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| DATE | HOME | RESULT | W/L/D | AWAY | COMPETITION |
| Jul-23 | | | | | |
| Sat 01 | Sturminster Marshall | 1-6 |  | Portland United Res | Pre-Season |
| Tue 18 | Portland Panthers | 2-3 | | Portland United Res | Pre-Season |
| Sat 22 | Bournemouth Manor | 1-3 | | Portland United Res | Pre-Season |
| Wed 26 | Portland United Res | 0-1 |  | Merley Cobham Res | Pre-Season |
| Sat 29 | Ridgeway | 0-3 | | Portland United Res | Pre-Season |
| Aug-23 | | | | | |
| Sat 12 | Swanage Town & Herston | 3-0 | | Portland United Res | DPL |
| Wed 16 | Portland United Res | 1-0 | | Dorchester Sports | DPL |
| Sat 19 | Bournemouth Sports | 1-1 |  | Portland United Res | DPL |
| Tue 22 | Balti Sports | 2-2 | | Portland United Res | DPL |
| Sat 26 | Sturminster Marshall | 0-4 | | Portland United Res | DPL |
| Sep-23 | | | | | |
| Sat 02 | Holt United | 4-1 | | Portland United Res | DPL |
| Sat 09 | Portland United Res | 4-2 | | Westland Sports | DPL |
| Wed 13 | Portland United Res | 2-1 | | Poole Borough | DPL |
| Sat 16 | Merley Cobham Sports | 2-2 | | Portland United Res | DPL |
| Sat 23 | Portland United Res | 7-1 | | Hamworthy United | DPL |
| Wed 27 | Sherborne Town Res | 0-5 | | Portland United Res | DPL Cup |
| Sat 30 | Wimborne Town Res | 3-0 | | Portland United Res | DPL |
| Oct-23 | | | | | |
| Sat 07 | Blandford United | 4-1 | | Portland United Res | DPL |
| Sat 14 | Shaftesbury Town Res | 0-5 | | Portland United Res | Expunged |
| Tue 17 | Bridport Res | 0-1 | | Portland United Res | DPL |
| Sat 21 | Portland United Res | 2-2 | | Sherborne Town Res | DPL |
| Sat 28 | Sturminster Newton | 3-2 | | Portland United Res | DPL |
| Nov-23 | | | | | |
| Sat 04 | Portland United Res | 1-2 | | Wimborne Town Res | Senior Trophy |
| Sat 11 | Portland United Res | 1-0 | | Swanage Town & Herston | DPL |
| Sat 18 | Hamworthy United | 0-3 | | Portland United Res | DPL |
| Sat 25 | Dorchester Sports | 2-2 | | Portland United Res | DPL |
| Dec-23 | | | | | |
| Sat 09 | Westland Sports | 5-3 | | Portland United Res | DPL |
| Sat 16 | Portland United Res | 0-2 | | Holt United | DPL Cup |
| Sat 23 | Poole Borough | 0-3 | | Portland United Res | DPL |
| Jan-24 | | | | | |
| Sat 06 | Sherborne Town Res | 1-4 | | Portland United Res | DPL |
| Sat 13 | Portland United Res | 19-0 | | Sturminster Marshall | DPL |
| Wed 17 | Portland United Res | 5-1 | | Balti Sports | DPL |
| Wed 24 | Portland United Res | 3-1 | | Bridport Res | DPL |
| Feb-24 | | | | | |
| Sat 03 | Portland United Res | 4-4 | | Bournemouth Sports | DPL |
| Sat 10 | Portland United Res | 1-1 | | Holt United | DPL |
| Mar-24 | | | | | |
| Wed 20 | Portland United Res | 1-6 | | Sturminster Newton | DPL |
| Sat 23 | Portland United Res | 1-3 | | Blandford United | DPL |
| Apr-24 | | | | | |
| Sat 06 | Portland United Res | 0-4 | | Wimborne Town Res | DPL |
| Sat 27 | Portland United Res | 0-0 | | Merley Cobham Sports | DPL |
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