| Date | Division | Match | String | Opponent | Result |
| 21/05/2019 | Division 4 | Old Wilsonians 1 v Maidstone 1 | 2 | Keith Hulbert | Lost 1-3 |
| 04/06/2019 | Division 4 | Old Wilsonians 1 v Bromley Sports 3 | 3 | Ross Beaumont | Won 3-1 |
| 11/06/2019 | Division 4 | Old Wilsonians 1 v Sundridge Park 1 | 3 | Ken Sheedy | Lost 1-3 |
| 24/07/2019 | Division 4 | Maidstone 1 v Old Wilsonians 1 | 3 | Mike Watson | Won 3-0 |
| 30/07/2019 | Division 4 | Blackheath 3 v Old Wilsonians 1 | 2 | Matthew Inglis | Lost 0-3 |
| 13/08/2019 | Division 4 | Sundridge Park 1 v Old Wilsonians 1 | 3 | Dave Hanson | Lost 2-3 |
| 20/08/2019 | Division 4 | Bromley Sports 3 v Old Wilsonians 1 | 3 | Ross Beaumont | Won 3-1 |
