FA Cup 2020/21, Extra Preliminary Round |
 | 02.09.2020 | | Blackstones | – | Boston Town | | 2:3 |
| Stamford |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | Kirby Muxloe | – | Boston Town | | 0:1 (0:1) |
| Kirby Muxloe |
FA Cup 2019/20, Preliminary Round |
| 27.08.2019 | | Leicester Nirvana | – | Boston Town | | 0:1 (0:1) * |
| Leicester |
FA Cup 2019/20, Extra Preliminary Round |
| 13.08.2019 | | Boston Town | – | Mulbarton Wanderers | | 4:2 (2:1) * |
| Boston |
FA Cup 2017/18, Second Qualifying Round |
| 16.09.2017 | | Dereham Town | – | Boston Town | | 1:2 (1:0) |
| Dereham |
FA Cup 2017/18, First Qualifying Round |
| 02.09.2017 | | Boston Town | – | Hednesford Town | | 2:0 (2:0) |
| Boston |
FA Cup 2017/18, Preliminary Round |
| 19.08.2017 | | Boston Town | – | Carlton Town | | 3:2 (3:1) |
| Boston |
FA Cup 2014/15, Preliminary Round |
| 30.08.2014 | | Holbeach United | – | Boston Town | | 2:4 |
| Holbeach |
FA Cup 2014/15, Extra Preliminary Round |
| 20.08.2014 | | Walsham-le-Willows | – | Boston Town | | 1:3 (1:1) * |
| Walsham-le-Willows |
FA Cup 2013/14, Extra Preliminary Round |
| 17.08.2013 | | Boston Town | – | Great Yarmouth Town | | 3:2 |
| Boston |
FA Cup 2011/12, Extra Preliminary Round |
| 20.08.2011 | | Glossop North End | – | Boston Town | | 2:4 |
| |
FA Cup 2010/11, Extra Preliminary Round |
| 14.08.2010 | | Gedling Town | – | Boston Town | | 2:4 |
| |
FA Cup 2009/10, Preliminary Round |
| 29.08.2009 | | Shirebrook Town | – | Boston Town | | 0:2 |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 16.08.2009 | | Hinckley Downes | – | Boston Town | | 1:4 |
| |
FA Cup 2008/09, Preliminary Round |
| 30.08.2008 | | Fakenham Town | – | Boston Town | | 0:4 |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 16.08.2008 | | Long Melford | – | Boston Town | | 2:5 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Ely City | – | Boston Town | | 0:1 |
| |
FA Cup 2006/07, Extra Preliminary Round |
| 19.08.2006 | | Staveley Miners Welfare | – | Boston Town | | 1:5 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Staveley Miners Welfare | – | Boston Town | | 0:1 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Boston Town | – | Borrowash Victoria | | 1:0 * |
| |
FA Cup 1999/00, Preliminary Round |
| | | Boston Town | – | Boldmere St Michaels | | 1:0 |
| |
FA Cup 1998/99, Preliminary Round |
| | | Boston Town | – | Blackstones | | 2:0 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Lowestoft Town | – | Boston Town | | 1:2 |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Boston Town | – | Bishop's Stortford | | 5:2 * |
| |
FA Cup 1995/96, Preliminary Round |
| | | Newmarket Town | – | Boston Town | | 0:1 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Boston Town | – | Basildon United | | 1:0 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Bury Town | – | Boston Town | | 0:4 |
| |
FA Cup 1992/93, Preliminary Round |
| | | Boston | – | Banbury United | | 4:1 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Boston | – | King's Lynn | | 2:0 |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Dudley Town | – | Boston | | 0:1 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Boston | – | Sutton Town | | 2:0 |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Gainsborough Trinity | – | Boston | | 1:2 * |
| |
FA Cup 1981/82, Preliminary Round |
| | | Boston | – | Holbeach United | | 5:0 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Holbeach United | – | Boston | | 0:3 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Boston | – | Spalding United | | 6:1 |
| |
FA Cup 1979/80, Third Qualifying Round |
| | | Boston | – | Skegness Town | | 1:0 * |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | North Ferriby United | – | Boston | | 1:3 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Bourne Town | – | Boston | | 0:2 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Barton Town | – | Boston | | 1:3 |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Holbeach United | – | Boston | | 0:1 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Parson Drove United | – | Boston | | 0:2 |
| |
FA Cup 1976/77, Fourth Qualifying Round |
| | | Boston | – | Bangor City | | 1:0 |
| |
FA Cup 1976/77, Third Qualifying Round |
| | | Boston | – | Stamford | | 1:0 |
| |
FA Cup 1976/77, Second Qualifying Round |
| | | Boston | – | King's Lynn | | 2:1 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Boston | – | Bourne Town | | 2:0 |
| |
FA Cup 1974/75, Second Qualifying Round |
| | | Skegness Town | – | Boston | | 1:2 * |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Boston | – | Spalding United | | 4:0 |
| |
FA Cup 1970/71, Second Qualifying Round |
| | | Boston | – | Spalding United | | 3:0 * |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Louth United | – | Boston | | 0:1 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Louth United | – | Boston | | 0:3 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Stamford | – | Boston | | 0:1 |
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