| Date | Division | Match | String | Opponent | Result |
| 19/05/2015 | Division 5 | Old Wilsonians 1 v Poult Wood 2 | 1 | Jake Wallis | Won 3-0 |
| 27/05/2015 | Division 5 | Bromley Sports 3 v Old Wilsonians 1 | 2 | Daniel Sweeney | Lost 2-3 |
| 04/06/2015 | Division 5 | Bexley 5 v Old Wilsonians 1 | 2 | Paul Wainwright | Lost 0-3 |
| 25/06/2015 | Division 5 | Wells Squash Club 1 v Old Wilsonians 1 | 2 | Stephen Edwards | Lost 1-3 |
| 30/06/2015 | Division 5 | Old Wilsonians 1 v Limpsfield 1 | 2 | Barry Gillam | Won 3-1 |
| 09/07/2015 | Division 5 | Wells Squash Club 2 v Old Wilsonians 1 | 2 | Chris Clear | Lost 2-3 |
| 14/07/2015 | Division 5 | Old Wilsonians 1 v Parklangley 5 | 2 | Trevor Young | Won 3-2 |
