Roll of Honour
Division 1
| Year | Champion | Runner Up |
|---|---|---|
| 1960 - 61 | Bicker Rangers | Spilsby Town |
| 1959 - 60 | Bicker Rangers | Wainfleet United |
| 1958 - 59 | Bicker Rangers | Croft United |
| 1957 - 58 | Bicker Rangers | Boston Amateurs |
| 1956 - 57 | Bicker Rangers | New Park Rangers |
| 1955 - 56 | Donington | Swineshead Institute |
| 1954 - 55 | Bicker Rangers | Donington |
| 1953 - 54 | Bicker Rangers | Old Bostonians |
| 1952 - 53 | Fishtoft | British Legion |
| 1951 - 52 | ||
| 1950 - 51 | Fishtoft | Boston Baptists |
| 1949 - 50 | Freiston | Fishtoft |
| 1948 - 49 | Freiston | Boston Baptists |
| 1947 - 48 | Spilsby Town | Alford United |
| 1946 - 47 | Old Leake | |
| 1945 - 46 | Old Leake | Fishtoft |
Premier Division
| Year | Champion | Runner Up |
|---|---|---|
| 2022 - 23 | Spilsby Town | Wyberton Reserves |
| 2021 - 22 | Pointon | Northgate Olympic |
| 2020 - 21 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2019 - 20 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2018 - 19 | Spilsby Town | Railway Athletic |
| 2017 - 18 | Pointon | Railway Athletic |
| 2016 - 17 | Swineshead Institute | Spilsby Town |
| 2015 - 16 | Wyberton Reserves | Spilsby Town |
| 2014 - 15 | Swineshead Institute | Spilsby Town |
| 2013 - 14 | Wyberton | Swineshead Institute |
| 2012 - 13 | Wyberton | Billinghay Athletic |
| 2011 - 12 | Tavern Colts | Old Leake |
| 2010 - 11 | Wyberton | Pointon |
| 2009 - 10 | Wyberton | Billinghay Athletic |
| 2008 - 9 | Coningsby | Swineshead Institute |
| 2007 - 8 | Wyberton | Spilsby Town |
| 2006 - 07 | Croft United | Billinghay Athletic |
| 2005 - 06 | Billinghay Athletic | Croft United |
| 2004 - 05 | Billinghay Athletic | Croft United |
| 2003 - 04 | Spilsby Town | Croft United |
| 2002 - 03 | Wyberton | Swineshead Institute |
| 2001 - 02 | Splisby Town | Croft United |
| 2000 - 01 | Wyberton | Cowbridge Rangers |
| 1999 - 0 | Cowbridge Rangers | Wainfleet United |
| 1998 - 99 | Wainfleet United | Cowbridge Rangers |
| 1997 - 98 | Billinghay Athletic | Coningsby |
| 1996 - 97 | Coningsby | Wainfleet United |
| 1995 - 96 | Coningsby | Horncastle Town |
| 1994 - 95 | Fishtoft | Horncastle Town |
| 1993 - 94 | Swineshead Institute | Coningsby |
| 1992 - 93 | Coningsby | Fishtoft |
| 1991 - 92 | Swineshead Institute | Fishtoft |
| 1990 - 91 | Swineshead Institute | Wyberton |
| 1989 - 90 | Swineshead Institute | Holbeach St. Marks |
| 1988 - 89 | Wyberton | Spilsby Town |
| 1987 - 88 | Wyberton | Holbeach St. Marks |
| 1986 - 87 | Swineshead Institute | Carlton Colts |
| 1985 - 86 | Old Doningtonians | Carlton Colts |
| 1984 - 85 | Croft United | Swineshead Institute |
| 1983 - 84 | Wrangle United | Swineshead Institute |
| 1982 - 83 | Swineshead Institute | Wrangle United |
| 1981 - 82 | Swineshead Institute | Wrangle United |
| 1980 - 81 | Wrangle United | Swineshead Institute |
| 1979 - 80 | Wrangle United | Swineshead Institute |
| 1978 - 79 | Wrangle United | Kirton School Old Boys |
| 1977 - 78 | Wrangle United | Swineshead Institute |
| 1976 - 77 | Swineshead Institute | Wrangle United |
| 1975 - 76 | Swineshead Institute | Wrangle United |
| 1974 - 75 | Wrangle United | Kirton Town |
| 1973 - 74 | Swineshead Institute | Wrangle United |
| 1972 - 73 | Wrangle United | Spilsby Town |
| 1971 - 72 | Wrangle United | |
| 1970 - 71 | Wrangle United | Friskney |
| 1969 - 70 | Carlton Colts | Wrangle United |
| 1968 - 69 | Real Towell | Wrangle United |
| 1967 - 68 | Real Towell | Old Doningtonians |
| 1966 - 67 | ||
| 1965 - 66 | Real Towell | |
| 1964 - 65 | British Railway | Spilsby Town |
| 1963 - 64 | Spilsby Town | |
| 1962 - 63 | Bicker Rangers | Swineshead Institute |
| 1961 - 62 | Bicker Rangers | Spilsby Town |
Division 1
| Year | Champion | Runner Up |
