| 26 Apr 2014 | First Round | Upminster v Chingford | Upminster Park, Upminster | Results |
| 26 Apr 2014 | First Round | Fives and Heronians v Billericay | The Paddock, Chigwell | Results |
| 26 Apr 2014 | First Round | Harlow Town v Ardleigh Green | Ash Tree Fields, Harlow | Results |
| 26 Apr 2014 | First Round | Brentwood v Hutton | Old County Ground, Brentwood | Results |
| 26 Apr 2014 | First Round | Hadleigh and Thundersley v Hainault and Clayhall | John H Burrows Recreation Ground, Hadleigh | Results |
| 26 Apr 2014 | First Round | Gidea Park and Romford v Buckhurst Hill | Gidea Park Sports Ground, Romford | Results |
| 26 Apr 2014 | First Round | Horndon-on-the-Hill v Ilford | The Recreation Ground, Horndon-on-the-Hill | Results |
| 26 Apr 2014 | First Round | Harold Wood v Harlow | Harold Wood Park, Harold Wood | Results |
| 26 Apr 2014 | First Round | Oakfield Parkonians v Old Southendian and Southchurch | Old Parkonians Association Ground, Barkingside | Results |
| 26 Apr 2014 | First Round | Woodford Green v South Woodford | The Green, Woodford Green | Results |
| 03 May 2014 | First Round | Wanstead v Southend-on-Sea and Ekco Monarchs and Trojans | Overton Drive, Wanstead | Results |
| 26 Apr 2014 | First Round | Basildon and Pitsea v Hornchurch | Mopsies Park, Basildon | Results |
| 26 Apr 2014 | First Round | Chelmsford v Loughton | Chelmer Park, Chelmsford | Results |
| 26 Apr 2014 | First Round | Wickford v Leigh-on-Sea | Dick Patmore Memorial Ground, Wickford | Results |
| 26 Apr 2014 | First Round | Old Brentwoods v Benfleet | Ashwells Road, Brentwood | Results |
| 26 Apr 2014 | First Round | Epping v Woodford Wells | Lower Bury Lane, Epping | Results |
| 26 Apr 2014 | First Round | Colchester and East Essex v Westcliff-on-Sea | Castle Park Cricket Ground, Colchester | Results |
| 26 Apr 2014 | First Round | West Essex v Belhus | The Rolls Sports Ground, Highams Park | Results |
| 03 May 2014 | Second Round | Chingford v Shenfield | Forest Side, Chingford | Results |
| 03 May 2014 | Second Round | Harold Wood v Old Southendian and Southchurch | Harold Wood Park, Harold Wood | Results |
| 08 Jun 2014 | Second Round | South Woodford v Wanstead | Highfield Road, Woodford Green | Results |
| 03 May 2014 | Second Round | Hornchurch v Chelmsford | Harrow Lodge Park, Hornchurch | Results |
| 03 May 2014 | Second Round | Leigh-on-Sea v Benfleet | Chalkwell Park, Westcliff-on-Sea | Results |
| 03 May 2014 | Second Round | Fives and Heronians v Ardleigh Green | The Paddock, Chigwell | Results |
| 03 May 2014 | Second Round | Brentwood v Hainault and Clayhall | Old County Ground, Brentwood | Results |
| 03 May 2014 | Second Round | Buckhurst Hill v Ilford | Roding Lane, Buckhurst Hill | Results |
| 03 May 2014 | Second Round | Woodford Wells v Colchester and East Essex | Monkham Lane, Woodford Wells | Results |
| 01 Jun 2014 | Third Round | Chelmsford v Leigh-on-Sea | Chelmer Park, Chelmsford | Results |
| 26 May 2014 | Third Round | Colchester and East Essex v Belhus | Castle Park Cricket Ground, Colchester | Results |
| 29 Jun 2014 | Quarter-Final | Shenfield v Fives and Heronians | Chelmsford Road, Shenfield | Results |
| 08 Jun 2014 | Quarter-Final | Brentwood v Ilford | Old County Ground, Brentwood | Results |
| 29 Jun 2014 | Quarter-Final | Harold Wood v Wanstead | Harold Wood Park, Harold Wood | Results |
| 20 Jul 2014 | Quarter-Final | Chelmsford v Colchester and East Essex | Chelmer Park, Chelmsford | Results |
| 17 Aug 2014 | Semi-Final | Fives and Heronians v Ilford | The Paddock, Chigwell | Results |
| 03 Aug 2014 | Semi-Final | Wanstead v Colchester and East Essex | Overton Drive, Wanstead | Results |
| 07 Sep 2014 | Final | Wanstead v Ilford | Overton Drive, Wanstead | Results |
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