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