FA Cup 2023/24, Fourth Round Proper |
 | 27.01.2024 | | Ipswich Town | – | Maidstone United | | 1:2 (0:1) |
| Ipswich |
FA Cup 2023/24, Third Round Proper |
| 06.01.2024 | | Maidstone United | – | Stevenage | | 1:0 (1:0) |
| Maidstone |
FA Cup 2023/24, Second Round Proper |
| 02.12.2023 | | Maidstone United | – | Barrow | | 2:1 (1:1) |
| Maidstone |
FA Cup 2023/24, First Round Proper |
| 04.11.2023 | | Chesham United | – | Maidstone United | | 0:2 (0:1) |
| Chesham |
FA Cup 2023/24, Fourth Qualifying Round |
| 14.10.2023 | | Torquay United | – | Maidstone United | | 0:2 (0:1) |
| Torquay |
FA Cup 2023/24, Third Qualifying Round |
| 30.09.2023 | | Winchester City | – | Maidstone United | | 0:2 (0:0) |
| Winchester |
FA Cup 2023/24, Second Qualifying Round |
| 16.09.2023 | | Steyning Town | – | Maidstone United | | 1:4 (1:2) |
| Steyning |
FA Cup 2021/22, Second qualifying round |
| 18.09.2021 | | Chichester City | – | Maidstone United | | 1:3 (0:0) |
| Chichester |
FA Cup 2020/21, Second Qualifying Round |
| 03.10.2020 | | Hendon | – | Maidstone United | | 0:1 |
| London |
FA Cup 2019/20, First Round Proper |
| 09.11.2019 | | Maidstone United | – | Torquay Town | | 1:0 (1:0) |
| Maidstone |
FA Cup 2019/20, Fourth Qualifying Round |
| 19.10.2019 | | Maidstone United | – | Kings Langley | | 4:1 (0:0) |
| Maidstone |
FA Cup 2019/20, Third Qualifying Round |
| 05.10.2019 | | Maidstone United | – | Hitchin Town | | 2:1 (2:1) |
| Maidstone |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | Maidstone United | – | Cheshunt | | 4:1 (2:0) |
| Maidstone |
FA Cup 2018/19, First Round Proper |
| 10.11.2018 | | Maidstone United | – | Macclesfield Town | | 2:1 (0:1) |
| Maidstone |
FA Cup 2018/19, Fourth Qualifying Round |
| 20.10.2018 | | Maidstone United | – | Leyton Orient | | 2:0 (0:0) |
| Maidstone |
FA Cup 2017/18, First Round Proper |
| 04.11.2017 | | Cheltenham Town | – | Maidstone United | | 2:4 (0:3) |
| Cheltenham |
FA Cup 2017/18, Fourth Qualifying Round |
| 17.10.2017 | | Enfield Town | – | Maidstone United | | 1:3 aet
(0:0, 1:1) * |
| London |
FA Cup 2016/17, Fourth Qualifying Round |
| 15.10.2016 | | Maidstone United | – | Billericay Town | | 3:1 |
| Maidstone |
FA Cup 2015/16, Fourth Qualifying Round |
| 24.10.2015 | | Chippenham Town | – | Maidstone United | | 0:2 (0:1) |
| Chippenham |
FA Cup 2015/16, Third Qualifying Round |
| 10.10.2015 | | Maidstone United | – | Dunstable Town | | 2:0 (0:0) |
| Maidstone |
FA Cup 2015/16, Second Qualifying Round |
| 26.09.2015 | | Maidstone United | – | South Park | | 6:2 (3:2) |
| Maidstone |
FA Cup 2014/15, First Round Proper |
| 20.11.2014 | | Maidstone United | – | Stevenage | | 2:1 (1:0) * |
| Maidstone |
FA Cup 2014/15, Fourth Qualifying Round |
| 25.10.2014 | | Maidstone United | – | Welling United | | 2:1 (1:0) |
| Maidstone |
FA Cup 2014/15, Third Qualifying Round |
| 11.10.2014 | | Biggleswade Town | – | Maidstone United | | 0:2 (0:0) |
| Biggleswade |
FA Cup 2014/15, Second Qualifying Round |
| 27.09.2014 | | Maidstone United | – | Brentwood Town | | 2:1 |
| Maidstone |
FA Cup 2014/15, First Qualifying Round |
| 13.09.2014 | | Maidstone United | – | Littlehampton Town | | 10:0 |
| Maidstone |
FA Cup 2013/14, Second Qualifying Round |
| 28.09.2013 | | Merstham | – | Maidstone United | | 1:4 |
| Merstham |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Three Bridges | – | Maidstone United | | 0:1 |
| Three Bridges |
FA Cup 2012/13, Second Qualifying Round |
| 22.09.2012 | | Grays Athletic | – | Maidstone United | | 0:5 |
| London |
FA Cup 2012/13, First Qualifying Round |
| 08.09.2012 | | Chipstead | – | Maidstone United | | 0:4 |
| Chipstead |
FA Cup 2012/13, Preliminary Round |
| 25.08.2012 | | Maidstone United | – | Colliers Wood United | | 4:1 |
| Maidstone |
FA Cup 2011/12, First Qualifying Round |
| 17.09.2011 | | Banstead Athletic | – | Maidstone United | | 1:9 |
| |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Corinthian | – | Maidstone United | | 0:9 |
| |
FA Cup 2009/10, Second Qualifying Round |
| 26.09.2009 | | Harefield United | – | Maidstone United | | 0:2 |
| |
FA Cup 2009/10, First Qualifying Round |
| 12.09.2009 | | Maidstone United | – | Bedfont | | 2:1 |
| |
FA Cup 2008/09, Third Qualifying Round |
| 11.10.2008 | | Halesowen Town | – | Maidstone United | | 1:4 (1:3) |
| |
FA Cup 2008/09, Second Qualifying Round |
| 27.09.2008 | | Maidstone United | – | Fisher Athletic | | 3:2 |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Maidstone United | – | Tooting & Mitcham United | | 2:1 |
| |
FA Cup 2007/08, First Qualifying Round |
| 15.09.2007 | | Maidstone United | – | Erith & Belvedere | | 3:0 |
| |
FA Cup 2006/07, Preliminary Round |
| 03.09.2006 | | Maidstone United | – | Burgess Hill Town | | 2:1 |
| |
FA Cup 2005/06, Preliminary Round |
| 27.08.2005 | | Winchester City | – | Maidstone United | | 0:3 |
| |
FA Cup 2004/05, Second Qualifying Round |
| | | Maidstone United | – | Redbridge | | 2:1 |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Maidstone United | – | Ash United | | 2:0 * |
| |
FA Cup 2004/05, Preliminary Round |
| | | Maidstone United | – | Chichester City United | | 3:1 |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Hythe Town | – | Maidstone United | | 0:4 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Maidstone United | – | Cowes Sports | | 4:0 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Maidstone United | – | Greenwich Borough | | 1:0 * |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Newport IOW | – | Maidstone United | | 0:4 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Tonbridge Angels | – | Maidstone United | | 2:3 |
| |
FA Cup 2002/03, Extra Preliminary Round |
| | | Maidstone United | – | Ramsgate | | 1:0 * |
| |
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