FA Cup 2023/24, Extra Preliminary Round |
 | 05.08.2023 |  | Cowes Sports | – | Melksham Town | | 2:4 (0:1) |
| Cowes |
FA Cup 2022/23, Preliminary Round |
| 24.08.2022 | | Larkhall Athletic | – | Cowes Sports | | 4:2 aet
(1:2, 2:2) * |
| Bath |
FA Cup 2021/22, Extra Preliminary Round |
| 07.08.2021 | | Blackfield & Langley | – | Cowes Sports | | 5:1 (3:0) |
| Blackfield |
FA Cup 2020/21, First Qualifying Round |
| 22.09.2020 | | Cowes Sports | – | Weston-super-Mare | | 0:5 |
| Cowes |
FA Cup 2019/20, Extra Preliminary Round |
| 10.08.2019 | | Cowes Sports | – | Lymington Town | | 0:4 (0:1) |
| Cowes |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Bemerton Heath Harlequins | – | Cowes Sports | | 1:0 (0:0) |
| Bemerton |
FA Cup 2017/18, Extra Preliminary Round |
| 05.08.2017 | | Bracknell Town | – | Cowes Sports | | 3:0 |
| Bracknell Larges Lane |
FA Cup 2016/17, Extra Preliminary Round |
| 06.08.2016 | | Cowes Sports | – | Brislington | | 0:3 |
| Cowes |
FA Cup 2015/16, Preliminary Round |
| 29.08.2015 | | Cowes Sports | – | Wimborne Town | | 0:5 |
| Cowes |
FA Cup 2014/15, Preliminary Round |
| 30.08.2014 | | Cowes Sports | – | Yate Town | | 0:1 |
| Cowes |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Yate Town | – | Cowes Sports | | 2:1 |
| Yate |
FA Cup 2012/13, Extra Preliminary Round |
| 12.08.2012 | | Christchurch | – | Cowes Sports | | 5:0 |
| |
FA Cup 2011/12, Extra Preliminary Round |
| 20.08.2011 | | Cowes Sports | – | Newport Isle of Wight | | 1:4 |
| |
FA Cup 2010/11, Extra Preliminary Round |
| 13.08.2010 | | Ringwood Town | – | Cowes Sports | | 5:0 |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 15.08.2009 | | New Milton Town | – | Cowes Sports | | 4:1 |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Fleet Town | – | Cowes Sports | | 3:0 |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 18.08.2007 | | VT | – | Cowes Sports | | 5:0 |
| |
FA Cup 2006/07, First Qualifying Round |
| 16.09.2006 | | Cowes Sports | – | Lymington & New Milton | | 1:2 |
| |
FA Cup 2005/06, First Qualifying Round |
| 10.09.2005 | | Margate | – | Cowes Sports | | 4:0 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Abingdon United | – | Cowes Sports | | 2:1 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Maidstone United | – | Cowes Sports | | 4:0 |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Herne Bay | – | Cowes Sports | | 3:2 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Cowes Sports | – | Greenwich Borough | | 0:3 * |
| |
FA Cup 2000/01, First Qualifying Round |
| | | Horsham YMCA | – | Cowes Sports | | 6:0 * |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Slough Town | – | Cowes Sports | | 3:1 |
| |
FA Cup 1998/99, Preliminary Round |
| | | Cowes Sports | – | Dorking | | 1:2 |
| |