|---|---|---|
| 2022 - 23 | Wyberton A | Horncastle Town Reserves |
| 2021 - 22 | Fishtoft | Bull Athletic |
| 2020 - 21 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2019 - 20 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2018 - 19 | Fishtoft | Friskney |
| 2017 - 18 | Kirton Town | Skegness United |
| 2016 - 17 | Railway Athletic | Fulbeck United |
| 2015 - 16 | Leverton | Boston College |
| 2014 - 15 | Swineshead Institute Reserves | Heckington Millers |
| 2013 - 14 | Wyberton Reserves | Woodhall Spa United |
| 2012 - 13 | Freiston Reserves | Wrangle United |
| 2011 - 12 | Benington | Fishtoft |
| 2010 - 11 | Tavern Colts | Boston Town Old Boys |
| 2009 - 10 | Old Doningtonians | Old Leake |
| 2008 - 9 | Swineshead Institute Reserves | Woodhall Spa United |
| 2007 - 8 | North Sea United | Freiston |
| 2006 - 07 | West End Tigers | Westside Rangers |
| 2005 - 06 | Sleaford Town Reserves | Gedney Drove End |
| 2004 - 05 | Wrangle United | Coningsby |
| 2003 - 04 | Boston Town Colts Reserves | Sutterton |
| 2002 - 03 | North Sea United | Kirton Town |
| 2001 - 02 | Axe & Cleaver | Old Leake |
| 2000 - 01 | Cowbridge Rangers Reserves | Wrangle United |
| 1999 - 0 | Boston Town Colts | Cowbridge Rangers Reserves |
| 1998 - 99 | Wyberton Reserves | C.f.c. Railway Boston |
| 1997 - 98 | Holbeach St. Marks | Newcastle Brasil |
| 1996 - 97 | Gedney Drove End | Wyberton Reserves |
| 1995 - 96 | Croft United | Carlton Colts |
| 1994 - 95 | Old Leake | Cowbridge Rangers |
| 1993 - 94 | Billinghay Athletic | Lutton Marsh |
| 1992 - 93 | Wyberton Reserves | West Pinchbeck |
| 1991 - 92 | Eagle Flyers | Coningsby |
| 1990 - 91 | Wyberton Reserves | Croft United |
| 1989 - 90 | Holbeach St. Marks Reserves | Spilsby Town |
| 1988 - 89 | Wainfleet United | Park Lane Wanderers |
| 1987 - 88 | Wyberton Reserves | Skegness Town Reserves |
| 1986 - 87 | Butterwick | Swineshead Institute Reserves |
| 1985 - 86 | Lutton Marsh | Wrangle United Reserves |
| 1984 - 85 | Sutterton | Wrangle United Reserves |
| 1983 - 84 | Old Doningtonians | Kirton School Old Boys |
| 1982 - 83 | Friskney | Wrangle United Reserves |
| 1981 - 82 | Wrangle United Reserves | Swineshead Institute Reserves |
| 1980 - 81 | Croft United | Wrangle United Reserves |
| 1979 - 80 | Wyberton | Wrangle United Reserves |
| 1978 - 79 | Wrangle United Reserves | Swineshead Institute Reserves |
| 1977 - 78 | Wrangle United Reserves | Swineshead Institute Reserves |
| 1976 - 77 | Wrangle United Reserves | Lutton Marsh |
| 1975 - 76 | Wrangle United Reserves | Croft United |
| 1974 - 75 | Taverners United | R.a.f. Coningsby |
| 1973 - 74 | Old Doningtonians | Kirton School Old Boys |
| 1972 - 73 | Leverton Sports | Coningsby |
| 1971 - 72 | Wrangle United Reserves | |
| 1970 - 71 | Coningsby | Wrangle United Reserves |
| 1969 - 70 | Leverton Sports | Kirton Town |
| 1968 - 69 | Old Bostonians | Fishers United |
| 1967 - 68 | Swineshead Institute | Surfleet |
| 1966 - 67 | Old Doningtonians | |
| 1965 - 66 | Butterwick | Real Towell |
| 1964 - 65 | Carlton Colts | |
| 1963 - 64 | Benington | Wainfleet United |
| 1962 - 63 | Spilsby Town | Boston Athletic |
| 1961 - 62 | Coningsby |
Division 2
| Year | Champion | Runner Up |
|---|---|---|
| 2022 - 23 | Ancaster Athletic United | Boston Bears |
| 2021 - 22 | Spilsby Town Reserves | Spalding Harriers |
| 2020 - 21 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2019 - 20 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2018 - 19 | Eagle United | Railway Athletic Reserves |
| 2017 - 18 | Park United | Fc Hammers |
| 2016 - 17 | Sibsey | Pointon Reserves |
| 2015 - 16 | Railway Athletic | Afc Tetford |
| 2014 - 15 | Leverton | Boston College |
| 2013 - 14 | Heckington Millers | Friskney |
