| Brentwood Town | | 2002 | | 1st Qualifying Round | 08-09-2002 | | Dagenham & Redbridge | Brentwood Town | 18-0 | | 2003 | | 1st Qualifying Round | 07-09-2003 | | Brentwood Town | Whitehawk | 1-4 | | 2004 | | 1st Qualifying Round | 05-09-2004 | | Brentwood Town | Haywards Heath Town | 3-2 | | 2nd Qualifying Round | 26-09-2004 | | Panthers | Brentwood Town | 4-0 | |
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| 2005 | | 1st Qualifying Round | 11-09-2005 | | Banbury United | Brentwood Town | 3-2 | | 2006 | | 1st Qualifying Round | 24-09-2006 | | Brentwood Town | Chelmsford City | 1-7 | | 2007 | | Preliminary Round | 02-09-2007 | | Rayleigh Raiders | Brentwood Town | 1-7 | | 1st Qualifying Round | 16-09-2007 | | Brentwood Town | Saffron Walden Town | 5-1 | | 2nd Qualifying Round | 30-09-2007 | | Billericay Town | Brentwood Town | 0-1 | | 3rd Qualifying Round | 07-10-2007 | | Brentwood Town | London Colney | 2-4 | | 2008 | | 1st Qualifying Round | 28-09-2008 | | Braintree Town | Brentwood Town | 2-5 | | 2nd Qualifying Round | 12-10-2008 | | Saffron Walden Town | Brentwood Town | 1-4 | | 3rd Qualifying Round | 26-10-2008 | | Brentwood Town | Dagenham & Redbridge | 0-1 | | 2009 | | 1st Qualifying Round | 27-09-2009 | | London Colney | Brentwood Town | O-W | | 2nd Qualifying Round | 11-10-2009 | | Brentwood Town | Chelmsford City | 1-4 | |
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| 2010 | | 1st Qualifying Round | 03-10-2010 | | Tring Athletic | Brentwood Town | 0-1 | | 2nd Qualifying Round | 24-10-2010 | | Hutton | Brentwood Town | 2-3 | | 3rd Qualifying Round | 14-11-2010 | | Brentwood Town | Tottenham Hotspur | 1-4 | | 2011 | | 3rd Qualifying Round | 13-11-2011 | | Peterborough Northern Star | Brentwood Town | 4-3 | |
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| 2012 | | 3rd Qualifying Round | 11-11-2012 | | Billericay Town | Brentwood Town | 2-4 | | First Round | 09-12-2012 | | Cambridge United | Brentwood Town | 4-0 | | 2013 | | 3rd Qualifying Round | 03-11-2013 | | C&K Basildon | Brentwood Town | 4-0 | | 2014 | | Preliminary Round | 07-09-2014 | | Bury Town | Brentwood Town | 1-1 | | 1st Qualifying Round | 28-09-2014 | | Brentwood Town | West Billericay | 2-1 | | 2nd Qualifying Round | 12-10-2014 | | Colchester Town | Brentwood Town | 2-0 | |
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| 2015 | | 1st Qualifying Round | 06-09-2015 | | Brentwood Town | Great Wakering Rovers | 0-4 | | 2016 | | 2nd Qualifying Round | 18-09-2016 | | Little Thurrock Dynamos | Brentwood Town | 1-2 | | 3rd Qualifying Round | 09-10-2016 | | Houghton Athletic | Brentwood Town | 0-3 | | Fourth Qualifying Round | 13-11-2016 | | Acle United | Brentwood Town | 3-0 | |
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| 2017 | | 1st Qualifying Round | 03-09-2017 | | Brentwood Town | Corringham Cosmos | 6-0 | | 2nd Qualifying Round | 17-09-2017 | | Brentwood Town | Billericay Town | 2-3 | | 2018 | | Preliminary Round | 26-08-2018 | | Frontiers | Brentwood Town | 0-4 | | 1st Qualifying Round | 02-09-2018 | | Brentwood Town | Harlow Town | 1-2 |
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