| 30 Apr 2016 | First Round | Chelmsford v Colchester and East Essex | Chelmer Park, Chelmsford | Results |
| 23 Apr 2016 | First Round | Gidea Park and Romford v Colchester and East Essex | Gidea Park Sports Ground, Romford | Results |
| 30 Apr 2016 | First Round | Hornchurch v Loughton | Harrow Lodge Park, Hornchurch | Results |
| 30 Apr 2016 | First Round | Old Brentwoods v Woodford Wells | Ashwells Road, Brentwood | Results |
| 23 Apr 2016 | First Round | Westcliff-on-Sea v Woodford Wells | Chalkwell Park, Westcliff-on-Sea | Results |
| 23 Apr 2016 | First Round | Woodford Green v Upminster | The Green, Woodford Green | Results |
| 23 Apr 2016 | Second Round | Belhus v South Woodford | The Village Green, North Stifford | Results |
| 30 Apr 2016 | Second Round | Benfleet v Hainault and Clayhall | Woodside Park, Thundersley | Results |
| 30 Apr 2016 | Second Round | Billericay v Buckhurst Hill | The Toby Howe Cricket Ground, Billericay | Results |
| 23 Apr 2016 | Second Round | Brentwood v Wanstead and Snaresbrook | Old County Ground, Brentwood | Results |
| 23 Apr 2016 | Second Round | Hainault and Clayhall v Epping | Oakfield Playing Fields, Barkingside | Results |
| 30 Apr 2016 | Second Round | Fives and Heronians v Oakfield Parkonians | The Paddock, Chigwell | Results |
| 23 Apr 2016 | Second Round | Chingford v Hadleigh and Thundersley | Forest Side, Chingford | Results |
| 30 Apr 2016 | Second Round | Harold Wood v Ardleigh Green | Harold Wood Park, Harold Wood | Results |
| 30 Apr 2016 | Second Round | South Woodford v Horndon-on-the-Hill | Highfield Road, Woodford Green | Results |
| 30 Apr 2016 | Second Round | Ilford v Upminster | Valentine's Park, Ilford | Results |
| 23 Apr 2016 | Second Round | Wickford v Harlow Town | Dick Patmore Memorial Ground, Wickford | Results |
| 23 Apr 2016 | Second Round | Fives and Heronians v Old Southendian and Southchurch | The Paddock, Chigwell | Results |
| 23 Apr 2016 | Second Round | Hutton v Horndon-on-the-Hill | The Polo Field Ground, Hutton | Results |
| 23 Apr 2016 | Second Round | Oakfield Parkonians v Orsett and Thurrock | Old Parkonians Association Ground, Barkingside | Results |
| 23 Apr 2016 | Second Round | Shenfield v Harlow | Chelmsford Road, Shenfield | Results |
| 30 Apr 2016 | Second Round | Wickford v Hadleigh and Thundersley | Dick Patmore Memorial Ground, Wickford | Results |
| 03 Jul 2016 | Third Round | Harold Wood v Shenfield | Harold Wood Park, Harold Wood | Results |
| 23 Apr 2016 | Third Round | Old Brentwoods v Walthamstow | Ashwells Road, Brentwood | Results |
| 23 Apr 2016 | Third Round | Chelmsford v Leigh-on-Sea | Chelmer Park, Chelmsford | Results |
| 26 Jun 2016 | Third Round | Chelmsford v Upminster | Chelmer Park, Chelmsford | Results |
| 26 Jun 2016 | Third Round | Wanstead and Snaresbrook v Billericay | Overton Drive, Wanstead | Results |
| 23 Apr 2016 | Third Round | Benfleet v West Essex | Woodside Park, Thundersley | Results |
| 23 Apr 2016 | Third Round | Hornchurch v Southend-on-Sea and Ekco Monarchs and Trojans | Harrow Lodge Park, Hornchurch | Results |
| 19 Jun 2016 | Third Round | Hornchurch v Woodford Wells | Harrow Lodge Park, Hornchurch | Results |
| 10 Jul 2016 | Quarter-Final | Hadleigh and Thundersley v Fives and Heronians | John H Burrows Recreation Ground, Hadleigh | Results |
| 07 Aug 2016 | Quarter-Final | South Woodford v Shenfield | Highfield Road, Woodford Green | Results |
| 17 Jul 2016 | Quarter-Final | Hornchurch v Chelmsford | Harrow Lodge Park, Hornchurch | Results |
| 17 Jul 2016 | Quarter-Final | Wanstead and Snaresbrook v Hainault and Clayhall | Overton Drive, Wanstead | Results |
| 14 Aug 2016 | Semi-Final | Wanstead and Snaresbrook v Hadleigh and Thundersley | Overton Drive, Wanstead | Results |
| 14 Aug 2016 | Semi-Final | Shenfield v Chelmsford | Chelmsford Road, Shenfield | Results |
| 29 Aug 2016 | Final | Wanstead and Snaresbrook v Chelmsford | Overton Drive, Wanstead | Results |
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