| 28 Apr 2019 | West Group | Kelvedon and Feering v Galleywood | Rye Mill Lane, Feering | Results |
| 18 Jun 2019 | West Group | Little Bardfield Village v Halstead | Church End, Little Bardfield | Results |
| 05 May 2019 | West Group | Galleywood v Halstead | Clarkes Field, Galleywood | Results |
| 06 May 2019 | West Group | Galleywood v Witham | Clarkes Field, Galleywood | Results |
| 19 May 2019 | West Group | Witham v Halstead | The Park, Witham | Results |
| 26 May 2019 | West Group | Coggeshall Town v Little Bardfield Village | Hare Field, Coggeshall | Results |
| 02 Jun 2019 | West Group | Coggeshall Town v Witham | Hare Field, Coggeshall | Results |
| 02 Jun 2019 | East Group | Frinton-on-Sea v Abberton and District | Ashlyns Road, Frinton-on-Sea | Results |
| 02 Jun 2019 | East Group | Frinton-on-Sea v Elmstead | Ashlyns Road, Frinton-on-Sea | Results |
| 09 Jun 2019 | West Group | Galleywood v Coggeshall Town | Clarkes Field, Galleywood | Results |
| 25 Jul 2019 | East Group | Wivenhoe Town v Elmstead | Rectory Road, Wivenhoe | Results |
| 13 Jun 2019 | East Group | Wivenhoe Town v Elmstead | Rectory Road, Wivenhoe | Results |
| 16 Jun 2019 | West Group | Coggeshall Town v Kelvedon and Feering | Hare Field, Coggeshall | Results |
| 16 Jun 2019 | West Group | Little Bardfield Village v Galleywood | Church End, Little Bardfield | Results |
| 20 Jun 2019 | East Group | Abberton and District v Wivenhoe Town | The Brow, Abberton | Results |
| 23 Jun 2019 | East Group | Colchester and East Essex v Frinton-on-Sea | Castle Park Cricket Ground, Colchester | Results |
| 23 Jun 2019 | West Group | Halstead v Kelvedon and Feering | Star Stile, Halstead | Results |
| 27 Jun 2019 | East Group | Mistley v Wivenhoe Town | Vicarage Meadow, Elmstead | Results |
| 04 Jul 2019 | East Group | Abberton and District v Mistley | The Brow, Abberton | Results |
| 04 Jul 2019 | East Group | Colchester and East Essex v Wivenhoe Town | Castle Park Cricket Ground, Colchester | Results |
| 07 Jul 2019 | West Group | Halstead v Coggeshall Town | Star Stile, Halstead | Results |
| 07 Jul 2019 | West Group | Kelvedon and Feering v Little Bardfield Village | Rye Mill Lane, Feering | Results |
| 11 Jul 2019 | East Group | Elmstead v Mistley | Vicarage Meadow, Elmstead | Results |
| 14 Jul 2019 | West Group | Witham v Little Bardfield Village | The Park, Witham | Results |
| 16 Jul 2019 | East Group | Wivenhoe Town v Frinton-on-Sea | Rectory Road, Wivenhoe | Results |
| 18 Jul 2019 | East Group | Elmstead v Colchester and East Essex | Vicarage Meadow, Elmstead | Results |
| 25 Jul 2019 | East Group | Colchester and East Essex v Mistley | Castle Park Cricket Ground, Colchester | Results |
| 01 Aug 2019 | East Group | Elmstead v Abberton and District | Vicarage Meadow, Elmstead | Results |
| 04 Aug 2019 | West Group | Kelvedon and Feering v Witham | Rye Mill Lane, Feering | Results |
| 09 Aug 2019 | East Group | Abberton and District v Colchester and East Essex | The Brow, Abberton | Results |
| 26 Aug 2019 | Semi-Final | Halstead v Colchester and East Essex | Star Stile, Halstead | Results |
| 26 Aug 2019 | Semi-Final | Coggeshall Town v Mistley | Star Stile, Halstead | Results |
| 26 Aug 2019 | Final | Halstead v Coggeshall Town | Star Stile, Halstead | Results |
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