| | 29/09/19 11 am | Round Tower Rovers | 1 | 4 | Slaney Rovers B | Ross Cole | Timahoe | |
| | 29/09/19 2 pm | Bagenalstown AFC | 4 | 0 | Baltinglass Town B | Mick Salter | McGrath Park Bagenalstown | |
| | 29/09/19 2 pm | St Joseph's FC | 2 | 4 | St Patricks Boys B | Christy Haughney | McArdle Cross Tinryland (St Josephs) | |
| | 29/09/19 2 pm | Killeshin FC B | 3 | 2 | Nurney Villa | Martin Murphy | Quakers Field, Killeshin | |
| | 29/09/19 2 pm | Burrin Celtic | 2 | 2 | Hanover Harps B | Luke Nolan | The Valley Ballon (Burrin Celtic) | |
| | 06/10/19 2 pm | Bagenalstown AFC | 1 | 0 | Vale Wanderers B | Mick Salter | McGrath Park Bagenalstown | |
| | 06/10/19 2 pm | Slaney Rovers B | 4 | 1 | St Joseph's FC | Luke Nolan | Rathvilly behind graveyard (Slaney Rovers | |
| | 06/10/19 2 pm | Hanover Harps B | 8 | 1 | Killeshin FC B | Pat Moran | The Plots (Hanover Harps) | |
| | 06/10/19 2 pm | Baltinglass Town B | 2 | 2 | St Patricks Boys B | Christy O' Rourke | Parkmore Baltinglass | |
| | 13/10/19 11 am | Slaney Rovers B | 2 | 0 | Killeshin FC B | Luke Nolan | Rathvilly behind graveyard (Slaney Rovers | |
| | 13/10/19 11 am | Nurney Villa | 1 | 2 | Round Tower Rovers | Mick Salter | Newtown Rd Nurney | |
| | 13/10/19 11 am | Hanover Harps B | 0 | 4 | St Joseph's FC | Ross Cole | The Plots (Hanover Harps) | |
| | 13/10/19 11 am | Bagenalstown AFC | 2 | 0 | Burrin Celtic | Mick Murphy | McGrath Park Bagenalstown | |
| | 13/10/19 2 pm | St Patricks Boys B | 6 | 2 | Vale Wanderers B | David Donegan | The Meadows Graiguecullen (St Pats Boys) | |
| | 20/10/19 11 am | Round Tower Rovers | 0 | 3 | Bagenalstown AFC | Ross Cole | Timahoe | |
| | 20/10/19 2 pm | Vale Wanderers B | 2 | 1 | Slaney Rovers B | David Donegan | Superbowl Leighlinbridge (Vale Wanderers) | |
| | 20/10/19 2 pm | St Patricks Boys B | 6 | 2 | Nurney Villa | Luke Nolan | The Meadows Graiguecullen (St Pats Boys) | |
| | 20/10/19 2 pm | Burrin Celtic | 6 | 0 | Killeshin FC B | Gerry Bickerstaffe | The Valley Ballon (Burrin Celtic) | |
| | 20/10/19 2 pm | Baltinglass Town B | 0 | 1 | Hanover Harps B | Christy O' Rourke | Parkmore Baltinglass | |
| | 27/10/19 11 am | Nurney Villa | 2 | 2 | Bagenalstown AFC | Mick Salter | Newtown Rd Nurney | |
| | 27/10/19 2 pm | Baltinglass Town B | 2 | 0 | Slaney Rovers B | Pat Moran | Parkmore Baltinglass | |
| | 27/10/19 2 pm | Vale Wanderers B | 1 | 0 | Hanover Harps B | Ross Cole | Superbowl Leighlinbridge (Vale Wanderers) | |
| | 27/10/19 2 pm | St Joseph's FC | 2 | 1 | Round Tower Rovers | David Donegan | McArdle Cross Tinryland (St Josephs) | |
| | 27/10/19 2 pm | Killeshin FC B | 0 | 3 | St Patricks Boys B | Mick Murphy | Quakers Field, Killeshin | |
