18 | JV Football | Coginchaug/Hale Ray/East Hampton | Home - Pierson Park, Cromwell [Directions] | Cancelled | ||
| Tue., 11/19 | V Girls Swimming and Diving | CIAC Girls Class S Finals | Away - Moore Field House, SCSU | 6:00 p.m. | ||
| Thu., 11/21 | V Girls Swimming and Diving | CIAC Girls State Open Diving | Away - Middletown HS-Pool | 5:30 p.m. | ||
| Sun., 11/24 | V Girls Swimming and Diving | CIAC Girls State Open Swimming | Away - Yale | 2:00 p.m. | ||
| Wed., 11/27 | V Football | Rocky Hill | Home - Pierson Park, Cromwell [Directions] | W 20-14 | ||
| Sat., 12/7 | V Wrestling | Wethersfield, Berlin, Middletown (Scrim.) | Away - Wethersfield HS-Gym B [Directions] | 9:00 a.m. | 8:00 AM | |
| Mon., 12/9 | V Boys Basketball | Lyman Hall (Scrim.) | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/10 | V Girls Basketball | Plainville (Scrim.) | Away - Plainville HS-Wood Gymnasium [Directions] | 4:30 p.m. | 3:30 PM | |
| Thu., 12/12 | V Boys Indoor Track | SLC League Developmental Meet | Away - Hillhouse HS-Field House | 5:00 p.m. | 3:45 PM | |
| Thu., 12/12 | V Girls Basketball | Windsor Locks (Scrim.) | Away - Windsor Locks HS-Gym [Directions] | 5:30 p.m. | 4:00 PM | |
| Thu., 12/12 | V Girls Indoor Track | SLC League Developmental Meet | Away - Hillhouse HS-Field House | 5:00 p.m. | 3:45 PM | |
| Fri., 12/13 | V Boys Basketball | Whitney Tech (Scrim.) | Home - Portland HS-PHS Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/14 | V Wrestling | Bacon Academy, RHAM (Scrim.) | Away - Bacon Academy-Jack Jackter [Directions] | 9:00 a.m. | 7:30 AM | |
| Mon., 12/16 | V Girls Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | W 55-14 | 4:45 PM | |
| Wed., 12/18 | V Wrestling | Rockville | Away - Rockville HS-Main gymnasium [Directions] | 6:00 p.m. | 4:00 PM | |
| Wed., 12/18 | V Girls Basketball | Haddam-Killingworth | Home - Portland HS-Portland HS [Directions] | L 50-39 | ||
| Wed., 12/18 | JV Girls Basketball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/19 | V Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | W 59-58 | 4:30 PM | |
| Thu., 12/19 | JV Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:30 p.m. | ||
| Sat., 12/21 | V Boys Basketball | Morgan | Home - Portland HS-Portland HS [Directions] | L 51-64 | ||
| Sat., 12/21 | JV Boys Basketball | Morgan | Home - Portland HS-PHS Gym [Directions] | 12:00 p.m. | ||
| Sat., 12/21 | FR Boys Basketball | Morgan | Home - Portland HS-PHS Gym [Directions] | 10:30 a.m. | ||
| Sat., 12/21 | V Wrestling | Mike O'Keefe Invitational Wrestling Tournament | Away - Pomperaug HS-Main Gym | 9:00 a.m. | ||
| Mon., 12/23 | V Wrestling | Coventry | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/27 | V Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | L 26-53 | 4:30 PM | |
| Fri., 12/27 | JV Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | Cancelled | ||
| Sat., 12/28 | V Wrestling | Rockville Duals | Away - Rockville HS-Main gymnasium | 9:00 a.m. | 7:00 AM | |
| Mon., 12/30 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | W 63-55 | 4:15 PM | |
| Mon., 12/30 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 5:15 p.m. | ||
| Mon., 12/30 | V Boys Swimming and Diving | Middletown | Home - Rocky Hill HS-Swimming Pool [Directions] | L | ||
| Mon., 12/30 | V Girls Basketball | Somers | Home - Portland HS-PHS Gym [Directions] | W 40-38 | ||
| Thu., 1/2 | V Boys Indoor Track | SLC League Meet #1 | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Thu., 1/2 | V Wrestling | Oxford | Away - Oxford HS-Main Gym [Directions] | 6:00 p.m. | 4:00 PM | |
| Thu., 1/2 | V Girls Indoor Track | SLC League Meet #1 | Away - Hillhouse HS-Field House | 5:00 p.m. | ||
