| Portland 2020-21 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 214 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 10/1 | V Boys Cross Country | Morgan, North Branford | Away - Indian River Complex-XC Course [Directions] | 3:45 p.m. | ||
| Thu., 10/1 | V Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 p.m. | L 0-3 | |
| Thu., 10/1 | JV Girls Soccer | Haddam-Killingworth | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/2 | JV Boys Soccer | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 3:45 p.m. | ||
| Fri., 10/2 | V Girls Cross Country | Morgan, North Branford | Away - Indian River Complex-XC Course [Directions] | 3:45 p.m. | ||
| Fri., 10/2 | V Girls Soccer | Haddam-Killingworth | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | L 1-4 | |
| Mon., 10/5 | V Boys Soccer | Old Lyme | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | T 2-2 | |
| Mon., 10/5 | JV Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Middle Field [Directions] | Postponed | ||
| Tue., 10/6 | V Boys Cross Country | Old Lyme | Home - Portland HS-HS Track [Directions] | 3:45 p.m. | ||
| Tue., 10/6 | V Girls Soccer | Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:45 p.m. | L 0-1 | |
| Wed., 10/7 | V Girls Swimming and Diving | Glastonbury | Away - Glastonbury HS-Pool [Directions] | 3:45 p.m. | L | |
| Wed., 10/7 | V Girls Swimming and Diving | Glastonbury | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | ||
| Thu., 10/8 | V Boys Soccer | Hale Ray | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | W 1-0 | |
| Thu., 10/8 | V Girls Cross Country | Old Lyme | Home - Portland HS-HS Track [Directions] | 3:45 p.m. | ||
| Fri., 10/9 | V Girls Soccer | Hale Ray | Away - Nathan Hale-Ray MS-Nathan Hale-Ray MS Soccer fields [Directions] | 3:45 p.m. | W 7-3 | |
| Mon., 10/12 | JV Girls Soccer | Valley Regional | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/14 | V Boys Cross Country | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | ||
| Wed., 10/14 | V Girls Swimming and Diving | East Catholic | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | T | |
| Wed., 10/14 | V Girls Swimming and Diving | East Catholic | Away - Indian Valley YMCA [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:20 p.m. | ||||||
| Wed., 10/14 | V Girls Swimming and Diving | East Catholic | Away - Star Hill Pool-Pool [Directions] | 7:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 7:20 p.m. | ||||||
| Thu., 10/15 | V Boys Soccer | Morgan | Away - Indian River Complex-Turf Field [Directions] | 3:45 p.m. | L 3-2 | |
| Thu., 10/15 | V Girls Cross Country | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 3:45 p.m. | ||
| Sat., 10/17 | V Boys Soccer | Valley Regional | Away - Valley Regional HS-Richard B. Blythe Field [Directions] | 3:00 p.m. | L 4-1 | |
| Mon., 10/19 | V Boys Soccer | Westbrook | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | W 4-1 | |
| Mon., 10/19 | V Girls Soccer | Morgan | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | T 0-0 | |
| Tue., 10/20 | V Boys Cross Country | East Hampton | Home - Portland HS-HS Track [Directions] | 3:45 p.m. | ||
| Tue., 10/20 | V Girls Soccer | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:45 p.m. | W 5-0 | |
| Wed., 10/21 | JV Boys Soccer | Morgan | Away - Morgan School-Soccer/Lax Field [Directions] | 3:45 p.m. | ||
| Wed., 10/21 | V Girls Swimming and Diving | Manchester/Bacon/Bolton/Coventry/Rockville | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Wed., 10/21 | V Girls Swimming and Diving | Manchester/Bacon/Bolton/Coventry/Rockville | Away - Manchester HS-Pool [Directions] | 3:45 p.m. | ||
| Thu., 10/22 | JV Boys Soccer | Old Saybrook | Home - Portland HS-JV Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/22 | V Girls Cross Country | East Hampton | Home - Portland HS-HS Track [Directions] | 3:45 p.m. | ||
| Thu., 10/22 | V Girls Soccer | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Soccer Field (Front) [Directions] | 3:45 p.m. | L 2-3 | |
| Fri., 10/23 | V Boys Soccer | Old Saybrook | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | L 3-0 | |
