| Preliminary Round | |||
| A | Wivenhoe Utd | 5-0 | Tey Old Fellas |
| B | Tollesbury Athletic | 3aet5 | Feering Village |
| First Round | |||
| 1 | Brooklands | 1-4 | Old Saints Utd |
| 2 | Great Oakley | 1-5 | Newtown Rovers |
| 3 | Clacton Ballers 43 | 2aet2 4pens3 | Feering Village |
| 4 | CO4 Ultras | 1-0 | Colchester Crusaders |
| 5 | Wivenhoe Utd | 0-2 | Pitchbury |
| 6 | Romania Athletic | AW | CUSA |
| 7 | Pathfields | 2-0 | Roman Colts |
| 8 | Brightlingsea Athletic | 0-8 | Fifteen Degrees |
| 9 | Marks Tey | 3-0 | Ramsey & Mistley |
| 10 | Iceni Wanderers | HW | Sokretez |
| 11 | North Essex Athletic | HW | Stone Island |
| 12 | Tendring Athletic | 0-3 | Madrid Wanderers |
| 13 | BYE | v | Kings Park |
| 14 | Queens Arms | HW | Great Horkesley |
| 15 | Clacton Villa | 1-2 | Sunday Shrimpers |
| 16 | Wormingford Wanderers | 0-2 | Clacton Rangers |
| Second Round | |||
| 17 | Old Saints Utd | 1-2 | Clacton Rangers |
| 18 | Newtown Rovers | 4-3 | Sunday Shrimpers |
| 19 | Clacton Ballers 43 | AW | Queens Arms |
| 20 | CO4 Ultras | 2-1 | Kings Park |
| 21 | Pitchbury | AW | Madrid Wanderers |
| 22 | CUSA | 1-3 | North Essex Athletic |
| 23 | Pathfields | HW | Iceni Wanderers |
| 24 | Fifteen Degrees | HW | Marks Tey |
| Quarter Final | |||
| 25 | Clacton Rangers | 1-4 | Fifteen Degrees |
| 26 | Newtown Rovers | 3-2 | Pathfields |
| 27 | Queens Arms | 5-2 | North Essex Athletic |
| 28 | CO4 Ultras | 1-5 | Madrid Wanderers |
| Semi Final | |||
| 29 | Fifteen Degrees | 2-0 | Madrid Wanderers |
| 30 | Newtown Rovers | 1-2 | Queens Arms |
| Final | |||
| 31 | Fifteen Degrees | 2 aet 1 | Queens Arms |
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