[11] Penybont 1-2 Barry Town [4] 2019-08-16 19:00
Stadium: Bryntirion Park Round: 1
Referee: Iwan Griffiths Home Manager: Rhys Griffiths Away Manager: Gavin Chesterfield
Head to Head
| Wales Cup | 2018/12/07 19:45 | Barry Town v Penybont | L | 4-1 |
| Wales League Division 1 | 2017/01/07 14:00 | Barry Town v Penybont | D | 1-1 |
| Wales Cup | 2016/11/05 14:00 | Barry Town v Penybont | W | 0-3 |
| Wales League Division 1 | 2016/08/20 13:30 | Penybont v Barry Town | D | 0-0 |
| Wales League Division 1 | 2015/12/12 14:00 | Barry Town v Penybont | W | 0-1 |
| Wales League Division 1 | 2015/08/22 13:30 | Penybont v Barry Town | L | 0-2 |
Home History
| Wales League Cup | 2019/08/09 18:45 | Penybont v Goytre United | W | 4-1 |
| World Club Friendlies | 2019/08/02 18:30 | Merthyr Town v Penybont | W | 0-2 |
| UK Friendlies | 2019/07/06 13:00 | Penybont v Ammanford AFC | W | 2-1 |
| Wales League Division 1 | 2019/05/11 13:30 | Cwmamman United v Penybont | W | 0-9 |
| Wales League Division 1 | 2019/05/07 18:30 | Ammanford AFC v Penybont | W | 1-3 |
| Wales League Division 1 | 2019/05/03 18:30 | Goytre United v Penybont | W | 1-5 |
| Wales League Division 1 | 2019/04/30 17:30 | Cwmbran Celtic v Penybont | W | 0-2 |
| Wales League Division 1 | 2019/04/27 13:30 | Port Talbot v Penybont | W | 0-2 |
Away History
| Wales League Cup | 2019/08/10 13:30 | Haverfordwest County v Barry Town | L | 5-4 |
| UK Friendlies | 2019/08/02 18:46 | Barry Town v Swansea U23 | L | 1-2 |
| UEFA Europa League Qualifying | 2019/07/04 18:45 | Cliftonville v Barry Town | L | 4-0 |
| UEFA Europa League Qualifying | 2019/06/27 17:30 | Barry Town v Cliftonville | D | 0-0 |
| Club Friendly List | 2019/06/22 12:00 | Ballymena Utd v Barry Town | L | 2-1 |
| Club Friendly List | 2019/06/18 18:15 | Barry Town v T.N.S. | L | 1-6 |
| World Club Friendlies | 2019/06/15 14:00 | Barry Town v Panjab FA | D | 1-1 |
| Wales Premier League | 2019/04/26 18:45 | Barry Town v Newtown | L | 1-3 |