| Mon., 10/26 | V Boys Soccer | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | 3:45 p.m. | W 8-0 | |
| Mon., 10/26 | V Girls Soccer | North Branford/Hale Ray | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 10/27 | V Boys Cross Country | Valley Regional | Away - John Winthrop MS [Directions] | 3:30 p.m. | ||
| Tue., 10/27 | JV Boys Soccer | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | 3:45 p.m. | ||
| Tue., 10/27 | V Girls Soccer | Valley Regional | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | W 4-1 | |
| Wed., 10/28 | V Girls Swimming and Diving | East Hartford | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | ||
| Thu., 10/29 | V Girls Cross Country | Valley Regional | Away - John Winthrop MS [Directions] | 3:30 p.m. | ||
| Fri., 10/30 | JV Girls Soccer | Coginchaug | Home - Portland HS-JV Soccer Field [Directions] | Canceled | Cancelled | |
| Mon., 11/2 | V Boys Soccer | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:00 p.m. | W 4-0 | |
| Mon., 11/2 | JV Boys Soccer | Cromwell | Home - Portland HS-JV Soccer Field [Directions] | 3:30 p.m. | ||
| Mon., 11/2 | V Girls Soccer | Cromwell | Away - Cromwell HS-Varsity field [Directions] | 3:15 p.m. | W 3-0 | |
| Wed., 11/4 | V Boys Soccer | Cromwell | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | W 3-2 | |
| Thu., 11/5 | V Girls Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | 3:45 p.m. | L 0-1 | |
| Fri., 11/6 | V Boys Cross Country | Coginchaug | Home - Coginchaug-Totoket Park in North Branford [Directions] | 11:00 a.m. | ||
| Fri., 11/6 | V Boys Soccer | East Hampton | Home - Portland HS-Varsity Soccer FIeld [Directions] | 6:00 p.m. | T 2-2 | |
| Fri., 11/6 | V Girls Cross Country | Coginchaug | Home - TBA-Totoket Park in North Branford [Directions] | 11:30 a.m. | ||
| Fri., 11/6 | V Girls Soccer | Coginchaug | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:45 p.m. | T 1-1 | |
| Fri., 11/6 | JV Girls Soccer | East Hampton | Away - East Hampton HS-Main Field [Directions] | Canceled | Cancelled | |
| Mon., 11/9 | V Boys Soccer | North Branford | Home - Portland HS-Varsity Soccer FIeld [Directions] | 3:30 p.m. | W 9-0 | |
| Wed., 2/10 | V Boys Swimming and Diving | E.O. Smith - Tolland Hammerheads | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Fri., 2/12 | V Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 5:30 p.m. | L 54-59 | |
| Fri., 2/12 | JV Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/12 | V Boys Swimming and Diving | E.O. Smith - Tolland Hammerheads | Away - Mansfield Community Center-Pool [Directions] | 3:45 p.m. | ||
| Fri., 2/12 | V Girls Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 13-56 | |
| Fri., 2/12 | JV Girls Basketball | Old Lyme | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/13 | FR Boys Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 9:00 a.m. | ||
| Tue., 2/16 | V Boys Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | W 59-24 | |
| Tue., 2/16 | JV Boys Basketball | Old Saybrook | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/16 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 5:30 p.m. | L 43-47 | |
| Tue., 2/16 | JV Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/22 | V Boys Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | W 69-51 | |
| Mon., 2/22 | JV Boys Basketball | Hale Ray | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/22 | V Girls Basketball | Hale Ray | Away - Nathan Hale Ray HS-Gym [Directions] | 4:00 p.m. | L 39-44 | |
| Wed., 2/24 | V Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 6:00 p.m. | W 67-42 | |
| Wed., 2/24 | JV Boys Basketball | Westbrook | Away - Westbrook HS-Westbrook HS Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/24 | V Boys Swimming and Diving | Manchester/RHAM | Away - Manchester HS-Pool [Directions] | 3:45 p.m. | ||
| Wed., 2/24 | V Boys Swimming and Diving | Manchester/RHAM | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | W | |
| Wed., 2/24 | V Boys Swimming and Diving | HK-Valley | Away - Haddam Killingworth HS (HK)-HKHS Pool - no diving [Directions] | 4:00 p.m. | W | |
