| Date | Division | Match | String | Opponent | Result |
| 23/10/2019 | Premier | Woodfield Squash 1 v Chapel Allerton 2 | 1 | Ian Chappell | Won 3-0 |
| 30/10/2019 | Premier | Hallamshire 2 v Woodfield Squash 1 | 2 | Lucas Hughes | Won 3-0 |
| 06/11/2019 | Premier | Woodfield Squash 1 v Queens 1 | 1 | Connor Sheen | Lost 2-3 |
| 13/11/2019 | Premier | Pontefract 1 v Woodfield Squash 1 | 2 | Taminder Gata-Aura | Won 3-1 |
| 04/12/2019 | Premier | Woodfield Squash 1 v Chapel Allerton 1 | 1 | Richie Fallows | Lost 0-3 |
| 22/01/2020 | Premier | Woodfield Squash 1 v Pontefract 2 | 1 | Sam Todd | Lost 0-3 |
| 19/02/2020 | Premier | Woodfield Squash 1 v Hallamshire 2 | 1 | Dan Lawrence | Won 3-0 |
| 04/03/2020 | Premier | Woodfield Squash 1 v Pontefract 1 | 1 | Lewis Doughty | Lost 1-3 |
| 11/03/2020 | Premier | Dunnington 1 v Woodfield Squash 1 | 1 | Chris Simpson | Lost 0-3 |