| 2012 - 13 | Ruskington Rovers | Fosdyke |
| 2011 - 12 | Wrangle United | Freiston Reserves |
| 2010 - 11 | Benington | Boston United Community |
| 2009 - 10 | Castle Colts | Billinghay Athletic Reserves |
| 2008 - 9 | Spalding Harriers | Wyberton Reserves |
| 2007 - 8 | Park Road Old Boys | Woodhall Spa United |
| 2006 - 07 | Freiston | Coningsby Reserves |
| 2005 - 06 | West End Tigers | Westside Rangers |
| 2004 - 05 | Tydd St. Mary | Spalding Town |
| 2003 - 04 | Swineshead Institute Reserves | Axe & Cleaver Reserves |
| 2002 - 03 | Holbeach St. Marks | Boston Town Colts Reserves |
| 2001 - 02 | Old Doningtonians | Kirton Town |
| 2000 - 01 | Old Leake Reserves | North Sea United |
| 1999 - 0 | Wainfleet United Reserves | Sutterton |
| 1998 - 99 | Boston Town Colts | Spilsby Town Reserves |
| 1997 - 98 | Cowbridge Rangers | Freiston |
| 1996 - 97 | Newcastle Brasil | Wrangle United Reserves |
| 1995 - 96 | Swineshead Institute Reserves | Rangers |
| 1994 - 95 | Gedney Drove End | Woodhall Spa United |
| 1993 - 94 | Newcastle | Old Leake |
| 1992 - 93 | King William Rangers | Sutterton |
| 1991 - 92 | West Pinchbeck | Lutton Marsh |
| 1990 - 91 | Eagles Flyers | Park United |
| 1989 - 90 | Fishtoft Reserves | Holbeach Bank |
| 1988 - 89 | R.a.f. Coningsby | Sibsey |
| 1987 - 88 | Wainfleet United | Park Lane Wanderers |
| 1986 - 87 | Wyberton Reserves | Moulton Seas End Reserves |
| 1985 - 86 | Butterwick | Spilsby Town Reserves |
| 1984 - 85 | Croft United Reserves | West Pinchbeck |
| 1983 - 84 | Sutterton | Lutton Marsh |
| 1982 - 83 | Carlton Colts Reserves | Kirton Town Reserves |
| 1981 - 82 | West Pinchbeck | Fishtoft |
| 1980 - 81 | Holbeach St. Marks | West End |
| 1979 - 80 | Kirton School Old Boys Reserves | Mareham United |
| 1978 - 79 | Park United | Wainfleet United |
| 1977 - 78 | Gedney United | Park United |
| 1976 - 77 | Kirton School Old Boys Reserves | Surfleet |
| 1975 - 76 | Lutton Marsh | Moulton Harrox |
| 1974 - 75 | Croft United | Swineshead Institute Reserves |
| 1973 - 74 | Old Leake | Freiston |
| 1972 - 73 | Taverners United | Wyberton |
| 1971 - 72 | ||
| 1970 - 71 | West End | Butterwick |
| 1969 - 70 | Park United | Wrangle United Reserves |
| 1968 - 69 | Mareham United | Ariel |
| 1967 - 68 | Carlton Colts | Fisher United |
| 1966 - 67 | ||
| 1965 - 66 | Fishtoft Reserves | Wrangle United Reserves |
| 1964 - 65 | Old Doningtonians | |
| 1963 - 64 | Butterwick | |
| 1962 - 63 | Benington | |
| 1961 - 62 | Gosberton | Algarkirk |
| 1960 - 61 | British Railway | Coningsby |
| 1959 - 60 | Unicorn Athletic | Wrangle United |
| 1958 - 59 | Cherry Corner | Boston Baptists |
| 1957 - 58 | Freiston | Cherry Corner |
| 1956 - 57 | Frithville | Unicorn Athletic |
| 1955 - 56 | Adkins Sports | Wrangle United |
| 1954 - 55 | Carrington | Gipsey Bridge |
| 1953 - 54 | Thompsons | Chapel Hill |
| 1952 - 53 | May & Hassell | New Park Rangers |
| 1951 - 52 | ||
| 1950 - 51 | Fishtoft Reserves | Unicorn Athletic |
| 1949 - 50 | British Legion | New Park Rangers |
| 1948 - 49 | Chapel Hill | Kirton Town |
| 1947 - 48 | ||
| 1946 - 47 | Moulton Seas End | Boston Athletic |
Division 3
| Year | Champion | Runner Up |
|---|---|---|
| 2021 - 22 | Eagle United Reserves | Sibsey |
| 2020 - 21 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2019 - 20 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2018 - 19 | Northgate Olympic | Bull Athletic |
| 2017 - 18 | Skegness Town A | Eagle United |
| 2016 - 17 | Wyberton A | Boston Athletic |
| 2015 - 16 | Spilsby Town Reserves | Fc Hammers |
| 2014 - 15 | Railway Athletic | Fishtoft Reserves |
| 2013 - 14 | Boston College | Swineshead Institute A |
| 2012 - 13 | Swineshead Institute Reserves | Friskney |
| 2011 - 12 | Queens Rangers | Old Doningtonians Reserves |