| Wed., 2/24 | V Girls Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | W 45-32 | |
| Wed., 2/24 | JV Girls Basketball | Westbrook | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/26 | V Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 6:00 p.m. | W 80-36 | |
| Fri., 2/26 | JV Boys Basketball | North Branford | Away - North Branford HS-NBHS Gym [Directions] | 4:30 p.m. | ||
| Fri., 2/26 | V Boys Swimming and Diving | East Hartford | Away - East Hartford HS-Pool [Directions] | 3:45 p.m. | W | |
| Fri., 2/26 | V Girls Basketball | North Branford | Home - Portland HS-PHS Gym [Directions] | 6:00 p.m. | L 60-56 | |
| Fri., 2/26 | JV Girls Basketball | North Branford | Home - Portland HS-PHS Gym [Directions] | 4:30 p.m. | ||
| Sat., 2/27 | FR Boys Basketball | Morgan | Home - Portland HS-PHS Gym [Directions] | 9:00 a.m. | ||
| Mon., 3/1 | V Boys Basketball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 60-64 | |
| Mon., 3/1 | JV Boys Basketball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Mon., 3/1 | V Girls Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 6:15 p.m. | L 71-35 | |
| Mon., 3/1 | JV Girls Basketball | Valley Regional | Away - Valley Regional HS-Valley Regional High School Gym [Directions] | 4:30 p.m. | ||
| Tue., 3/2 | V Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 6:00 p.m. | W 60-44 | |
| Tue., 3/2 | JV Boys Basketball | Coginchaug | Away - Coginchaug Regional HS-Maynard Stender Gymnasium @ CRHS [Directions] | 4:30 p.m. | ||
| Tue., 3/2 | V Girls Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 60-33 | |
| Tue., 3/2 | JV Girls Basketball | Coginchaug | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Wed., 3/3 | V Boys Swimming and Diving | East Catholic | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Wed., 3/3 | V Boys Swimming and Diving | East Catholic | Away - Indian Valley YMCA [Directions] | 3:45 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:20 p.m. | ||||||
| Wed., 3/3 | V Boys Swimming and Diving | East Catholic | Away - Star Hill Pool-Pool [Directions] | 7:30 p.m. | ||
| Thu., 3/4 | V Boys Basketball | Cromwell | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | W 65-62 | |
| Thu., 3/4 | JV Boys Basketball | Cromwell | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Thu., 3/4 | V Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:30 p.m. | L 47-68 | |
| Thu., 3/4 | JV Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 3/5 | FR Boys Basketball | North Branford | Home - Portland HS-PHS Gym [Directions] | 3:30 p.m. | ||
| Sat., 3/6 | FR Boys Basketball | Old Lyme | Away - Lyme-Old Lyme HS-High School Gym [Directions] | 9:00 a.m. | ||
| Mon., 3/8 | V Boys Basketball | East Hampton | Away - East Hampton [Directions] | 6:00 p.m. | L 61-45 | |
| Mon., 3/8 | JV Boys Basketball | East Hampton | Away - East Hampton [Directions] | 4:30 p.m. | ||
| Mon., 3/8 | V Girls Basketball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 19-57 | |
| Mon., 3/8 | JV Girls Basketball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Wed., 3/10 | V Boys Swimming and Diving | South Windsor | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | L | |
| Thu., 3/11 | V Boys Basketball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | W 54-50 | |
| Thu., 3/11 | JV Boys Basketball | Haddam-Killingworth | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Thu., 3/11 | V Girls Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:30 p.m. | W 45-43 | |
| Thu., 3/11 | JV Girls Basketball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 4:00 p.m. | ||
| Fri., 3/12 | V Boys Swimming and Diving | South Windsor | Away - Star Hill Pool-Pool [Directions] | 3:45 p.m. | ||
| Sun., 3/14 | FR Boys Basketball | East Hampton | Away - East Hampton [Directions] | 3:30 p.m. | ||
| Mon., 3/15 | V Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 6:00 p.m. | L 65-76 | |
| Mon., 3/15 | JV Boys Basketball | Morgan | Away - Morgan School-Gym [Directions] | 4:30 p.m. | ||
| Mon., 3/15 | V Girls Basketball | Morgan | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | L 48-45 | |
