2020 to 2021 Cup Fixtures - Portsmouth Football Club
| Date | Opponent | Venue | Competition | Result | Attendance |
|---|---|---|---|---|---|
| 29th Aug | Stevenage | Away | EFL Carabao Cup 1st Round | D 3 - 3 AET (Pens: W 1 - 3) | N/A |
| 8th Sep | Colchester United | Home | EFL Trophy Group I | W 2 - 0 | N/A |
| 17th Sep | Brighton & Hove Albion | Away | EFL Carabao Cup 2nd Round | L 4 - 0 | N/A |
| 6th Oct | Southend United | Away | EFL Trophy Group I | W 0 - 3 | N/A |
| 7th Nov | Ipswich Town | Away | FA Cup 1st Round | W 2 - 3 | N/A |
| 10th Nov | West Ham United U21 | Home | EFL Trophy Group I | L 0 - 1 | N/A |
| 28th Nov | Kings Lynn Town | Away | FA Cup 2nd Round | W 6 - 1 | N/A |
| 8th Dec | Cheltenham Town | Away | EFL Trophy Round 2 | W 0 - 3 | N/A |
| 10th Jan | Bristol City | Away | FA Cup 3rd Round | L 2 - 1 | N/A |
| 12th Jan | Peterborugh United | Away | EFL Trophy Round 3 | L 1 - 5 | N/A |