| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 12/14 | 6:00 p.m. | Varsity | League | Normal | Away | Stafford | Loss | 47-19 | | Stafford High School-Gymnasium | |
| FRI 12/16 | 6:00 p.m. | Varsity | League | Normal | Home | LymeOldLyme | Loss | 46-43 | | Portland High School-PHS Gym | |
| TUE 12/20 | 7:00 p.m. | Varsity | League | Normal | Home | CoginchaugReg | Loss | 60-21 | | Portland High School-PHS Gym | |
| WED 12/28 | 7:00 p.m. | Varsity | League | Normal | Home | Suffield | Loss | 53-26 | | Portland High School-PHS Gym | |
| TUE 1/3 | 6:30 p.m. | Varsity | League | Normal | Away | Westbrook | Loss | 52-31 | | Westbrook High School-Westbrook HS Gym | |
| FRI 1/6 | 7:00 p.m. | Varsity | League | Normal | Home | OldSaybrook | Loss | 40-22 | | Portland High School-PHS Gym | |
| TUE 1/10 | 7:00 p.m. | Varsity | League | Normal | Away | Cromwell | Loss | 72-22 | | Cromwell High School-Jake Salafia Gymnasium | |
| THU 1/12 | 7:00 p.m. | Varsity | League | Normal | Home | StBernard | Loss | 46-37 | | Portland High School-PHS Gym | |
| SAT 1/14 | 6:00 p.m. | Varsity | League | Normal | Home | ValleyReg | Loss | 88-24 | | Portland High School-PHS Gym | |
| TUE 1/17 | 7:00 p.m. | Varsity | League | Normal | Home | Morgan | Loss | 65-21 | | Portland High School-PHS Gym | |
| FRI 1/20 | 7:00 p.m. | Varsity | League | Normal | Away | EastHampton | Loss | 62-20 | | East Hampton High School-Gym | |
| THU 1/26 | 6:30 p.m. | Varsity | League | Normal | Away | CantonJrSr | Loss | 49-23 | | Canton High School-Gym | |
| FRI 1/27 | 7:00 p.m. | Varsity | League | Normal | Home | HaddamKillingworth | Loss | 63-28 | | Portland High School-PHS Gym | |
| MON 1/30 | 6:00 p.m. | Varsity | League | Normal | Away | LymeOldLyme | Win | 56-36 | | Lyme-Old Lyme High School-High School Gym | |
| WED 2/1 | 6:30 p.m. | Varsity | League | Normal | Away | NorthBranford | Loss | 59-28 | | North Branford High School-NBHS Gym | |
| FRI 2/3 | 7:00 p.m. | Varsity | League | Normal | Away | CoginchaugReg | Loss | 55-20 | | Coginchaug Regional High School-Maynard Stender Gymnasium @ CRHS | |
| TUE 2/7 | 7:00 p.m. | Varsity | League | Normal | Home | NathanHaleRay | Win | 36-26 | | Portland High School-PHS Gym | |
| FRI 2/10 | 7:00 p.m. | Varsity | League | Normal | Home | Westbrook | Loss | 51-26 | | Portland High School-PHS Gym | |
| TUE 2/14 | 7:00 p.m. | Varsity | League | Normal | Away | OldSaybrook | Loss | 54-25 | | Old Saybrook High School-OSHS Gymnasium | |
| FRI 2/17 | 6:00 p.m. | Varsity | League | Normal | Away | NathanHaleRay | Loss | 40-19 | | Nathan Hale Ray High School-Gym | |