FA Cup 2023/24, Extra Preliminary Round |
 | 08.08.2023 |  | Anstey Nomads | – | Boston Town | | 2:2 aet
(2:2, 2:2),
pen. 5:3 * |
| Anstey |
FA Cup 2023/24, Extra Preliminary Round |
| 05.08.2023 | | Boston Town | – | Anstey Nomads | | 0:0 |
| Boston |
FA Cup 2022/23, Extra Preliminary Round |
| 06.08.2022 | | Boston Town | – | Harborough Town | | 0:0 |
| Boston |
FA Cup 2021/22, Extra Preliminary Round |
| 07.08.2021 | | Sherwood Colliery | – | Boston Town | | 1:1 (0:0) |
| Mansfield Woodhouse |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Boston Town | – | Leicester Nirvana | | 0:0 |
| Boston |
FA Cup 2019/20, Extra Preliminary Round |
| 10.08.2019 | | Mulbarton Wanderers | – | Boston Town | | 0:0 |
| Mulbarton |
FA Cup 2017/18, Extra Preliminary Round |
| 15.08.2017 | | Radford | – | Boston Town | | 2:2 aet
(0:0, 1:1),
pen. 3:4 * |
| Nottingham |
FA Cup 2017/18, Extra Preliminary Round |
| 05.08.2017 | | Boston Town | – | Radford | | 2:2 |
| Boston |
FA Cup 2014/15, Extra Preliminary Round |
| 16.08.2014 | | Boston Town | – | Walsham-le-Willows | | 1:1 |
| Boston |
FA Cup 2010/11, Preliminary Round |
| 28.08.2010 | | Lincoln United | – | Boston Town | | 2:2 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Belper Town | – | Boston Town | | 2:2 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Belper Town | – | Boston Town | | 1:1 |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Boston Town | – | Sutton Coldfield Town | | 1:1 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Boston Town | – | Borrowash Victoria | | 2:2 |
| |
FA Cup 1999/00, First Qualifying Round |
| | | Northampton Spencer | – | Boston Town | | 1:1 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Bishop's Stortford | – | Boston Town | | 2:2 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Witton Albion | – | Boston | | 0:0 |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Boston | – | Gainsborough Trinity | | 0:0 |
| |
FA Cup 1979/80, Fourth Qualifying Round |
| | | Boston | – | AP Leamington | | 2:2 |
| |
FA Cup 1979/80, Third Qualifying Round |
| | | Boston | – | Skegness Town | | 2:2 aet * |
| |
FA Cup 1979/80, Third Qualifying Round |
| | | Skegness Town | – | Boston | | 1:1 |
| |
FA Cup 1975/76, Preliminary Round |
| | | Corby Town | – | Boston | | 0:0 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Boston | – | Skegness Town | | 1:1 |
| |
FA Cup 1970/71, Second Qualifying Round |
| | | Spalding United | – | Boston | | 2:2 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Boston | – | Louth United | | 0:0 |
| |
