| Date | Division | Match | String | Opponent | Result |
| 08/10/2019 | League 1 | Kendal Squash Club A v Penrith Squash Club A | 1 | Andy Chant | Won 3-0 |
| 15/10/2019 | League 1 | Penrith Squash Club A v Wigton Squash Club A | 1 | Jonathan Honeyman | Lost 2-3 |
| 29/10/2019 | League 1 | Windscale Squash Club A v Penrith Squash Club A | 1 | Chris Musson | Lost 2-3 |
| 05/11/2019 | League 1 | Penrith Squash Club A v Carlisle Squash Club A | 1 | Victoria Bell | Lost 1-3 |
| 19/11/2019 | League 1 | Penrith Squash Club A v Carlisle Squash Club B | 1 | Joseph Broadley | Lost 2-3 |
| 26/11/2019 | League 1 | Wigton Squash Club A v Penrith Squash Club A | 1 | Jonathan Honeyman | Lost 1-3 |
| 03/12/2019 | League 1 | Penrith Squash Club A v Kendal Squash Club A | 1 | Russ Lilliebridge | Won 3-1 |
| 10/12/2019 | League 1 | Carlisle Squash Club A v Penrith Squash Club A | 1 | James Worsick | Lost 0-3 |
| 07/01/2020 | League 1 | Penrith Squash Club A v Windscale Squash Club A | 1 | Chris Musson | Lost 1-3 |
| 14/01/2020 | League 1 | Carlisle Squash Club B v Penrith Squash Club A | 1 | Dave Box | Lost 0-3 |
| 28/01/2020 | League 1 | Penrith Squash Club A v Wigton Squash Club A | 1 | Jonathan Honeyman | Lost 2-3 |
| 04/02/2020 | League 1 | Kendal Squash Club A v Penrith Squash Club A | 1 | Andy Chant | Won 3-0 |
| 25/02/2020 | League 1 | Penrith Squash Club A v Carlisle Squash Club A | 1 | James Worsick | Lost 1-3 |
| 03/03/2020 | League 1 | Penrith Squash Club A v Carlisle Squash Club B | 1 | Joseph Broadley | Lost 0-3 |
