| DATE | HOME | RESULT/KO | W/L/D | AWAY | VENUE | COMPETITION |
|---|---|---|---|---|---|---|
| Jul-23 | ||||||
| Sun 30 | Portland United U18 | 6-2 |  | Hamworthy U18 | Camp & Satherley Stadium | Pre-Season |
| Aug-23 | ||||||
| Sun 13 | Portland United U18 | 7-2 | | Sturminster Marshall | Redlands | Pre-Season |
| Sun 27 | Portland United U18 | 2-2 |  | Weymouth u18 | Redlands | Pre-Season |
| Sep-23 | ||||||
| Sun 03 | Christchurch U18 | 3-2 |  | Portland United U18 | Hurn Bridge Sports Club | U18 Division One |
| Wed 06 | US Portsmouth U18 | 1-3 | | Portland United U18 | Burnaby Road Sports Ground | FA Youth Cup |
| Sun 10 | Portland United U18 | 3-4 | | Hamworthy Rec U18 | Camp & Satherley Stadium | U18 Division One |
| Sun 17 | Holt United Youth U18 | 3-4 | | Portland United U18 | Holt FC. Petersham Lane | U18 Division One |
| Thur 21 | Hamble Club Youth FC | 6-2 | | Portland United U18 | Hamble Club - SO31 4BU | FA Youth Cup 1Q |
| Sun 24 | Portland United U18 | 2-1 | | Merley Cobham Spts U18 | Camp & Satherley Stadium | U18 Division One |
| Oct-23 | ||||||
| Sun 01 | Poole Town Wessex U18 | 2:00pm | Portland United U18 | Turlin Moor Blandford Road | U18 Division One | |
| Sun 08 | Portland United U18 | 2:00pm | Sturminster Marshall U18 | Camp & Satherley Stadium | U18 Division One | |
| Sun 15 | Portland United U18 | 2:00pm | Ringwood Town Youth U18 | Camp & Satherley Stadium | U18 Division One | |
| Sun 29 | Portland United U18 | 2:00pm | Weymouth FC U18 | Camp & Satherley Stadium | U18 Division One | |
Please be reminded that the above fixtures are subject to change