| 02 May 2009 | First Round | Basildon and Pitsea v West Essex | Mopsies Park, Basildon | Results |
| 25 Apr 2009 | First Round | Benfleet v Gidea Park and Romford | Woodside Park, Thundersley | Results |
| 25 Apr 2009 | First Round | Billericay v Walthamstow | The Toby Howe Cricket Ground, Billericay | Results |
| 25 Apr 2009 | First Round | Colchester and East Essex v Chingford | Castle Park Cricket Ground, Colchester | Results |
| 25 Apr 2009 | First Round | Fives and Heronians v Epping | The Paddock, Chigwell | Results |
| 25 Apr 2009 | First Round | Hornchurch v Old Southendian and Southchurch | Harrow Lodge Park, Hornchurch | Results |
| 02 May 2009 | First Round | Hutton v Hadleigh and Thundersley | The Polo Field Ground, Hutton | Results |
| 25 Apr 2009 | First Round | Ilford v Woodford Green | Valentine's Park, Ilford | Results |
| 02 May 2009 | First Round | Leigh-on-Sea v Harlow | Chalkwell Park, Westcliff-on-Sea | Results |
| 02 May 2009 | First Round | Loughton v Brentwood | The Uplands, Loughton | Results |
| 25 Apr 2009 | First Round | Old Parkonians v Hainault and Clayhall | Old Parkonians Association Ground, Barkingside | Results |
| 25 Apr 2009 | First Round | Ongar v Old Brentwoods | Love Lane, Ongar | Results |
| 25 Apr 2009 | First Round | South Woodford v Belhus | Highfield Road, Woodford Green | Results |
| 25 Apr 2009 | First Round | Southend-on-Sea v Shenfield | Southchurch Park, Southend-on-Sea | Results |
| 25 Apr 2009 | First Round | Upminster v Harold Wood | Upminster Park, Upminster | Results |
| 25 Apr 2009 | First Round | Wanstead v Horndon-on-the-Hill | Overton Drive, Wanstead | Results |
| 25 Apr 2009 | First Round | Westcliff-on-Sea v Buckhurst Hill | Chalkwell Park, Westcliff-on-Sea | Results |
| 25 Apr 2009 | First Round | Wickford v Chelmsford | Dick Patmore Memorial Ground, Wickford | Results |
| 25 Apr 2009 | First Round | Woodford Wells v Ardleigh Green | Monkham Lane, Woodford Wells | Results |
| 07 Jun 2009 | Second Round | Ardleigh Green v Hainault and Clayhall | Central Park, Harold Hill | Results |
| 02 May 2009 | Second Round | Colchester and East Essex v Hornchurch | Castle Park Cricket Ground, Colchester | Results |
| 01 Jun 2009 | Second Round | Hadleigh and Thundersley v Gidea Park and Romford | John H Burrows Recreation Ground, Hadleigh | Results |
| 07 Jun 2009 | Second Round | Loughton v Harlow | The Uplands, Loughton | Results |
| 02 May 2009 | Second Round | Ongar v South Woodford | Love Lane, Ongar | Results |
| 02 May 2009 | Second Round | Shenfield v Walthamstow | Chelmsford Road, Shenfield | Results |
| 07 Jun 2009 | Second Round | West Essex v Ilford | The Rolls Sports Ground, Highams Park | Results |
| 02 May 2009 | Second Round | Westcliff-on-Sea v Wanstead | Chalkwell Park, Westcliff-on-Sea | Results |
| 02 May 2009 | Second Round | Wickford v Upminster | Dick Patmore Memorial Ground, Wickford | Results |
| 05 Jul 2009 | Third Round | Colchester and East Essex v Fives and Heronians | Castle Park Cricket Ground, Colchester | Results |
| 09 Aug 2009 | Quarter-Final | Gidea Park and Romford v Hainault and Clayhall | Gidea Park Sports Ground, Romford | Results |
| 19 Jul 2009 | Quarter-Final | Upminster v Fives and Heronians | Upminster Park, Upminster | Results |
| 14 Jun 2009 | Third Round | South Woodford v Upminster | Highfield Road, Woodford Green | Results |
| 28 Jun 2009 | Quarter-Final | Walthamstow v Loughton | Buck Walk, Walthamstow | Results |
| 26 Jul 2009 | Quarter-Final | Wanstead v Ilford | Overton Drive, Wanstead | Results |
| 09 Aug 2009 | Semi-Final | Walthamstow v Upminster | Buck Walk, Walthamstow | Results |
| 16 Aug 2009 | Semi-Final | Gidea Park and Romford v Wanstead | Gidea Park Sports Ground, Romford | Results |
| 30 Aug 2009 | Final | Upminster v Wanstead | Roding Lane, Buckhurst Hill | Results |
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