| Date | Division | Match | String | Opponent | Result |
| 07/11/2019 | Div 2 East | The Northern 3 v Crewe Vagrants 2 | 3 | Henry Worrall | Lost 0-3 |
| 14/11/2019 | Div 2 East | Crewe Vagrants 2 v The Northern 2 | 5 | Lemmie Green | Lost 2-3 |
| 21/11/2019 | Div 3 South West | Crewe Vagrants 3 v Heswall 4 | 1 | Gareth Buckley | Won 3-0 |
| 28/11/2019 | Div 3 South West | Cheshire Officers 2 v Crewe Vagrants 3 | 1 | Paul Williams | Won 3-0 |
| 05/12/2019 | Div 2 East | Warrington 2 v Crewe Vagrants 2 | 5 | Pete Kelly | Won 3-2 |
| 12/12/2019 | Div 3 South West | Neston 2 v Crewe Vagrants 3 | 2 | Adam Mitchell | Won 3-2 |
| 09/01/2020 | Div 2 East | Crewe Vagrants 2 v Hyde 1 | 5 | Steve Korny | Won 3-0 |
| 16/01/2020 | Div 2 East | Knutsford Sports 1 v Crewe Vagrants 2 | 4 | Charles Keeble | Lost 0-3 |
| 23/01/2020 | Div 2 East | Crewe Vagrants 2 v Prestbury 1 | 5 | Brian Lomas | Lost 1-3 |
| 30/01/2020 | Div 2 East | Marple 1 v Crewe Vagrants 2 | 5 | Nick Hague | Won 3-1 |
| 06/02/2020 | Div 3 South West | Wrexham Brymbo 3 v Crewe Vagrants 3 | 1 | William Silvester | Won 3-2 |
| 20/02/2020 | Div 2 East | Crewe Vagrants 2 v Congleton 1 | 5 | William Westhead | Won 3-0 |
| 05/03/2020 | Div 3 South West | Winsford 1 v Crewe Vagrants 3 | 1 | Toby Mather | Won 3-1 |
| 12/03/2020 | Div 2 East | The Northern 2 v Crewe Vagrants 2 | 4 | Andrew Laing | Lost 1-3 |
