Premier Division Winners
| SEASON | TEAM | SEASON | TEAM |
| 1892/93 | AYLESBURY PRINTING WORKS FC | 1959/60 | LONG MARSTON FC |
| 1893/94 | NORTH MARSTON FC | 1960/61 | LONG MARSTON FC |
| 1894/95 | AYLESBURY PRINTING WORKS FC | 1961/62 | WADDESDON FC |
| 1895/96 | AYLESBURY PRINTING WORKS FC | 1962/63 | BIERTON FC |
| 1896/97 | WENDOVER FC | 1963/64 | WADDESDON FC |
| 1897/98 | CHESHAM GENERALS RESERVES FC | 1964/65 | BIERTON FC |
| 1898/99 | WADDESDON FC | 1965/66 | BIERTON FC |
| 1899/00 | CHESHAM TOWN RESERVES FC | 1966/67 | WING VILLAGE FC |
| 1900/01 | CHESHAM TOWN RESERVES FC | 1967/68 | BUCKINGHAM TOWN FC |
| 1901/02 | CHESHAM TOWN RESERVES FC | 1968/69 | HADDENHAM UNITED FC |
| 1902/03 | BUCKINGHAM FC | 1969/70 | HADDENHAM UNITED FC |
| 1903/04 | CHESHAM TOWN RESERVES FC | 1970/71 | HADDENHAM UNITED FC |
| 1904/05 | AYLESBURY UNITED RESERVES FC | 1971/72 | STONE UNITED FC |
| 1905/06 | CHESHAM TOWN RESERVES FC | 1972/73 | STONE UNITED FC |
| 1906/07 | AYLESBURY UNITED RESERVES FC | 1973/74 | ST JOHNS HOSPITAL FC |
| 1907/08 | WADDESDON FC | 1974/75 | HADDENHAM UNITED FC |
| 1908/09 | AMERSHAM FC | 1975/76 | HADDENHAM UNITED FC |
| 1909/10 | AMERSHAM FC | 1976/77 | HADDENHAM UNITED FC |
| 1910/11 | WYCOMBE TRINITY FC | 1977/78 | WING VILLAGE FC |
| 1911/12 | QUAINTON FC | 1978/79 | STEWKLEY FC |
| 1912/13 | RIVET WORKS FC | 1979/80 | WING VILLAGE FC |
| 1913/14 | RIVET WORKS FC | 1980/81 | OVING FC |
| 1914/19 | FIRST WORLD WAR | 1981/82 | LONG MARSTON FC |
| 1919/20 | AMERSHAM FC | 1982/83 | OVING FC |
| 1920/21 | AMERSHAM FC | 1983/84 | OVING FC |
| 1921/22 | No.2 SEC RAF FC | 1984/85 | BLETCHLEY TOWN FC |
| 1922/23 | No.4 SEC RAF FC | 1985/86 | BLETCHLEY TOWN FC |
| 1923/24 | HAZELLS FC | 1986/87 | CBS RECORDS FC |
| 1924/25 | No.5 SEC RAF FC & WADDESDON FC | 1987/88 | CBS RECORDS FC |
| 1925/26 | WADDESDON FC | 1988/89 | CBS RECORDS FC |
| 1926/27 | WADDESDON FC | 1989/90 | CBS RECORDS FC |
| 1927/28 | QUAINTON FC | 1990/91 | STEWKLEY FC |
| 1928/29 | QUAINTON FC | 1991/92 | STONE FC |
| 1929/30 | LONG CRENDON FC | 1992/93 | STONE FC |
| 1930/31 | STONE FC | 1993/94 | STONE FC |
| 1931/32 | STONE FC | 1994/95 | STONE FC |
| 1932/33 | RIVET WORKS FC | 1995/96 | STONE FC |
| 1933/34 | WENDOVER FC | 1996/97 | WING FC |
| 1934/35 | LONG CRENDON FC | 1997/98 | WING FC |
| 1935/36 | WENDOVER FC | 1998/99 | WING FC |
| 1936/37 | BUCKINGHAM FC | 1999/00 | HADDENHAM UNITED FC |
| 1937/38 | QUAINTON FC | 2000/01 | WENDOVER FC |
| 1938/39 | QUAINTON FC | 2001/02 | WINGRAVE FC |
| 1939/46 | SECOND WORLD WAR | 2002/03 | ASTON CLINTON OLD BOYS FC |
| 1946/47 | QUAINTON FC | 2003/04 | ASTON CLINTON FC |
| 1947/48 | BIERTON FC | 2004/05 | ASTON CLINTON FC |
| 1948/49 | BIERTON FC | 2005/06 | BEDGROVE UNITED FC |
| 1949/50 | BIERTON FC | 2006/07 | ASTON PARK FC |
