| Date | Division | Match | String | Opponent | Result |
| 03/10/2018 | Division 1 | Woodfield Squash 1 v Queens 2 | 4 | Chris Morse | Won 3-0 |
| 04/10/2018 | Division 2 | Hull & ER 2 v Woodfield Squash 2 | 1 | Paul Norton | Lost 0-3 |
| 17/10/2018 | Division 2 | Woodfield Squash 2 v Chapel Allerton 4 | 1 | Ross Williamson | Won 3-1 |
| 24/10/2018 | Division 2 | Barnsley 2 v Woodfield Squash 2 | 1 | Josh Greaves | Lost 1-3 |
| 24/10/2018 | Division 1 | Woodfield Squash 1 v Abbeydale 2 | 3 | Michael Kipling | Won 3-1 |
| 31/10/2018 | Division 2 | Woodfield Squash 2 v Harrogate 1 | 1 | Simon Myring | Lost 0-3 |
| 08/11/2018 | Division 2 | Fulwood 1 v Woodfield Squash 2 | 1 | Rahul Bansal | Lost 0-3 |
| 15/11/2018 | Division 2 | Woodfield Squash 2 v Norwood SC 1 | 1 | Ian Taylor | Lost 1-3 |
| 21/11/2018 | Division 2 | Scunthorpe@AppFrod 1 v Woodfield Squash 2 | 1 | Dave Ball | Lost 2-3 |
| 29/11/2018 | Division 2 | Woodfield Squash 2 v York RI 1 | 1 | Tom Howell | Lost 1-3 |
| 17/01/2019 | Division 2 | Woodfield Squash 2 v Hull & ER 2 | 1 | Mike Reid | Won 3-0 |
| 24/01/2019 | Division 1 | Chapel Allerton 3 v Woodfield Squash 1 | 4 | Ross Williamson | Lost 0-3 |
| 31/01/2019 | Division 2 | Chapel Allerton 4 v Woodfield Squash 2 | 1 | Tom Kirby | Lost 1-3 |
| 07/02/2019 | Division 2 | Woodfield Squash 2 v Barnsley 2 | 1 | Jack Walmsley | Lost 1-3 |
| 21/02/2019 | Division 2 | Woodfield Squash 2 v Fulwood 1 | 1 | Owen Bailey | Won 3-0 |
| 27/02/2019 | Division 2 | Norwood SC 1 v Woodfield Squash 2 | 1 | George Bannister | Lost 1-3 |
| 06/03/2019 | Division 1 | Doncaster 1 v Woodfield Squash 1 | 4 | Shaun Bradley | Won 3-0 |
| 07/03/2019 | Division 2 | Woodfield Squash 2 v Scunthorpe@AppFrod 1 | 1 | Dave Ball | Lost 1-3 |
| 13/03/2019 | Division 2 | York RI 1 v Woodfield Squash 2 | 1 | Tom Howell | Lost 2-3 |
| 20/03/2019 | Division 2 | Harrogate 1 v Woodfield Squash 2 | 1 | Ross Kneller | Won 3-2 |