| Fri., 1/3 | V Boys Basketball | Old Lyme | Home - Portland HS-Portland HS [Directions] | L 44-61 | ||
| Fri., 1/3 | JV Boys Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/3 | V Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | L 28-32 | 4:30 PM | |
| Fri., 1/3 | JV Girls Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 6:00 p.m. | ||
| Sat., 1/4 | FR Boys Basketball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/4 | V Wrestling | Windham Duals | Away - Windham HS-Callahan Gymnasium | 9:30 a.m. | 7:00 AM | |
| Tue., 1/7 | V Boys Basketball | Cromwell | Home - Portland HS-Portland HS [Directions] | L 44-46 | ||
| Tue., 1/7 | JV Boys Basketball | Cromwell | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/7 | V Boys Swimming and Diving | Manchester/RHAM | Home - Rocky Hill HS-Swimming Pool [Directions] | W | ||
| Tue., 1/7 | V Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | L 42-65 | 4:30 PM | |
| Tue., 1/7 | JV Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 6:00 p.m. | 12:00 PM | |
| Wed., 1/8 | FR Boys Basketball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/8 | V Wrestling | Granby Memorial | Away - Granby Memorial HS-Community Gym [Directions] | 6:00 p.m. | 4:00 PM | |
| Thu., 1/9 | V Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | W 54-36 | 4:20 PM | |
| Thu., 1/9 | JV Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/10 | V Boys Swimming and Diving | Berlin | Home - Rocky Hill HS-Swimming Pool [Directions] | L | ||
| Fri., 1/10 | V Girls Basketball | Westbrook | Home - Portland HS-Portland HS [Directions] | W 56-46 | ||
| Fri., 1/10 | JV Girls Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/11 | FR Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 10:00 a.m. | 8:45 AM | |
| Sat., 1/11 | V Boys Indoor Track | SLC Coaches Invite | Away - Hillhouse HS-Field House | 10:00 a.m. | 8:00 AM | |
| Sat., 1/11 | V Wrestling | Casey Yates Invitational | Away - Lyman Memorial HS-Gym | 9:00 a.m. | ||
| Sat., 1/11 | V Girls Indoor Track | SLC Coaches Invite | Away - Hillhouse HS-Field House | 10:00 a.m. | ||
| Mon., 1/13 | V Boys Indoor Track | Old Saybrook Qualifier | Away - Hillhouse HS-Field House | 5:00 p.m. | 3:45 PM | |
| Mon., 1/13 | V Girls Indoor Track | Old Saybrook Qualifier | Away - Hillhouse HS-Field House | 5:00 p.m. | 3:45 PM | |
| Tue., 1/14 | V Boys Basketball | North Branford | Home - Portland HS-Portland HS [Directions] | W 60-57 | ||
| Tue., 1/14 | JV Boys Basketball | North Branford | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/14 | V Boys Swimming and Diving | Meriden Co-op | Home - Rocky Hill HS-Swimming Pool [Directions] | L | TBA | |
| Tue., 1/14 | V Girls Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | L 34-47 | 4:30 PM | |
| Tue., 1/14 | JV Girls Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/15 | V Wrestling | Somers | Home - Portland HS-PHS Gym [Directions] | 6:30 p.m. | ||
| Thu., 1/16 | V Boys Basketball | East Hampton | Home - Portland HS-Portland HS [Directions] | L 34-61 | ||
| Thu., 1/16 | JV Boys Basketball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/17 | V Boys Swimming and Diving | Bulkeley Cooperative Swim Team | Home - Rocky Hill HS-Swimming Pool [Directions] | W | ||
| Fri., 1/17 | V Girls Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | L 21-38 | 4:45 PM | |
| Fri., 1/17 | JV Girls Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | Cancelled | 12:00 PM | |
| Sat., 1/18 | V Wrestling | The Colter Abely Mid-Season Classic | Away - Mercy HS-Gym 1 | 9:00 a.m. | 7:00 AM | |
| Mon., 1/20 | V Girls Basketball | Tourtellotte | Away - Tourtellotte Memorial HS-TMHS-Canty Gym [Directions] | W 62-37 | 2:15 PM | |
