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	3-1	Bocking Social
Quarter-Final
10/02/2019 10.30am	Braintree Iron	4-3	Academy Soccer Sunday Sceptre First
Semi-Final
03/03/2019 10.30am	Braintree Iron	1-3	Palmers