| Date | Division | Match | String | Opponent | Result |
| 02/10/2019 | Premier | Woodfield Squash 1 v Abbeydale 1 | 4 | Nick Wall | Lost 0-3 |
| 16/10/2019 | Division 2 | Woodfield Squash 3 v Woodfield Squash 2 | 1 | Alec Tomlinson | Won 3-2 |
| 24/10/2019 | Division 2 | Woodfield Squash 2 v Rothwell 1 | 1 | Jermaine Manners | Won 3-1 |
| 31/10/2019 | Division 2 | Pontefract 5 v Woodfield Squash 2 | 1 | Lauren Siddall | Won 3-1 |
| 20/11/2019 | Premier | Woodfield Squash 1 v Dunnington 1 | 5 | Kieran Heaphy | Lost 0-3 |
| 28/11/2019 | Division 2 | Woodfield Squash 2 v Pontefract 4 | 1 | Jordan Stewart | Won 3-1 |
| 12/12/2019 | Division 2 | Woodfield Squash 2 v Wakefield 2 | 1 | Danny Hall | Won 3-0 |
| 18/12/2019 | Division 2 | Norwood SC 2 v Woodfield Squash 2 | 1 | Dan Roberts | Lost 1-3 |
| 15/01/2020 | Premier | Abbeydale 1 v Woodfield Squash 1 | 5 | Phil Scully | Lost 0-3 |
| 19/02/2020 | Premier | Woodfield Squash 1 v Hallamshire 2 | 5 | Jack Smith | Won 3-1 |
| 26/02/2020 | Premier | Queens 1 v Woodfield Squash 1 | 4 | Finnlay Withington | Lost 0-3 |
