1 – Sporting Club Woodham 1-5 Old Chelmsfordians
2 – Great Danes L-W Manford Way
3 – Westhamians 2-0 Leigh Ramblers
4 – Dunmow Vets 9-0 Newport Veterans
5 – Hannakins Farm 3-2 Ryan
6 – Hullbridge Sports 3-5 Sporting Club Henderson Vets
7 – Metpol Chigwell NE W-L Springfield
8 – Fobs (East Hanningfield) 2-3 Glassmasters Vets
9 – Great Baddow 1-2 Hutton Old Boys (aet)
10 – Cricketers (Horndon) A 3-4 Chipping Ongar Vets (aet)
11 – Writtle 6-0 Sanders Vets
12 – Leigh Town 3-1 Wickford Town
13 – Rochford Town 0-7 Witham CML Vets
14 – Hornminster Vets 4-2 Horndon Veterans (aet)
15 – Ludlows 1-0 Shenfield Association
16 – Lawford Lads 2-1 Frenford Senior
17 – Sungate 2-0 Benfleet
18 – Hockley & Hawkwell 2-1 Ford (Basildon)
19 – Britannia 5-1 Old Parmiterians (aet)
20 – Doddinghurst Olympic 4-5 Bishop’s Stortford Community (aet)
21 – Grays Athletic 6-2 Helions Bumpstead
22 – Lowhall 1-5 Herongate Athletic
23 – Great Berry Rangers W-L Essex Police
24 – Beacon Hill Rovers L-W Hawkwell Athletic
25 – Vichouse Sports 4-0 West Billericay
Round Two (14th November 2009)
26 – White Notley 4-2 Glassmasters
27 – Grays Athletic 7-1 Runwell Hospital
28 – Lawford Lads 2-5 Runwell Old Boys
29 – West Essex 1-5 Port of London
30 – Pavillion United Vets 1-5 Herongate Athletic
31 – Maidonians 2-0 Britannia
32 – Great Berry Rangers 4-3 Ludlows (aet)
33 – Old Chelmsfordians 1-7 Writtle
34 – Hornminster 0-5 Metpol Chigwell NE
35 – Hannakins Farm 2-3 Dunmow
36 – Social Club Henderson Vets 2-1 Hockley & Hawkwell
37 – Manford Way 3-1 Witham CML Vets
38 – Sungate 1-8 Bishop's Stortford Community Vets
39 – Hawkwell Athletic 5-4 Chipping Ongar Vets
40 – Hutton Old Boys 3-1 Leigh Town
41 – Westhamians 5-3 Vichouse Sports
Round Three (5th December 2009)
42 – Westhamians 2-0 Hutton Old Boys
43 – Grays Athletic 0-1 Maidonians
44 – Social Club Henderson Vets 1-4 Port of London
45 – Hawkwell Athletic 2-7 Metpol Chigwell NE
46 – Bishop's Stortford Community Vets 2-8 Writtle
47 – Dunmow 2-0 Great Berry Rangers
48 – White Notley 3-4 Runwell Old Boys
49 – Herongate Athletic 2-3 Manford Way (aet)
Quarter-Finals (23rd January 2010)
50 - Runwell Old Boys 4-2 Maidonians
51 - Manford Way 5-1 Writtle
52 - Metpol Chigwell NE 4-1 Westhamians
53 - Port of London 5-1 Dunmow
Semi-Finals (20th February 2010)
54 - Metpol Chigwell NE 1-2 Port of London
55 - Manford Way 2-1 Runwell Old Boys (aet)
Final (Wednesday 24th March 2010, Heybridge Swifts FC)
56 - Manford Way vs Port of London
Key
W-L - Home win by Walkover
L-W - Away win by Walkover
P-P - Match Postponed
L-L - Late Result