| Tue., 1/21 | V Boys Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | L 43-51 | 4:30 PM | |
| Tue., 1/21 | JV Boys Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/21 | V Boys Swimming and Diving | Simsbury | Home - Rocky Hill HS-Swimming Pool [Directions] | L | ||
| Tue., 1/21 | V Girls Basketball | Valley Regional | Home - Portland HS-Portland HS [Directions] | W 39-36 | ||
| Tue., 1/21 | JV Girls Basketball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | Cancelled | ||
| Wed., 1/22 | FR Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:00 p.m. | 4:00 PM | |
| Wed., 1/22 | V Wrestling | Stafford | Home - Portland HS-Portland HS [Directions] | 5:00 p.m. | ||
| Thu., 1/23 | V Boys Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | L 39-50 | ||
| Thu., 1/23 | JV Boys Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/24 | V Boys Indoor Track | H-K Invitational | Away - Hillhouse HS-Field House | 4:30 p.m. | 2:25 PM | |
| Fri., 1/24 | V Girls Indoor Track | H-K Invitational | Away - Hillhouse HS-Field House | 4:30 p.m. | ||
| Sat., 1/25 | FR Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 12:00 p.m. | 10:45 AM | |
| Sat., 1/25 | V Wrestling | TBA, Griswold | Away - TBA | 9:00 a.m. | 7:00 AM | |
| Mon., 1/27 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | W 51-45 | 2:25 PM | |
| Mon., 1/27 | JV Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 1/28 | V Boys Basketball | Old Saybrook | Home - Portland HS-Portland HS [Directions] | W 79-74 | ||
| Tue., 1/28 | JV Boys Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/29 | V Wrestling | Canton | Home - Portland HS-Portland HS [Directions] | 6:30 p.m. | ||
| Thu., 1/30 | V Boys Basketball | Platt Tech | Away - Platt Tech.-Gym [Directions] | L 44-58 | 4:30 PM | |
| Thu., 1/30 | JV Boys Basketball | Platt Tech | Away - Platt Tech.-Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/30 | FR Boys Basketball | Platt Tech | Away - Platt Tech.-Gym [Directions] | 3:45 p.m. | 2:25 PM | |
| Thu., 1/30 | V Girls Basketball | Coginchaug | Home - Portland HS-Portland HS [Directions] | L 57-25 | ||
| Thu., 1/30 | JV Girls Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/31 | V Boys Swimming and Diving | Plainville Boys Swimming | Home - Rocky Hill HS-Swimming Pool [Directions] | L | ||
| Sat., 2/1 | FR Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 4:00 p.m. | 2:30 PM | |
| Sat., 2/1 | V Wrestling | 6th Annual Highlander Invitational (3 Mats) (3 mats) | Home - Portland HS-PHS Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/1 | V Competitive Cheerleading | CCSU Compettion | Home - Portland HS-PHS Gym [Directions] | TBA | 10:00 AM | |
| Mon., 2/3 | V Girls Basketball | Hale Ray | Home - Portland HS-Portland HS [Directions] | W 56-18 | ||
| Tue., 2/4 | V Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | L 60-73 | ||
| Tue., 2/4 | JV Boys Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/4 | V Boys Swimming and Diving | Wethersfield | Away - Wethersfield HS-Backman Pool [Directions] | L | 3:30 PM | |
| Tue., 2/4 | V Girls Basketball | St. Bernard | Home - Portland HS-PHS Gym [Directions] | W 42-40 | ||
| Tue., 2/4 | JV Girls Basketball | St. Bernard | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/4 | Unified Sports Basketball | Cromwell | Home - Portland HS-Portland HS [Directions] | 3:15 p.m. | ||
| Wed., 2/5 | V Wrestling | Suffield Windsor Locks Wrestling Co Op | Away - Suffield HS [Directions] | 6:00 p.m. | 4:00 PM | |
| Thu., 2/6 | V Girls Basketball | East Hampton | Home - Portland HS-Portland HS [Directions] | L 45-20 | ||
| Thu., 2/6 | JV Girls Basketball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/7 | V Boys Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | L 50-77 | 4:40 PM | |
