FA Cup 2019/20, Preliminary Round |
 | 25.08.2019 |  | Dunstable Town | – | Shortwood United | | 4:1 (2:0) |
| Dunstable |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Ardley United | – | Shortwood United | | 7:0 (3:0) |
| Ardley |
FA Cup 2017/18, Preliminary Round |
| 19.08.2017 | | Colney Heath | – | Shortwood United | | 2:0 (1:0) |
| Colney Heath |
FA Cup 2016/17, Preliminary Round |
| 20.08.2016 | | Shortwood United | – | Ashford Town | | 0:2 |
| Nailsworth |
FA Cup 2015/16, Second Qualifying Round |
| 26.09.2015 | | Oxford City | – | Shortwood United | | 3:1 (1:0) |
| Marston |
FA Cup 2014/15, Third Qualifying Round |
| 14.10.2014 | | Shortwood United | – | Bath City | | 1:3 (0:2) * |
| Nailsworth |
FA Cup 2013/14, First Round Proper |
| 11.11.2013 | | Shortwood United | – | Port Vale | | 0:4 (0:2) |
| Nailsworth |
FA Cup 2012/13, Preliminary Round |
| 26.08.2012 | | Highworth Town | – | Shortwood United | | 1:0 |
| Highworth |
FA Cup 2011/12, Preliminary Round |
| 06.09.2011 | | Bishop Sutton | – | Shortwood United | | 4:1 * |
| |
FA Cup 2010/11, Preliminary Round |
| 31.08.2010 | | Shortwood United | – | Totton & Eling | | 1:3 aet * |
| |
FA Cup 2009/10, First Qualifying Round |
| 15.09.2009 | | Witney United | – | Shortwood United | | 2:1 * |
| |
FA Cup 2008/09, Second Qualifying Round |
| 30.09.2008 | | Shortwood United | – | Havant & Waterlooville | | 0:1 * |
| |
FA Cup 2007/08, Third Qualifying Round |
| 13.10.2007 | | Maidenhead United | – | Shortwood United | | 3:0 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Shortwood United | – | Truro City | | 0:5 |
| |
FA Cup 2005/06, Preliminary Round |
| 27.08.2005 | | Shortwood United | – | Bodmin Town | | 2:3 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Mangotsfield United | – | Shortwood United | | 3:2 |
| |
FA Cup 2003/04, Extra Preliminary Round |
| | | Highworth Town | – | Shortwood United | | 3:1 |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Bemerton Heath Harlequins | – | Shortwood United | | 2:1 |
| |
FA Cup 2001/02, First Qualifying Round |
| | | St Blazey | – | Shortwood United | | 5:0 |
| |
FA Cup 2000/01, Second Qualifying Round |
| | | Tiverton Town | – | Shortwood United | | 2:0 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Shortwood United | – | Weston-Super-Mare | | 1:3 |
| |
FA Cup 1992/93, Preliminary Round |
| | | Shortwood United | – | Brockenhurst | | 0:4 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Gloucester City | – | Shortwood United | | 4:1 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Shortwood United | – | St Blazey | | 1:2 |
| |
FA Cup 1989/90, Second Qualifying Round |
| | | Worcester City | – | Shortwood United | | 3:0 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Maesteg Park Athletic | – | Shortwood United | | 1:0 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Shortwood United | – | Waterlooville | | 1:6 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Shortwood United | – | Melksham Town | | 2:3 |
| |
FA Cup 1985/86, Preliminary Round |
| | | Sharpness | – | Shortwood United | | 5:1 * |
| |
