Home History
| Club Friendly List | 2024/07/13 14:00 | Chepstow Town v Tytherington Rocks FC | L | 1-2 |
| 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
| Club Friendly List | 2024/07/06 12:00 | Hereford Pegasus FC v Bewdley | W | 4-0 |