| Date | Division | Match | String | Opponent | Result |
| 19/05/2016 | Division 4 | Dulwich 4 v Nuffield Health 1 | 5 | Peter Young | Won 3-0 |
| 26/05/2016 | Division 4 | Bromley LTC 2 v Dulwich 4 | 5 | Mark Winkless | Won 3-0 |
| 01/06/2016 | Division 4 | Tunbridge Wells SRC 3 v Dulwich 4 | 4 | Colin Atkins | Lost 0-3 |
| 09/06/2016 | Division 4 | Dulwich 4 v Blackheath 3 | 5 | David Foster | Won 3-0 |
| 23/06/2016 | Division 4 | Wells Squash Club 1 v Dulwich 4 | 4 | Stephen Edwards | Won 3-2 |
| 30/06/2016 | Division 4 | Dulwich 4 v Poult Wood 2 | 5 | Barry Prescott | Lost 1-3 |
| 05/07/2016 | Division 4 | Bexley Park 2 v Dulwich 4 | 5 | Steve Tucker | Won 3-1 |
| 14/07/2016 | Division 4 | Dulwich 4 v Parklangley 5 | 5 | Erdal Niyazoglu | Won 3-0 |
| 19/07/2016 | Division 4 | Nuffield Health 1 v Dulwich 4 | 3 | Luke Bennett | Lost 0-3 |
| 25/08/2016 | Division 4 | Dulwich 4 v Wells Squash Club 1 | 5 | John Binns | Lost 2-3 |
| 30/08/2016 | Division 4 | Poult Wood 2 v Dulwich 4 | 5 | Andrew Boshoff | Lost 2-3 |
| 08/09/2016 | Division 4 | Dulwich 4 v Bexley Park 2 | 4 | Paul Roberts | Lost 2-3 |
| 13/09/2016 | Division 4 | Parklangley 5 v Dulwich 4 | 5 | Erdal Niyazoglu | Lost 0-3 |