| 2010 - 11 | Mareham United Reserves | Freiston Reserves |
| 2009 - 10 | Benington | Friskney |
| 2008 - 9 | Fishtoft Reserves | Spalding Town Reserves |
| 2007 - 8 | Wyberton Reserves | Skegness Working Mens Club |
| 2006 - 07 | Marshalls | Wrangle United Reserves |
| 2005 - 06 | Woodhall Spa United | Shodfriars |
| 2004 - 05 | Holbeach St. Marks Reserves | Spalding Harriers |
| 2003 - 04 | Park Road Old Boys | Holbeach St. Marks Reserves |
| 2002 - 03 | Wainfleet United | Axe & Cleaver Reserves |
| 2001 - 02 | Cavern Athletic | Great Northern |
| 2000 - 01 | Old Doningtonians | Seas End Rangers |
| 1999 - 0 | Old Leake Reserves | North Sea United |
| 1998 - 99 | Broadgate | South Kyme United |
| 1997 - 98 | Newcastle Brasil | Croft United Reserves |
| 1996 - 97 | Billinghay Athetic Reserves | Old Leake Reserves |
| 1995 - 96 | Spalding United Colts | Newcastle Brasil |
| 1994 - 95 | Swineshead Institute Reserves | Fogarty |
| 1993 - 94 | Rosebery Rangers | Coningsby Reserves |
| 1992 - 93 | Wrangle United Reserves | Holbeach Bank Reserves |
| 1991 - 92 | Post Office | Old Doningtonians Reserves |
| 1990 - 91 | North Sea United | Wainfleet United Reserves |
| 1989 - 90 | Eagle Flyers | Norprint |
| 1988 - 89 | Billinghay Athletic | Coloroll |
| 1987 - 88 | Fishtoft Reserves | Woodhall Spa United |
| 1986 - 87 | Freiston | Sibsey |
| 1985 - 86 | Fishtoft Reserves | Carlton Colts "A" |
| 1984 - 85 | Holbeach Bank | Park Lane Wanderers |
| 1983 - 84 | Sibsey | Royal George |
| 1982 - 83 | Sutterton | Butterwick |
| 1981 - 82 | Kirton Town Reserves | Old Doningtonians Reserves |
| 1980 - 81 | Spilsby Town Reserves | Bulldog |
| 1979 - 80 | Park United Reserves | West Pinchbeck |
| 1978 - 79 | Sibsey | Fishtoft |
| 1977 - 78 | Park United Reserves | West Pinchbeck |
| 1976 - 77 | Carlton Colts Reserves | Old Doningtonians Reserves |
| 1975 - 76 | Surfleet | Kirton School Old Boys Reserves |
| 1974 - 75 | Holbeach Bank | Moulton Harrox |
| 1973 - 74 | Taverners United Reserves | Kirton Town Reserves |
| 1972 - 73 | Calders | Surfleet |
| 1971 - 72 | ||
| 1970 - 71 | Swineshead Institute Reserves | Old Doningtonians Reserves |
| 1969 - 70 | Taverners United | Vivo Dynamo |
| 1968 - 69 | Surfleet Reserves | Friskney Reserves |
| 1967 - 68 | ||
| 1966 - 67 | ||
| 1965 - 66 | ||
| 1964 - 65 | ||
| 1963 - 64 | ||
| 1962 - 63 | Tagcraft | |
| 1961 - 62 | Boston Athletics Reserves | Tagcraft |
| 1960 - 61 | Algakirk | Gosberton Reserves |
| 1959 - 60 | North Sea Camp | Fosdyke |
| 1958 - 59 | Freiston Reserves | North Sea Camp |
| 1957 - 58 | Fogartys | Bicker Rangers Reserves |
| 1956 - 57 | Algakirk | Kitwood Old Boys |
| 1955 - 56 | Frithville | Wigtoft |
| 1954 - 55 | Adkins Sports | United Canners |
| 1953 - 54 | United Canners | Algakirk |
| 1952 - 53 | Thompsons | Frithville |
| 1951 - 52 | ||
| 1950 - 51 | Gipsy Bridge | Fosdyke Reserves |
| 1949 - 50 | General Post Office | Quadring Athletic |
| 1948 - 49 | British Legion | Boston Baptists Reserves |
| 1947 - 48 | ||
| 1946 - 47 | Boston Baptists | Kirton Town |
Division 4
| Year | Champion | Runner Up |
|---|---|---|
| 1989 - 90 | Wyberton A | Kirton School Old Boys Reserves |
| 1988 - 89 | Holbeach Bank Reserves | Old Leake Reserves |
| 1987 - 88 | Billinghay Athletic | Wheatsheaf Hubberts Bridge |
| 1986 - 87 | Woodhall Spa United | Kirton School Old Boys Reserves |
| 1985 - 86 | Spilsby Town A | North Sea United |
| 1984 - 85 | Fishtoft Reserves | Park United Reserves |
| 1983 - 84 | Carlton Colts A | West End |
| 1982 - 83 | Barge Hotel | Fleet Fen |
| 1981 - 82 | The Eagles | Mareham United Reserves |
| 1980 - 81 | Spilsby Town A | Fishtoft Reserves |
| 1979 - 80 | Friskney Reserves | Holbeach Bank Reserves |
| 1978 - 79 | West Pinchbeck | Sutterton |
