| 23 August 2019 | |||
| Oak FC | 2 | 2 | Usk Town |
| 24 August 2019 | |||
| Crickhowell | 4 | 1 | Tranch |
| Cwmcarn Athletic | 0 | 0 | Cromwell Youth |
| Trinant | 2 | 1 | Ponthir |
| 25 August 2019 | |||
| Cefn Fforest | 4 | 1 | Gilwern & District |
| 31 August 2019 | |||
| Cromwell Youth | 2 | 1 | Oak FC |
| Gilwern & District | 1 | 3 | Crickhowell |
| Nantyglo | 3 | 1 | Ponthir |
| Tranch | 2 | 1 | Cwmcarn Athletic |
| Trinant | 4 | 6 | Cefn Fforest |
| 7 September 2019 | |||
| Cefn Fforest | 3 | 1 | Nantyglo |
| Crickhowell | 4 | 3 | Trinant |
| Cwmcarn Athletic | 2 | 3 | Gilwern & District |
| Oak FC | 3 | 1 | Tranch |
| Usk Town | 0 | 6 | Cromwell Youth |
| 14 September 2019 | |||
| Gilwern & District | 5 | 1 | Oak FC |
| Nantyglo | 0 | 1 | Crickhowell |
| Ponthir | 0 | 2 | Cefn Fforest |
| Tranch | 0 | 6 | Usk Town |
| 21 September 2019 | |||
| Crickhowell | 2 | 2 | Ponthir |
| Cromwell Youth | 6 | 0 | Tranch |
| Cwmcarn Athletic | 2 | 3 | Nantyglo |
| Oak FC | 2 | 3 | Trinant |
| Usk Town | 2 | 2 | Gilwern & District |
| 28 September 2019 | |||
| Cefn Fforest | 2 | 0 | Crickhowell |
| Gilwern & District | 2 | 3 | Cromwell Youth |
| Nantyglo | 1 | 1 | Oak FC |
| Ponthir | 1 | 2 | Cwmcarn Athletic |
| Trinant | 7 | 8 | Usk Town |
| 5 October 2019 | |||
| Cromwell Youth | 5 | 1 | Trinant |
| Cwmcarn Athletic | 1 | 1 | Cefn Fforest |
| Oak FC | 3 | 3 | Ponthir |
| Tranch | 2 | 3 | Gilwern & District |
| 19 October 2019 | |||
| Gilwern & District | 1 | 2 | Trinant |
| Oak FC | 3 | 0 | Crickhowell |
| 2 November 2019 | |||
| Gilwern & District | 1 | 1 | Ponthir |
| 9 November 2019 | |||
| Cwmcarn Athletic | 3 | 2 | Usk Town |
| Nantyglo | 5 | 1 | Trinant |
| 23 November 2019 | |||
| Oak FC | 2 | 5 | Cwmcarn Athletic |
| Usk Town | 5 | 5 | Crickhowell |
| 30 November 2019 | |||
| Cefn Fforest | 5 | 1 | Usk Town |
| Crickhowell | 2 | 0 | Oak FC |
| Nantyglo | 4 | 1 | Tranch |
| Ponthir | 1 | 5 | Cromwell Youth |
| Trinant | 3 | 2 | Gilwern & District |
| 7 December 2019 | |||
| Cromwell Youth | 1 | 2 | Nantyglo |
| Cwmcarn Athletic | 2 | 0 | Crickhowell |
| Oak FC | 2 | 3 | Cefn Fforest |
| Usk Town | 2 | 1 | Ponthir |
| 28 December 2019 | |||
| Ponthir | 1 | 2 | Crickhowell |
| Trinant | 1 | 4 | Oak FC |
| Teams | P | W | D | L | GD | Pts | |
| Cefn Fforest | 8 | 7 | 1 | 0 | +16 | 22 | |
| Crickhowell | 11 | 6 | 2 | 3 | +3 | 20 | |
| Cromwell Youth | 8 | 6 | 1 | 1 | +21 | 19 | |
| Nantyglo | 8 | 5 | 1 | 2 | +8 | 16 | |
| Cwmcarn Athletic | 9 | 4 | 2 | 3 | +4 | 14 | |
| Usk Town | 9 | 3 | 3 | 3 | -3 | 12 | |
| Oak FC | 12 | 3 | 3 | 6 | -4 | 12 | |
| Trinant | 10 | 4 | 0 | 6 | -11 | 12 | |
| Gilwern & District | 10 | 3 | 2 | 5 | -2 | 11 | |
| Ponthir | 10 | 0 | 3 | 7 | -12 | 3 | |
| Tranch | 7 | 1 | 0 | 6 | -20 | 3 |
| 4 January 2020 | ||||
| Cefn Fforest | v | Ponthir | ||
| Crickhowell | v | Nantyglo | ||
| Cwmcarn Athletic | v | Trinant | ||
| Oak FC | v | Gilwern & District | ||
| Oak FC | v | Tranch |
| 11 January 2020 | ||||
| Cromwell Youth | v | Usk Town | ||
| Gilwern & District | v | Cwmcarn Athletic | ||
| Nantyglo | v | Cefn Fforest | ||
| Tranch | v | Oak FC | ||
| Trinant | v | Crickhowell |
| 18 January 2020 | ||||
| Cefn Fforest | v | Trinant | ||
| Crickhowell | v | Gilwern & District | ||
| Cwmcarn Athletic | v | Tranch | ||
| Oak FC | v | Cromwell Youth | ||
| Ponthir | v | Nantyglo |
| 25 January 2020 | ||||
| Cromwell Youth | v | Cwmcarn Athletic | ||
| Gilwern & District | v | Cefn Fforest | ||
| Tranch | v | Crickhowell | ||
| Trinant | v | Ponthir | ||
| Usk Town | v | Oak FC |
