Summary of previous matches between the team of Chepstow Town and the team of Monmouth Town since 2025-07-05:
Chepstow Town won 0 matches against Monmouth Town, lost 1 matches, and 0 matches were draws.
| Time | League | Home Team | Score | Away Team |
|---|---|---|---|---|
| 2025-07-05 | International Club Friendly | Chepstow Town | 0 : 2 | Monmouth Town |
| 2025-07-02 | International Club Friendly | Chepstow Town | 1 : 2 | Clevedon Town |
| 2024-09-21 | Wales Cup | Chepstow Town | 0 : 1 | PILL AFC |
| 2023-11-11 | Wales Cup | South Gower | 2 : 2 | Chepstow Town |
| 2023-10-14 | Wales Cup | Chepstow Town | 4 : 0 | Abercarn United |
| 2023-09-16 | Wales Cup | Chepstow Town | 7 : 0 | PILL AFC |
| 2022-10-08 | Wales Cup | Chepstow Town | 1 : 2 | Pontypridd |
| 2022-09-17 | Wales Cup | Chepstow Town | 1 : 0 | Rockspur |
| 2021-08-14 | Wales Cup | Undy Athletic | 3 : 0 | Chepstow Town |
| 2019-11-16 | Wales Cup | Chepstow Town | 0 : 5 | STM Sports |
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