FIRST ROUND - 21 September 2019 2:00 p.m. K.O
| Home | Away | Result | ||
| FC Hamlets | v | Wadham College Old Boys | 6 - 0 |
SECOND ROUND - 19 October 2019 1:30 p.m. K.O.
| Home | Away | Result | ||
| Canning Town Reserves | v | Catford F.C. | 5 - 0 | |
| FC Hamlets | v | St. Francis | 3 - 1 |
THIRD ROUND - 16 November 2019 1:30 p.m. K.O.
| Home | v | Away | Result | |
| Canning Town Reserves | v | FC Baresi | 0 - 2 | |
| FC Hamlets | v | Battersea Boys | 2 - 1 |
FOURTH ROUND - 07 December 2019
| Home | Away | Result | ||
| F.C. Roast | v | F.C. Hamlets | 2 - 4 |
QUARTER-FINAL - 11 January 2020
| Home | Away | Result | ||
| FC Hamlets | v | Rapid Chingford | 4 - 0 |
SEMI-FINAL - 15 February 2020
| Home | Away | Result | ||
| UCC Diaspora | v | FC Hamlets |