| 1974 - 75 | Croft United Reserves | Wainfleet United Reserves |
| 1973 - 74 | Holbeach Bank | North Sea Camp |
| 1972 - 73 | Taverners United Reserves | Ariel Reserves |
| 1971 - 72 | ||
| 1970 - 71 | Park United Reserves | Mareham United Reserves |
| 1954 - 55 | Kitwood Old Boys | Sibsey |
Reserve Cup
| Year | Champion | Runner Up |
|---|---|---|
| 2022 - 23 | Boston College Reserves | Bull Athletic Reserves |
| 2021 - 22 | Eagle United Reserves | Spilsby Town Reserves |
| 2020 - 21 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2019 - 20 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2018 - 19 | Railway Athletic Reserves | Woodhall Spa United Reserves |
| 2017 - 18 | Coningsby Reserves | Pointon Reserves |
| 2016 - 17 | Swineshead Institute Reserves | Fishtoft Reserves |
| 2015 - 16 | Spilsby Town Reserves | Swineshead Institute Reserves |
| 2014 - 15 | Swineshead Institute Reserves | A.f.c. Tetford Reserves |
| 2013 - 14 | Wyberton Reserves | Freiston Reserves |
| 2012 - 13 | Freiston Reserves | Wyberton Reserves |
| 2011 - 12 | Wyberton Reserves | Freiston Reserves |
| 2010 - 11 | Freiston Reserves | Billinghay Athletic Reserves |
| 2009 - 10 | Fishtoft Reserves | Spalding Town Reserves |
| 2008 - 9 | Billinghay Athletic Reserves | Swineshead Institute Reserves |
| 2007 - 8 | Coningsby Reserves | Swineshead Institute Reserves |
| 2006 - 07 | Coningsby Reserves | Swineshead Institute Reserves |
| 2005 - 06 | Kirton Town Reserves | Swineshead Institute Reserves |
| 2004 - 05 | Kirton Town Reserves | Croft United Reserves |
| 2003 - 04 | Axe & Cleaver Reserves | Swineshead Institute Reserves |
| 2002 - 03 | Boston Town Colts Reserves | Axe & Cleaver Reserves |
| 2001 - 02 | Wyberton Reserves | Swineshead Institute Reserves |
| 2000 - 01 | Cowbridge Rangers Reserves | Spilsby Town Reserves |
| 1999 - 0 | Cowbridge Rangers Reserves | Wyberton Reserves |
| 1998 - 99 | Wyberton Reserves | Billinghay Athletic Reserves |
| 1997 - 98 | Swineshead Institute Reserves | Cowbridge Rangers Reserves |
| 1996 - 97 | Swineshead Institute Reserves | Wyberton Reserves |
| 1995 - 96 | Spilsby Town Reserves | Wrangle United Reserves |
| 1994 - 95 | Fishtoft Reserves | Wyberton Reserves |
| 1993 - 94 | Fishtoft Reserves | Holbeach Bank Reserves |
| 1992 - 93 | Fishtoft Reserves | Wrangle United Reserves |
| 1991 - 92 | Wyberton Reserves | Old Doningtonians Reserves |
| 1990 - 91 | Wyberton Reserves | Swineshead Institute Reserves |
| 1989 - 90 | Wyberton Reserves | Holbeach Bank Reserves |
| 1988 - 89 | Wyberton Reserves | Swineshead Institute Reserves |
| 1987 - 88 | Wyberton Reserves | Holbeach Bank Reserves |
| 1986 - 87 | Croft United Reserves | Carlton Colts Reserves |
| 1985 - 86 | Spilsby Town Reserves | Croft United Reserves |
| 1984 - 85 | Wyberton Reserves | Wrangle United Reserves |
| 1983 - 84 | Croft United Reserves | Holbeach St. Marks Reserves |
| 1982 - 83 | Swineshead Institute Reserves | Spilsby Town Reserves |
| 1981 - 82 | Kirton Town Reserves | Swineshead Institute Reserves |
| 1980 - 81 | Wrangle United Reserves | Spilsby Town Reserves |
| 1979 - 80 | Park United Reserves | Spilsby Town Reserves |
| 1978 - 79 | Swineshead Institute Reserves | Wrangle United Reserves |
| 1977 - 78 | Wrangle United Reserves | Swineshead Institute Reserves |
| 1976 - 77 | Wrangle United Reserves | Kirton School Old Boys Reserves |
| 1975 - 76 | Taverners United Reserves | Swineshead Institute Reserves |
| 1974 - 75 | ||
| 1973 - 74 | ||
| 1972 - 73 | Wrangle United Reserves | Spilsby Town Reserves |
Challenge Cup
| Year | Champion | Runner Up |
|---|---|---|
| 2022 - 23 | Wyberton A | Billinghay Athletic |
| 2021 - 22 | Eagle United | Boston Bears |
