1 - Milton Athletic 1-3 Eversley Park
2 - Hullbridge Sports 2-4 William de Ferrers (aet)
3 - Chalkwell United 4-3 Ekco Social & Sports Club
4 - Pegasus (Coryton) 4-2 Styles
5 - Castle Rangers 2-0 Sutton Sports
6 - Ford (Basildon) 3-2 Simco Asbestco
7 - Old Southendian 3-2 Southend Collegians
8 - Foulness 3-1 Inn on the Green
9 - AFC Corringham 5-3 Eversley Sports
10 - Wheatleys 2-5 Brit Academicals
11 - Catholic United L-W Tag United
Round Two (29th November 2009)
12 - Great Wakering Rovers Veterans 9-1 Eversley Park
13 - Concord Rangers 6-2 AFC Corringham
14 - Foulness 7-1 Nicholas Colts
15 - Earls Hall United 3-5 Brit Academicals
16 - Rayleigh Olympiads 0-2 Castle Rangers
17 - Pegasus (Coryton) 7-1 William De Ferrers
18 - Old Southendian 1-3 Ford (Basildon)
19 - Chalkwell United 3-4 Tag United
Quarter-Finals (10th January 2010)
20 - Foulness 0-2 Tag United
21 - Concord Rangers W-L Brit Academicals
22 - Castle Rangers 4-1 Ford (Basildon)
23 - Great Wakering Rovers Vets 4-0 Pegasus (Coryton)
Semi-Finals (21st February 2010)
24 - Great Wakering Rovers 2-0 Concord Rangers
25 - Tag United 7-3 Castle Rangers
Final (Sunday 11th April 2010, kick-off 2:30pm, Great Wakering Rovers FC)
26 - Great Wakering Rovers vs Tag United
Key
W-L - Home win by Walkover
L-W - Away win by Walkover
P-P - Match Postponed
L-L - Late Result