FA Cup 2023/24, Fourth Qualifying Round |
 | 14.10.2023 |  | Worksop Town | – | Boston United | | 3:2 (1:1) |
| Retford |
FA Cup 2021/22, Fourth Qualifying Round |
| 19.10.2021 | | Stratford Town | – | Boston United | | 3:2 (1:0) * |
| Stratford-upon-Avon |
FA Cup 2019/20, Second Round Proper |
| 16.12.2019 | | Boston United | – | Rochdale | | 1:2 (0:1) * |
| Boston |
FA Cup 2018/19, Second Qualifying Round |
| 22.09.2018 | | Boston United | – | Peterborough Sports | | 0:2 (0:2) |
| Boston |
FA Cup 2017/18, Fourth Qualifying Round |
| 17.10.2017 | | Boston United | – | Chorley | | 3:4 aet
(1:0, 3:3) * |
| Boston |
FA Cup 2016/17, Third Qualifying Round |
| 01.10.2016 | | Kettering Town | – | Boston United | | 2:0 |
| Kettering |
FA Cup 2015/16, Second Qualifying Round |
| 26.09.2015 | | Gainsborough Trinity | – | Boston United | | 2:0 |
| Gainsborough |
FA Cup 2014/15, Third Qualifying Round |
| 11.10.2014 | | Leek Town | – | Boston United | | 2:0 (0:0) |
| Leek |
FA Cup 2013/14, Third Qualifying Round |
| 12.10.2013 | | Brackley Town | – | Boston United | | 2:0 (1:0) |
| Brackley |
FA Cup 2012/13, Fourth Qualifying Round |
| 20.10.2012 | | Boston United | – | Altrincham | | 1:3 (1:0) |
| Boston |
FA Cup 2011/12, Second Qualifying Round |
| 04.10.2011 | | Kidsgrove Athletic | – | Boston United | | 2:0 * |
| Kidsgrove |
FA Cup 2010/11, Second Qualifying Round |
| 25.09.2010 | | Boston United | – | Worcester City | | 2:3 |
| |
FA Cup 2009/10, Second Qualifying Round |
| 26.09.2009 | | Lowestoft Town | – | Boston United | | 1:0 |
| |
FA Cup 2008/09, Fourth Qualifying Round |
| 25.10.2008 | | Boston United | – | Cambridge United | | 2:3 |
| |
FA Cup 2007/08, Fourth Qualifying Round |
| 27.10.2007 | | Workington | – | Boston United | | 1:0 (0:0) |
| |
FA Cup 2006/07, First Round Proper |
| 11.11.2006 | | AFC Bournemouth | – | Boston United | | 4:0 (2:0) |
| Bournemouth |
FA Cup 2005/06, Second Round Proper |
| 04.12.2005 | | Boston United | – | Doncaster Rovers | | 1:2 (0:1) |
| Boston |
FA Cup 2004/05, Third Round Proper |
| 19.01.2005 | | Boston United | – | Hartlepool United | | 0:1 (0:0) |
| |
FA Cup 2003/04, First Round Proper |
| 08.11.2003 | | Macclesfield Town | – | Boston United | | 3:0 (1:0) |
| Macclesfield |
FA Cup 2002/03, First Round Proper |
| 16.11.2002 | | Northampton Town | – | Boston United | | 3:2 (2:0) |
| Northampton |
FA Cup 2001/02, Fourth Qualifying Round |
| | | Boston United | – | Brigg Town | | 0:1 (0:1) |
| |
FA Cup 2000/01, Fourth Qualifying Round |
| | | Burton Albion | – | Boston United | | 3:2 (0:1) * |
| |
FA Cup 1999/00, Fourth Qualifying Round |
| | | Boston United | – | Kingstonian | | 0:3 (0:1) * |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Congleton Town | – | Boston United | | 1:0 |
| |
FA Cup 1997/98, First Round Proper |
| 15.11.1997 | | Ilkeston Town | – | Boston United | | 2:1 (1:0) |
| |
FA Cup 1996/97, Second Round Proper |
| 07.12.1996 | | Chester City | – | Boston United | | 1:0 (1:0) |
| Chester |
FA Cup 1995/96, First Qualifying Round |
| | | Boston United | – | Wisbech Town | | 1:2 |
| |
FA Cup 1994/95, Third Qualifying Round |
| | | Heybridge Swifts | – | Boston United | | 3:0 |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Boston United | – | Canvey Island | | 2:3 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Boston United | – | Aveley | | 1:2 |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Tamworth | – | Boston United | | 1:0 * |
| |
FA Cup 1990/91, First Round Proper |
| 21.11.1990 | | Wycombe Wanderers | – | Boston United | | 4:0 * |
| |
FA Cup 1989/90, Third Qualifying Round |
| | | Boston United | – | Matlock Town | | 0:1 * |
| |
FA Cup 1988/89, Third Qualifying Round |
| | | Boston United | – | Hinckley Town | | 3:4 |
| |
FA Cup 1987/88, Fourth Qualifying Round |
| | | Welling United | – | Boston United | | 3:2 * |
| |
FA Cup 1986/87, First Round Proper |
| 19.11.1986 | | Boston United | – | Runcorn | | 1:2 (0:0) * |
| Boston |
FA Cup 1985/86, First Round Proper |
| 25.11.1985 | | Runcorn | – | Boston United | | 4:1 * |
| |
FA Cup 1984/85, Fourth Qualifying Round |
| | | Barnet | – | Boston United | | 3:1 |
| |
