FA Cup 2023/24, Second Qualifying Round |
 | 16.09.2023 |  | Highworth Town | – | Weymouth | | 1:3 (0:1) |
| Highworth |
FA Cup 2022/23, Extra Preliminary Round |
| 06.08.2022 | | Highworth Town | – | Reading City | | 0:2 (0:0) |
| Highworth |
FA Cup 2021/22, First Qualifying Round |
| 07.09.2021 | | Shaftesbury | – | Highworth Town | | 4:2 (2:1) * |
| Shaftesbury |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | Tavistock | – | Highworth Town | | 4:0 (1:0) |
| Tavistock |
FA Cup 2018/19, Extra Preliminary Round |
| 15.08.2018 | | Highworth Town | – | Windsor | | 1:2 (0:2) * |
| Highworth |
FA Cup 2017/18, Preliminary Round |
| 20.08.2017 | | Highworth Town | – | Marlow | | 2:3 (0:1) |
| Highworth |
FA Cup 2016/17, Second Qualifying Round |
| 17.09.2016 | | Havant & Waterlooville | – | Highworth Town | | 5:1 |
| Havant |
FA Cup 2015/16, Preliminary Round |
| 29.08.2015 | | Farnham Town | – | Highworth Town | | 4:2 |
| Thame |
FA Cup 2014/15, Preliminary Round |
| 30.08.2014 | | Blackfield & Langley | – | Highworth Town | | 4:0 |
| Blackfield |
FA Cup 2013/14, Extra Preliminary Round |
| 17.08.2013 | | Bournemouth | – | Highworth Town | | 3:1 |
| Bournemouth |
FA Cup 2012/13, First Qualifying Round |
| 07.09.2012 | | Wootton Bassett Town | – | Highworth Town | | 3:1 |
| Wootton Bassett |
FA Cup 2011/12, Extra Preliminary Round |
| 21.08.2011 | | Highworth Town | – | Odd Down | | 1:4 |
| |
FA Cup 2010/11, First Qualifying Round |
| 14.09.2010 | | Salisbury City | – | Highworth Town | | 5:0 * |
| |
FA Cup 2009/10, First Qualifying Round |
| 12.09.2009 | | Highworth Town | – | Abingdon United | | 0:3 |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 16.08.2008 | | Aylesbury Vale | – | Highworth Town | | 4:2 aet |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 21.08.2007 | | Wootton Bassett Town | – | Highworth Town | | 2:1 * |
| |
FA Cup 2006/07, Extra Preliminary Round |
| 19.08.2006 | | Witney United | – | Highworth Town | | 2:1 |
| |
FA Cup 2005/06, Second Qualifying Round |
| 24.09.2005 | | Highworth Town | – | Tiverton Town | | 1:7 |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Highworth Town | – | Bishop's Cleeve | | 3:5 |
| |
FA Cup 2003/04, Third Qualifying Round |
| | | Lymington & New Milton | – | Highworth Town | | 2:0 (0:0) |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Highworth Town | – | Cinderford Town | | 2:3 |
| |
FA Cup 2001/02, Second Qualifying Round |
| | | Highworth Town | – | Weymouth | | 0:3 |
| |
