| Date | Division | Match | String | Opponent | Result |
| 19/09/2019 | Div 3 North West | Woolston 2 v Wigan Squash 3 | 1 | Conal Duffy | Lost 1-3 |
| 26/09/2019 | Div 3 North West | Northern Crosby 2 v Woolston 2 | 1 | Jon Fell | Lost 0-3 |
| 03/10/2019 | Div 3 North West | Woolston 2 v Liverpool CC 5 | 1 | James Hewitt | Won 3-1 |
| 10/10/2019 | Div 3 North West | Woolston 2 v Warrington 4 | 1 | Shayne Byron | Won 3-1 |
| 17/10/2019 | Div 3 North West | Xaverian 2 v Woolston 2 | 1 | Ian Noble | Lost 2-3 |
| 24/10/2019 | Div 3 North West | Woolston 2 v Southport & Birkdale 3 | 1 | Lee Collins | Won 3-2 |
| 31/10/2019 | Div 3 North West | David Lloyd Knowsley 1 v Woolston 2 | 1 | Pietro Di Tondo | Won 3-1 |
| 07/11/2019 | Div 3 North West | Woolston 2 v Liverpool CC 4 | 1 | Katie Cox | Won 3-2 |
| 14/11/2019 | Div 3 North West | Northern Crosby 3 v Woolston 2 | 1 | Paul Salt | Won 3-2 |
| 21/11/2019 | Div 3 North West | Woolston 2 v Capitol Squash 2 | 1 | Paul McNally | Lost 1-3 |
| 28/11/2019 | Div 3 North West | Warrington 5 v Woolston 2 | 1 | Kevin O'Neill | Lost 2-3 |
| 05/12/2019 | Div 3 North West | Woolston 2 v Xaverian 3 | 1 | Rob Kyle | Won 3-0 |
| 09/01/2020 | Div 3 North West | Wigan Squash 3 v Woolston 2 | 1 | Gary Connolly | Lost 1-3 |
| 16/01/2020 | Div 3 North West | Woolston 2 v Northern Crosby 2 | 1 | Ade Taiwo | Won 3-2 |
| 23/01/2020 | Div 3 North West | Liverpool CC 5 v Woolston 2 | 1 | Paul Robertson | Lost 1-3 |
| 20/02/2020 | Div 3 North West | Southport & Birkdale 3 v Woolston 2 | 1 | Nick Higgs | Won 3-0 |
| 05/03/2020 | Div 3 North West | Liverpool CC 4 v Woolston 2 | 1 | Katie Cox | Lost 0-3 |
| 12/03/2020 | Div 3 North West | Woolston 2 v Northern Crosby 3 | 1 | Gary Powell | Lost 2-3 |
