| 26 May 2014 | Group C | Ardleigh Green v Benfleet | Central Park, Harold Hill | Results |
| 18 May 2014 | Group C | Ardleigh Green v Fives and Heronians | Central Park, Harold Hill | Results |
| 06 Jun 2014 | Group G | Basildon and Pitsea v Hadleigh and Thundersley | Mopsies Park, Basildon | Results |
| 30 May 2014 | Group G | Basildon and Pitsea v Upminster | Mopsies Park, Basildon | Results |
| 27 Jun 2014 | Group E | Belhus v Ilford | The Village Green, North Stifford | Results |
| 25 Jun 2014 | Group C | Benfleet v Harold Wood | Woodside Park, Thundersley | Results |
| 20 Jun 2014 | Group D | Billericay v Horndon-on-the-Hill | The Toby Howe Cricket Ground, Billericay | Results |
| 23 May 2014 | Group D | Billericay v Stanford-le-Hope | The Toby Howe Cricket Ground, Billericay | Results |
| 05 May 2014 | Group B | Brentwood v Hutton | Old County Ground, Brentwood | Results |
| 29 Jun 2014 | Group B | Brentwood v Wickford | Old County Ground, Brentwood | Results |
| 08 Jun 2014 | Group D | Buckhurst Hill v Billericay | Roding Lane, Buckhurst Hill | Results |
| 26 Jun 2014 | Group D | Buckhurst Hill v Horndon-on-the-Hill | Roding Lane, Buckhurst Hill | Results |
| 27 Jun 2014 | Group D | Chelmsford v Billericay | Chelmer Park, Chelmsford | Results |
| 11 May 2014 | Group D | Chelmsford v Buckhurst Hill | Chelmer Park, Chelmsford | Results |
| 20 May 2014 | Group H | Chingford v Loughton | Forest Side, Chingford | Results |
| 10 Jun 2014 | Group H | Chingford v West Essex | Forest Side, Chingford | Results |
| 05 Jun 2014 | Group A | Colchester and East Essex v Leigh-on-Sea | Castle Park Cricket Ground, Colchester | Results |
| 29 Jun 2014 | Group A | Colchester and East Essex v Orsett | Castle Park Cricket Ground, Colchester | Results |
| 25 Jun 2014 | Group H | Epping v Chingford | Lower Bury Lane, Epping | Results |
| 08 Jun 2014 | Group C | Fives and Heronians v Benfleet | The Paddock, Chigwell | Results |
| 29 Jun 2014 | Group B | Gidea Park and Romford v Brentwood | Gidea Park Sports Ground, Romford | Results |
| 05 May 2014 | Group B | Gidea Park and Romford v Old Southendian and Southchurch | Gidea Park Sports Ground, Romford | Results |
| 20 Jun 2014 | Group G | Hadleigh and Thundersley v Southend-on-Sea and Ekco Monarchs and Trojans | John H Burrows Recreation Ground, Hadleigh | Results |
| 29 May 2014 | Group G | Hadleigh and Thundersley v Westcliff-on-Sea | John H Burrows Recreation Ground, Hadleigh | Results |
| 10 Jun 2014 | Group F | Hainault and Clayhall v Harlow Town | Oakfield Playing Fields, Barkingside | Results |
| 20 Jun 2014 | Group F | Harlow Town v South Woodford | Ash Tree Fields, Harlow | Results |
| 12 Jun 2014 | Group C | Harold Wood v Ardleigh Green | Harold Wood Park, Harold Wood | Results |
| 18 Jun 2014 | Group C | Harold Wood v Fives and Heronians | Harold Wood Park, Harold Wood | Results |
| 05 Jun 2014 | Group E | Hornchurch v Belhus | Harrow Lodge Park, Hornchurch | Results |
| 12 Jun 2014 | Group D | Horndon-on-the-Hill v Chelmsford | The Recreation Ground, Horndon-on-the-Hill | Results |
| 01 Jun 2014 | Group D | Horndon-on-the-Hill v Stanford-le-Hope | The Recreation Ground, Horndon-on-the-Hill | Results |
| 29 Jun 2014 | Group B | Hutton v Gidea Park and Romford | The Polo Field Ground, Hutton | Results |
| 18 Jun 2014 | Group B | Hutton v Old Southendian and Southchurch | The Polo Field Ground, Hutton | Results |
| 12 Jun 2014 | Group E | Ilford v Hornchurch | Valentine's Park, Ilford | Results |
| 29 May 2014 | Group E | Ilford v Wanstead | Valentine's Park, Ilford | Results |
| 08 May 2014 | Group A | Leigh-on-Sea v Shenfield | Chalkwell Park, Westcliff-on-Sea | Results |
| 11 Jun 2014 | Group H | Loughton v Epping | The Uplands, Loughton | Results |
| 04 Jun 2014 | Group H | Loughton v West Essex | The Uplands, Loughton | Results |
