| 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 |
| 22.11.20162016-11-22 20:45:00 | 20:45 | FA Trophy Qualification | 3. R | Chalfont St Peter - Burgess Hill Town | 8:9 (0:0) |
| 15.11.20162016-11-15 20:45:00 | 20:45 | FA Trophy Qualification | 3. R | Burgess Hill Town - Chalfont St Peter | 2:2 (1:0) |
| 29.10.20162016-10-29 16:00:00 | 16:00 | FA Trophy Qualification | 2. R | Chalfont St Peter - Corinthian Casuals | 3:2 (2:1) |
| 11.10.20162016-10-11 20:45:00 | 20:45 | FA Trophy Qualification | 1. R | Chalfont St Peter - Arlesey Town | 6:0 |
| 8.10.20162016-10-8 16:00:00 | 16:00 | FA Trophy Qualification | 1. R | Arlesey Town - Chalfont St Peter | 2:2 |
| 3.9.20162016-9-3 16:00:00 | 16:00 | FA Cup Qualification | 1. R | Chalfont St Peter - Potters Bar Town | 0:3 |