Home History
| Wales League Division 1 | 2016/09/23 18:30 | Penybont v Afan Lido | L | 0-3 |
| Wales League Division 1 | 2016/09/17 13:30 | Haverfordwest County v Penybont | W | 1-4 |
| Wales League Division 1 | 2016/09/10 13:30 | Penybont v Monmouth Town | W | 6-1 |
| Wales League Division 1 | 2016/09/03 13:30 | Penybont v Goytre United | L | 1-2 |
| Wales League Division 1 | 2016/08/27 13:30 | Undy Athletic v Penybont | L | 4-0 |
| Wales League Division 1 | 2016/08/20 13:30 | Penybont v Barry Town | D | 0-0 |
| Wales League Division 1 | 2016/08/13 13:30 | Ton Pentre v Penybont | L | 3-2 |
| Club Friendly List | 2016/07/05 18:30 | Penybont v Carmarthen | W | 3-1 |
Away History
| Wales League Division 1 | 2016/10/08 13:30 | Caldicot Town v Undy Athletic | L | 0-3 |
| Wales League Division 1 | 2016/09/24 13:30 | Barry Town v Caldicot Town | L | 5-2 |
| Wales League Division 1 | 2016/09/17 13:30 | Ton Pentre v Caldicot Town | L | 3-2 |
| Wales League Division 1 | 2016/09/10 13:30 | Caldicot Town v Caerau Ely | W | 1-0 |
| Wales League Division 1 | 2016/09/03 13:30 | Taffs Well v Caldicot Town | L | 3-0 |
| Wales League Division 1 | 2016/08/27 13:30 | Caldicot Town v Cambrian United | L | 2-3 |
| Wales League Division 1 | 2016/08/20 13:30 | Port Talbot v Caldicot Town | L | 2-1 |
| Wales League Division 1 | 2016/08/13 13:30 | Caldicot Town v Goytre | L | 3-4 |