| Fri., 2/7 | JV Boys Basketball | East Hampton | Away - East Hampton HS-Gym [Directions] | 5:30 p.m. | ||
| Sat., 2/8 | FR Boys Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 10:00 a.m. | 8:45 AM | |
| Sat., 2/8 | V Boys Indoor Track | SLC Conference Championship | Away - Hillhouse HS-Field House | 10:00 a.m. | 8:00 AM | |
| Sat., 2/8 | V Wrestling | Bobcat Classic | Away - Bacon Academy | 9:00 a.m. | 7:00 AM | |
| Sat., 2/8 | V Girls Indoor Track | SLC Conference Championship | Away - Hillhouse HS-Field House | 10:00 a.m. | ||
| Mon., 2/10 | V Girls Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | W 49-35 | 4:30 PM | |
| Mon., 2/10 | JV Girls Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 5:45 p.m. | ||
| Tue., 2/11 | V Boys Basketball | Westbrook | Home - Portland HS-Portland HS [Directions] | L 64-73 | ||
| Tue., 2/11 | JV Boys Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/11 | V Boys Swimming and Diving | Hartford Public | Away - Hartford Public HS-Pool [Directions] | W | 2:30 PM | |
| Tue., 2/11 | Unified Sports Basketball | Old Saybrook, Westbrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 3:15 p.m. | 2:25 PM | |
| Wed., 2/12 | FR Boys Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 7:00 p.m. | 5:45 PM | |
| Wed., 2/12 | V Wrestling | Gilbert/Torrington | Home - Portland HS-Portland HS [Directions] | 6:30 p.m. | ||
| Thu., 2/13 | V Girls Basketball | Cheney Tech | Away - Cheney Tech.-Gym [Directions] | W 46-12 | 2:25 PM | |
| Thu., 2/13 | JV Girls Basketball | Cheney Tech | Away - Cheney Tech.-Gym [Directions] | Cancelled | TBA | |
| Thu., 2/13 | V | SLC Unified Basketball Tournament | Away - Westbrook HS-Westbrook HS Gym | 3:00 p.m. | 2:25 PM | |
| Fri., 2/14 | V Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | L 71-72 | 4:20 PM | |
| Fri., 2/14 | JV Boys Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/14 | V Boys Swimming and Diving | Avon | Home - Rocky Hill HS-Swimming Pool [Directions] | L | 1:00 PM | |
| Fri., 2/14 | V Girls Basketball | Old Saybrook | Home - Portland HS-Portland HS [Directions] | W 48-26 | ||
| Fri., 2/14 | JV Girls Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Sat., 2/15 | FR Boys Basketball | Cromwell | Home - Portland HS-PHS Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/15 | V Wrestling | NCCC Wrestling Championships | Away - Suffield HS | 9:00 a.m. | 7:00 AM | |
| Tue., 2/18 | V Boys Swimming and Diving | Newington | Home - Rocky Hill HS-Swimming Pool [Directions] | L | ||
| Wed., 2/19 | FR Boys Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 3:30 p.m. | ||
| Wed., 2/19 | V Girls Basketball | Old Lyme | Home - Portland HS-Portland HS [Directions] | L 31-47 | ||
| Wed., 2/19 | JV Girls Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/21 | V Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | L 49-66 | 4:20 PM | |
| Fri., 2/21 | JV Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | 4:15 PM | |
| Fri., 2/21 | V Boys Swimming and Diving | Windham | Home - Rocky Hill HS-Swimming Pool [Directions] | W | ||
| Fri., 2/21 | V Wrestling | CIAC Class S Divisional Championship | Away - Killingly HS-Gym | 3:00 p.m. | ||
| Sat., 2/22 | V Wrestling | CIAC Class S Divisional Championship | Away - Killingly HS-Gym | 9:00 a.m. | ||
| Sat., 2/22 | V Competitive Cheerleading | SLC Cheer Championships- Westbrook HS | Home - Portland HS-PHS Gym [Directions] | 10:00 a.m. | 7:30 AM | |
| Sat., 2/22 | V Girls Basketball | Morgan | Away - Morgan School-Gym [Directions] | 6:00 p.m. | 4:30 PM | |
| Mon., 2/24 | V Boys Basketball | Amistad | Away - Amistad HS-Gym [Directions] | L 43-70 | 4:20 PM | |
