Division Two Cup Draw - 2021/22
| 1st Round | ||||
| A | Ryan U23 | 1-3 | Loughton Lions | |
| B | Rainham Working Mens Club | 6-1 | Royal Forest | |
| C | Fairlop Rovers | 3-2 | St Francis | |
| D | Newbury East | 4-4 | Emerson & Upminster Reserves | 7-6 on pens Awarded to Emerson following protest |
| Quarter Finals | ||||
| 1 | Loughton Lions | 5-2 | FHN Athletic | |
| 2 | Redbridge Community | 1-3 | Rainham Working Mens Club | |
| 3 | Fairlop Rovers | 1-1 | Unitey | 2-3 on pens |
| 4 | Old Esthameians | 1-4 | Emerson & Upminster Reserves | |
| Semi Finals | ||||
| A | Loughton Lions | 0-1 | Rainham Working Mens Club | |
| B | Unitey | 6-1 | Emerson & Upminster Reserves | |
| The Final - Saturday 21st May 2022, 2pm at Dagenham & Redbridge FC | ||||
| RAINHAM WORKING MENS CLUB | 2-2 | UNITEY | 2-3 on pens | |