| Date/Time | Home | Score | Away | Other Info | Referee |
|---|---|---|---|---|---|
1st Round | |||||
| 16/09/2018 10.30am | CFC Shalford | 0-3 | East London Old boys | ||
| 23/09/2018 10.30am | Brays Athletic | 4-0 | Nags Head Celtic | ||
| 23/09/2018 10.30am | Imara | 6-3 | Great Bradfords | ||
| 23/09/2018 10.30am | Witham United | 5-3 A-E-T | Pools Athletic | ||
| 23/09/2018 10.30am | Braintree Iron | 3-1 A-E-T | Ockendon Manor | ||
| 23/09/2018 10.30am | Ultimate Vision | 3-4 | Bocking Social | ||
2nd Round | |||||
| 04/11/2018 10.30am | Legends | 2-1 | Flitch United Sunday | ||
| 04/11/2018 10.30am | Palmers | 6-2 | Witham United | ||
| 04/11/2018 10.30am | West Horndon United | 3-3 (A-E-T) | Bocking Social | Bocking Social won 5-3 on penalties | |
| 04/11/2018 10.30am | Pitsea Athletic Sunday | 0-3 | Braintree Iron | ||
3rd Round | |||||
| 18/11/2018 10.30am | Wickford Town | 2-4 | Braintree Iron | ||
| 25/11/2018 10.30am | Vikings Flag | v | Bocking Social |
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