| Date | Division | Match | String | Opponent | Result |
| 20/09/2018 | Div 5 South West | Winsford 3 v Winsford 2 | 2 | Max Birkenhead | Won 3-1 |
| 18/10/2018 | Div 5 South West | Whitby 2 v Winsford 2 | 4 | Kevin James | Won 3-0 |
| 01/11/2018 | Div 5 South West | Neston 4 v Winsford 2 | 3 | Pete Townsend | Won 3-1 |
| 08/11/2018 | Div 5 South West | Holywell Leisure SC 2 v Winsford 2 | 4 | Chris Bunnel | Won 3-1 |
| 15/11/2018 | Div 5 South West | Winsford 2 v Cheshire Officers 4 | 5 | (walkover) | Won 3-0 |
| 22/11/2018 | Div 5 South West | New Brighton 2 v Winsford 2 | 3 | John Price | Won 3-0 |
| 29/11/2018 | Div 3 South West | Village Wirral 1 v Winsford 1 | 5 | Mark Whitfield | Won 3-2 |
| 06/12/2018 | Div 5 South West | Barnton CC 3 v Winsford 2 | 2 | Rod Howell | Lost 0-3 |
| 13/12/2018 | Div 5 South West | Winsford 2 v Delamere Park 1 | 3 | Andrew Bryson | Won 3-0 |
| 03/01/2019 | Div 5 South West | Winsford 2 v Winsford 3 | 1 | Max Birkenhead | Won 3-2 |
| 10/01/2019 | Div 5 South West | Cheshire Officers 3 v Winsford 2 | 1 | Nigel Bailey | Lost 0-3 |
| 24/01/2019 | Div 3 South West | Winsford 1 v Chester Rugby 2 | 3 | Mark Strefford | Lost 0-3 |
| 31/01/2019 | Div 5 South West | Winsford 2 v Whitby 2 | 4 | Steve Jones | Won 3-0 |
| 21/02/2019 | Div 5 South West | Winsford 2 v Neston 4 | 5 | (walkover) | Won 3-0 |
| 28/02/2019 | Div 5 South West | Winsford 2 v Holywell Leisure SC 2 | 4 | Paul Day | Lost 1-3 |
| 14/03/2019 | Div 5 South West | Winsford 2 v New Brighton 2 | 5 | Damian Ryan | Won 3-1 |
| 21/03/2019 | Div 5 South West | Chester Rugby 4 v Winsford 2 | 2 | Wayne Lawrence | Lost 1-3 |
| 28/03/2019 | Div 5 South West | Winsford 2 v Barnton CC 3 | 3 | David Vaughan | Won 3-0 |
| 04/04/2019 | Div 5 South West | Delamere Park 1 v Winsford 2 | 3 | Andrew Bryson | Won 3-1 |
