| 27 Apr 2019 | First Round | Brentwood v Benfleet | Old County Ground, Brentwood | Results |
| 27 Apr 2019 | First Round | Buckhurst Hill v Belhus | Roding Lane, Buckhurst Hill | Results |
| 27 Apr 2019 | First Round | Chelmsford v West Essex | Chelmer Park, Chelmsford | Results |
| 27 Apr 2019 | First Round | Chingford v Hutton | Forest Side, Chingford | Results |
| 27 Apr 2019 | First Round | Colchester and East Essex v South Woodford | Castle Park Cricket Ground, Colchester | Results |
| 27 Apr 2019 | First Round | Epping v Billericay | Lower Bury Lane, Epping | Results |
| 27 Apr 2019 | First Round | Hadleigh and Thundersley v Old Brentwoods | John H Burrows Recreation Ground, Hadleigh | Results |
| 27 Apr 2019 | First Round | Harlow Town v Southend-on-Sea and Ekco Monarchs and Trojans | Ash Tree Fields, Harlow | Results |
| 27 Apr 2019 | First Round | Harold Wood v Upminster | Harold Wood Park, Harold Wood | Results |
| 27 Apr 2019 | First Round | Horndon-on-the-Hill v Goresbrook | The Recreation Ground, Horndon-on-the-Hill | Results |
| 27 Apr 2019 | First Round | Ilford v Hornchurch | Valentine's Park, Ilford | Results |
| 27 Apr 2019 | First Round | Loughton v Wanstead and Snaresbrook | The Uplands, Loughton | Results |
| 27 Apr 2019 | First Round | Oakfield Parkonians v Gidea Park and Romford | Old Parkonians Association Ground, Barkingside | Results |
| 27 Apr 2019 | First Round | Old Southendian and Southchurch v Walthamstow | Garon Park, Southend-on-Sea | Results |
| 27 Apr 2019 | First Round | Orsett and Thurrock v Harlow | School Lane, Orsett | Results |
| 27 Apr 2019 | First Round | Shenfield v Leigh-on-Sea | Chelmsford Road, Shenfield | Results |
| 27 Apr 2019 | First Round | Stanford-le-Hope v Frenford | Stanford Recreation Ground, Stanford-le-Hope | Results |
| 27 Apr 2019 | First Round | Wickford v Ardleigh Green | Dick Patmore Memorial Ground, Wickford | Results |
| 27 Apr 2019 | First Round | Woodford Green v Fives and Heronians | The Green, Woodford Green | Results |
| 27 Apr 2019 | First Round | Woodford Wells v Westcliff-on-Sea | Monkham Lane, Woodford Wells | Results |
| 04 May 2019 | Second Round | Chelmsford v Woodford Wells | Chelmer Park, Chelmsford | Results |
| 04 May 2019 | Second Round | Fives and Heronians v Colchester and East Essex | The Paddock, Chigwell | Results |
| 04 May 2019 | Second Round | Hadleigh and Thundersley v Shenfield | John H Burrows Recreation Ground, Hadleigh | Results |
| 04 May 2019 | Second Round | Oakfield Parkonians v Old Southendian and Southchurch | Old Parkonians Association Ground, Barkingside | Results |
| 04 May 2019 | Second Round | Southend-on-Sea and Ekco Monarchs and Trojans v Wanstead and Snaresbrook | Southchurch Park, Southend-on-Sea | Results |
| 04 May 2019 | Second Round | Wickford v Belhus | Dick Patmore Memorial Ground, Wickford | Results |
| 04 May 2019 | Second Round | Billericay v Orsett and Thurrock | The Toby Howe Cricket Ground, Billericay | Results |
| 04 May 2019 | Second Round | Chingford v Frenford | Forest Side, Chingford | Results |
| 04 May 2019 | Second Round | Goresbrook v Hornchurch | May and Baker Annexe, Dagenham | Results |
| 04 May 2019 | Second Round | Harold Wood v Brentwood | Harold Wood Park, Harold Wood | Results |
| 23 Jun 2019 | Third Round | Belhus v Hadleigh and Thundersley | The Village Green, North Stifford | Results |
| 23 Jun 2019 | Third Round | Chelmsford v Wanstead and Snaresbrook | Chelmer Park, Chelmsford | Results |
| 23 Jun 2019 | Quarter-Final | Brentwood v Oakfield Parkonians | Old County Ground, Brentwood | Results |
| 14 Jul 2019 | Quarter-Final | Hadleigh and Thundersley v Wanstead and Snaresbrook | John H Burrows Recreation Ground, Hadleigh | Results |
| 21 Jul 2019 | Quarter-Final | Billericay v Hornchurch | The Toby Howe Cricket Ground, Billericay | Results |
| 21 Jul 2019 | Quarter-Final | Chingford v Colchester and East Essex | Forest Side, Chingford | Results |
| 11 Aug 2019 | Semi-Final | Brentwood v Hadleigh and Thundersley | Old County Ground, Brentwood | Results |
| 11 Aug 2019 | Semi-Final | Hornchurch v Colchester and East Essex | Harrow Lodge Park, Hornchurch | Results |
| 26 Aug 2019 | Final | Brentwood v Hornchurch | Southchurch Park, Southend-on-Sea | Results |
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