| 26.11.20162016-11-26 16:00:00 | 16:00 | FA Trophy Qualification | 4. R | Winchester City - Dulwich Hamlet | 0:1 (0:1) |
| 12.11.20162016-11-12 16:00:00 | 16:00 | FA Trophy Qualification | 3. R | Phoenix Sports - Winchester City | 1:3 (1:2) |
| 29.10.20162016-10-29 16:00:00 | 16:00 | FA Trophy Qualification | 2. R | Fleet Town - Winchester City | 1:2 (1:1) |
| 11.10.20162016-10-11 20:45:00 | 20:45 | FA Trophy Qualification | 1. R | Petersfield Town - Winchester City | 1:3 |
| 8.10.20162016-10-8 16:00:00 | 16:00 | FA Trophy Qualification | 1. R | Winchester City - Petersfield Town | 1:1 |
| 1.10.20162016-10-1 16:00:00 | 16:00 | FA Cup Qualification | 3. R | Harrow Borough - Winchester City | 2:1 |
| 10.12.20162016-12-10 16:00:00 | 16:00 | FA Trophy | 1. R | Dulwich Hamlet - Royston Town/Hampton & Richmond | -:- |
| 26.11.20162016-11-26 16:00:00 | 16:00 | FA Trophy Qualification | 4. R | Winchester City - Dulwich Hamlet | 0:1 (0:1) |
| 12.11.20162016-11-12 16:00:00 | 16:00 | FA Trophy Qualification | 3. R | Dulwich Hamlet - Chesham United | 4:0 (1:0) |
| 29.10.20162016-10-29 16:00:00 | 16:00 | FA Trophy Qualification | 2. R | Lowestoft Town - Dulwich Hamlet | 1:2 (0:1) |
| 17.9.20162016-9-17 16:00:00 | 16:00 | FA Cup Qualification | 2. R | Dulwich Hamlet - Hendon | 0:2 |
| 3.9.20162016-9-3 16:00:00 | 16:00 | FA Cup Qualification | 1. R | Pagham - Dulwich Hamlet | 0:3 |
| 16.1.20162016-1-16 16:00:00 | 16:00 | FA Trophy | 2. R | Dulwich Hamlet - Guiseley | 1:2 |