| 22 Apr 2023 | First Round | Belhus v Fives and Heronians | The Village Green, North Stifford | Results |
| 22 Apr 2023 | First Round | Brentwood v Bentley | Old County Ground, Brentwood | Results |
| 22 Apr 2023 | First Round | Chelmsford v Springfield | Chelmer Park, Chelmsford | Results |
| 22 Apr 2023 | First Round | Colchester and East Essex v Buckhurst Hill | Castle Park Cricket Ground, Colchester | Results |
| 22 Apr 2023 | First Round | Hornchurch v Rainham | Harrow Lodge Park, Hornchurch | Results |
| 22 Apr 2023 | First Round | Old Southendian and Southchurch v Neo | Garon Park, Southend-on-Sea | Results |
| 29 Apr 2023 | Second Round | Brentwood v Belhus | Old County Ground, Brentwood | Results |
| 29 Apr 2023 | Second Round | Chelmsford v Neo | Chelmer Park, Chelmsford | Results |
| 29 Apr 2023 | First Round | Frenford v Hawks | Oakfield Playing Fields, Barkingside | Results |
| 29 Apr 2023 | First Round | Harlow v Redbridge | Marigolds, Harlow | Results |
| 29 Apr 2023 | First Round | Harlow Town v London Eagles | Ash Tree Fields, Harlow | Results |
| 29 Apr 2023 | First Round | Harold Wood v Loughton | Harold Wood Park, Harold Wood | Results |
| 29 Apr 2023 | Second Round | Hornchurch v Chingford | Harrow Lodge Park, Hornchurch | Results |
| 29 Apr 2023 | First Round | Hornchurch Athletic v Aztecs | Hylands Park, Hornchurch | Results |
| 29 Apr 2023 | First Round | Leigh-on-Sea v Benfleet | Chalkwell Park, Westcliff-on-Sea | Results |
| 29 Apr 2023 | First Round | Oakfield Parkonians v Hutton | Old Parkonians Association Ground, Barkingside | Results |
| 29 Apr 2023 | First Round | Old Brentwoods v Newham | Ashwells Road, Brentwood | Results |
| 29 Apr 2023 | First Round | Roding Valley v Ardleigh Green and Havering-atte-Bower | River Playing Field, Buckhurst Hill | Results |
| 29 Apr 2023 | First Round | Shenfield v Epping | Chelmsford Road, Shenfield | Results |
| 29 Apr 2023 | First Round | Westcliff-on-Sea v Ilford | Chalkwell Park, Westcliff-on-Sea | Results |
| 29 Apr 2023 | First Round | Wickford v Walthamstow | Dick Patmore Memorial Ground, Wickford | Results |
| 29 Apr 2023 | First Round | Woodford Wells v Wanstead and Snaresbrook | Monkham Lane, Woodford Wells | Results |
| 07 May 2023 | First Round | Billericay v Orsett and Thurrock | The Toby Howe Cricket Ground, Billericay | Results |
| 07 May 2023 | First Round | Upminster v South Woodford | Upminster Park, Upminster | Results |
| 08 May 2023 | Second Round | Ilford v Harlow | Valentine's Park, Ilford | Results |
| 14 May 2023 | First Round | Hadleigh and Thundersley v Goresbrook | John H Burrows Recreation Ground, Hadleigh | Results |
| 28 May 2023 | Second Round | Hadleigh and Thundersley v Hawks | John H Burrows Recreation Ground, Hadleigh | Results |
| 28 May 2023 | Second Round | Old Brentwoods v Shenfield | Ashwells Road, Brentwood | Results |
| 04 Jun 2023 | Second Round | Aztecs v Ardleigh Green and Havering-atte-Bower | London Marathon Playing Fields, Barkingside | Results |
| 04 Jun 2023 | Second Round | Benfleet v Wanstead and Snaresbrook | Woodside Park, Thundersley | Results |
| 04 Jun 2023 | Second Round | Buckhurst Hill v Hutton | Roding Lane, Buckhurst Hill | Results |
| 04 Jun 2023 | Second Round | Upminster v Orsett and Thurrock | Upminster Park, Upminster | Results |
| 11 Jun 2023 | Third Round | Brentwood v Harlow | Old County Ground, Brentwood | Results |
| 18 Jun 2023 | Second Round | Harlow Town v Wickford | Ash Tree Fields, Harlow | Results |
| 25 Jun 2023 | Third Round | Aztecs v Hadleigh and Thundersley | London Marathon Playing Fields, Barkingside | Results |
| 25 Jun 2023 | Third Round | Harold Wood v Hornchurch | Harold Wood Park, Harold Wood | Results |
| 25 Jun 2023 | Third Round | Wanstead and Snaresbrook v Upminster | Overton Drive, Wanstead | Results |
| 23 Jul 2023 | Quarter-Final | Brentwood v Old Brentwoods | Old County Ground, Brentwood | Results |
| 16 Jul 2023 | Quarter-Final | Chelmsford v Hadleigh and Thundersley | Chelmer Park, Chelmsford | Results |
| 06 Aug 2023 | Quarter-Final | Hutton v Hornchurch | The Polo Field Ground, Hutton | Results |
| 23 Jul 2023 | Quarter-Final | Wanstead and Snaresbrook v Harlow Town | Overton Drive, Wanstead | Results |
| 20 Aug 2023 | Semi-Final | Wanstead and Snaresbrook v Hadleigh and Thundersley | Overton Drive, Wanstead | Results |
| 03 Sep 2023 | Semi-Final | Brentwood v Hornchurch | Old County Ground, Brentwood | Results |
| 09 Sep 2023 | Final | Hadleigh and Thundersley v Hornchurch | Dick Patmore Memorial Ground, Wickford | Results |
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