FA Cup 2022/23, Extra Preliminary Round |
 | 09.08.2022 | | Harborough Town | – | Boston Town | | 3:0 (1:0) * |
| Market Harborough |
FA Cup 2021/22, Extra Preliminary Round |
| 10.08.2021 | | Boston Town | – | Sherwood Colliery | | 0:1 (0:1) * |
| Boston |
FA Cup 2020/21, Preliminary Round |
| 12.09.2020 | | Boston Town | – | Coalville Town | | 0:3 |
| Boston |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | Boston Town | – | Leek Town | | 0:4 (0:2) |
| Boston |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Staveley Miners Welfare | – | Boston Town | | 4:2 (3:0) |
| Staveley |
FA Cup 2017/18, Third Qualifying Round |
| 30.09.2017 | | Boston Town | – | Hyde | | 2:3 (1:1) |
| Boston |
FA Cup 2016/17, Extra Preliminary Round |
| 06.08.2016 | | Boston Town | – | Wisbech Town | | 1:4 |
| Boston |
FA Cup 2015/16, Extra Preliminary Round |
| 15.08.2015 | | Deeping Rangers | – | Boston Town | | 6:1 |
| Market Deeping |
FA Cup 2014/15, First Qualifying Round |
| 13.09.2014 | | King's Lynn Town | – | Boston Town | | 7:0 (2:0) |
| King's Lynn |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Boston Town | – | Dereham Town | | 1:3 |
| Boston |
FA Cup 2012/13, Extra Preliminary Round |
| 11.08.2012 | | Boston Town | – | Quorn | | 0:2 |
| |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Heanor Town | – | Boston Town | | 2:1 |
| |
FA Cup 2010/11, Preliminary Round |
| 31.08.2010 | | Boston Town | – | Lincoln United | | 2:4 * |
| |
FA Cup 2009/10, First Qualifying Round |
| 12.09.2009 | | Bourne Town | – | Boston Town | | 3:1 |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Bury Town | – | Boston Town | | 3:1 |
| |
FA Cup 2007/08, First Qualifying Round |
| 15.09.2007 | | Boston Town | – | Soham Town Rangers | | 0:4 |
| |
FA Cup 2006/07, Preliminary Round |
| 05.09.2006 | | Boston Town | – | Belper Town | | 1:2 * |
| |
FA Cup 2005/06, Preliminary Round |
| 27.08.2005 | | Long Eaton United | – | Boston Town | | 4:2 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Boston Town | – | Stone Dominoes | | 1:2 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Boston Town | – | Belper Town | | 0:1 * |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Sutton Coldfield Town | – | Boston Town | | 2:0 * |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Stafford Town | – | Boston Town | | 2:1 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Boston Town | – | Leek County School Old Boys | | 2:3 |
| |
FA Cup 1999/00, First Qualifying Round |
| | | Boston Town | – | Northampton Spencer | | 4:6 * |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Boston Town | – | Eastwood Town | | 0:5 |
| |
FA Cup 1997/98, Preliminary Round |
| | | Boston Town | – | Stapenhill | | 0:2 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Grantham Town | – | Boston Town | | 2:0 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | King's Lynn | – | Boston Town | | 5:1 |
| |
FA Cup 1994/95, Second Qualifying Round |
| | | Boston Town | – | Billericay Town | | 1:2 |
| |
FA Cup 1993/94, Preliminary Round |
| | | Bishop's Stortford | – | Boston | | 4:0 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Boston | – | Stourbridge | | 3:4 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Boston | – | Harrogate Town | | 2:3 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Boston | – | Bromsgrove Rovers | | 0:3 |
| |
FA Cup 1989/90, Second Qualifying Round |
| | | Boston | – | Grantham Town | | 1:2 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Boston | – | Witton Albion | | 0:2 * |
| |
FA Cup 1985/86, Preliminary Round |
| | | Boston | – | Atherstone United | | 0:2 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Boston | – | Matlock Town | | 1:4 |
| |
FA Cup 1983/84, Preliminary Round |
| | | Boston | – | Gresley Rovers | | 1:3 |
| |
FA Cup 1982/83, Preliminary Round |
| | | Boston | – | Bourne Town | | 1:3 |
| |
FA Cup 1981/82, Second Qualifying Round |
| | | Boston | – | North Ferriby United | | 1:2 |
| |
FA Cup 1980/81, Third Qualifying Round |
| | | Boston | – | Corby Town | | 0:1 |
| |
FA Cup 1979/80, Fourth Qualifying Round |
| | | AP Leamington | – | Boston | | 1:0 * |
| |
FA Cup 1978/79, Second Qualifying Round |
| | | Boston | – | Grantham | | 0:1 |
| |
FA Cup 1977/78, Third Qualifying Round |
| | | Arnold | – | Boston | | 2:0 |
| |
FA Cup 1976/77, First Round Proper |
| 20.11.1976 | | Barnsley | – | Boston | | 3:1 |
| Barnsley |
FA Cup 1975/76, Preliminary Round |
| | | Boston | – | Corby Town | | 1:2 * |
| |
FA Cup 1974/75, Third Qualifying Round |
| | | King's Lynn | – | Boston | | 1:0 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Boston | – | Holbeach United | | 0:2 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Corby Town | – | Boston | | 3:1 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Boston | – | Bourne Town | | 1:5 |
| |
FA Cup 1970/71, Third Qualifying Round |
| | | Boston | – | Boston United | | 0:4 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Boston | – | King's Lynn | | 2:3 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Louth United | – | Boston | | 3:1 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Louth United | – | Boston | | 4:0 * |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | King's Lynn | – | Boston | | 2:1 |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Grantham | – | Boston | | 7:0 |
| |
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