| | 03/11/19 11 am | Nurney Villa | 3 | 0 | Vale Wanderers B | Willie Bowes | Newtown Rd Nurney | |
| | 03/11/19 11 am | Killeshin FC B | 5 | 4 | St Joseph's FC | David Donegan | Quakers Field, Killeshin | |
| | 03/11/19 2 pm | Baltinglass Town B | 1 | 0 | Round Tower Rovers | Christy O' Rourke | Parkmore Baltinglass | |
| | 03/11/19 2 pm | St Patricks Boys B | 5 | 2 | Burrin Celtic | Mick Salter | The Meadows Graiguecullen (St Pats Boys) | |
| | 10/11/19 11:30 am | Round Tower Rovers | 4 | 0 | Killeshin FC B | Pat Moran | Timahoe | |
| | 10/11/19 2 pm | Vale Wanderers B | 4 | 1 | Baltinglass Town B | Mick Murphy | Superbowl Leighlinbridge (Vale Wanderers) | |
| | 10/11/19 2 pm | Nurney Villa | 1 | 1 | Hanover Harps B | Luke Nolan | Newtown Rd Nurney | |
| | 10/11/19 2 pm | Burrin Celtic | 3 | 0 | Slaney Rovers B | David Donegan | The Valley Ballon (Burrin Celtic) | |
| | 17/11/19 11 am | Nurney Villa | 0 | 2 | Burrin Celtic | Christy O' Rourke | Newtown Rd Nurney | |
| | 17/11/19 2 pm | St Patricks Boys B | 3 | 0 | Round Tower Rovers | Mick Salter | The Meadows Graiguecullen (St Pats Boys) | |
| | 17/11/19 2 pm | Hanover Harps B | 1 | 1 | Bagenalstown AFC | Gerry Bickerstaffe | The Plots (Hanover Harps) | |
| | 24/11/19 2 pm | Vale Wanderers B | 3 | 5 | St Joseph's FC | Luke Nolan | Superbowl Leighlinbridge (Vale Wanderers) | |
| | 24/11/19 2 pm | Hanover Harps B | 1 | 4 | St Patricks Boys B | David Donegan | The Plots (Hanover Harps) | |
| | 01/12/19 11 am | St Joseph's FC | 0 | 2 | Nurney Villa | Martin Murphy | McArdle Cross Tinryland (St Josephs) | |
| | 01/12/19 2 pm | Killeshin FC B | 1 | 1 | Hanover Harps B | David Donegan | Quakers Field, Killeshin | |
| | 15/12/19 11 am | Round Tower Rovers | 2 | 2 | Vale Wanderers B | Gerry Bickerstaffe | Timahoe | |
| | 15/12/19 11 am | Bagenalstown AFC | 2 | 1 | St Patricks Boys B | Seamus Ivers | McGrath Park Bagenalstown | |
| | 15/12/19 2 pm | Killeshin FC B | 1 | 1 | Baltinglass Town B | Martin Murphy | Quakers Field, Killeshin | |
| | 29/12/19 11 am | Slaney Rovers B | 2 | 7 | Bagenalstown AFC | Gerry Bickerstaffe | Rathvilly behind graveyard (Slaney Rovers | |
| | 29/12/19 11 am | Burrin Celtic | 1 | 2 | Baltinglass Town B | Luke Nolan | The Valley Ballon (Burrin Celtic) | |
| | 05/01/20 11 am | St Joseph's FC | 1 | 5 | Bagenalstown AFC | Ross Cole | McArdle Cross Tinryland (St Josephs) | |
| | 05/01/20 11 am | Burrin Celtic | 3 | 1 | Round Tower Rovers | Martin Murphy | The Valley Ballon (Burrin Celtic) | |
| | 05/01/20 2 pm | Slaney Rovers B | 0 | 3 | St Patricks Boys B | David Donegan | Rathvilly behind graveyard (Slaney Rovers | |
| | 05/01/20 2 pm | Killeshin FC B | 0 | 3 | Vale Wanderers B | Ross Cole | Quakers Field, Killeshin | |