| Mon., 2/24 | JV Boys Basketball | Amistad | Away - Amistad HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/25 | V Boys Swimming and Diving | E.O. Smith - Tolland Hammerheads | Home - Rocky Hill HS-Swimming Pool [Directions] | L | ||
| Wed., 2/26 | V Boys Basketball | Cheney Tech | Home - Portland HS-PHS Gym [Directions] | L 47-58 | ||
| Wed., 2/26 | JV Boys Basketball | Cheney Tech | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/27 | V Boys Basketball | Hale Ray | Home - Portland HS-Portland HS [Directions] | L 50-57 | ||
| Thu., 2/27 | JV Boys Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/28 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-Field House | 3:00 p.m. | ||
| Sat., 2/29 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-Field House | 9:00 a.m. | ||
| Sat., 2/29 | V Competitive Cheerleading | NECA Competition- East Haven HS | Home - Portland HS-PHS Gym [Directions] | TBA | TBA | |
| Tue., 3/3 | V Girls Basketball | Somers | Home - Portland HS-PHS Gym [Directions] | 7:00 p.m. | ||
| Fri., 3/6 | V Boys Swimming and Diving | Newington, Avon, E.O. Smith/Tolland, Hartford Public, Wethersfield | Away - Newington HS-Pool | 4:30 p.m. | 2:30 PM | |
| Fri., 3/6 | V Girls Basketball | Putnam | Away - Putnam HS-Gym [Directions] | Postponed | 4:00 PM | |
| Sat., 3/7 | V Competitive Cheerleading | CIAC State Championships- F. Little Field Hous | Home - Portland HS-PHS Gym [Directions] | Postponed | TBA | |
| Wed., 3/11 | V Boys Swimming and Diving | CIAC Boys Class S Diving Championship | Away - Plainville HS-Pool | Cancelled | ||
| Sat., 3/14 | V Boys Swimming and Diving | CIAC Boys Class S Trials | Away - Cheshire Community Pool | Cancelled | ||
| Wed., 3/18 | V Boys Swimming and Diving | CIAC Boys Class S Finals | Away - Wesleyan University-Pool | Cancelled | ||
| Thu., 3/19 | V Boys Swimming and Diving | CIAC Boys State Open Diving | Away - Bulkeley HS-Pool | Cancelled | ||
| Sat., 3/21 | V Boys Swimming and Diving | CIAC Boys State Open Swimming | Away - Yale | Cancelled | ||
| Thu., 3/26 | V Girls Tennis | TBA | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Tue., 3/31 | V Baseball | Haddam-Killingworth (Scrim.) | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | Cancelled | 2:25 PM; 1 Bus | |
| Thu., 4/2 | V Baseball | Rocky Hill (Scrim.) | Away - Rocky Hill HS-Griswold MS [Directions] | Cancelled | 2:25 PM; 1 Bus | |
| Sat., 4/4 | V Girls Tennis | North Branford | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Mon., 4/6 | V Baseball | ValleyReg/Westbrook | Home - Portland HS-Portland HS [Directions] | Cancelled | ||
| Mon., 4/6 | V Boys Tennis | Morgan | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Mon., 4/6 | V Softball | Valley Regional | Home - Nolan Field [Directions] | Cancelled | ||
| Mon., 4/6 | V Girls Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Tue., 4/7 | JV Baseball | ValleyReg/Westbrook | Away - Valley Regional HS-Baseball Diamond [Directions] | Cancelled | 2:25 PM | |
| Tue., 4/7 | V Boys Golf | Old Saybrook | Home - Portland Golf Course [Directions] | Cancelled | ||
| Wed., 4/8 | V Baseball | Westbrook | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | Cancelled | 2:25 PM | |
| Wed., 4/8 | V Boys Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | Cancelled | 2:25 PM | |
| Wed., 4/8 | V Softball | Westbrook/Old Saybrook | Away - Westbrook HS-Westbrook HS Field #5 - Softball [Directions] | Cancelled | 2:25 PM | |
| Wed., 4/8 | V Girls Tennis | Coginchaug | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Thu., 4/9 | V Boys Golf | Glastonbury | Away - Glastonbury Hills Country Club [Directions] | Cancelled | 2:25 PM | |
