| Date | Division | Match | String | Opponent | Result |
| 19/09/2019 | Div 3 Central North | David Lloyd Chorley 2 v Preston Grasshoppers 2 | 2 | David Abberley | Lost 1-3 |
| 26/09/2019 | Div 3 Central North | Preston Grasshoppers 2 v Lancon 1 | 1 | Mark Woolston | Lost 2-3 |
| 03/10/2019 | Div 3 Central North | St Annes 2 v Preston Grasshoppers 2 | 1 | Tom Millar | Lost 1-3 |
| 10/10/2019 | Div 2 Central | Southport & Birkdale 2 v Preston Grasshoppers 1 | 4 | Alex Gould | Lost 0-3 |
| 24/10/2019 | Div 3 Central North | Preston Grasshoppers 2 v Blackburn Northern 1 | 2 | Jeremy Clarkson | Lost 1-3 |
| 31/10/2019 | Div 3 Central North | Markland Hill 1 v Preston Grasshoppers 2 | 1 | Johnathan Shacklady | Lost 1-3 |
| 07/11/2019 | Div 3 Central North | Preston Grasshoppers 2 v East Lancs 1 | 2 | (walkover) | Won 3-0 |
| 14/11/2019 | Div 3 Central North | YMCA Thornton 2 v Preston Grasshoppers 2 | 2 | Nick Stafford | Lost 0-3 |
| 28/11/2019 | Div 3 Central North | Preston Grasshoppers 2 v Blackpool CC 2 | 4 | Grant Leitch | Lost 2-3 |
| 12/12/2019 | Div 3 Central North | Preston Grasshoppers 2 v 3-1-5 Squash Club 3 | 3 | max castaldi | Won 3-2 |
| 09/01/2020 | Div 3 Central North | Preston Grasshoppers 2 v David Lloyd Chorley 2 | 3 | David Abberley | Won 3-1 |
| 23/01/2020 | Div 3 Central North | Preston Grasshoppers 2 v St Annes 2 | 2 | Adrian Vickers | Lost 0-3 |
| 30/01/2020 | Div 3 Central North | 3-1-5 Squash Club 2 v Preston Grasshoppers 2 | 1 | Paul Mcallister | Won 3-0 |
| 06/02/2020 | Div 3 Central North | Preston Grasshoppers 2 v Lancaster University 1 | 1 | Tom Williamson | Lost 0-3 |
| 27/02/2020 | Div 3 Central North | Preston Grasshoppers 2 v Markland Hill 1 | 1 | Andy Jones | Won 3-2 |
| 05/03/2020 | Div 3 Central North | East Lancs 1 v Preston Grasshoppers 2 | 3 | Steve Goodwin-Allen | Lost 0-3 |