| 2020 - 21 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2019 - 20 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2018 - 19 | Park United | Skegness Town A |
| 2017 - 18 | Woodhall Spa United | Kirton Town |
| 2016 - 17 | Fishtoft | Wyberton A |
| 2015 - 16 | Boston College | Leverton |
| 2014 - 15 | F.c. Kirton | Coningsby |
| 2013 - 14 | Swineshead Institute A | Ruskington Rovers |
| 2012 - 13 | Fosdyke | Coningsby |
| 2011 - 12 | Benington | Spalding Harriers |
| 2010 - 11 | Tavern Colts | Sutterton |
| 2009 - 10 | Boston Town Old Boys | Benington |
| 2008 - 9 | Old Doningtonians | Woodhall Spa United |
| 2007 - 8 | Fishtoft | Kirton Town |
| 2006 - 07 | Wainfleet United | Marshalls |
| 2005 - 06 | Sleaford Town | West End Tigers |
| 2004 - 05 | Gedney Drove End | Old Doningtonians |
| 2003 - 04 | Wainfleet United | Park Road Old Boys |
| 2002 - 03 | Gedney Drove End | Holbeach Bank |
| 2001 - 02 | Old Leake | Axe & Cleaver |
| 2000 - 01 | Old Leake | Skegness Town |
| 1999 - 0 | Carlton Colts | Skegness Town |
| 1998 - 99 | C.f.c. Railway | Holbeach Bank |
| 1997 - 98 | Old Leake | Holbeach Bank |
| 1996 - 97 | Holbeach St. Marks | Newcastle Brasil |
| 1995 - 96 | Croft United | Gedney Drove End |
| 1994 - 95 | Cowbridge Rangers | Mareham United |
| 1993 - 94 | Cowbridge Rangers | Orchard Park Mariners |
| 1992 - 93 | Carlton Colts | Sutterton |
| 1991 - 92 | Sutterton | Lutton Marsh |
| 1990 - 91 | Eagles Flyers | North Sea United |
| 1989 - 90 | Eagles Flyers | Wheat Sheaf Hubberts Bridge |
| 1988 - 89 | Billinghay Athletic | R.a.f. Coningsby |
| 1987 - 88 | Coningsby | Wainfleet United |
| 1986 - 87 | Moulton Seas End | Holbeach Bank |
| 1985 - 86 | Butterwick | Old Leake |
| 1984 - 85 | Coningsby | West Pinchbeck |
| 1983 - 84 | Sutterton | Coningsby |
| 1982 - 83 | Lutton Marsh | Gedney Drove End |
| 1981 - 82 | West Pinchbeck | Bulldog |
| 1980 - 81 | Coningsby | Fishtoft |
| 1979 - 80 | Fishtoft | Sutterton |
Sports Cup
| Year | Champion | Runner Up |
|---|---|---|
| 2022 - 23 | Spilsby Town | Wyberton Reserves |
| 2021 - 22 | Pointon | Spilsby Town |
| 2020 - 21 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2019 - 20 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2018 - 19 | Spilsby Town | Skegness Town Reserves |
| 2017 - 18 | Benington | Kirton Town |
| 2016 - 17 | Swineshead Institute | Spilsby Town |
| 2015 - 16 | Wyberton Reserves | Old Leake |
| 2014 - 15 | Leverton | Railway Athletic |
| 2013 - 14 | Swineshead Institute | Benington |
| 2012 - 13 | Wyberton | Ruskington Rovers |
| 2011 - 12 | Wrangle United | Old Leake |
| 2010 - 11 | Pointon | Wyberton |
| 2009 - 10 | Wyberton | Billinghay Athletic |
| 2008 - 9 | Swineshead Institute | Freiston |
| 2007 - 8 | Swineshead Institute | West End Tigers |
| 2006 - 07 | Croft United | Coningsby |
| 2005 - 06 | Croft United | Billinghay Athletic |
| 2004 - 05 | Billinghay Athletic | Skegness Town Reserves |
| 2003 - 04 | Skegness Town Reserves | C.f.c. Napoleon |
| 2002 - 03 | Spilsby Town | Croft United |
| 2001 - 02 | Coningsby | Boston Town Colts |
| 2000 - 01 | Wyberton | Billinghay Athletic |
| 1999 - 0 | Spilsby Town | Swineshead Institute |
| 1998 - 99 | Cowbridge Rangers | Croft United |
| 1997 - 98 | Billinghay Athletic | Swineshead Institute |
| 1996 - 97 | Billinghay Athletic | Wrangle United |
| 1995 - 96 | Croft United | Wyberton |
| 1994 - 95 | Swineshead Institute | Horncastle Town |
| 1993 - 94 | Swineshead Institute | Lutton Marsh |
| 1992 - 93 | Swineshead Institute | Fishtoft |
| 1991 - 92 | Swineshead Institute | Wyberton |
| 1990 - 91 | Wyberton | Old Doningtonians |
| 1989 - 90 | Wyberton | Swineshead Institute |
| 1988 - 89 | Wyberton | Wainfleet United |
| 1987 - 88 | Holbeach St. Marks | Carlton Colts |
| 1986 - 87 | Butterwick | Wyberton |
| 1985 - 86 | Croft United | Fishtoft |
