FA Cup 2023/24, First Qualifying Round |
 | 02.09.2023 | | Reading City | – | Shaftesbury | | 3:1 (2:0) |
| Reading |
FA Cup 2023/24, Preliminary Round |
| 19.08.2023 | | Shaftesbury | – | Hamble Club | | 5:2 (1:1) |
| Shaftesbury |
FA Cup 2023/24, Extra Preliminary Round |
| 05.08.2023 | | Brislington | – | Shaftesbury | | 0:1 (0:0) |
| Brislington |
FA Cup 2022/23, Extra Preliminary Round |
| 17.08.2022 | | Camberley Town | – | Shaftesbury | | 2:1 (0:1) * |
| Camberley |
FA Cup 2022/23, Extra Preliminary Round |
| 09.08.2022 | | Shaftesbury | – | Camberley Town | | 2:2 (2:0) |
| Shaftesbury |
FA Cup 2021/22, Second qualifying round |
| 18.09.2021 | | Shaftesbury | – | Bath City | | 0:1 (0:0) |
| Shaftesbury |
FA Cup 2021/22, First Qualifying Round |
| 07.09.2021 | | Shaftesbury | – | Highworth Town | | 4:2 (2:1) * |
| Shaftesbury |
FA Cup 2021/22, First Qualifying Round |
| 04.09.2021 | | Highworth Town | – | Shaftesbury | | 1:1 (0:1) |
| Highworth |
FA Cup 2021/22, Preliminary Round |
| 21.08.2021 | | Shaftesbury | – | AFC Stoneham | | 6:1 (4:1) |
| Shaftesbury |
FA Cup 2021/22, Extra Preliminary Round |
| 07.08.2021 | | Amesbury Town | – | Shaftesbury | | 1:4 (1:1) |
| Amesbury |
FA Cup 2020/21, Extra Preliminary Round |
| 01.09.2020 | | Shaftesbury | – | Fawley | | 2:2,
pen. 5:6 |
| Shaftesbury |
FA Cup 2019/20, Extra Preliminary Round |
| 10.08.2019 | | Shaftesbury | – | Knaphill | | 1:4 (1:4) |
| Shaftesbury |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Shaftesbury | – | Poole Town | | 0:1 (0:1) |
| Shaftesbury |
FA Cup 2018/19, Preliminary Round |
| 25.08.2018 | | Barnstaple Town | – | Shaftesbury | | 0:1 (0:1) |
| Barnstaple |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Wells City | – | Shaftesbury | | 2:5 (1:4) |
| Wells |
FA Cup 2017/18, Preliminary Round |
| 19.08.2017 | | Tavistock | – | Shaftesbury | | 2:1 |
| Tavistock |
FA Cup 2017/18, Extra Preliminary Round |
| 09.08.2017 | | Exmouth Town | – | Shaftesbury | | 1:2 aet
(1:1) * |
| Exmouth |
FA Cup 2017/18, Extra Preliminary Round |
| 05.08.2017 | | Shaftesbury | – | Exmouth Town | | 0:0 |
| Shaftesbury |
FA Cup 2009/10, Extra Preliminary Round |
| 15.08.2009 | | Alresford Town | – | Shaftesbury | | 8:0 |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 20.08.2008 | | Falmouth Town | – | Shaftesbury | | 4:2 * |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 16.08.2008 | | Shaftesbury | – | Falmouth Town | | 2:2 |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 21.08.2007 | | Shaftesbury | – | Liskeard Athletic | | 0:3 * |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 18.08.2007 | | Liskeard Athletic | – | Shaftesbury | | 2:2 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Portland United | – | Shaftesbury | | 11:1 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Portland United | – | Shaftesbury | | 3:1 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Shaftesbury | – | Poole Town | | 1:4 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Shaftesbury | – | Alton Town | | 1:5 |
| |
FA Cup 1950/51, Extra Preliminary Round |
| | | Shaftesbury | – | Bournemouth Gasworks Athletic | | 2:1 |
| |
