| Date | Division | Match | String | Opponent | Result |
| 19/09/2019 | Division 5 | Kirkbymoorside 2 v Stillington 5 | 2 | Fraser Thomson | Won 3-1 |
| 24/09/2019 | Division 5 | Stillington 5 v Malton 3 | 1 | Rob Harper | Lost 1-3 |
| 06/10/2019 | Division 5 | York RI 4 v Stillington 5 | 1 | Michael Abbotson | Lost 1-3 |
| 08/10/2019 | Division 5 | Stillington 5 v St Peters 1 | 2 | Josh Wood | Lost 1-3 |
| 27/10/2019 | Division 5 | Thornton Le Dale 3 v Stillington 5 | 1 | Geoff Gibson | Lost 2-3 |
| 29/10/2019 | Division 5 | Stillington 5 v Wigginton 6 | 2 | Scott Codrai | Won 3-1 |
| 11/11/2019 | Division 5 | Dunnington 5 v Stillington 5 | 2 | Chris Martin | Lost 2-3 |
| 19/11/2019 | Division 5 | Stillington 5 v University Students 2 | 2 | Billy Macleod | Lost 1-3 |
| 14/01/2020 | Division 5 | Stillington 5 v Kirkbymoorside 2 | 1 | Jake Duncombe | Lost 1-3 |
| 19/01/2020 | Division 2 | Stillington 3 v Stillington 2 | 4 | Nick Peel | Lost 1-3 |
| 22/01/2020 | Division 5 | Malton 3 v Stillington 5 | 1 | Rob Harper | Lost 0-3 |
| 28/01/2020 | Division 5 | Stillington 5 v York RI 4 | 2 | James Brunton | Lost 0-3 |
| 28/01/2020 | Division 4 | York 6 v Stillington 4 | 3 | Miles Dewhurst | Lost 0-3 |
| 04/02/2020 | Division 5 | St Peters 1 v Stillington 5 | 1 | Ben Dunsmore | Lost 0-3 |
| 12/02/2020 | Division 4 | Thornton Le Dale 2 v Stillington 4 | 4 | Andrew Mansfield | Lost 2-3 |
| 18/02/2020 | Division 5 | Stillington 5 v Dunnington 5 | 1 | Kevin Johnson | Won 3-2 |
| 08/03/2020 | Division 5 | Wigginton 6 v Stillington 5 | 1 | Scott Codrai | Lost 1-3 |
| 10/03/2020 | Division 5 | Stillington 5 v York 8 | 1 | Tim Wardman | Lost 2-3 |
