| First Round | ||||
|---|---|---|---|---|
| Oct 7 | CFC Shalford 'A' FC | 2 - 1 | Maypole Sports | |
| Hullbridge Sports 2nd | 1 - 5 | Witham Galacticos FC | ||
| Sporting 77 FC | 8 - 2 | Converso | ||
| New Angel Bradford Street FC | 5 - 1 | Hillford | ||
| Braintree Town Supporters Club FC | 2 - 0 | Writtle | ||
| Witham Phoenix FC | 1 - 2 | Area Boys | ||
| Notley Reserves FC | 3 - 1 | Grove & Hove Albion | ||
| Elm Park Eagles | 8 - 0 | Horse and Groom FC | ||
| Second Round | ||||
| Oct 28 | Witham Galacticos FC | 2 - 3 | Hatfield Heath Reserves | |
| Bell United FC | 1 - 6 | AFC Colchester | ||
| Braintree Town Supporters Club FC | 3 - 3 | FC Flare Reserves (AET: 8 - 7 on pens) | ||
| Loughton Town | 3 - 4 | Notley Reserves FC | ||
| New Angel Bradford Street FC | 3 - 7 | Old Chelmsfordians 2nds | ||
| Howbridge Swifts Reserves | 11 - 0 | CFC Shalford 'A' FC | ||
| Sporting 77 FC | A - A | Becontree Soccer | ||
| Nov 4 | Sporting 77 FC | 11 - 0 | Becontree Soccer | |
| Third Round | ||||
| Nov 25 | City Saints | 0 - 1 | Braintree Town Supporters Club FC | |
| Fourth Round | ||||
| Jan 13 | Braintree Town Supporters Club FC | 0 - 4 | Boreham | |