| 1984 - 85 | Swineshead Institute | Spilsby Town |
| 1983 - 84 | Croft United | Carlton Colts |
| 1982 - 83 | Wrangle United | Holbeach St. Marks |
| 1981 - 82 | Wrangle United | Swineshead Institute |
| 1980 - 81 | Swineshead Institute | Wrangle United |
| 1979 - 80 | Wrangle United | Old Doningtonians |
| 1978 - 79 | Wrangle United | Kirton School Old Boys |
| 1977 - 78 | Wrangle United | Swineshead Institute |
| 1976 - 77 | Wrangle United | Taverners United |
| 1975 - 76 | Wrangle United | Kirton Town |
| 1974 - 75 | Wrangle United | |
| 1973 - 74 | Wrangle United | |
| 1972 - 73 | Holbeach St. Marks | |
| 1971 - 72 | Swineshead Institute | |
| 1970 - 71 | Kirton Town | |
| 1969 - 70 | Spilsby Town | |
| 1968 - 69 | Wrangle United | |
| 1967 - 68 | Carlton Colts | |
| 1966 - 67 | Wrangle United | |
| 1965 - 66 | ||
| 1964 - 65 | ||
| 1963 - 64 | Spilsby Town | |
| 1962 - 63 | Bicker Rangers | |
| 1961 - 62 | Spilsby Town | |
| 1960 - 61 | Bicker Rangers | |
| 1959 - 60 | Bicker Rangers | |
| 1958 - 59 | Bicker Rangers | |
| 1957 - 58 | Bicker Rangers | |
| 1956 - 57 | Bicker Rangers | |
| 1955 - 56 | ||
| 1954 - 55 | Swineshead Institute | |
| 1953 - 54 | Bicker Rangers | |
| 1952 - 53 | Boston Baptists | Bicker Rangers |
| 1951 - 52 | ||
| 1950 - 51 | British Legion | New Bolingbroke |
| 1949 - 50 | Boston Baptists | Freiston |
| 1948 - 49 | Freiston | Spilsby Town |
| 1947 - 48 | Freiston | Boston Baptists |
| 1946 - 47 | Old Leake | Boston Amateurs |
| 1945 - 46 | Boston Reserves + Old Leake (Shared for 6 Months Each) |
The Horncastle Parliamentary Division Football Challenge Cup Known as "The Willoughby Cup"
| Year | Champion | Runner Up |
|---|---|---|
| 2022 - 23 | Spilsby Town | Northgate Olympic |
| 2021 - 22 | Pointon | Wyberton Reserves |
| 2020 - 21 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2019 - 20 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2018 - 19 | Skegness Town Reserves | Kirton Town |
| 2017 - 18 | Pointon | Coningsby |
| 2016 - 17 | Woodhall Spa United | Kirton Town |
| 2016 - 17 | Swineshead Institute | Leverton |
| 2015 - 16 | Spilsby Town | Old Leake |
| 2014 - 15 | Swineshead Institute | Coningsby |
| 2013 - 14 | Wyberton | Woodhall Spa United |
| 2012 - 13 | Billinghay Athletic | Swineshead Istitute |
| 2011 - 12 | Spilsby Town | Fishtoft |
| 2010 - 11 | Wyberton | Kirton Town |
| 2009 - 10 | Billinghay Athletic | Swineshead Institute |
| 2008 - 9 | Freiston | Skegness Town Reserves |
| 2007 - 8 | Wyberton | Spilsby Town |
| 2006 - 07 | Wyberton | Billinghay Athletic |
| 2005 - 06 | Billinghay Athletic | Spilsby Town |
| 2004 - 05 | C.f.c. Napoleon | Billinghay Athletic |
| 2003 - 04 | C.f.c. Napoleon | Swineshead Institute |
| 2002 - 03 | Wyberton | Spilsby Town |
| 2001 - 02 | Spilsby Town | Billinghay Athletic |
| 2000 - 01 | Wyberton | Cowbridge Rangers |
| 1999 - 0 | Cowbridge Rangers | |
| 1998 - 99 | Cowbridge Rangers | |
| 1997 - 98 | Wainfleet United | |
| 1996 - 97 | Wyberton | |
| 1995 - 96 | Wrangle United | |
| 1994 - 95 | Horncastle Town | |
| 1993 - 94 | C.f.c. Boston | |
| 1992 - 93 | Old Doningtonians | Swineshead Institute |
| 1991 - 92 | Wainfleet United | |
| 1990 - 91 | Wyberton | |
| 1989 - 90 | Spilsby Town | |
| 1988 - 89 | Carlton Colts | |
| 1987 - 88 | Wainfleet United | |
| 1986 - 87 | Horncastle Town | |
| 1985 - 86 | ||
| 1984 - 85 | Croft United | |
| 1983 - 84 | ||
| 1982 - 83 | ||
| 1981 - 82 | ||
| 1980 - 81 | ||
| 1979 - 80 | ||
| 1978 - 79 | ||
| 1977 - 78 | ||
| 1976 - 77 | ||
| 1975 - 76 | ||
| 1974 - 75 | ||
| 1973 - 74 | ||
| 1972 - 73 | ||
| 1971 - 72 | ||
| 1970 - 71 | ||
| 1969 - 70 | ||
| 1968 - 69 | ||
| 1967 - 68 | Real Towell | |
| 1966 - 67 | Boston Athletic | |
| 1965 - 66 | ||
| 1964 - 65 | ||
| 1963 - 64 | ||
