FA Cup 2023/24, Third Qualifying Round |
 | 30.09.2023 |  | Winchester City | – | Maidstone United | | 0:2 (0:0) |
| Winchester |
FA Cup 2022/23, Second Qualifying Round |
| 17.09.2022 | | Winchester City | – | Weymouth | | 1:3 (1:3) |
| Winchester |
FA Cup 2021/22, Preliminary Round |
| 21.08.2021 | | Winchester City | – | Chichester City | | 1:3 (0:2) |
| Winchester |
FA Cup 2020/21, Second Qualifying Round |
| 03.10.2020 | | Bath City | – | Winchester City | | 3:2 |
| Bath |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | Winchester City | – | Taunton Town | | 0:3 (0:1) |
| Winchester |
FA Cup 2018/19, Fourth Qualifying Round |
| 20.10.2018 | | Torquay United | – | Winchester City | | 4:1 (3:0) |
| Torquay |
FA Cup 2017/18, First Qualifying Round |
| 02.09.2017 | | Paulton Rovers | – | Winchester City | | 1:0 (1:0) |
| Paulton |
FA Cup 2016/17, Third Qualifying Round |
| 01.10.2016 | | Harrow Borough | – | Winchester City | | 2:1 |
| London |
FA Cup 2015/16, Second Qualifying Round |
| 29.09.2015 | | Maidenhead United | – | Winchester City | | 4:2 (2:1) * |
| Maidenhead |
FA Cup 2014/15, Third Qualifying Round |
| 11.10.2014 | | Concord Rangers | – | Winchester City | | 3:2 (2:1) |
| Canvey Island |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Winchester City | – | Mangotsfield United | | 1:2 |
| Winchester |
FA Cup 2012/13, First Qualifying Round |
| 08.09.2012 | | Winchester City | – | Yate Town | | 1:2 (0:1) |
| Winchester |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Winchester City | – | Blackfield & Langley | | 1:3 |
| |
FA Cup 2010/11, Extra Preliminary Round |
| 14.08.2010 | | Hallen | – | Winchester City | | 4:1 |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 15.08.2009 | | Winchester City | – | Bemerton Heath Harlequins | | 1:4 |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Winchester City | – | AFC Totton | | 0:3 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Winchester City | – | Moneyfields | | 0:2 |
| |
FA Cup 2005/06, Preliminary Round |
| 27.08.2005 | | Winchester City | – | Maidstone United | | 0:3 |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Tonbridge Angels | – | Winchester City | | 2:1 |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Chippenham Town | – | Winchester City | | 2:1 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Winchester City | – | Basingstoke Town | | 0:3 * |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Winchester City | – | Fareham Town | | 1:4 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Andover | – | Winchester City | | 4:1 |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Winchester City | – | Cowes | | 0:1 * |
| |
FA Cup 1956/57, Third Qualifying Round |
| | | Winchester City | – | Andover | | 0:2 |
| |
FA Cup 1955/56, Second Qualifying Round |
| | | Andover | – | Winchester City | | 2:1 |
| |
FA Cup 1954/55, Fourth Qualifying Round |
| | | Winchester City | – | Dorchester Town | | 0:1 |
| |
FA Cup 1953/54, Second Qualifying Round |
| | | Newport IOW | – | Winchester City | | 7:0 |
| |
FA Cup 1952/53, Second Qualifying Round |
| | | Winchester City | – | Newport IOW | | 1:3 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Alton Town | – | Winchester City | | 3:1 * |
| |
FA Cup 1950/51, Preliminary Round |
| | | Newport IOW | – | Winchester City | | 5:1 |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Winchester City | – | Newport IOW | | 1:2 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Longfleet St Mary's | – | Winchester City | | 4:2 |
| |
FA Cup 1947/48, Extra Preliminary Round |
| | | Winchester City | – | Salisbury | | 0:1 |
| |
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