FA Cup 2024/25, Second Qualifying Round |
 | 17.09.2024 |  | Leiston | – | Brentwood Town | | 3:1 (1:0) * |
| Leiston |
FA Cup 2023/24, First Qualifying Round |
| 02.09.2023 | | Hashtag United | – | Brentwood Town | | 1:0 (0:0) |
| Pitsea |
FA Cup 2021/22, First Qualifying Round |
| 04.09.2021 | | Brentwood Town | – | Cheshunt | | 0:2 (0:0) |
| Brentwood |
FA Cup 2020/21, Second Qualifying Round |
| 03.10.2020 | | Bishop's Stortford | – | Brentwood Town | | 1:0 |
| Bishop's Stortford |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | Bowers & Pitsea | – | Brentwood Town | | 2:1 (0:1) |
| Pitsea |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Brentwood Town | – | Haringey Borough | | 2:3 (1:1) |
| Brentwood |
FA Cup 2017/18, Preliminary Round |
| 19.08.2017 | | AFC Hornchurch | – | Brentwood Town | | 2:0 (0:0) |
| London |
FA Cup 2016/17, Preliminary Round |
| 20.08.2016 | | Brentwood Town | – | Tilbury | | 1:2 |
| Brentwood |
FA Cup 2015/16, Fourth Qualifying Round |
| 24.10.2015 | | Didcot Town | – | Brentwood Town | | 4:2 (2:2) |
| Didcot |
FA Cup 2014/15, Second Qualifying Round |
| 27.09.2014 | | Maidstone United | – | Brentwood Town | | 2:1 |
| Maidstone |
FA Cup 2013/14, First Qualifying Round |
| 17.09.2013 | | Clacton | – | Brentwood Town | | 2:1 (1:0) * |
| Clacton-on-Sea |
FA Cup 2012/13, Third Qualifying Round |
| 06.10.2012 | | South Park | – | Brentwood Town | | 3:1 (2:0) |
| Reigate |
FA Cup 2010/11, Third Qualifying Round |
| 12.10.2010 | | Woking | – | Brentwood Town | | 1:0 * |
| |
FA Cup 2009/10, Preliminary Round |
| 29.08.2009 | | East Thurrock United | – | Brentwood Town | | 2:0 |
| |
FA Cup 2008/09, First Qualifying Round |
| 16.09.2008 | | Arlesey Town | – | Brentwood Town | | 1:0 * |
| |
FA Cup 2007/08, Third Qualifying Round |
| 13.10.2007 | | Brentwood Town | – | Staines Town | | 0:3 |
| |
FA Cup 2006/07, Extra Preliminary Round |
| 19.08.2006 | | Dereham Town | – | Brentwood Town | | 3:1 |
| |
FA Cup 2005/06, Second Qualifying Round |
| 24.09.2005 | | Brentwood Town | – | Windsor & Eton | | 1:2 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Bury Town | – | Brentwood | | 2:1 |
| |
FA Cup 2003/04, Extra Preliminary Round |
| | | Brentwood | – | Haringey Borough | | 0:2 |
| |
FA Cup 2002/03, Preliminary Round |
| | | AFC Wallingford | – | Brentwood | | 4:1 * |
| |
FA Cup 2001/02, Preliminary Round |
| | | Aylesbury United | – | Brentwood | | 10:1 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Brentwood | – | Staines Town | | 2:4 |
| |
FA Cup 1969/70, Third Round Proper |
| 12.01.1970 | | Brentwood Town | – | Northampton Town | | 0:1 (0:1) |
| |
FA Cup 1968/69, Second Round Proper |
| 07.12.1968 | | Southend United | – | Brentwood Town | | 10:1 |
| |
FA Cup 1967/68, Fourth Qualifying Round |
| | | Brentwood Town | – | Walthamstow Avenue | | 1:3 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Bexley United | – | Brentwood Town | | 3:2 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Brentwood Town | – | Tilbury | | 0:2 |
| |
FA Cup 1885/86, Sixth Round |
| 27.02.1886 | | Brentwood | – | Blackburn Rovers | | 1:3 |
| |
FA Cup 1885/86, Fifth Round |
| 16.01.1886 | | Burslem Port Vale | – | Brentwood | | 2:1 * |
| |
FA Cup 1884/85, Second Round |
| 20.12.1884 | | Old Etonians | – | Brentwood | | 6:1 * |
| |
FA Cup 1883/84, Fourth Round |
| 19.01.1884 | | Northwich Victoria | – | Brentwood | | 3:0 |
| |
FA Cup 1882/83, Second Round |
| 02.12.1882 | | Old Etonians | – | Brentwood | | 2:1 |
| |
FA Cup 1881/82, First Round |
| 22.10.1881 | | Marlow | – | Brentwood | | 3:1 |
| |
FA Cup 1880/81, First Round |
| 06.11.1880 | | Brentwood | – | Old Etonians | | 0:10 |
| |
FA Cup 1879/80, First Round |
| 01.11.1879 | | South Norwood | – | Brentwood | | 4:2 |
| |
FA Cup 1878/79, First Round |
| 09.11.1878 | | Brentwood | – | Pilgrims | | 1:3 |
| |