| 1962 - 63 | ||
| 1961 - 62 | ||
| 1960 - 61 | ||
| 1959 - 60 | ||
| 1958 - 59 | ||
| 1957 - 58 | ||
| 1956 - 57 | ||
| 1955 - 56 | Wainfleet United | |
| 1954 - 55 | Wainfleet United | |
| 1953 - 54 | Spilsby Town | |
| 1952 - 53 | Wainfleet United | |
| 1951 - 52 | Wainfleet United | |
| 1950 - 51 | ||
| 1949 - 50 | ||
| 1948 - 49 | ||
| 1947 - 48 | ||
| 1946 - 47 | ||
| 1945 - 46 | ||
| 1944 - 45 | ||
| 1943 - 44 | ||
| 1942 - 43 | ||
| 1941 - 42 | ||
| 1940 - 41 | ||
| 1939 - 40 | ||
| 1938 - 39 | ||
| 1937 - 38 | ||
| 1936 - 37 | ||
| 1935 - 36 | ||
| 1934 - 35 | ||
| 1933 - 34 | ||
| 1932 - 33 | Horncastle Town | |
| 1931 - 32 | Skegness United | |
| 1930 - 31 | Wainfleet United | |
| 1929 - 30 | Skegness United | |
| 1928 - 29 | Skegness United | |
| 1927 - 28 | Skegness United | |
| 1926 - 27 | Skegness United | |
| 1925 - 26 | Alford United | |
| 1924 - 25 | Skegness United | |
| 1923 - 24 | Skegness United | |
| 1922 - 23 | Spilsby United | |
| 1921 - 22 | Skegness United | |
| 1920 - 21 | Skegness United | |
| 1919 - 20 | Horncastle Town | |
| 1918 - 19 | ||
| 1917 - 18 | ||
| 1916 - 17 | ||
| 1915 - 16 | ||
| 1914 - 15 | ||
| 1913 - 14 | Skegness United | |
| 1912 - 13 | Skegness United | |
| 1911 - 12 | Horncastle United | |
| 1910 - 11 | Horncastle United | |
| 1909 - 10 | Horncastle United | |
| 1908 - 9 | Woodhall Spa Rovers | |
| 1907 - 8 | Woodhall Spa Rovers | |
| 1906 - 07 | Horncastle United | |
| 1905 - 06 | Woodhall Spa Rovers | |
| 1904 - 05 | Alford United | |
| 1903 - 04 | Alford United | |
| 1902 - 03 | Alford United | |
| 1901 - 02 | Horncastle United | |
| 1900 - 01 | Skegness & District | |
| 1899 - 0 | Alford United |
Willoughby Shield
| Year | Champion | Runner Up |
|---|---|---|
| 2022 - 23 | Spilsby Town Reserves | Fishtoft Reserves |
| 2021 - 22 | Boston College Reserves | Swineshead Institute Reserves |
| 2020 - 21 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2019 - 20 | Null & Void (Coronavirus Pandemic) | Null & Void (Coronavirus Pandemic) |
| 2018 - 19 | Pointon Reserves | Woodhall Spa United Reserves |
| 2017 - 18 | Railway Athletic Reserves | Skegness Town A |
| 2016 - 17 | Swineshead Institute Reserves | Benington Reserves |
| 2015 - 16 | Spilsby Town Reserves | Coningsby Reserves |
| 2014 - 15 | Fishtoft Reserves | Billinghay Athletic Reserves |
| 2013 - 14 | Swineshead Institute Reserves | Coningsby Reserves |
| 2013 - 14 | Swineshead Institute Reserves | Coningsby Reserves |
| 2012 - 13 | Freiston Reserves | Kirton Town Reserves |
| 2011 - 12 | Coningsby Reserves | Swineshead Institute Reserves |
| 2010 - 11 | Woodhall Spa United Reserves | Billinghay Athletic Reserves |
| 2010 - 11 | Woodhall Spa United Reserves | Billinghay Athletic Reserves |
| 2009 - 10 | Fishtoft Reserves | Billinghay Athletic Reserves |
| 2008 - 9 | Swineshead Institute Reserves | Old Doningtonians Reserves |
| 2007 - 8 | Swineshead Institute Reserves | Wyberton Reserves |
| 2006 - 07 | Swineshead Institute Reserves | Coningsby Reserves |
| 2005 - 06 | Kirton Town Reserves | Coningsby Reserves |
| 2004 - 05 | Kirton Town Reserves | Park United Reserves |
| 2003 - 04 | Boston Town Colts Reserves | Swineshead Institute Reserves |
| 2002 - 03 | Swineshead Institute Reserves | Croft United Reserves |
| 2001 - 02 | Wyberton Reserves | Spilsby Town Reserves |
| 2000 - 01 | Cowbridge Rangers Reserves | Old Leake Reserves |
| 1999 - 0 | Cowbridge Rangers Reserves | |
| 1998 - 99 | Coningsby Reserves | |
| 1997 - 98 | Wyberton Reserves | |
| 1996 - 97 | Cowbridge Rangers Reserves | Wrangle United Reserves |
| 1995 - 96 | Wrangle United Reserves | Wainfleet United Reserves |
| 1994 - 95 | Swineshead Institute Reserves | |
| 1993 - 94 | Spilsby Town Reserves | |
| 1992 - 93 | Horncastle Town Reserves |