FA Cup 1983/84, First Round Proper |
| 19.11.1983 | | Boston United | – | Bury | | 0:3 |
| |
FA Cup 1982/83, Second Round Proper |
| 14.12.1982 | | Sheffield United | – | Boston United | | 5:1 * |
| |
FA Cup 1981/82, First Round Proper |
| 21.11.1981 | | Boston United | – | Kettering Town | | 0:1 |
| |
FA Cup 1980/81, First Round Proper |
| 22.11.1980 | | Boston United | – | Rotherham United | | 0:4 |
| |
FA Cup 1979/80, Fourth Qualifying Round |
| | | Nuneaton Borough | – | Boston United | | 2:1 * |
| |
FA Cup 1978/79, First Round Proper |
| 25.11.1978 | | Tranmere Rovers | – | Boston United | | 2:1 |
| |
FA Cup 1977/78, Fourth Qualifying Round |
| | | Boston United | – | AP Leamington | | 1:2 |
| |
FA Cup 1976/77, Fourth Qualifying Round |
| | | Boston United | – | Goole Town | | 1:3 * |
| |
FA Cup 1975/76, First Round Proper |
| 22.11.1975 | | Boston United | – | Lincoln City | | 0:1 |
| |
FA Cup 1974/75, First Round Proper |
| 23.11.1974 | | Chesterfield | – | Boston United | | 3:1 |
| |
FA Cup 1973/74, Third Round Proper |
| 09.01.1974 | | Boston United | – | Derby County | | 1:6 * |
| |
FA Cup 1972/73, First Round Proper |
| 18.11.1972 | | Boston United | – | Lancaster City | | 1:2 |
| |
FA Cup 1971/72, Third Round Proper |
| 15.01.1972 | | Boston United | – | Portsmouth | | 0:1 |
| |
FA Cup 1970/71, Second Round Proper |
| 12.12.1970 | | Boston United | – | York City | | 1:2 |
| |
FA Cup 1969/70, Third Qualifying Round |
| | | King's Lynn | – | Boston United | | 2:1 |
| |
FA Cup 1968/69, Fourth Qualifying Round |
| | | Grantham | – | Boston United | | 2:1 * |
| |
FA Cup 1967/68, Second Round Proper |
| 15.01.1968 | | Orient | – | Boston United | | 2:1 * |
| |
FA Cup 1966/67, Fourth Qualifying Round |
| | | Boston United | – | Grantham | | 1:4 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Skegness Town | – | Boston United | | 3:2 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Boston United | – | Spalding United | | 0:14 |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Boston United | – | Holbeach United | | 0:1 * |
| |
FA Cup 1962/63, First Round Proper |
| 03.11.1962 | | Boston United | – | King's Lynn | | 1:2 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Boston United | – | Louth United | | 3:4 |
| |
FA Cup 1960/61, Fourth Qualifying Round |
| | | Boston United | – | Kettering Town | | 1:3 * |
| |
FA Cup 1959/60, Fourth Qualifying Round |
| | | Kettering Town | – | Boston United | | 1:0 |
| |
FA Cup 1958/59, First Round Proper |
| 15.11.1958 | | Chester | – | Boston United | | 3:2 |
| |
FA Cup 1957/58, Second Round Proper |
| 07.12.1957 | | Darlington | – | Boston United | | 5:3 |
| |
FA Cup 1956/57, First Round Proper |
| 17.11.1956 | | Boston United | – | Bradford Park Avenue | | 0:2 |
| |
FA Cup 1955/56, Third Round Proper |
| 07.01.1956 | | Tottenham Hotspur | – | Boston United | | 4:0 |
| |
FA Cup 1954/55, First Round Proper |
| 24.11.1954 | | Blyth Spartans | – | Boston United | | 5:4 * |
| |
FA Cup 1953/54, First Round Proper |
| 21.11.1953 | | Scunthorpe United | – | Boston United | | 9:0 |
| |
FA Cup 1952/53, First Round Proper |
| 22.11.1952 | | Boston United | – | Oldham Athletic | | 1:2 |
| |
FA Cup 1951/52, Third Qualifying Round |
| | | Skegness Town | – | Boston United | | 2:1 |
| |
FA Cup 1950/51, Second Qualifying Round |
| | | Boston United | – | Linby Colliery | | 0:4 |
| |
FA Cup 1949/50, First Qualifying Round |
| | | Boston United | – | Grantham | | 2:3 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Spalding United | – | Boston United | | 2:1 |
| |
FA Cup 1947/48, Second Qualifying Round |
| | | Ilkeston Town | – | Boston United | | 1:0 |
| |
FA Cup 1946/47, Fourth Qualifying Round |
| | | Scunthorpe United | – | Boston United | | 4:1 |
| |
FA Cup 1945/46, Second Qualifying Round |
| | | Ollerton Colliery | – | Boston United | | 4:2 |
| |
FA Cup 1936/37, First Round Proper |
| 02.12.1936 | | Spennymoor United | – | Boston United | | 2:0 * |
| |
FA Cup 1935/36, First Round Proper |
| 30.11.1935 | | Crewe Alexandra | – | Boston United | | 4:2 |
| |
FA Cup 1934/35, Second Round Proper |
| 08.12.1934 | | Bath City | – | Boston United | | 2:1 |
| |