| | 05/01/20 2 pm | Baltinglass Town B | 1 | 1 | Nurney Villa | Christy O' Rourke | Parkmore Baltinglass | |
| | 12/01/20 11 am | Bagenalstown AFC | 3 | 0 | Killeshin FC B | Gerry Bickerstaffe | McGrath Park Bagenalstown | |
| | 12/01/20 11 am | Vale Wanderers B | 2 | 3 | Burrin Celtic | Chris Coleman | Superbowl Leighlinbridge (Vale Wanderers) | |
| | 12/01/20 11 am | Round Tower Rovers | 3 | 3 | Hanover Harps B | Ross Cole | Timahoe | |
| | 12/01/20 2 pm | St Joseph's FC | 2 | 2 | Baltinglass Town B | Christy O' Rourke | McArdle Cross Tinryland (St Josephs) | |
| | 19/01/20 12 pm | Nurney Villa | 3 | 2 | St Joseph's FC | Chris Coleman | Newtown Rd Nurney | |
| | 19/01/20 12 pm | Bagenalstown AFC | 2 | 0 | Round Tower Rovers | David Donegan | McGrath Park Bagenalstown | |
| | 19/01/20 2:30 pm | Vale Wanderers B | 1 | 2 | St Patricks Boys B | Gerry Bickerstaffe | Superbowl Leighlinbridge (Vale Wanderers) | |
| | 19/01/20 2:30 pm | Hanover Harps B | 0 | 1 | Slaney Rovers B | Christy O' Rourke | The Plots (Hanover Harps) | |
| | 26/01/20 2 pm | Baltinglass Town B | 3 | 1 | St Joseph's FC | Christy O' Rourke | Parkmore Baltinglass | |
| | 26/01/20 2 pm | Killeshin FC B | 3 | 1 | Round Tower Rovers | Jim Wynne | Quakers Field, Killeshin | |
| | 02/02/20 11 am | Bagenalstown AFC | 4 | 1 | St Joseph's FC | Ross Cole | McGrath Park Bagenalstown | |
| | 02/02/20 11 am | Nurney Villa | 1 | 0 | Slaney Rovers B | Christy O' Rourke | Newtown Rd Nurney | |
| | 02/02/20 2 pm | St Patricks Boys B | 4 | 2 | Killeshin FC B | Mick Murphy | The Meadows Graiguecullen (St Pats Boys) | |
| | 02/02/20 2 pm | Hanover Harps B | 3 | 0 | Round Tower Rovers | David Donegan | The Plots (Hanover Harps) | |
| | 02/02/20 2 pm | Baltinglass Town B | 0 | 3 | Burrin Celtic | Jim Wynne | Parkmore Baltinglass | |
| | 23/02/20 2 pm | Baltinglass Town B | 3 | 1 | Killeshin FC B | Christy O' Rourke | Parkmore Baltinglass | |
| | 23/02/20 2 pm | St Patricks Boys B | 3 | 0 | Hanover Harps B | Pat Moran | The Meadows Graiguecullen (St Pats Boys) | |
| | 23/02/20 2 pm | Vale Wanderers B | 2 | 5 | Round Tower Rovers | Mick Monaghan | Superbowl Leighlinbridge (Vale Wanderers) | |
| | 01/03/20 11 am | Vale Wanderers B | | | Killeshin FC B | Luke Nolan | Superbowl Leighlinbridge (Vale Wanderers) | |
| | 01/03/20 11 am | Burrin Celtic | | | Bagenalstown AFC | David Donegan | The Valley Ballon (Burrin Celtic) | |
| | 01/03/20 2 pm | St Patricks Boys B | | | St Joseph's FC | Luke Nolan | The Meadows Graiguecullen (St Pats Boys) | |
| | 01/03/20 2 pm | Slaney Rovers B | | | Hanover Harps B | Christy O' Rourke | Rathvilly behind graveyard (Slaney Rovers | |
| | 01/03/20 2 pm | Nurney Villa | | | Baltinglass Town B | Martin Murphy | Newtown Rd Nurney | |