| Thu., 4/9 | V Softball | Comp Sci | Away - Civic Leadership HS-Civic Leadership Turf Field [Directions] | Cancelled | 2:25 PM | |
| Sat., 4/11 | V Baseball | Morgan | Away - Morgan School-Baseball Field [Directions] | Cancelled | 2:25 PM | |
| Sat., 4/11 | V Softball | Morgan | Away - Morgan School-Softball Field [Directions] | Cancelled | 2:25 PM | |
| Mon., 4/13 | V Baseball | North Branford | Home - Portland HS-Portland HS [Directions] | Cancelled | ||
| Mon., 4/13 | V Boys Tennis | East Hampton | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Mon., 4/13 | V Softball | North Branford | Home - Nolan Field [Directions] | Cancelled | ||
| Mon., 4/13 | V Girls Tennis | East Hampton | Away - East Hampton HS-Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Wed., 4/15 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Baseball Diamond [Directions] | Cancelled | 2:25 PM | |
| Wed., 4/15 | V Boys Tennis | Old Lyme | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Wed., 4/15 | V Softball | Old Lyme | Away - Lyme-Old Lyme HS-Softball Diamond [Directions] | Cancelled | 2:25 PM | |
| Wed., 4/15 | V Girls Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Thu., 4/16 | JV Baseball | Old Lyme | Home - Portland HS-Portland HS [Directions] | Cancelled | ||
| Fri., 4/17 | V Boys Tennis | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Fri., 4/17 | V Girls Tennis | Old Saybrook | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Mon., 4/20 | V Baseball | Old Saybrook | Away - Old Saybrook HS-OSHS Baseball Field [Directions] | Cancelled | 2:25 PM | |
| Mon., 4/20 | V Softball | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Softball Field [Directions] | Cancelled | 2:25 PM | |
| Tue., 4/21 | JV Baseball | Old Saybrook | Away - Old Saybrook HS-OSHS Baseball Field [Directions] | Cancelled | 2:25 PM | |
| Tue., 4/21 | V Boys Golf | East Hampton, Haddam-Killingworth | Home - Portland Golf Course [Directions] | Cancelled | ||
| Wed., 4/22 | V Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | Cancelled | 2:25 PM | |
| Wed., 4/22 | V Boys Golf | Conard | Away - Rockledge Golf Club West Hartford [Directions] | Cancelled | ||
| Wed., 4/22 | JV Boys Golf | Conard | Away - Rockledge Golf Club West Hartford [Directions] | Cancelled | ||
| Wed., 4/22 | V Boys Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Wed., 4/22 | V Softball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Varsity Softball Field [Directions] | Cancelled | 2:25 PM | |
| Wed., 4/22 | V Girls Tennis | Westbrook | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Thu., 4/23 | V Baseball | Middletown | Away - Palmer Field-Baseball Diamond [Directions] | Cancelled | 4:45 PM, Return 7:45 PM; 1 Bus | |
| Thu., 4/23 | V Boys Golf | Coginchaug | Away - Coginchaug-Lyman Orchards Golf course [Directions] | Cancelled | 2:15 PM | |
| Fri., 4/24 | V Baseball | Hale Ray | Home - Portland HS-Portland HS [Directions] | Cancelled | ||
| Fri., 4/24 | V Boys Tennis | Cromwell | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Fri., 4/24 | V Softball | Hale Ray | Home - Nolan Field [Directions] | Cancelled | ||
| Fri., 4/24 | V Girls Tennis | Cromwell | Away - Watrous park [Directions] | Cancelled | 2:25 PM | |
| Mon., 4/27 | V Baseball | Coginchaug | Home - Portland HS-Portland HS [Directions] | Cancelled | ||
| Mon., 4/27 | V Boys Golf | Old Lyme | Home - Portland Golf Course [Directions] | Cancelled | ||
| Mon., 4/27 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Mon., 4/27 | V Softball | Coginchaug | Home - Nolan Field [Directions] | Cancelled | ||
| Mon., 4/27 | V Girls Tennis | Haddam-Killingworth | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Tue., 4/28 | JV Baseball | Coginchaug | Away - Coginchaug Regional HS-Field #1 - Brookside Field @ CRHS [Directions] | Cancelled | 2:25 PM | |
