| 07 May 2023 | First Round | Roding Valley v Hawks | River Playing Field, Buckhurst Hill | Results |
| 08 May 2023 | First Round | Orsett and Thurrock v Rainham | School Lane, Orsett | Results |
| 21 May 2023 | First Round | Woodford Wells v Walthamstow | Monkham Lane, Woodford Wells | Results |
| 24 May 2023 | First Round | Redbridge v West Essex | Clayhall Park, Clayhall | Results |
| 28 May 2023 | First Round | Benfleet v Wickford | Woodside Park, Thundersley | Results |
| 29 May 2023 | First Round | London Eagles v Neo | London Eagles Ground, Ilford | Results |
| 29 May 2023 | First Round | Oakfield Parkonians v Aztecs | Old Parkonians Association Ground, Barkingside | Results |
| 31 May 2023 | First Round | Epping v Harlow | Lower Bury Lane, Epping | Results |
| 31 May 2023 | First Round | Frenford v Barking | Oakfield Playing Fields, Barkingside | Results |
| 31 May 2023 | First Round | Gidea Park and Romford v Bentley | Gidea Park Sports Ground, Romford | Results |
| 31 May 2023 | First Round | Old Brentwoods v Ardleigh Green and Havering-atte-Bower | Ashwells Road, Brentwood | Results |
| 09 Jun 2023 | Second Round | Goresbrook v Hornchurch Athletic | May and Baker Annexe, Dagenham | Results |
| 20 Jun 2023 | Second Round | Aztecs v Barking | London Marathon Playing Fields, Barkingside | Results |
| 14 Jun 2023 | Second Round | Harlow Town v Gidea Park and Romford | Ash Tree Fields, Harlow | Results |
| 21 Jun 2023 | Second Round | Hawks v Redbridge | Jubilee Sports Ground, Highams Park | Results |
| 22 Jun 2023 | Second Round | London Eagles v South Woodford | London Eagles Ground, Ilford | Results |
| 21 Jun 2023 | Second Round | Newham v Woodford Wells | Bobby Moore Sports Pavilion, East Ham | Results |
| 12 Jul 2023 | Second Round | Old Brentwoods v Epping | Ashwells Road, Brentwood | Results |
| 27 Jun 2023 | Second Round | Orsett and Thurrock v Wickford | School Lane, Orsett | Results |
| 21 Jul 2023 | Quarter-Final | Goresbrook v Orsett and Thurrock | May and Baker Annexe, Dagenham | Results |
| 10 Aug 2023 | Quarter-Final | Harlow Town v Epping | Ash Tree Fields, Harlow | Results |
| 19 Jul 2023 | Quarter-Final | Woodford Wells v Barking | Monkham Lane, Woodford Wells | Results |
| 19 Jul 2023 | Quarter-Final | Hawks v London Eagles | Jubilee Sports Ground, Highams Park | Results |
| 16 Aug 2023 | Semi-Final | Orsett and Thurrock v Epping | School Lane, Orsett | Results |
| 09 Aug 2023 | Semi-Final | Woodford Wells v Hawks | Monkham Lane, Woodford Wells | Results |
| 09 Sep 2023 | Final | Epping v Hawks | Monkham Lane, Woodford Wells | Results |
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