| DATE | HOME | RESULT | W/L/D | AWAY | COMPETITION |
|---|---|---|---|---|---|
| JUL 23 | |||||
| Thur 06 | Blandford United | 0-4 |  | Portland United | Pre-Season |
| Tue 11 | Portland United | 0-2 |  | Dorchester Town | Pre-Season |
| Thur 13 | Holt United | 3-3 |  | Portland United | Pre-Season |
| Sat 15 | Portland United | 2-0 | | Hamworthy United | Pre-Season |
| Mon 24 | Hamworthy Recreation | 2-3 | | Portland United | Pre-Season |
| Sat 29 | Crediton United | 1-2 | | Portland United | Pre-Season |
| Aug-23 | |||||
| Tue 01 | Laverstock & Ford | 1-1 | | Portland United | Premier Division |
| Sat 05 | Horndean | 3-0 | | Portland United | Emirates FA Cup (ExPR) |
| Sat 12 | Portland United | 2-2 | | Lymington Town | Premier Division |
| Tue 15 | Shaftesbury Town | 0-0 | | Portland United | Premier Division |
| Sat 19 | Portland United | 1-1 | | Baffins Milton Rovers | Premier Division |
| Sat 26 | Portland United | 1-0 | | US Portsmouth | Isuzu FA Vase (1Q) |
| Tue 29 | Portland United | 5-3 | | Totton & Eling | League Cup |
| Sep-23 | |||||
| Sat 02 | Brockenhurst | 3-2 | | Portland United | Premier Division |
| Sat 16 | Portland United | 5-1 | | Cowes Sports | Premier Division |
| Sat 23 | Wincanton Town | 2-4 | | Portland United | Isuzu FA Vase (2Q) |
| Sat 30 | Portland United | 2-0 | | Bournmouth Poppies | Premier Division |
| Oct-23 | |||||
| Tue 03 | Portland United | 7-0 | | Romsey Town | League Cup |
| Sat 07 | Hythe & Dibden | 0-4 | | Portland United | Premier Division |
| Sat 14 | Portland United | 6-1 | | Blackfield & Langley | Premier Division |
| Tue 17 | Portland United | 1-0 | | Sherborne Town | Premier Division |
| Sat 21 | Torpoint Athletic | 0-0 (2-4 Pens) | | Portland United | Isuzu FA Vase |
| Sat 28 | Portland United | 0-3 | | Moneyfields | Premier Division |
| Tue 31 | Portland United | 0-3 | | AFC Portchester | League Cup |
| Nov-23 | |||||
| Sat 11 | Wells City | 1-1 (4-3 Pens) | | Portland United | Isuzu FA Vase |
| Wed 15 | Sherborne Town | 2-1 | | Portland United | Dorset Senior Cup (1R) |
| Sat 18 | Portland United | 1-0 | | Fareham Town | Premier Division |
| Sat 25 | Portland United | 2-1 | | Andover New Street | Premier Division |
| Dec-23 | |||||
| Sat 02 | AFC Stoneham | 1-0 | | Portland United | Premier Division |
| Sat 09 | Portland United | 0-0 | | Hythe & Dibden | Premier Division |
| Sat 16 | Cowes Sports | 4-2 | | Portland United | Premier Division |
| Sat 23 | Portland United | 3-0 | | Christchurch | Premier Division |
| Sat 30 | Bournemouth Poppies | 1-2 | | Portland United | Premier Division |
| Jan-24 | |||||
| Sat 06 | Portland United | 2-1 | | US Portsmouth | Premier Division |
| Sat 13 | Lymington Town | 0-6 | | Portland United | Premier Division |
| Sat 20 | Portland United | 1-1 | | Hamble Club | Premier Division |
| Sat 27 | Portland United | 0-1 | | AFC Portchester | Premier Division |
| Tue 30 | Christchurch | 1-1 | | Portland United | Premier Division |
| Feb-24 | |||||
| Sat 03 | Baffins Milton Rovers | 3-2 | | Portland United | Premier Division |
| Sat 17 | Portland United | 0-2 | | AFC Stoneham | Premier Division |
| Mar-24 | |||||
| Sat 02 | AFC Portchester | 2-0 | | Portland United | Premier Division |
| Tue 05 | Portland United | 2-0 | | Laverstock & Ford | Premier Division |
| Sat 09 | US Portsmouth | 1-2 | | Portland United | Premier Division |
| Sat 16 | Portland United | 0-0 | | Peterfield Town | Premier Division |
| Tue 19 | Blackfield & Langley | 2-3 | | Portland United | Premier Division |
| Fri 22 | Moneyfields | 2-0 | | Portland United | Premier Division |
| Sat 30 | Sherborne Town | 1-3 | | Portland United | Premier Division |
| Apr-24 | |||||
| Sat 06 | Petersfield Town | 1-2 | | Portland United | Premier Division |
| Tue 09 | Andover New Street | 0-3 | | Portland United | Premier Division |
| Sat 13 | Hamble Club | 1-2 | | Portland United | Premier Division |
| Mon 15 | Fareham Town | 0-1 | | Portland United | Premier Division |
| Thu 18 | Portland United | 1-2 | | Shaftesbury Town | Premier Division |
| Sat 20 | Portland United | 1-2 | | Brockenhurst | Premier Division |
