| DATE | HOME | RESULT | W/L/D | AWAY | COMPETITION |
|---|---|---|---|---|---|
| Aug-25 | |||||
| Tue 05 | Portland United Res | 2-1 |  | Portland United U18 | Friendly |
| Sun 10 | Porland United U18 | 4-1 |  | Bournemouth Sports U18 | Friendly |
| Sun 17 | Portland United U18 | 9-0 | | Weymouth FC U18 | Friendly |
| Wed 20 | Portland United Panthers | 2-1 | | Porland United U18 | Friendly |
| Thur 28 | Portland United U18 | 5-0 | | Beaminster FC | Friendly |
| Sep-25 | |||||
| Wed 03 | Portland United U18 | 3-0 | | Millbrook U18 (Hampshire) | FA Youth Cup (PR) |
| Sun 07 | Portland United U18 | 3-3 |  | Swanage Town & Herston | U18 Division 1 |
| Sun 14 | Portland United U18 | 3-1 | | Holt United Youth | U18 Division 1 |
| Wed 17 | Portland United U18 | 5-3 | | Hamworthy Recreation U18 | FA Youth Cup (1Q) |
| Sun 21 | Portland United U18 | 4-0 | | Dorchester Sports U18 | Friendly |
| Tue 30 | Portland United U18 | 3-1 | | Yeovil Town U18 | FA Youth Cup (2Q) |
| Oct-25 | |||||
| Sun 05 | Portland United U18 | 2-0 | | Hamworthy Recreation U18 | U18 Division 1 |
| Tue 14 | Portland United U18 | 0-4 |  | Oxford City U18 | FA Youth Cup (3Q) |
| Sun 26 | Holt United U18 | 4-3 | | Portland United U18 | U18 Division 1 |
| Nov-25 | |||||
| Sun 02 | Portland United U18 | 1-2 | | Lilliput Athletic U18 | U18 Division 1 |
| Sun 09 | Westland Sports U18 | 2-3 | | Portland United U18 | U18 Dorset Youth Cup |
| Sun 30 | Portland United U18 | 1-2 | | Christchurch U18 | U18 Division 1 |
| Dec-25 | |||||
| Sun 14 | Portland United U18 | 3-1 | | Weymouth FC U18 Terras | U18 Dorset Youth Cup (R2) |
| Jan-26 | |||||
| Sun 11 | Shaftesbury U18 | 1-4 | | Portland United U18 | U18 Dorset Youth Cup |
| Feb-26 | |||||
| Sun 01 | Portland United U18 | 1-1 | | Poole Town Wessex Colts | U18 Division 1 |
| Sun 22 | Poole Town Wessex Colts | 0-3 | | Portland United U18 | U18 Division 1 |
| Mar-26 | |||||
| Sun 01 | Portland United U18 | 2-0 | | Westland Sports U18 | U18 Division 1 |
| Sun 08 | Portland United U18 | 3-1 | | Lilliput U18 Athletic | Dorset U18 Youth Cup |
| Sun 15 | Westland Sports U18 | 3-0 | | Portland United U18 | U18 Division 1 |
| Sun 22 | Lilliput U18 Athletic | 3-2 | | Portland United U18 | U18 Division 1 |
| Sun 29 | Swanage Town & Herston | 1-1 | | Portland United U18 | U18 Division 1 |
| Apr-26 | |||||
| Sun 12 | Weymouth U18 | 0-3 | | Portland United U18 | U18 League Cup |
| Thur 16 | Cobham Sports U18 | 4-1 | | Portland United U18 | County Youth Cup Final |
| Sun 19 | Hamworthy Recreation U18 | 1-3 | | Portland United U18 | U18 Division 1 |
| Sun 26 | Christchurch U18 | 1-7 | | Portland United U18 | U18 Division 1 |
| May-26 | |||||
| Sun 10 | Poole Town Wessex Colts | 0-2 | | Portland United U18 | U18 League Cup Semi Final |
| Sun 17 | Hamworthy Recreation U18 | 0-2 | | Portland United U18 | U18 League Cup Final |
