| Date/Time | Home | Score | Away | Other Info | Referee |
|---|---|---|---|---|---|
1st Round | |||||
| 30/09/2018 10.30am | Onley Arms | 1-3 | Manor Works | ||
| 21/10/2018 10.30am | Witham White Horse | 2-4 | Witham Phoenix | ||
| 21/10/2018 10.30am | Heybridge Harriers | 1-4 | Dunmow Rhodes | ||
2nd Round | |||||
| 04/11/2018 10.30am | Braintree Legends | 1-3 | Great Bradfords | ||
| 02/12/2018 10.30am | CFC Shalford | 4-2 | Bocking Social | ||
| 04/11/2018 10.30am | Notley Sunday First | 1-1 (A-E-T) | Tolleshunt Knights Eagles | Notley Sunday First won 5-3 on pens | |
| 04/11/2018 10.30am | Nags Head Celtic | 6-3 | Panfield Bell | ||
| 25/11/2018 10.30am | Braintree Iron | P-P | Witham United | ||
| 04/11/2018 10.30am | Tiptree Jobserve | 4-2 | Witham Nomads | ||
| 04/11/2018 10.30am | Tiptree Elite | 1-4 | Western Arms | ||
| 04/11/2018 10.30am | Manor Works | 1-2 | Witham Town | ||
3rd Round | |||||
| 06/01/2019 10.30am | Finchingfield Rovers | v | Bocking Eagles | ||
| 09/12/2018 10.30am | Dunmow Rhodes | 2-3 | Great Bardfield | ||
| 06/01/2019 10.30am | CFC Shalford | v | Tiptree Jobserve | ||
| 06/01/2018 10.30am | Great Bradfords | v | Flitch United | ||
| 09/12/2018 10.30am | Nags Head Celtic | 4-3 | Western Arms | ||
| 06/01/2018 10.30am | Notley Sunday First | v | Sporting 77 | ||
| 09/12/2018 10.30am | Great Notley | 4-1 | Witham Town | ||
| 06/01/2018 10.30am | Witham Phoenix | v | Braintree Iron or Witham United |
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