| 1950/51 | BIERTON FC | 2007/08 | BIERTON FC |
| 1951/52 | HADDENHAM UNITED FC | 2008/09 | HALE LEYS FC |
| 1952/53 | AYLESBURY EASTERN ELECT FC | 2009/10 | BUCKS CC FC |
| 1953/54 | GDYNIA STAR FC (POLISH HOSTEL) | 2010/11 | BIERTON FC |
| 1954/55 | BIERTON FC | 2011/12 | BUCKS CC FC |
| 1955/56 | AYLESBURY TOWN CORINTHIANS FC | 2012/13 | BUCKS CC FC |
| 1956/57 | BIERTON FC (Trophy not engraved) | 2013/14 | WALTON COURT WANDERERS |
| 1957/58 | LONG MARSTON FC | ||
| 1958/59 | LONG MARSTON FC |
Division 1 Winners
| SEASON | TEAM | SEASON | TEAM |
| 1960/61 | WESTON TURVILLE FC | 1988/89 | WATER EATON FC |
| 1961/62 | TRING CORINTHIANS RESERVES FC | 1989/90 | HALFEN FC |
| 1962/63 | HADDENHAM UNITED FC | 1990/91 | STONE RESERVES FC |
| 1963/64 | PITSTONE AND IVINGHOE FC | 1991/92 | WALTON COURT RESERVES FC |
| 1964/65 | OAKLEY FC | 1992/93 | WENDOVER FC |
| 1965/66 | BEDGROVE FC | 1993/94 | WATERMEAD FC |
| 1966/67 | CHINNOR FC | 1994/95 | AYLESBURY WEST INDIANS FC |
| 1967/68 | MONKS RISBOROUGH FC | 1995/96 | TRING CORINTHIANS FC |
| 1968/69 | ELLESBOROUGH FC | 1996/97 | BIERTON FC |
| 1969/70 | RAF HALTON FC | 1997/98 | DAYLA FC |
| 1970/71 | ST JOHNS HOSPITAL FC | 1998/99 | LINK UP CARRIERS FC |
| 1971/72 | LONGWICK FC / TRING CORINTHIANS FC | 1999/00 | RISBOROUGH UNITED FC |
| 1972/73 | HAZELLS ‘A’ FC | 2000/01 | WINGRAVE FC |
| 1973/74 | RISBOROUGH TENANTS FC | 2001/02 | ASTON CLINTON OLD BOYS RES. FC |
| 1974/75 | HADDENHAM RESERVES FC | 2002/03 | LONG MARSTON FC |
| 1975/76 | WING RESERVES FC | 2003/04 | ELMHURST FC |
| 1976/77 | AYLESBURY ATHLETIC FC | 2004/05 | ASTON CLINTON RES. FC |
| 1977/78 | MONKS RISBOROUGH FC | 2005/06 | WENDOVER FC |
| 1978/79 | STONE UNITED FC | 2006/07 | WALTON COURT WANDERERS FC |
| 1979/80 | C.B.S. FC | 2007/08 | HALE LEYS FC |
| 1980/81 | POST OFFICE FC | 2008/09 | BERKHAMSTED SPORTS FC |
| 1981/82 | CUDDINGTON FC | 2009/10 | P & IC UNITED FC |
| 1982/83 | WING RESERVES FC | 2010/11 | BEDGROVE UNITED FC |
| 1983/84 | SPRINGHILL FC | 2011/12 | BEDGROVE DYNAMOS FC |
| 1984/85 | AYLESBURY WEST INDIANS FC | 2012/13 | BIERTON FC WANDERERS |
| 1985/86 | WALTON COURT FC | 2013/14 | LONG MARSTON FC |
| 1986/87 | STONE FC | ||
| 1987/88 | WALTON COURT RESERVES FC |
Division 2 Winners
| SEASON | TEAM | SEASON | TEAM |
| 1991/92 | MONKS RISBOROUGH FC | 2004/05 | BRITANNIA FC |
| 1992/93 | WADDESDON RESERVES FC | 2005/06 | DAIRYMAID FC |
| 1993/94 | AYLESBURY WEST INDIANS FC | 2006/07 | NEW ZEALAND FC |
| 1994/95 | RISBOROUGH UNITED FC | 2007/08 | CHEDDINGTON RESERVES FC |
| 1995/96 | CUDDINGTON FC | 2008/09 | BRITANNIA FC |
| 1996/97 | DAYLA FC | 2009/10 | P & IC UNITED RESERVES FC |
| 1997/98 | BRICKLAYERS ARMS RESERVES FC | 2010/11 | FC BEDGROVE |
| 1998/99 | RISBOROUGH UNITED RESERVES FC | 2011/12 | AFC VICTORIA |
