| 2020-03-07 14:00:47March 7, 2020 | AFC Rhoose | Quarter Finals 1 - 0 | Tynewydd | Ceri Road, Rhoose |
| 2020-02-08 14:00:28February 8, 2020 | Vale United | 2nd Rd 4 - 4 (1-3 pens) | Cadoxton Barry | Corntown |
| 2020-02-08 14:00:16February 8, 2020 | Rhoose Social | 2nd Round 3 - 2 | Island Marine | Barry Sports Centre |
| 2019-11-09 14:00:42November 9, 2019 | Cogan Coronation | 2nd Round 0 - 2 | AFC Rhoose | Cogan Leisure Centre |
| 2019-11-09 14:00:26November 9, 2019 | Cardiff Airport | 2nd Round 1 - 3 | | Ceri Road, Rhoose |
| 2019-11-09 14:00:24November 9, 2019 | Holton Road | 2nd Round 4 - 1 | St Athan | Barry Sports Centre |
| 2019-11-09 14:00:04November 9, 2019 | Cwm Talwg | 2nd Round 1 - 7 | Penarth Town | Barry Sports Centre |
| 2019-09-14 14:00:20September 14, 2019 | Rhoose Social | 1st Round 2 - 1 | Barry Athletic | Barry Sports Centre |
| 2019-09-14 14:00:11September 14, 2019 | Holton Road | 1st Round 3 - 0 | Cowbridge Town | Barry Sports Centre |
