| Date | Division | Match | String | Opponent | Result |
| 10/10/2019 | Div 4 South East | Grove Park 5 v Prestbury 5 | 3 | Jack Wright | Lost 1-3 |
| 17/10/2019 | Div 4 South East | Prestbury 5 v Hyde 4 | 1 | Andy Berry | Lost 1-3 |
| 31/10/2019 | Div 4 South East | Prestbury 5 v Alderley Edge 6 | 2 | Stephen Chalmers-Morris | Lost 0-3 |
| 14/11/2019 | Div 4 Central South | The Northern 6 v Prestbury 4 | 4 | Brian Parfitt | Won 3-0 |
| 21/11/2019 | Div 5 South East | Alderley Edge 7 v Prestbury 6 | 1 | James Parker | Lost 1-3 |
| 28/11/2019 | Div 4 South East | Prestbury 5 v Hyde 3 | 4 | Benjamin Rubin | Lost 0-3 |
| 05/12/2019 | Div 5 South East | Marple 4 v Prestbury 6 | 5 | John Dillon | Won 3-0 |
| 12/12/2019 | Div 4 South East | Prestbury 5 v Buxton 1 | 3 | Steve Coates | Lost 0-3 |
| 09/01/2020 | Div 4 South East | Marple 3 v Prestbury 5 | 2 | Rob Stanbridge | Lost 0-3 |
| 16/01/2020 | Div 4 South East | Prestbury 5 v Stockport 1 | 2 | Richard Fogarty | Lost 1-3 |
| 23/01/2020 | Div 4 South East | Disley 2 v Prestbury 5 | 4 | Jordan Sargeant | Won 3-1 |
| 30/01/2020 | Div 4 Central South | Bowdon 5 v Prestbury 4 | 4 | joss Atkinson | Lost 1-3 |
| 06/02/2020 | Div 5 South East | Prestbury 6 v Bollington 4 | 1 | Rob Harland | Lost 0-3 |
| 05/03/2020 | Div 4 South East | Prestbury 5 v Bollington 3 | 4 | Tom Grimes | Lost 0-3 |
| 12/03/2020 | Div 4 South East | City of Manchester 3 v Prestbury 5 | 4 | George Worton | Lost 0-3 |
