| Date | Division | Match | String | Opponent | Result |
| 22/09/2022 | Division 2 West | Woolston 1 v Tattenhall 1 | 3 | Jonny Jones | Won 3-1 |
| 29/09/2022 | Division 2 West | Woolston 1 v Chester Rugby 1 | 3 | Joe Edwards | Lost 0-3 |
| 06/10/2022 | Division 2 West | Heswall 1 v Woolston 1 | 3 | Richard McLaughlin | Lost 0-3 |
| 13/10/2022 | Division 2 West | Woolston 1 v Capitol Squash 1 | 3 | Lee Atherton | Won 3-0 |
| 20/10/2022 | Division 2 West | Xaverian 1 v Woolston 1 | 3 | Nick Jones | Lost 1-3 |
| 27/10/2022 | Division 2 West | Woolston 1 v Neston 1 | 3 | Joe Shill | Lost 0-3 |
| 03/11/2022 | Division 2 West | Barnton CC 1 v Woolston 1 | 3 | Lee Washburn | Lost 0-3 |
| 17/11/2022 | Division 2 West | Wrexham Brymbo 2 v Woolston 1 | 3 | John Ashton | Lost 1-3 |
| 24/11/2022 | Division 2 West | Woolston 1 v Heswall 2 | 3 | Peter Barton | Won 3-0 |
| 01/12/2022 | Division 2 West | Northern Crosby 1 v Woolston 1 | 3 | Steve Nieman | Lost 2-3 |
| 08/12/2022 | Division 2 West | Woolston 1 v Liverpool CC 2 | 3 | Simon Jeffreys | Won 3-0 |
| 15/12/2022 | Division 2 West | Neston 2 v Woolston 1 | 3 | Graham Lea-Swain | Lost 0-3 |
| 12/01/2023 | Division 2 West | Tattenhall 1 v Woolston 1 | 2 | Tom Hulse | Lost 1-3 |
| 19/01/2023 | Division 2 West | Chester Rugby 1 v Woolston 1 | 2 | Steve Glenton | Lost 1-3 |
| 26/01/2023 | Division 2 West | Woolston 1 v Heswall 1 | 2 | Andy Corran | Lost 0-3 |
| 02/02/2023 | Division 2 West | Capitol Squash 1 v Woolston 1 | 3 | Lee Atherton | Won 3-0 |
| 09/02/2023 | Division 2 West | Woolston 1 v Xaverian 1 | 3 | Paul Morris | Lost 1-3 |
| 23/02/2023 | Division 2 West | Neston 1 v Woolston 1 | 3 | Joe Shill | Lost 2-3 |
| 02/03/2023 | Division 2 West | Woolston 1 v Barnton CC 1 | 3 | Matt Uren | Lost 1-3 |
| 20/04/2023 | Division 2 West | Liverpool CC 2 v Woolston 1 | 3 | Luke Mercer | Lost 0-3 |
| 27/04/2023 | Division 2 West | Woolston 1 v Neston 2 | 3 | Elin Harlow | Lost 2-3 |
