| Date | Division | Match | String | Opponent | Result |
| 25/05/2016 | Division 5 | Blackheath 4 v Old Wilsonians 1 | 2 | Greg Smart | Won 3-1 |
| 31/05/2016 | Division 5 | Old Wilsonians 1 v Limpsfield 1 | 2 | Peter Vines | Won 3-0 |
| 07/06/2016 | Division 5 | Knole Park 2 v Old Wilsonians 1 | 2 | Tim Handel | Lost 2-3 |
| 14/06/2016 | Division 5 | Old Wilsonians 1 v Bromley Sports 4 | 2 | Steve Pusey | Lost 0-3 |
| 23/06/2016 | Division 5 | Bromley Sports 3 v Old Wilsonians 1 | 2 | Kevin Gimenez | Won 3-2 |
| 05/07/2016 | Division 5 | Bexley 6 v Old Wilsonians 1 | 2 | Adam Willis | Won 3-0 |
| 12/07/2016 | Division 5 | Old Wilsonians 1 v Wells Squash Club 2 | 2 | Nick Hughes | Won 3-0 |
| 21/07/2016 | Division 5 | Bexley 5 v Old Wilsonians 1 | 2 | Steve Spring | Won 3-0 |
| 26/07/2016 | Division 5 | Old Wilsonians 1 v Blackheath 4 | 2 | Leigh Hutchings | Won 3-1 |
| 02/08/2016 | Division 5 | Limpsfield 1 v Old Wilsonians 1 | 2 | Colin Bruce | Lost 1-3 |
| 09/08/2016 | Division 5 | Old Wilsonians 1 v Knole Park 2 | 2 | Tim Handel | Won 3-1 |
| 23/08/2016 | Division 5 | Old Wilsonians 1 v Bromley Sports 3 | 2 | Tony Davies | Lost 1-3 |
| 30/08/2016 | Division 5 | Nuffield Health 2 v Old Wilsonians 1 | 2 | Darren Norton | Lost 2-3 |
| 06/09/2016 | Division 5 | Old Wilsonians 1 v Bexley 6 | 2 | (walkover) | Won 3-0 |
| 15/09/2016 | Division 5 | Wells Squash Club 2 v Old Wilsonians 1 | 2 | Ben Smith | Lost 2-3 |
| 21/09/2016 | Division 5 | Bromley Sports 4 v Old Wilsonians 1 | 2 | Steve Pusey | Lost 2-3 |
