| DATE | HOME | RESULT | W/L/D | AWAY | COMPETITION |
|---|---|---|---|---|---|
| Jul-23 | |||||
| Sun 30 | Portland United U18 | 6-2 |  | Hamworthy U18 | Pre-Season |
| Aug-23 | |||||
| Sun 13 | Portland United U18 | 7-2 | | Sturminster Marshall | Pre-Season |
| Sun 27 | Portland United U18 | 2-2 |  | Weymouth u18 | Pre-Season |
| Sep-23 | |||||
| Sun 03 | Christchurch U18 | 3-2 |  | Portland United U18 | U18 Division One |
| Wed 06 | US Portsmouth U18 | 1-3 | | Portland United U18 | FA Youth Cup |
| Sun 10 | Portland United U18 | 3-4 | | Hamworthy Rec U18 | U18 Division One |
| Sun 17 | Holt United Youth U18 | 3-4 | | Portland United U18 | U18 Division One |
| Thur 21 | Hamble Club Youth FC | 6-2 | | Portland United U18 | FA Youth Cup 1Q |
| Sun 24 | Portland United U18 | 2-1 | | Merley Cobham U18 | U18 Division One |
| Oct-23 | |||||
| Sun 01 | Poole Town Wessex U18 | 1-7 | | Portland United U18 | U18 Division One |
| Sun 08 | Sturminster Marshall U18 | 2-4 | | Portland United U18 | U18 Division One |
| Sun 15 | Portland United U18 | 8-2 | | Ringwood Town U18 | U18 Division One |
| Nov-23 | |||||
| Sun 05 | Portland United U18 | 4-3 | | Bashley FC U18 | U18 Division One |
| Sun 12 | Hamworthy United U18 | 5-2 | | Portland United U18 | County FA Youth Cup |
| Sun 19 | Dorchester Town U18 | 4-1 | | Portland United U18 | U18 Division One |
| Sun 26 | Bournemouth Sports U18 | 3-6 | | Portland United U18 | U18 Division One |
| Dec-23 | |||||
| Wed 06 | Portland United U18 | 1-2 | | Weymouth FC U18 | U18 Division One |
| Sun 10 | Portland United U18 | 8-2 | | Poole Town Wessex U18 | U18 Division One |
| Sun 17 | Portland United U18 | 1-6 | | Holt United U18 | U18 Division One |
| Jan-24 | |||||
| Sun 07 | Ringwood Town Youth | 4-6 | | Portland United U18 | U18 Division One |
| Sun 14 | Portland United U18 | 2-2 | | Bournemouth Youth U18 | U18 Division One |
| Sun 21 | Hamworthy Rec U18 | 2-3 | | Portland United U18 | U18 Division One |
| Feb-24 | |||||
| Sun 04 | Merley Cobham U18 | 6-0 | | Portland United U18 | U18 Division One |
| Mar-24 | |||||
| Sun 10 | Portland United U18 | 2-2 | | Dorchester Town FC U18 | U18 Division One |
| Apr-24 | |||||
| Sun 14 | Bournemouth Poppies | 1-1 | | Portland United U18 | U18 Division One |
| Sun 21 | Portland United U18 | 1-3 | | Christchurch U18 | U18 Division One |
| Sun 28 | Weymouth FC U18 | 3-1 | | Portland United U18 | U18 Division One |
| May-24 | |||||
| Tue 07 | Portland United U18 | 9-0 | | Sturminster Marshall U18 | U18 Division One |