| Mon., 3/15 | JV Girls Basketball | Morgan | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Wed., 3/17 | V Boys Swimming and Diving | Glastonbury | Home - Rocky Hill HS-Swimming Pool [Directions] | 3:45 p.m. | Virtual Meet | |
| Pending change awaiting acceptance by one or more parties involved: Date to 3/18 | ||||||
| Wed., 3/17 | V Boys Swimming and Diving | Glastonbury | Away - Glastonbury HS-Pool [Directions] | 3:45 p.m. | ||
| Thu., 3/18 | V Boys Basketball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | W 47-40 | |
| Thu., 3/18 | JV Boys Basketball | East Hampton | Home - Portland HS-PHS Gym [Directions] | 4:00 p.m. | ||
| Thu., 3/18 | V Girls Basketball | East Hampton | Away - East Hampton [Directions] | 6:00 p.m. | L 22-51 | |
| Thu., 3/18 | JV Girls Basketball | East Hampton | Away - East Hampton [Directions] | 4:30 p.m. | ||
| Sat., 3/20 | V Boys Basketball | North Branford | Home - Portland HS-PHS Gym [Directions] | 5:30 p.m. | W 69-47 | |
| Sat., 3/20 | FR Boys Basketball | Valley Regional | Home - Portland HS-PHS Gym [Directions] | Postponed | ||
| Sat., 3/20 | V Girls Basketball | Old Saybrook | Away - Old Saybrook HS-OSHS Gymnasium [Directions] | 6:00 p.m. | ||
| Mon., 3/22 | V Girls Basketball | East Hampton | Away - East Hampton-Gym [Directions] | 6:00 p.m. | L 27-34 | |
| Tue., 3/23 | V Boys Basketball | East Hampton | Away - East Hampton-Gym [Directions] | 6:00 p.m. | L 50-54 | |
| Sat., 4/10 | V Baseball | Coginchaug | Away - Coginchaug Regional HS-Helmuth H. Brown Varsity Baseball Field @ CRHS [Directions] | 11:00 a.m. | L 14-0 | |
| Sat., 4/10 | V Boys Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 11:00 a.m. | W 5-2 [Detailed Results] | |
| Sat., 4/10 | V Girls Tennis | Haddam-Killingworth | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Mon., 4/12 | V Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | 4:00 p.m. | L 13-3 | |
| Tue., 4/13 | JV Baseball | Hale Ray | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | L 13-1 | |
| Tue., 4/13 | V Girls Tennis | Westbrook | Home - Portland HS-Tennis Courts [Directions] | 12:00 p.m. | L 3-4 | |
| Wed., 4/14 | V Baseball | Westbrook | Home - Portland HS-Portland HS [Directions] | 11:00 a.m. | W 6-2 | |
| Wed., 4/14 | V Boys Golf | Morgan | Away - Clinton Country Club [Directions] | 2:00 p.m. | Portland: 162 Morgan: 175 (non-league) | |
| Wed., 4/14 | V Boys Tennis | Westbrook | Home - Portland HS-Tennis Courts [Directions] | 10:00 a.m. | L 0-7 [Detailed Results] | |
| Sat., 4/17 | V Boys Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 1:00 p.m. | L 0-7 [Detailed Results] | |
| Sun., 4/18 | V Baseball | Old Saybrook | Home - Portland HS-Portland HS [Directions] | 1:00 p.m. | L 10-2 | |
| Mon., 4/19 | V Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Baseball Diamond [Directions] | 4:00 p.m. | L 4-3 | |
| Mon., 4/19 | V Boys Golf | North Branford | Away - Indian Springs Golf Course-Indian Springs CC [Directions] | 3:00 p.m. | Portland:168 North Branford: 199 (league) | |
| Mon., 4/19 | V Boys Tennis | Old Lyme | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Mon., 4/19 | V Girls Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 4/20 | JV Baseball | Old Lyme | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | ||
| Tue., 4/20 | V Boys Golf | Old Lyme | Away - Black Hall Golf Club [Directions] | 3:00 p.m. | Portland: 172 Old Lyme: 204 (league) | |
| Tue., 4/20 | V Boys Outdoor Track | Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:30 p.m. | ||
| Tue., 4/20 | V Girls Outdoor Track | Old Lyme | Away - Lyme-Old Lyme HS-Track Field [Directions] | 3:30 p.m. | ||
| Thu., 4/22 | JV Boys Golf | Xavier | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Thu., 4/22 | V Girls Tennis | East Hampton | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 4/23 | V Baseball | ValleyReg/Westbrook | Home - Portland HS-Portland HS [Directions] | 3:45 p.m. | L 11-0 | |
| Fri., 4/23 | V Boys Tennis | Coginchaug | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/23 | V Girls Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 3:30 p.m. | W 5-2 | |
