| 26 Apr 2008 | First Round | Basildon and Pitsea v Ongar | Mopsies Park, Basildon | Results |
| 26 Apr 2008 | First Round | Benfleet v Epping | Woodside Park, Thundersley | Results |
| 26 Apr 2008 | First Round | Brentwood v Billericay | Old County Ground, Brentwood | Results |
| 26 Apr 2008 | First Round | Buckhurst Hill v Harlow | Roding Lane, Buckhurst Hill | Results |
| 26 Apr 2008 | First Round | Colchester and East Essex v Hadleigh and Thundersley | Castle Park Cricket Ground, Colchester | Results |
| 26 Apr 2008 | First Round | Hainault and Clayhall v Woodford Wells | Oakfield Playing Fields, Barkingside | Results |
| 26 Apr 2008 | First Round | Harold Wood v Saffron Walden | Harold Wood Park, Harold Wood | Results |
| 26 Apr 2008 | First Round | Hornchurch v Horndon-on-the-Hill | Harrow Lodge Park, Hornchurch | Results |
| 26 Apr 2008 | First Round | Hutton v Chingford | The Polo Field Ground, Hutton | Results |
| 26 Apr 2008 | First Round | Ilford v Fives and Heronians | Valentine's Park, Ilford | Results |
| 26 Apr 2008 | First Round | Leigh-on-Sea v Old Parkonians | Chalkwell Park, Westcliff-on-Sea | Results |
| 26 Apr 2008 | First Round | Old Brentwoods v Gidea Park and Romford | Ashwells Road, Brentwood | Results |
| 26 Apr 2008 | First Round | Upminster v Chelmsford | Upminster Park, Upminster | Results |
| 26 Apr 2008 | First Round | Walthamstow v Loughton | Buck Walk, Walthamstow | Results |
| 26 Apr 2008 | First Round | Wanstead v South Woodford | Overton Drive, Wanstead | Results |
| 26 Apr 2008 | First Round | West Essex v Woodford Green | The Rolls Sports Ground, Highams Park | Results |
| 26 Apr 2008 | First Round | Westcliff-on-Sea v Stanford-le-Hope | Chalkwell Park, Westcliff-on-Sea | Results |
| 03 May 2008 | Second Round | Benfleet v Basildon and Pitsea | Woodside Park, Thundersley | Results |
| 03 May 2008 | Second Round | Brentwood v Chingford | Old County Ground, Brentwood | Results |
| 03 May 2008 | Second Round | Colchester and East Essex v Gidea Park and Romford | Castle Park Cricket Ground, Colchester | Results |
| 03 May 2008 | Second Round | Fives and Heronians v Wickford | The Paddock, Chigwell | Results |
| 03 May 2008 | Second Round | Leigh-on-Sea v Woodford Wells | Chalkwell Park, Westcliff-on-Sea | Results |
| 03 May 2008 | Second Round | Loughton v Westcliff-on-Sea | The Uplands, Loughton | Results |
| 03 May 2008 | Second Round | Wanstead v Saffron Walden | Overton Drive, Wanstead | Results |
| 01 Jun 2008 | Second Round | Buckhurst Hill v Ardleigh Green | Roding Lane, Buckhurst Hill | Results |
| 08 Jun 2008 | Third Round | Brentwood v Wickford | Old County Ground, Brentwood | Results |
| 08 Jun 2008 | Third Round | Colchester and East Essex v Southend-on-Sea | Castle Park Cricket Ground, Colchester | Results |
| 13 Jul 2008 | Third Round | Loughton v Upminster | The Uplands, Loughton | Results |
| 27 Jul 2008 | Quarter-Final | not known v not known | not known | Results |
| 27 Jul 2008 | Quarter-Final | not known v not known | not known | Results |
| 27 Jul 2008 | Quarter-Final | Upminster v Brentwood | Upminster Park, Upminster | Results |
| 27 Jul 2008 | Quarter-Final | Woodford Wells v Colchester and East Essex | Monkham Lane, Woodford Wells | Results |
| 10 Aug 2008 | Semi-Final | Colchester and East Essex v Saffron Walden | Castle Park Cricket Ground, Colchester | Results |
| 10 Aug 2008 | Semi-Final | not known v not known | not known | Results |
| 25 Aug 2008 | Final | Colchester and East Essex v Hornchurch | Monkham Lane, Woodford Wells | Results |
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