| | | St Joseph's FC | | | Burrin Celtic | Christy O' Rourke | McArdle Cross Tinryland (St Josephs) | |
| | | Hanover Harps B | | | Burrin Celtic | | The Plots (Hanover Harps) | |
| | | Nurney Villa | | | Killeshin FC B | | Newtown Rd Nurney | |
| | | Slaney Rovers B | | | Round Tower Rovers | | Rathvilly behind graveyard (Slaney Rovers | |
| | | Baltinglass Town B | | | Bagenalstown AFC | | Parkmore Baltinglass | |
| | | Round Tower Rovers | | | St Patricks Boys B | | Timahoe | |
| | | Killeshin FC B | | | Slaney Rovers B | | Quakers Field, Killeshin | |
| | | Burrin Celtic | | | Nurney Villa | | The Valley Ballon (Burrin Celtic) | |
| | | Bagenalstown AFC | | | Hanover Harps B | | McGrath Park Bagenalstown | |
| | | Baltinglass Town B | | | Vale Wanderers B | Mick Murphy | Parkmore Baltinglass | |
| | | Hanover Harps B | | | Vale Wanderers B | | The Plots (Hanover Harps) | |
| | | Bagenalstown AFC | | | Nurney Villa | | McGrath Park Bagenalstown | |
| | | Killeshin FC B | | | Bagenalstown AFC | | Quakers Field, Killeshin | |
| | | Burrin Celtic | | | St Joseph's FC | Luke Nolan | The Valley Ballon (Burrin Celtic) | |
| | | Round Tower Rovers | | | Baltinglass Town B | | Timahoe | |
| | | Bagenalstown AFC | | | Slaney Rovers B | | McGrath Park Bagenalstown | |
| | | St Joseph's FC | | | Hanover Harps B | Mick Monaghan | McArdle Cross Tinryland (St Josephs) | |
| | | Burrin Celtic | | | St Patricks Boys B | | The Valley Ballon (Burrin Celtic) | |
| | | Slaney Rovers B | | | Vale Wanderers B | | Rathvilly behind graveyard (Slaney Rovers | |
| | | St Joseph's FC | | | Slaney Rovers B | | McArdle Cross Tinryland (St Josephs) | |
| | | Round Tower Rovers | | | Nurney Villa | | Timahoe | |
| | | Nurney Villa | | | St Patricks Boys B | | Newtown Rd Nurney | |
| | | St Joseph's FC | | | Killeshin FC B | | McArdle Cross Tinryland (St Josephs) | |
| | | Round Tower Rovers | | | Burrin Celtic | Martin Murphy | Timahoe | |
| | | Vale Wanderers B | | | Bagenalstown AFC | | Superbowl Leighlinbridge (Vale Wanderers) | |
| | | Slaney Rovers B | | | Nurney Villa | Pat Moran | Rathvilly behind graveyard (Slaney Rovers | |
| | | Burrin Celtic | | | Vale Wanderers B | | The Valley Ballon (Burrin Celtic) | |
| | | St Patricks Boys B | | | Baltinglass Town B | Ross Cole | The Meadows Graiguecullen (St Pats Boys) | |
| | | St Patricks Boys B | | | Slaney Rovers B | | The Meadows Graiguecullen (St Pats Boys) | |
| | | Killeshin FC B | | | Burrin Celtic | | Quakers Field, Killeshin | |
| | | Hanover Harps B | | | Nurney Villa | | The Plots (Hanover Harps) | |
| | | Slaney Rovers B | | | Baltinglass Town B | | Rathvilly behind graveyard (Slaney Rovers | |
| | | St Joseph's FC | | | Vale Wanderers B | | McArdle Cross Tinryland (St Josephs) | |
| Total : 105 |