| Mon., 4/26 | V Baseball | Cromwell | Home - Portland HS-Portland HS [Directions] | 3:45 p.m. | L 7-2 | |
| Mon., 4/26 | V Boys Outdoor Track | Cromwell | Away - Cromwell HS-Don Luke Track [Directions] | 3:30 p.m. | ||
| Mon., 4/26 | V Boys Tennis | Valley Regional | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 [Detailed Results] | |
| Mon., 4/26 | V Girls Outdoor Track | Cromwell | Away - Cromwell HS-Don Luke Track [Directions] | 3:30 p.m. | ||
| Mon., 4/26 | V Girls Tennis | Valley Regional | Away - Valley Regional HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Tue., 4/27 | JV Baseball | Cromwell | Away - Cromwell HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 4/27 | V Boys Golf | Coventry | Home - Portland Golf Course [Directions] | 2:30 p.m. | Portland: 163 Coventry: 185 | |
| Tue., 4/27 | JV Boys Golf | Coventry | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Tue., 4/27 | V Boys Tennis | East Hampton | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 2-5 [Detailed Results] | |
| Wed., 4/28 | V Baseball | East Hampton | Away - East Hampton HS-Dunkin Donuts Park [Directions] | 6:30 p.m. | L 3-1 | |
| Wed., 4/28 | V Boys Golf | Haddam-Killingworth | Home - Portland Golf Course [Directions] | 2:45 p.m. | Portland: 165 Haddam-Killingworth: 207 (non-league) | Non-league |
| Wed., 4/28 | V Boys Tennis | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/28 | V Girls Tennis | Old Saybrook | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Thu., 4/29 | V Boys Golf | Valley Regional | Home - Portland Golf Course [Directions] | 2:45 p.m. | Portland: 163 Valley Regional: 222 (league) | |
| Fri., 4/30 | V Baseball | Haddam-Killingworth | Home - Portland HS-Portland HS [Directions] | 3:45 p.m. | L 7-1 | |
| Fri., 4/30 | V Girls Tennis | Morgan | Away - Morgan School-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Sat., 5/1 | V Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 2:00 p.m. | L 16-2 | |
| Sat., 5/1 | JV Baseball | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Baseball Field [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Mon., 5/3 | V Baseball | Morgan | Away - Morgan School-Baseball Field [Directions] | 4:00 p.m. | L 10-5 | |
| Tue., 5/4 | V Boys Tennis | Morgan | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 [Detailed Results] | |
| Wed., 5/5 | V Boys Golf | Cromwell | Home - Portland Golf Course [Directions] | 2:45 p.m. | Portland: 163 Cromwell: 195 (league) | |
| Thu., 5/6 | V Boys Golf | Haddam-Killingworth | Away - Black Birch Golf Course [Directions] | 3:00 p.m. | Portland: 167 Haddam-Killingworth: 213 (league) | |
| Thu., 5/6 | JV Boys Golf | Coventry | Home - Portland West [Directions] | 3:00 p.m. | ||
| Thu., 5/6 | V Boys Tennis | Cromwell | Away - Watrous park [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Thu., 5/6 | V Girls Tennis | Cromwell | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Fri., 5/7 | V Baseball | Hale Ray | Home - Portland HS-Portland HS [Directions] | 4:00 p.m. | L 12-4 | |
| Fri., 5/7 | V Boys Outdoor Track | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:00 p.m. | ||
| Fri., 5/7 | V Girls Outdoor Track | Old Saybrook | Away - Old Saybrook HS-Old Saybrook Track (HS) [Directions] | 3:00 p.m. | ||
| Fri., 5/7 | V Girls Tennis | Westbrook | Away - Westbrook HS-Westbrook HS / MS Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | |
| Sat., 5/8 | V Baseball | Coginchaug | Home - Portland HS-Portland HS [Directions] | 11:00 a.m. | L 18-4 | |
| Sat., 5/8 | JV Baseball | Hale Ray | Away - Nathan Hale Ray HS-Baseball # 1 [Directions] | Postponed | ||
| Tue., 5/11 | V Boys Golf | Morgan | Home - Portland Golf Course [Directions] | 2:45 p.m. | Portland:161 Morgan: 193 (league) | |
| Tue., 5/11 | V Boys Outdoor Track | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:30 p.m. | ||
| Tue., 5/11 | V Girls Outdoor Track | Coginchaug | Away - Coginchaug Regional HS-CRHS Stadium Field & Track [Directions] | 3:45 p.m. | ||
