First Round (2nd October)

1 - Rowhedge L-W Witham Town (Over 45s)
2 - Old Chelmsfordians (Over 45s) vs Sporting Club Woodham (Over 45s)
3 - Woodham Radars (Over 45s) vs Chipping Ongar (Over 45s)
4 - Newport (Over 45s) vs White Roding Sports (Over 45s)
5 - Blackmore (Over 45s) vs Ravens Legends (Supervets)
6 - Pavilion United (Over 45s) vs Ford (Basildon) Veterans Reserves
7 - Old Parmiterians (Over 45s) vs Harold Hill Vets (Over 45s)
8 - May & Baker Eastbrook Community (Over 45s) vs West Essex
9 - Jubilee Sports (Over 45s) vs Old Parmiterians (Over 45s Reserves)

Second Round (16th October)

10 - Bocking (Over 45s Reserves) vs Bocking (Over 45s First Team)
11 - First City Wanderers (Over 45s) vs Witham Town (Over 45s)
12 - Herongate Athletic (Over 45s Reserves) vs Stansted
13 - Broomfield (Over 45s) vs Winners of Match 2
14 - White Roding Sports (Over 45s Reserves) vs Shenfield Association (Over 45s)
15 - Springfield (Over 45s) vs Paringdon (Over 45s)
16 - Winners of Match 5 vs Chelmer (Over 45s)
17 - Herongate Athletic (Over 45s First Team) vs Winners of Match 4
18 - Great Baddow (Over 45s) vs Winners of Match 3
19 - Basildon Town vs Horndon Veterans (First Team)
20 - Winners of Match 6 vs Hullbridge Sports (Supervets)
21 - Winners of Match 9 vs Sungate Veterans (Over 45s)
22 - Winners of Match 7 vs Frenford (Over 45s)
23 - Harold Wood Athletic (Over 45s) vs Winners of Match 8
24 - Chigwell (Over 45s) vs Archer (Over 45s)
25 - Old Parmiterians (Over 45s A Team) W-L Westhamians

Third Round (13th November)

26 - Winners of Match 10 vs Winners of Match 12
27 - Winners of Match 17 vs Winners of Match 18
28 - Winners of Match 11 vs Old Parmiterians (Over 45s A Team)
29 - Winners of Match 23 vs Winners of Match 24
30 - Winners of Match 20 vs Winners of Match 15
31 - Winners of Match 14 vs Winners of Match 19
32 - Winners of Match 13 vs Winners of Match 21
33 - Winners of Match 16 vs Winners of Match 22

Quarter-Finals (15th January)

34 - Winners of Match 29 vs Winners of Match 31
35 - Winners of Match 26 vs Winners of Match 27
36 - Winners of Match 33 vs Winners of Match 30
37 - Winners of Match 32 vs Winners of Match 28

Semi-Finals (5th February)

38 - Winners of Match 35 vs Winners of Match 34
39 - Winners of Match 36 vs Winners of Match 37

Final (TBC)

40 - TBC vs TBC