FIRST ROUND - 15 September 2018
| Home | Away | Result | ||
| Canning Town Reserves | v | Broomwood (Withdrawn) | Bye | |
| Hackney Wick Reserves | v | F.C. Hamlets | 1 - 3 |
SECOND ROUND - 13 October 2018
| Home | Away | Result | ||
| Canning Town Reserves | v | Rygas | 1 - 2 | |
| Johnson & Phillips | v | F.C. Hamlets | 0 - 3 | |
| Newham United | v | AFC Battersea (Wimbledon) | 5 - 0 |
THIRD ROUND - 10 November 2018
| Home | v | Away | Result | |
| F.C. Hamlets | v | Bridon Ropes Res. | 4 - 1 | |
| Hilltop | v | Newham United | 5 - 1 |
FOURTH ROUND - 08 December 2018
| Home | Away | Result | ||
| UCC Diaspora | v | FC Hamlets | 2 - 1 |