| Tue., 4/28 | V Boys Golf | Cromwell | Away - TPC River Highlands [Directions] | Cancelled | 2:25 PM | |
| Tue., 4/28 | V Boys Outdoor Track | Old Lyme, Old Saybrook | Away - Lyme-Old Lyme HS-Track Field [Directions] | Cancelled | 2:25 PM | |
| Tue., 4/28 | V Girls Outdoor Track | Old Lyme, Old Saybrook | Away - Lyme-Old Lyme HS-Track Field [Directions] | Cancelled | 2:25 PM | |
| Wed., 4/29 | JV Baseball | East Hampton | Home - Portland HS-Portland HS [Directions] | Cancelled | ||
| Wed., 4/29 | V Boys Tennis | Valley Regional | Away - Valley Regional HS-Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Wed., 4/29 | V Softball | East Hampton | Away - East Hampton HS-Softball Field [Directions] | Cancelled | 2:25 PM | |
| Wed., 4/29 | V Girls Tennis | Valley Regional | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Thu., 4/30 | V Baseball | East Hampton | Away - Dunkin Donuts Park (Hartford, CT)-Baseball Field [Directions] | Cancelled | 2:15 PM | |
| Thu., 4/30 | V Boys Golf | North Branford | Home - Portland Golf Course [Directions] | Cancelled | ||
| Thu., 4/30 | V Softball | St. Bernard | Home - Nolan Field [Directions] | Cancelled | ||
| Fri., 5/1 | V Baseball | Cromwell | Away - Cromwell HS-Baseball Field [Directions] | Cancelled | 2:25 PM | |
| Fri., 5/1 | V Softball | Cromwell | Away - Cromwell HS-Softball Field [Directions] | Cancelled | 2:25 PM | |
| Fri., 5/1 | V Girls Tennis | North Branford | Away - North Branford HS-NBHS Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Sat., 5/2 | JV Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | Cancelled | 2:25 PM | |
| Mon., 5/4 | V Baseball | Westbrook | Home - Portland HS-Portland HS [Directions] | Cancelled | ||
| Mon., 5/4 | V Boys Golf | Wildcat Invitational | Home - Portland Golf Course [Directions] | Cancelled | ||
| Mon., 5/4 | V Boys Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Mon., 5/4 | V Softball | Westbrook/Old Saybrook | Home - Nolan Field [Directions] | Cancelled | ||
| Mon., 5/4 | V Girls Tennis | Morgan | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Tue., 5/5 | JV Baseball | Westbrook | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | Cancelled | 2:25 PM | |
| Tue., 5/5 | V Boys Golf | Haddam-Killingworth | Away - Black Birch Golf Course [Directions] | Cancelled | 2:25 PM | |
| Tue., 5/5 | V Boys Outdoor Track | Hale Ray, Valley Regional | Home - Portland HS-HS Track [Directions] | Cancelled | ||
| Tue., 5/5 | V Girls Outdoor Track | Hale Ray, Valley Regional | Home - Portland HS-HS Track [Directions] | Cancelled | ||
| Wed., 5/6 | V Baseball | Old Lyme | Home - Palmer Field-Baseball Diamond [Directions] | Cancelled | 2:15 PM | |
| Wed., 5/6 | V Boys Tennis | Coginchaug | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Wed., 5/6 | V Softball | Old Lyme | Home - Nolan Field [Directions] | Cancelled | ||
| Wed., 5/6 | V Girls Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | Cancelled | 2:25 PM | |
| Thu., 5/7 | JV Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Baseball Diamond [Directions] | Cancelled | 2:25 PM | |
| Fri., 5/8 | V Baseball | Old Saybrook | Home - Portland HS-Portland HS [Directions] | Cancelled | ||
| Fri., 5/8 | V Boys Tennis | East Hampton | Away - East Hampton HS-Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Fri., 5/8 | V Softball | Old Saybrook | Home - Nolan Field [Directions] | Cancelled | 2:25 PM | |
| Fri., 5/8 | V Girls Tennis | East Hampton | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Sat., 5/9 | JV Baseball | Old Saybrook | Away - Old Saybrook HS-OSHS Baseball Field [Directions] | Cancelled | 8:20 AM | |
