FA Cup 2023/24, Second Qualifying Round |
 | 19.09.2023 |  | Winchester City | – | Reading City | | 4:1 (1:1) * |
| Winchester |
FA Cup 2023/24, First Qualifying Round |
| 02.09.2023 | | Winchester City | – | Evesham United | | 3:2 (1:0) |
| Winchester |
FA Cup 2022/23, First Qualifying Round |
| 02.09.2022 | | Baffins Milton Rovers | – | Winchester City | | 1:5 (0:2) |
| Portsmouth |
FA Cup 2020/21, First Qualifying Round |
| 22.09.2020 | | Winchester City | – | Clevedon Town | | 3:2 |
| Winchester |
FA Cup 2020/21, Preliminary Round |
| 12.09.2020 | | Winchester City | – | Corsham Town | | 2:0 |
| Winchester |
FA Cup 2019/20, Preliminary Round |
| 03.09.2019 | | AFC Stoneham | – | Winchester City | | 1:3 (0:2) * |
| Eastleigh |
FA Cup 2018/19, Third Qualifying Round |
| 06.10.2018 | | Winchester City | – | Cirencester Town | | 3:0 (2:0) |
| Winchester |
FA Cup 2018/19, Second Qualifying Round |
| 22.09.2018 |  | Merthyr Town | – | Winchester City | | 1:4 (0:2) |
| Merthyr Tydfil |
FA Cup 2018/19, First Qualifying Round |
| 11.09.2018 | | Winchester City | – | Frome Town | | 2:1 aet
(1:1, 1:1) * |
| Winchester |
FA Cup 2018/19, Preliminary Round |
| 25.08.2018 | | Winchester City | – | Bournemouth | | 1:0 (0:0) |
| Winchester |
FA Cup 2017/18, Preliminary Round |
| 19.08.2017 | | Bracknell Town | – | Winchester City | | 0:4 (0:2) |
| Bracknell Larges Lane |
FA Cup 2016/17, Second Qualifying Round |
| 17.09.2016 | | Winchester City | – | Truro City | | 4:0 |
| Winchester |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Winchester City | – | Street | | 4:2 |
| Winchester |
FA Cup 2016/17, Preliminary Round |
| 20.08.2016 | | United Services Portsmouth | – | Winchester City | | 0:3 |
| Portsmouth |
FA Cup 2015/16, First Qualifying Round |
| 12.09.2015 | | Swindon Supermarine | – | Winchester City | | 0:4 (0:1) |
| Swindon |
FA Cup 2015/16, Preliminary Round |
| 29.08.2015 | | Winchester City | – | Wincanton Town | | 5:1 |
| Winchester |
FA Cup 2014/15, Second Qualifying Round |
| 30.09.2014 | | Newport Isle of Wight | – | Winchester City | | 0:1 (0:1) * |
| Newport |
FA Cup 2014/15, First Qualifying Round |
| 13.09.2014 | | Winchester City | – | Bemerton Heath Harlequins | | 3:0 |
| Winchester |
FA Cup 2014/15, Preliminary Round |
| 30.08.2014 | | Bashley | – | Winchester City | | 0:2 |
| Bashley |
FA Cup 2014/15, Extra Preliminary Round |
| 16.08.2014 | | Lymington Town | – | Winchester City | | 2:5 |
| Lymington |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Winchester City | – | Swindon Supermarine | | 3:0 (2:0) |
| Winchester |
FA Cup 2013/14, Extra Preliminary Round |
| 16.08.2013 | | Alresford Town | – | Winchester City | | 0:3 |
| New Alresford |
FA Cup 2012/13, Preliminary Round |
| 25.08.2012 | | Winchester City | – | Alton Town | | 3:0 |
| Winchester |
FA Cup 2011/12, Extra Preliminary Round |
| 20.08.2011 | | Winchester City | – | Ringwood Town | | 5:0 |
| |
FA Cup 2008/09, Preliminary Round |
| 30.08.2008 | | Flackwell Heath | – | Winchester City | | 3:4 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Winchester City | – | Chatham Town | | 4:3 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Corinthian-Casuals | – | Winchester City | | 0:3 |
| |
FA Cup 2004/05, Extra Preliminary Round |
| | | Lordswood | – | Winchester City | | 1:4 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Metropolitan Police | – | Winchester City | | 2:3 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Banstead Athletic | – | Winchester City | | 0:2 |
| |
FA Cup 1956/57, Second Qualifying Round |
| | | Winchester City | – | Gosport Borough Athletic | | 3:0 |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Chichester City | – | Winchester City | | 1:3 * |
| |
FA Cup 1954/55, Third Qualifying Round |
| | | Winchester City | – | Gosport Borough Athletic | | 3:0 |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Basingstoke Town | – | Winchester City | | 0:2 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Winchester City | – | Gosport Borough Athletic | | 1:0 |
| |
FA Cup 1948/49, Extra Preliminary Round |
| | | Botley | – | Winchester City | | 1:3 |
| |