| 16 May 2014 | Group B | Old Southendian and Southchurch v Brentwood | Southchurch Park, Southend-on-Sea | Results |
| 29 Jun 2014 | Group B | Old Southendian and Southchurch v Wickford | Southchurch Park, Southend-on-Sea | Results |
| 29 Jun 2014 | Group A | Orsett v Leigh-on-Sea | School Lane, Orsett | Results |
| 10 Jun 2014 | Group A | Shenfield v Colchester and East Essex | Chelmsford Road, Shenfield | Results |
| 03 Jun 2014 | Group A | Shenfield v Orsett | Chelmsford Road, Shenfield | Results |
| 18 May 2014 | Group F | South Woodford v Hainault and Clayhall | Highfield Road, Woodford Green | Results |
| 25 May 2014 | Group F | South Woodford v Woodford Wells | Highfield Road, Woodford Green | Results |
| 13 Jun 2014 | Group G | Southend-on-Sea and Ekco Monarchs and Trojans v Basildon and Pitsea | Southchurch Park, Southend-on-Sea | Results |
| 29 Jun 2014 | Group G | Southend-on-Sea and Ekco Monarchs and Trojans v Westcliff-on-Sea | Southchurch Park, Southend-on-Sea | Results |
| 04 May 2014 | Group D | Stanford-le-Hope v Buckhurst Hill | Stanford Recreation Ground, Stanford-le-Hope | Results |
| 18 Jun 2014 | Group D | Stanford-le-Hope v Chelmsford | Stanford Recreation Ground, Stanford-le-Hope | Results |
| 12 Jun 2014 | Group G | Upminster v Hadleigh and Thundersley | Upminster Park, Upminster | Results |
| 03 Jun 2014 | Group G | Upminster v Southend-on-Sea and Ekco Monarchs and Trojans | Upminster Park, Upminster | Results |
| 12 Jun 2014 | Group E | Wanstead v Belhus | Overton Drive, Wanstead | Results |
| 26 Jun 2014 | Group E | Wanstead v Hornchurch | Overton Drive, Wanstead | Results |
| 18 Jun 2014 | Group H | West Essex v Epping | The Rolls Sports Ground, Highams Park | Results |
| 29 Jun 2014 | Group G | Westcliff-on-Sea v Basildon and Pitsea | Chalkwell Park, Westcliff-on-Sea | Results |
| 29 Jun 2014 | Group G | Westcliff-on-Sea v Upminster | Chalkwell Park, Westcliff-on-Sea | Results |
| 29 Jun 2014 | Group B | Wickford v Gidea Park and Romford | Dick Patmore Memorial Ground, Wickford | Results |
| 29 Jun 2014 | Group B | Wickford v Hutton | Dick Patmore Memorial Ground, Wickford | Results |
| 08 Jun 2014 | Group F | Woodford Wells v Hainault and Clayhall | Monkham Lane, Woodford Wells | Results |
| 22 Jun 2014 | Group F | Woodford Wells v Harlow Town | Monkham Lane, Woodford Wells | Results |
| 16 Jul 2014 | Second Round | Wanstead v Hutton | Overton Drive, Wanstead | Results |
| 14 Jul 2014 | Second Round | Upminster v Billericay | Upminster Park, Upminster | Results |
| 03 Jul 2014 | Second Round | Chingford v Southend-on-Sea and Ekco Monarchs and Trojans | Forest Side, Chingford | Results |
| 02 Jul 2014 | Second Round | Colchester and East Essex v Loughton | Castle Park Cricket Ground, Colchester | Results |
| 13 Jul 2014 | Second Round | Brentwood v Fives and Heronians | Old County Ground, Brentwood | Results |
| 09 Jul 2014 | Second Round | Harold Wood v Hornchurch | Harold Wood Park, Harold Wood | Results |
| 16 Jul 2014 | Second Round | Chelmsford v South Woodford | Chelmer Park, Chelmsford | Results |
| 15 Jul 2014 | Second Round | Harlow Town v Shenfield | Ash Tree Fields, Harlow | Results |
| 15 Jul 2014 | Quarter-Final | Harold Wood v Brentwood | Harold Wood Park, Harold Wood | Results |
| 24 Jul 2014 | Quarter-Final | Wanstead v Upminster | Overton Drive, Wanstead | Results |
| 24 Jul 2014 | Quarter-Final | Shenfield v South Woodford | Chelmsford Road, Shenfield | Results |
| 16 Jul 2014 | Quarter-Final | Chingford v Colchester and East Essex | Forest Side, Chingford | Results |
| 27 Jul 2014 | Semi-Final | Colchester and East Essex v Wanstead | The Polo Field Ground, Hutton | Results |
| 27 Jul 2014 | Semi-Final | Brentwood v South Woodford | The Polo Field Ground, Hutton | Results |
| 27 Jul 2014 | Final | Brentwood v Wanstead | The Polo Field Ground, Hutton | Results |
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