FA Cup 2021/22, Extra Preliminary Round |
 | 07.08.2021 | | Long Eaton United | – | Holbeach United | | 4:1 (2:1) |
| Long Eaton |
FA Cup 2020/21, Preliminary Round |
| 12.09.2020 | | Holbeach United | – | Sheffield | | 0:4 |
| Holbeach |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Corby Town | – | Holbeach United | | 4:0 (2:0) |
| Corby |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Deeping Rangers | – | Holbeach United | | 3:2 (2:0) |
| Market Deeping |
FA Cup 2017/18, First Qualifying Round |
| 02.09.2017 | | Grantham Town | – | Holbeach United | | 2:1 (2:1) |
| Grantham |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Dereham Town | – | Holbeach United | | 2:1 |
| Dereham |
FA Cup 2015/16, Second Qualifying Round |
| 29.09.2015 | | Worcester City | – | Holbeach United | | 2:0 (1:0) * |
| Worcester |
FA Cup 2014/15, Preliminary Round |
| 30.08.2014 | | Holbeach United | – | Boston Town | | 2:4 |
| Holbeach |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Spalding United | – | Holbeach United | | 4:0 |
| Spalding |
FA Cup 2012/13, First Qualifying Round |
| 08.09.2012 | | Holbeach United | – | Stamford | | 1:2 (0:1) |
| Holbeach |
FA Cup 2011/12, Preliminary Round |
| 07.09.2011 | | Holbeach United | – | Hucknall Town | | 1:3 * |
| |
FA Cup 2010/11, Extra Preliminary Round |
| 14.08.2010 | | Holbeach United | – | Radcliffe Olympic | | 0:1 |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 19.08.2009 | | Holbeach United | – | Shirebrook Town | | 1:2 * |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 16.08.2008 | | St Neots Town | – | Holbeach United | | 7:1 |
| |
FA Cup 2007/08, First Qualifying Round |
| 15.09.2007 | | Holbeach United | – | Debenham LC | | 0:2 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Gedling Town | – | Holbeach United | | 4:0 |
| |
FA Cup 2005/06, Preliminary Round |
| 27.08.2005 | | Holbeach United | – | Boldmere St Michaels | | 0:2 |
| |
FA Cup 2004/05, Extra Preliminary Round |
| | | Holbeach United | – | Alvechurch | | 0:1 |
| |
FA Cup 2003/04, Extra Preliminary Round |
| | | Staveley Miners Welfare | – | Holbeach United | | 3:2 * |
| |
FA Cup 2002/03, Preliminary Round |
| | | Nantwich Town | – | Holbeach United | | 4:0 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Matlock Town | – | Holbeach United | | 3:1 |
| |
FA Cup 2000/01, Second Qualifying Round |
| | | Holbeach United | – | Belper Town | | 1:3 |
| |
FA Cup 1999/00, First Qualifying Round |
| | | Eastwood Town | – | Holbeach United | | 3:0 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Rocester | – | Holbeach United | | 3:0 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Holbeach United | – | Gresley Rovers | | 3:6 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Haverhill Rovers | – | Holbeach United | | 5:1 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Chelmsford City | – | Holbeach United | | 3:1 * |
| |
FA Cup 1994/95, Preliminary Round |
| | | Holbeach United | – | Heybridge Swifts | | 1:2 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Holbeach United | – | Hinckley Athletic | | 2:3 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Holbeach United | – | Potton United | | 1:2 |
| |
FA Cup 1989/90, Second Qualifying Round |
| | | Tamworth | – | Holbeach United | | 1:0 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Holbeach United | – | Banbury United | | 1:4 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Holbeach United | – | Walsall Wood | | 1:4 |
| |
FA Cup 1986/87, First Qualifying Round |
| | | Bromsgrove Rovers | – | Holbeach United | | 2:0 |
| |
FA Cup 1985/86, Preliminary Round |
| | | Rushden Town | – | Holbeach United | | 1:0 * |
| |
FA Cup 1984/85, Preliminary Round |
| | | Stevenage Borough | – | Holbeach United | | 8:0 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Great Yarmouth Town | – | Holbeach United | | 3:1 |
| |
FA Cup 1982/83, First Round Proper |
| 20.11.1982 | | Holbeach United | – | Wrexham | | 0:4 |
| |
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 1979/80, Preliminary Round |
| | | Skegness Town | – | Holbeach United | | 2:1 * |
| |
FA Cup 1978/79, Preliminary Round |
| | | Holbeach United | – | Louth United | | 0:3 |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Holbeach United | – | Boston | | 0:1 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Stamford | – | Holbeach United | | 3:2 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Great Yarmouth Town | – | Holbeach United | | 1:0 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Skegness Town | – | Holbeach United | | 3:0 |
| |
FA Cup 1973/74, Second Qualifying Round |
| | | Stamford | – | Holbeach United | | 3:1 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Holbeach United | – | Bourne Town | | 0:1 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Holbeach United | – | Stamford | | 1:4 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Boston United | – | Holbeach United | | 4:0 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Holbeach United | – | Bourne Town | | 1:2 |
| |
FA Cup 1968/69, Second Qualifying Round |
| | | Wisbech Town | – | Holbeach United | | 3:1 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Holbeach United | – | Boston United | | 0:2 * |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Spalding United | – | Holbeach United | | 5:2 |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Holbeach United | – | Skegness Town | | 0:1 * |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Holbeach United | – | Grantham | | 0:1 * |
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FA Cup 1963/64, Second Qualifying Round |
| | | Grantham | – | Holbeach United | | 2:0 |
| |
FA Cup 1962/63, Second Qualifying Round |
| | | Holbeach United | – | Skegness Town | | 2:3 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Holbeach United | – | Grantham | | 0:2 |
| |
FA Cup 1960/61, Fourth Qualifying Round |
| | | Holbeach United | – | Loughborough United | | 1:2 |
| |
FA Cup 1959/60, Second Qualifying Round |
| | | Cambridge United | – | Holbeach United | | 3:0 |
| |
FA Cup 1958/59, Third Qualifying Round |
| | | Wisbech Town | – | Holbeach United | | 4:0 |
| |
FA Cup 1957/58, Preliminary Round |
| | | King's Lynn | – | Holbeach United | | 2:1 |
| |
FA Cup 1956/57, Preliminary Round |
| | | Cambridge United | – | Holbeach United | | 5:0 * |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Holbeach United | – | Wisbech Town | | 0:2 * |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | King's Lynn | – | Holbeach United | | 3:1 * |
| |
FA Cup 1953/54, Preliminary Round |
| | | Holbeach United | – | Histon | | 0:1 |
| |
FA Cup 1952/53, Preliminary Round |
| | | Retford Town | – | Holbeach United | | 2:1 |
| |
FA Cup 1951/52, Second Qualifying Round |
| | | Skegness Town | – | Holbeach United | | 4:0 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Langold WMC | – | Holbeach United | | 2:1 |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Boston United | – | Holbeach United | | 7:0 |
| |
FA Cup 1948/49, Preliminary Round |
| | | South Normanton Miners Welfare | – | Holbeach United | | 5:1 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Gedling Colliery | – | Holbeach United | | 6:1 |
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