| Date | Step H | Home | HS | – | AS | Away | Step A |
|---|---|---|---|---|---|---|---|
| Round 1 | |||||||
| Sun, Sep 8, 2024 | 3 | Wimborne Town | w/o | – | Poole Town | 3 | |
| Tue, Oct 8, 2024 | 3 | Dorchester Town | 4 | – | 2 | Bridport | 6 |
| Tue, Oct 8, 2024 | 6 | Verwood Town | 1 | – | 5 | Hamworthy United | 6 |
| Tue, Oct 15, 2024 | 5 | Portland United | 0 | – | 3 | Weymouth | 2 |
| Tue, Oct 15, 2024 | 6 | Sturminster Newton United | 4 | – | 2 | Gillingham Town | 6 |
| Wed, Nov 6, 2024 | 5 | Sherborne Town | 0 | – | 4 | Shaftesbury | 4 |
| Quarter Final | |||||||
| Tue, Nov 12, 2024 | 5 | Hamworthy Recreation | 4 | 1 | Swanage Town & Herston | 7 | |
| Tue, Nov 12, 2024 | 6 | Hamworthy United | 1 | 2 | Shaftesbury | 4 | |
| Tue, Nov 12, 2024 | 3 | Wimborne Town | 0 | 3 | Weymouth | 2 | |
| Tue, Nov 19, 2024 | 3 | Dorchester Town | 0 | 0p | Sturminster Newton United | 6 | |
| Semi Final | |||||||
| Tue, Jan 14, 2025 | 2 | Weymouth | 3 | 1 | Sturminster Newton United | 6 | |
| Tue, Jan 14, 2025 | 5 | Hamworthy Recreation | 2p | 2 | Shaftesbury | 4 | |
| Final | |||||||
| Tue, Mar 25, 2025 | 5 | Hamworthy Recreation | 1 | 2 | Weymouth | 2 | |
| CHAMPIONS | |||||||
| Sun, Jun 1, 2025 | WEYMOUTH | ||||||