| Round One |
| |
| - | NOT | v | PLAYED |
| |
| Round Two |
| |
| 1 | Tollesbury | v | bye |
| 2 | Highwaymen | v | bye |
| 3 | Brightlingsea Regent | v | bye |
| 4 | Pitchbury | v | bye |
| 5 | Stone Island | v | bye |
| 6 | Centurion | v | bye |
| 7 | City Saints | v | bye |
| 8 | Harwich & Wix Athletic | v | bye |
| 10 | Colchester Athletic | 1-4 | Romania Athletic |
| 11 | St Johns | 5-0 | Newtown Rovers |
| 12 | Mill (The) | HW | Wimpole 2000 |
| 13 | Bridgelink | 1-1
1aet2 | Fox & Fiddler |
| Romania Ath fielded an ineligible player, are expelled from the competition and are replaced in the next round by Colchester Ath. |
| |
| Round Three |
| |
| 15 | Mill (The) | 1-4 | City Saints |
| 16 | Harwich & Wix Athletic | 6-3 | Iceni Wanderers |
| 17 | Tollesbury Legion | 2-0 | St Osyth |
| 18 | AFC Colchester | 5-3 | Marks Tey |
| 19 | Feering Utd | 9-3 | Colchester Athletic |
| 20 | Corecalona | 5-0 | Sunday Shrimpers |
| 21 | Wivenhoe Old Boys | 3-0 | Centurion |
| 22 | CUSA | 2-1 | Copford |
| 23 | Fox & Fiddler | 6-0 | Ramsey Utd |
| 24 | Pitchbury | 0-17 | AFC Pegasus |
| 25 | Duckpond | 1-0 | Botolphs |
| 26 | Highwaymen | 1-14 | FC Byair |
| 27 | Brightlingsea Regent | 13-1 | Stone Island |
| 28 | Langham Utd | 4-1 | Prettygate |
| 29 | Colchester Villa | 1-3 | Greenstead Social Club |
| 30 | St Johns | 12-0 | Ramsey Mill |
| Harwich & Wix Ath. fielded two ineligible players, are expelled from the competition and are replaced in the next round by Iceni Wanderers. |
| Fox & Fiddler fielded an ineligible player, are expelled from the competition and are replaced in the next round by Ramsey Utd. |
| |
| Round Four |
| |
| 31 | St Johns | 4-4
6aet4 | Feering Utd |
| 32 | Langham Utd | 3-0 | CUSA |
| 33 | AFC Pegasus | HW | Tollesbury Legion |
| (Tollesbury Legion failed to raise a side) |
| 34 | FC Byair | 9-1 | Brightlingsea Regent |
| 35 | Greenstead Social Club | 0-2 | AFC Colchester |
| 36 | Ramsey Utd | 1-3 | Wivenhoe Old Boys |
| 37 | City Saints | 0-6 | Duckpond |
| 38 | Iceni Wanderers | AW | Corecalona |
| (Iceni Wanderers failed to raise a side) |
| |
| Quarter Finals |
| |
| 39 | Duckpond | 4-2 | Wivenhoe Old Boys |
| 40 | AFC Pegasus | 5aet5
4pens2 | Corecalona |
| 41 | St Johns | 2aet2
1pens3 | Langham Utd |
| 42 | AFC Colchester | AW | FC Byair |
| (AFC Colchester failed to raise a side) |
| |
| Semi Finals |
| |
| 43 | Langham Utd | 0-0
0aet4 | Duckpond |
| 44 | AFC Pegasus | 1aet1
4pens5 | FC Byair |
| |
| Final |
| |
| 45 | Duckpond | 1 - 2 | FC Byair |
| |
| Match Report & Photos |