| Mon., 5/11 | V Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | Cancelled | 2:25 PM | |
| Mon., 5/11 | V Boys Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Mon., 5/11 | V Softball | Hale Ray | Away - Nathan Hale Ray HS-Lou Milardo Field [Directions] | Cancelled | 2:25 PM | |
| Mon., 5/11 | V Girls Tennis | Old Lyme | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Tue., 5/12 | JV Baseball | Hale Ray | Home - Portland HS-Portland HS [Directions] | Cancelled | ||
| Tue., 5/12 | V Boys Golf | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Campus [Directions] | Cancelled | 2:25 PM | |
| Wed., 5/13 | V Baseball | East Hampton | Home - Palmer Field-Baseball Diamond [Directions] | Cancelled | 4:30 PM | |
| Wed., 5/13 | V Boys Golf | Morgan, Branford | Away - Clinton Country Club [Directions] | Cancelled | 2:15 PM | |
| Wed., 5/13 | V Boys Tennis | Old Saybrook | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Wed., 5/13 | V Softball | East Hampton | Home - Nolan Field [Directions] | Cancelled | ||
| Wed., 5/13 | V Girls Tennis | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Thu., 5/14 | JV Baseball | East Hampton | Away - East Hampton HS-Main Field [Directions] | Cancelled | 2:25 PM | |
| Thu., 5/14 | V Boys Golf | Hale Ray | Home - Portland Golf Course [Directions] | Cancelled | ||
| Thu., 5/14 | V Softball | Cromwell | Home - Nolan Field [Directions] | Cancelled | ||
| Mon., 5/18 | V Baseball | Bolton | Home - Portland HS-Portland HS [Directions] | Cancelled | ||
| Mon., 5/18 | V Boys Tennis | Westbrook | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Mon., 5/18 | V Girls Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Tue., 5/19 | V Boys Golf | Valley Regional | Away - Black Hall Golf Club [Directions] | Cancelled | 2:25 PM | |
| Tue., 5/19 | V Softball | International | Home - Nolan Field [Directions] | Cancelled | ||
| Wed., 5/20 | V Baseball | Ellington | Home - Portland HS-Portland HS [Directions] | Cancelled | ||
| Wed., 5/20 | V Boys Golf | Morgan | Home - Portland Golf Course [Directions] | Cancelled | ||
| Wed., 5/20 | V Boys Tennis | Cromwell | Away - Watrous park [Directions] | Cancelled | 2:25 PM | |
| Wed., 5/20 | V Girls Tennis | Cromwell | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Thu., 5/21 | V Baseball | Morgan | Away - Indian River Complex-Baseball Field [Directions] | Cancelled | 4:45 PM | |
| Thu., 5/21 | V Boys Golf | Coventry | Home - Portland Golf Course [Directions] | Cancelled | ||
| Fri., 5/22 | V Boys Tennis | Haddam-Killingworth | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Fri., 5/22 | V Girls Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | Cancelled | 2:25 PM | |
| Sat., 5/23 | V Boys Tennis | Valley Regional | Home - Portland HS-Tennis Courts [Directions] | Cancelled | ||
| Sat., 5/23 | V Girls Tennis | Valley Regional | Away - Valley Regional HS-Tennis Courts [Directions] | Cancelled | 9:00 AM | |
| Tue., 5/26 | V Boys Tennis | SLC Boys Tennis Tournament | Away - Not Listed | Cancelled | TBA, Dismiss TBA | |
| Tue., 5/26 | V Girls Tennis | SLC Girls Tennis Tournament | Away - Not Listed | Cancelled | ||
| Wed., 5/27 | V Boys Outdoor Track | SLC Outdoor Track and Field Championship | Away - Old Saybrook HS-Old Saybrook Track (HS) | Cancelled | TBA | |
| Wed., 5/27 | V Boys Tennis | SLC Boys Tennis Tournament | Away - Westbrook HS-Westbrook HS / MS Tennis Courts | Cancelled | TBA | |
| Wed., 5/27 | V Girls Outdoor Track | SLC Outdoor Track and Field Championship | Away - Old Saybrook HS-Old Saybrook Track (HS) | Cancelled | TBA | |
| Thu., 5/28 | V Boys Golf | SLC Golf Tournament | Away - Stanley Golf Course | Cancelled | 12:00 PM | |