Home History
| Wales Cup | 2023/11/11 14:00 | South Gower AFC v Chepstow Town | L | 7-6 |
| Wales Cup | 2023/10/14 13:00 | Chepstow Town v Abercarn United AFC | W | 4-0 |
| Wales Cup | 2023/09/16 13:00 | Chepstow Town v Pill AFC | W | 7-0 |
| Wales Cup | 2022/10/08 13:30 | Chepstow Town v Pontypridd Utd | L | 1-2 |
| Wales Cup | 2022/09/17 13:30 | Chepstow Town v Rockspur Fords Club | W | 1-0 |
| Wales Cup | 2021/08/13 17:45 | Undy Athletic v Chepstow Town | L | 3-0 |
Away History
| Wales Cup | 2023/12/09 14:00 | Flint Mountain FC v South Gower AFC | L | 2-1 |
| Wales Cup | 2023/11/11 14:00 | South Gower AFC v Chepstow Town | W | 7-6 |
| Wales Cup | 2023/10/14 13:00 | South Gower AFC v Rockspur Fords Club | W | 5-3 |
| Wales Cup | 2023/09/16 13:00 | Penydarren BGC v South Gower AFC | W | 4-5 |