| 1999/00 | MANDEVILLE OLD BOYS FC | 2012/13 | GREAT MILTON |
| 2000/01 | ASTON CLINTON OLD BOYS FC | 2013/14 | NORTHCHURCH FC |
| 2001/02 | ST JOHNS FC | ||
| 2002/03 | TRING BELL RANGERS FC | ||
| 2003/04 | WENDOVER RESERVES FC |
Thomas Field Shield Winners
| SEASON | TEAM | SEASON | TEAM |
| 1923/24 | RAF No.5 SEC FC | 1973/74 | ST JOHNS HOSPITAL FC |
| 1924/25 | RAF No.5 SEC FC | 1974/75 | HADDENHAM UNITED FC |
| 1925/26 | WADDESDON FC | 1975/76 | HADDENHAM UNITED FC |
| 1926/27 | WADDESDON FC | 1976/77 | LONG CRENDON FC |
| 1927/28 | CHESHAM UNITED RESERVES FC | 1977/78 | LONG CRENDON FC |
| 1928/29 | BLETCHLEY SPORTS CLUB FC | 1978/79 | LONG CRENDON FC |
| 1929/30 | STOKE MANDEVILLE FC | 1979/80 | WING VILLAGE FC |
| 1930/31 | PRINCES RISBOROUGH FC | 1980/81 | OVING FC |
| 1931/32 | HAZELLS SPORTS AND SOCIAL FC | 1981/82 | OVING FC |
| 1932/33 | LONG CRENDON FC | 1982/83 | MONKS RISBOROUGH FC |
| 1933/34 | LONG CRENDON FC | 1983/84 | RIVETS FC |
| 1934/35 | LONG CRENDON FC | 1984/85 | ST JOHNS HOSPITAL FC |
| 1935/36 | WENDOVER FC | 1985/86 | MOLINS SPORTS FC |
| 1936/37 | QUAINTON FC | 1986/87 | WING VILLAGE FC |
| 1937/38 | QUAINTON FC | 1987/88 | MOLINS SPORTS FC |
| 1938/39 | BIERTON FC | 1988/89 | CBS RECORDS FC |
| 1939/46 | SECOND WORLD WAR | 1989/90 | CBS RECORDS FC |
| 1946/47 | QUAINTON FC | 1990/91 | WALTON COURT FC |
| 1947/48 | PRINCESS MARY HOSPITAL FC | 1991/92 | WING VILLAGE FC |
| 1948/49 | BIERTON FC | 1992/93 | ASTON CLINTON FC |
| 1949/50 | ASTON CLINTON FC | 1993/94 | HADDENHAM UNITED FC |
| 1950/51 | LONG CRENDON FC | 1994/95 | HADDENHAM UNITED FC |
| 1951/52 | HADDENHAM UNITED FC | 1995/96 | STONE FC |
| 1952/53 | HADDENHAM UNITED FC | 1996/97 | STONE FC |
| 1953/54 | BIERTON FC | 1997/98 | WING FC |
| 1954/55 | AYLESBURY TOWN CORINTHIANS FC | 1998/99 | WING FC |
| 1955/56 | WENDOVER FC | 1999/00 | BELGRAVE FC |
| 1956/57 | LONG MARSTON FC | 2000/01 | STONE FC |
| 1957/58 | WENDOVER FC / ELLESBOROUGH FC | 2001/02 | STONE FC |
| 1958/59 | BIERTON FC | 2002/03 | BUCKS CC FC |
| 1959/60 | LONG MARSTON FC | 2003/04 | BUCKS CC FC |
| 1960/61 | BIERTON FC | 2004/05 | ASTON CLINTON FC |
| 1961/62 | TRING CORINTHIANS FC | 2005/06 | ST JOHNS FC |
| 1962/63 | RIVETS FC | 2006/07 | WALTON COURT WANDERERS FC |
| 1963/64 | STEWKLEY FC | 2007/08 | HADDENHAM UNITED FC |
| 1964/65 | RISBOROUGH TENANTS FC | 2008/09 | AYLESBURY DYNAMOS FC |
| 1965/66 | BIERTON FC | 2009/10 | BIERTON FC |
| 1966/67 | STEWKLEY FC | 2010/11 | BIERTON FC |
| 1967/68 | BIERTON FC | 2011/12 | P & IC UNITED FC |
| 1968/69 | WING VILLAGE FC | 2012/13 | OAKLEY FC |
| 1969/70 | HADDENHAM UNITED FC | 2013/14 | BUCKS CC FC |
| 1970/71 | ST JOHNS HOSPITAL FC | ||
| 1971/72 | STONE UNITED FC | ||
| 1972/73 | HADDENHAM UNITED FC |