| Tue., 5/11 | V Girls Tennis | North Branford | Away - North Branford HS-NBHS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Wed., 5/12 | V Baseball | Old Saybrook | Away - Old Saybrook HS-OSHS Baseball Field [Directions] | 4:30 p.m. | L 3-2 | |
| Wed., 5/12 | V Boys Golf | Hale Ray | Home - Portland Golf Course [Directions] | 2:45 p.m. | Portland: 179 Hale Ray: 199 (league) | |
| Wed., 5/12 | V Girls Tennis | North Branford | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Thu., 5/13 | V Boys Golf | Coginchaug | Away - Coginchaug-Lyman Orchards Golf course [Directions] | 3:05 p.m. | Portland:184 Coginchaug: 193 (non-league) | |
| Fri., 5/14 | V Baseball | Old Lyme | Home - Palmer Field-Baseball Diamond [Directions] | 6:30 p.m. | L 15-4 | |
| Fri., 5/14 | V Boys Tennis | Old Lyme | Away - Lyme-Old Lyme HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Fri., 5/14 | V Girls Tennis | Old Lyme | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Sat., 5/15 | JV Baseball | Old Lyme | Away - Lyme-Old Lyme HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Mon., 5/17 | V Baseball | Morgan | Home - Palmer Field-Baseball Diamond [Directions] | 6:30 p.m. | L 12-3 | |
| Mon., 5/17 | V Boys Golf | Hale Ray | Away - Nathan Hale Ray HS-Black Birch [Directions] | 3:20 p.m. | Portland: 177 Hale Ray: 207 (non-league) | |
| Pending change awaiting acceptance by one or more parties involved: Time to 3:00 p.m. | ||||||
| Mon., 5/17 | V Boys Tennis | East Hampton | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Mon., 5/17 | V Girls Tennis | East Hampton | Home - Portland HS-Tennis Courts [Directions] | 5:30 p.m. | W 5-2 | |
| Tue., 5/18 | V Baseball | Middletown | Home - Palmer Field-Baseball Diamond [Directions] | 3:30 p.m. | L 14-6 | |
| Tue., 5/18 | V Boys Outdoor Track | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:30 p.m. | ||
| Tue., 5/18 | V Boys Tennis | Haddam-Killingworth | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 2-5 [Detailed Results] | |
| Tue., 5/18 | V Girls Outdoor Track | Westbrook | Away - Westbrook HS-Westbrook HS Soccer Field #2 - Track / Soccer [Directions] | 3:30 p.m. | ||
| Tue., 5/18 | V Girls Tennis | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Wed., 5/19 | V Baseball | Cromwell | Away - Cromwell HS-Baseball Diamond [Directions] | 4:00 p.m. | L 11-1 | |
| Wed., 5/19 | V Boys Golf | Coginchaug | Away - Coginchaug-Lyman Orchards Golf course [Directions] | 3:10 p.m. | Portland: 172 Coginchaug: 183 (league) | |
| Wed., 5/19 | JV Boys Golf | Glastonbury | Home - Portland Golf Course [Directions] | 2:45 p.m. | ||
| Wed., 5/19 | V Boys Tennis | Coginchaug | Away - Coginchaug Regional HS-Tennis Courts @ CRHS [Directions] | 3:30 p.m. | W 6-1 [Detailed Results] | |
| Wed., 5/19 | V Girls Tennis | Coginchaug | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Thu., 5/20 | V Boys Golf | Old Saybrook | Home - Portland Golf Course [Directions] | 2:45 p.m. | Portland: 154 Old Saybrook: 193 (league) | |
| Thu., 5/20 | V Boys Outdoor Track | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track [Directions] | 3:30 p.m. | ||
| Thu., 5/20 | V Girls Outdoor Track | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Track [Directions] | 3:30 p.m. | ||
| Fri., 5/21 | V Baseball | Westbrook | Away - Westbrook HS-Westbrook HS Field #7 - Baseball / Field Hockey [Directions] | 3:45 p.m. | L 8-7 (8 inn) | |
| Sat., 5/22 | V Baseball | ValleyReg/Westbrook | Away - Valley Regional HS-Baseball Diamond [Directions] | 11:00 a.m. | L 13-0 | |
| Wed., 5/26 | JV Boys Golf | Xavier | Home - Portland Golf Course [Directions] | 2:45 a.m. | ||
| Wed., 5/26 | V Boys Tennis | Old Saybrook | Home - Portland HS-Tennis Courts [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Thu., 5/27 | V Boys Golf | Glastonbury | Home - Portland Golf Course [Directions] | 2:30 p.m. | Portland: 166 Glastonbury: 152 | |
| Thu., 5/27 | JV Boys Golf | Glastonbury, TBA | Away - Minnechaug Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 6/2 | V Boys Golf | Old Saybrook | Away - Old Saybrook HS-Fenwick Golf Course [Directions] | 3:00 p.m. | Portland: 161 Old Saybrook: 185 | |