| 24 Apr 2021 | First Round | Belhus v Harold Wood | The Village Green, North Stifford | Results |
| 24 Apr 2021 | First Round | Chelmsford v Colchester and East Essex | Chelmer Park, Chelmsford | Results |
| 24 Apr 2021 | First Round | Chingford v Woodford Wells | Forest Side, Chingford | Results |
| 24 Apr 2021 | First Round | Fives and Heronians v Buckhurst Hill | The Paddock, Chigwell | Results |
| 24 Apr 2021 | First Round | Frenford v Oakfield Parkonians | Oakfield Playing Fields, Barkingside | Results |
| 24 Apr 2021 | First Round | Hadleigh and Thundersley v Benfleet | John H Burrows Recreation Ground, Hadleigh | Results |
| 24 Apr 2021 | First Round | Horndon-on-the-Hill v Orsett and Thurrock | The Recreation Ground, Horndon-on-the-Hill | Results |
| 24 Apr 2021 | First Round | Hutton v Shenfield | The Polo Field Ground, Hutton | Results |
| 24 Apr 2021 | First Round | Ilford v Wanstead and Snaresbrook | Valentine's Park, Ilford | Results |
| 24 Apr 2021 | First Round | Loughton v Harlow Town | The Uplands, Loughton | Results |
| 24 Apr 2021 | First Round | Old Southendian and Southchurch v Southend-on-Sea and Ekco Monarchs and Trojans | Garon Park, Southend-on-Sea | Results |
| 24 Apr 2021 | First Round | Upminster v Gidea Park and Romford | Upminster Park, Upminster | Results |
| 24 Apr 2021 | First Round | Westcliff-on-Sea v Leigh-on-Sea | Chalkwell Park, Westcliff-on-Sea | Results |
| 24 Apr 2021 | First Round | Wickford v Billericay | Dick Patmore Memorial Ground, Wickford | Results |
| 01 May 2021 | Second Round | Belhus v Loughton | The Village Green, North Stifford | Results |
| 01 May 2021 | Second Round | Billericay v Chelmsford | The Toby Howe Cricket Ground, Billericay | Results |
| 01 May 2021 | Second Round | Fives and Heronians v Chingford | The Paddock, Chigwell | Results |
| 01 May 2021 | Second Round | Frenford v Wanstead and Snaresbrook | Oakfield Playing Fields, Barkingside | Results |
| 01 May 2021 | Second Round | Hadleigh and Thundersley v Horndon-on-the-Hill | John H Burrows Recreation Ground, Hadleigh | Results |
| 01 May 2021 | Second Round | Old Southendian and Southchurch v Westcliff-on-Sea | Garon Park, Southend-on-Sea | Results |
| 01 May 2021 | Second Round | Shenfield v Brentwood | Chelmsford Road, Shenfield | Results |
| 01 May 2021 | Second Round | Upminster v Hornchurch | Upminster Park, Upminster | Results |
| 20 Jun 2021 | Quarter-Final | Belhus v Brentwood | The Village Green, North Stifford | Results |
| 11 Jul 2021 | Quarter-Final | Westcliff-on-Sea v Wanstead and Snaresbrook | Chalkwell Park, Westcliff-on-Sea | Results |
| 18 Jul 2021 | Quarter-Final | Hadleigh and Thundersley v Chelmsford | John H Burrows Recreation Ground, Hadleigh | Results |
| 20 Jun 2021 | Quarter-Final | Hornchurch v Chingford | Harrow Lodge Park, Hornchurch | Results |
| 22 Aug 2021 | Semi-Final | Wanstead and Snaresbrook v Hornchurch | Overton Drive, Wanstead | Results |
| 30 Aug 2021 | Semi-Final | Hadleigh and Thundersley v Brentwood | John H Burrows Recreation Ground, Hadleigh | Results |
| 05 Sep 2021 | Final | Brentwood v Wanstead and Snaresbrook | Roding Lane, Buckhurst Hill | Results |
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