FIRST ROUND - 18 September 2021
| MATCH NO. | HOME | AWAY | RESULT | |
|---|---|---|---|---|
| 1 | Old Southendian Res | v | Herongate Athletic | 1 - 3 |
| 2 | Takeley Res. | v | ACD United | 2 - 4 |
| 3 | Barnston | v | Sungate | 0 - 3 |
| 4 | Walthamstow Res | v | DT | 2 - 5 |
| 5 | Harold Wood Athletic | v | Tiptree Heath | 2 - 4 aet |
| 6 | May & Baker E.C. Res. | v | Chigwell Town | 2 - 1 |
| 7 | Dunmow Town | v | Springfield | 4 - 4 aet |
| Dunmow Town Won on Penalties | 7 - 6 | |||
| 8 | Shoebury Town | v | West Bergholt | 4 - 0 |
| 9 | Lawford Lads | v | Leyton Royal | 1 - 3 |
| 10 | Lynmore Gardens | v | Epping Town | 1 - 2 |
| 11 | Corinthians | v | Halstead Town Res. | 2 - 1 |
| 12 | Basildon Town | v | Earls Colne | 5 - 1 |
| 13 | Old Southendian | v | Dedham Old Boys | H - W |
| 14 | Toby | v | Old Chelmsfordians | 2 - 0 |
| 15 | Little Oakley | v | Waltham Abbey Res. | A - W |
SECOND ROUND - 16 October 2021
| MATCH NO | HOME | AWAY | RESULT | |
| 16 | Hashtag United Res. | v | Dunmow Town | |
| 17 | Hutton Res. | v | Frenford Res. | On 09 October |
| 18 | Tiptree Heath | v | Leyton Royal | |
| 19 | Brentwood Town Res. | v | May & Baker E.C. Res | |
| 20 | Redbridge Res. | v | West Essex Dev. | |
| 21 | Clapton Community | v | Wakebury | |
| 22 | Manford Way | v | Runwell Sports | |
| 23 | Waltham Abbey Res. | v | Snaresbrook | |
| 24 | Chadwell Heath Spartans | v | Leigh Town | |
| 25 | Harold Wood Athletic Res. | v | AS Rawreth | |
| 26 | Epping Town | v | Wakering Sports | |
| 27 | Colne Athletic | v | Kelvedon Hatch | |
| 28 | Shenfield A.F.C. | v | Basildon Town | |
| 29 | Rayleigh Town Res. | v | CSM London | |
| 30 | Barkingside Res. | v | Cornard Rangers Res. | |
| 31 | Stanway Pegasus | v | Gas Recreation | |
| 32 | Wivenhoe Town Res. | v | Sungate | |
| 33 | Arlesford Colne Rangers | v | Witham Town Res. | |
| 34 | Canning Town | v | Saffron Walden Town Res. | |
| 35 | Herongate Athletic | v | Catholic United | |
| 36 | DT | v | Holland Res. | |
| 37 | White Ensign Res. | v | Woodford East | |
| 38 | Toby | v | Corinthians/ | |
| 39 | Hutton | v | Rochford Town | |
| 40 | Grays Athletic Res. | v | Ongar Town | At Lakeside |
| 41 | Galleywood | v | Leigh Ramblers | |
| 42 | White Notley | v | Chingford Athletic | |
| 43 | Old Foresters | v | Chelmsford City Res. | |
| 44 | Beacon Hill Rovers | v | Harold Hill | |
| 45 | Shoebury Town | v | May & Baker E.C. 'A' | |
| 46 | Billericay Town Res | v | Old Southendian | |
| 47 | Rayleigh Town | v | ACD United | On 09 October |
THIRD ROUND - 20 November 2021
| MATCH NO. | HOME | AWAY | RESULT | |
|---|---|---|---|---|
| 48 | Manford Way/Runwell Sports | v | Rayleigh Town/ACD United | |
| 49 | Herongate Athletic/Catholic United | v | Redbridge Res./West Essex Dev. | |
| 50 | Billericay Town Res./Old Southendian | v | Harold Wood Ath. Res/AS Rawreth | |
| 51 | Toby/Corinthians | v | Stanwat Pegasus/Gas Recreation | |
| 52 | Wivenhoe Town Res./Sungate | v | Epping Town/Wakering Sports | |
| 53 | Tiptree Heath/Leyton Royals | v | Old Foresters/Chelmsford City Res. | |
| 54 | White Notley/Chingford Athletic | v | Canning Town/Saffron Walden Town Res | |
| 55 | Beacon Hill Rivers/ Harold Hill | v | Grays Ath. Res/Ongar Town | |
| 56 | Colne Athletic/Kelvedon Hatch | v | DT/Holland Res. | |
| 57 | Galleywood/Leigh Ramblers | v | Brentwood Town Res./May & Baker Res | |
| 58 | Chadwell Heath Spartans/Leigh Town | v | Clapton Community/Wakebury | |
| 59 | Hutton/Rochford Town | v | Rayleigh Town Res./CSM London | |
| 60 | Waltham Abbey Res./Snaresbrook | v | Shenfield AFC/Basildon Town | |
| 61 | Arlesford Colne Rangers/Witham Town Res. | v | Barkingside Res./Concord Rangers Res. | |
| 62 | Shoebury Town/May & Baker 'A' | v | White Ensign Res/Woodford East | |
| 63 | Hashtag United Res/Dunmow Town | v | Hutton Res./Frenford Res |