| DATE | HOME | RESULT/KO | W/L/D | AWAY | VENUE | COMPETITION |
|---|---|---|---|---|---|---|
| Sep-24 | ||||||
| Mon 02 | Alton Youth | 0-0 (2-4 Pens) |  | Portland United U18 | Exclusive Networks Stadium | FA Youth Cup |
| Tue 17 | Wimborne Town | 1-1 (5-4 Pens) |  | Portland United U18 | New Cuthbury 3G | FA Youth Cup |
| Sun 22 | Portland United U18 | 6-1 | | Poole Borough U18 | Camp & Satherley Stadium | League |
| Sun 29 | Portland United U18 | 3-1 | | Weymouth FC U18 | Camp & Satherley Stadium | League |
| Oct 24 | ||||||
| Sun 06 | Portland United U18 | 4-0 | | Ringwood Town | Camp & Satherley Stadium | League |
| Sun 13 | Holt United Youth | 0-3 | | Portland United U18 | (Away Walkover) | Dorset U18 Youth Cup |
| Nov 24 | ||||||
| Sun 10 | Weymouth FC U18 | 1-3 | | Portland United U18 | Weymouth FC | Dorset U18 Youth Cup |
| Sun 24 | Ringwood Town U18 | 2-4 | | Portland United U18 | League | |
| Dec 24 | ||||||
| Sun 01 | Poole Borough U18 | 1-8 | | Portland United U18 | Poole | League |
| Sun 15 | Poole Town Wessex U18 | 5-0 |  | Portland United U18 | Poole | Dorset U18 Youth Cup (QF) |
| Jan 25 | ||||||
| Sun 05 | Bournemouth Sports U18 | 2-3 | | Portland United U18 | BU Sports Campus | League |
| Sun 19 | Bournemouth Poppies U18 | 2-4 | | Portland United U18 | Victoria Park | League |
| Feb 25 | ||||||
| Sun 02 | Portland United U18 | 3-0 | | Bournemouth Sports U18 | Camp & Satherley Stadium | League |
| Sun 09 | Poole Town Youth U18 | 0-3 | | Portland United U18 | King George Playing Field | League |
| Mar 25 | ||||||
| Sun 02 | Portland United U18 | 4-4 |  | Bournemouth Poppies U18 | Camp & Satherley Stadium | League |
| Sun 16 | Portland United U18 | 3-1 | | Poole Town Youth U18 | Camp & Satherley Stadium | League |
| Sun 23 | Weymouth FC U18 | 1-0 | | Portland United U18 | Camp & Satherley Stadium | league |
| Sun 30 | Bournemouth Poppies U18 | 0-1 | | Portland United U18 | Victoria Park | League Cup |
| Apr 25 | ||||||
| Sun 13 | Portland United U18 | 2-2 | | Ringwood Town U18 | Camp & Satherley Stadium | League Cup |
| May 25 | ||||||
| Wed 07 | Weymouth FC U18 | 1-2 | | Portland United U18 | Weymouth FC | League Cup |
| Sun 18 | Ringwood Town U18 | 2-3 | | Portland United U18 | Ringwood Hub | League Cup (Semi Final) |
| Sun 25 | Portland United U18 | 1-1 (7-6 Pens) | | Weymouth FC U18 | Milborne ST Andrew | League Cup (Final) |
Please be reminded that the above fixtures are subject to change