| Date | Division | Match | String | Opponent | Result |
| 20/09/2018 | Div 5 South West | Chester Rugby 4 v Holywell Leisure SC 2 | 2 | Wayne Lawrence | Lost 2-3 |
| 27/09/2018 | Div 5 South West | Holywell Leisure SC 2 v Whitby 2 | 1 | John Hamilton | Lost 1-3 |
| 04/10/2018 | Div 5 South West | Barnton CC 3 v Holywell Leisure SC 2 | 1 | James Powlson | Won 3-0 |
| 11/10/2018 | Div 5 South West | Holywell Leisure SC 2 v Heswall 6 | 1 | Rob Wright | Won 3-2 |
| 25/10/2018 | Div 5 South West | Holywell Leisure SC 2 v Neston 4 | 2 | Darren Reid | Won 3-0 |
| 01/11/2018 | Div 5 South West | Winsford 3 v Holywell Leisure SC 2 | 2 | Rueben Mather | Won 3-0 |
| 08/11/2018 | Div 5 South West | Holywell Leisure SC 2 v Winsford 2 | 2 | James Andrew | Lost 2-3 |
| 15/11/2018 | Div 5 South West | Cheshire Officers 3 v Holywell Leisure SC 2 | 1 | Keith Flanigan | Lost 0-3 |
| 22/11/2018 | Div 5 South West | Holywell Leisure SC 2 v Cheshire Officers 4 | 2 | Trevor Jones | Won 3-1 |
| 06/12/2018 | Div 5 South West | Holywell Leisure SC 2 v New Brighton 2 | 3 | (walkover) | Won 3-0 |
| 06/12/2018 | Div 5 South West | Holywell Leisure SC 2 v New Brighton 2 | 2 | (walkover) | Won 3-0 |
| 03/01/2019 | Div 5 South West | Holywell Leisure SC 2 v Chester Rugby 4 | 3 | Richard Chisholm | Won 3-0 |
| 10/01/2019 | Div 5 South West | Whitby 2 v Holywell Leisure SC 2 | 3 | (walkover) | Won 3-0 |
| 17/01/2019 | Div 5 South West | Holywell Leisure SC 2 v Barnton CC 3 | 2 | Rod Howell | Won 3-2 |
| 24/01/2019 | Div 5 South West | Heswall 6 v Holywell Leisure SC 2 | 2 | Martin Williams | Won 3-1 |
| 07/02/2019 | Div 5 South West | Neston 4 v Holywell Leisure SC 2 | 1 | Jim Anderson | Lost 0-3 |
| 21/02/2019 | Div 5 South West | Holywell Leisure SC 2 v Winsford 3 | 2 | Moxy Thompson | Won 3-0 |
| 28/02/2019 | Div 5 South West | Winsford 2 v Holywell Leisure SC 2 | 2 | James Andrew | Lost 1-3 |
| 07/03/2019 | Div 5 South West | Holywell Leisure SC 2 v Cheshire Officers 3 | 1 | Keith Flanigan | Lost 0-3 |
| 14/03/2019 | Div 5 South West | Cheshire Officers 4 v Holywell Leisure SC 2 | 2 | Graham Hill | Won 3-0 |
| 21/03/2019 | Div 3 South West | Heswall 3 v Holywell Leisure SC 1 | 5 | Roy Finney | Lost 2-3 |
| 28/03/2019 | Div 5 South West | New Brighton 2 v Holywell Leisure SC 2 | 1 | Andy Watson | Lost 0-3 |
