Home History
| 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 | 2022/11/12 14:00 | Pontardawe Town v Pill AFC | L | 3-1 |
| Wales Cup | 2022/10/08 13:30 | Pill AFC v Cardiff MU | W | 2-1 |
| Wales Cup | 2022/09/17 13:30 | Pill AFC v Caldicot Town | W | 4-0 |