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| Winners | Runners-up | |||||
| CHARITY SHIELD | ||||||
| 1908 | Manchester United | 4 | v | 0 | Queens Park Rangers | (after 1-1 draw) |
| 1909 | Newcastle United | 2 | v | 0 | Northampton Town | |
| 1910 | Brighton Hove Albion | 1 | v | 0 | Aston Villa | |
| 1911 | Manchester United | 8 | v | 4 | Swindon Town | |
| 1912 | Blackburn Rovers | 2 | v | 1 | Queen Park Rangers | |
| 1913 | Professionals | 7 | v | 2 | Amateurs | |
| 1920 | West Bromwich Albion | 2 | v | 0 | Tottenham Hotspur | |
| 1921 | Tottenham Hotspur | 2 | v | 0 | Burnley | |
| 1922 | Huddersfield Town | 1 | v | 0 | Liverpool | |
| 1923 | Professionals | 2 | v | 0 | Amateurs | |
| 1924 | Professionals | 3 | v | 1 | Amateurs | |
| 1925 | Amateurs | 6 | v | 1 | Professionals | |
| 1926 | Amateurs | 6 | v | 3 | Professionals | |
| 1927 | Cardiff City | 2 | v | 1 | Corinthians | |
| 1928 | Everton | 2 | v | 1 | Blackburn Rovers | |
| 1929 | Professionals | 3 | v | 0 | Amateurs | |
| 1930 | Arsenal | 2 | v | 1 | Sheffield Wednesday | |
| 1931 | Arsenal | 1 | v | 0 | West Bromwich | |
| 1932 | Everton | 5 | v | 3 | Newcastle United | |
| 1933 | Arsenal | 3 | v | 0 | Everton | |
| 1934 | Arsenal | 4 | v | 0 | Manchester City | |
| 1935 | Sheffield Wednesday | 1 | v | 0 | Arsenal | |
| 1936 | Sunderland | 2 | v | 1 | Arsenal | |
| 1937 | Manchester City | 2 | v | 0 | Sunderland | |
| 1938 | Arsenal | 2 | v | 1 | Preston North End | |
| 1948 | Arsenal | 4 | v | 3 | Manchester United | |
| 1949 | Portsmouth | 1 | v | 1 | Wolverhampton Wand's | (each held shield for 6 months) |
| 1950 | World Cup Team | 4 | v | 2 | Canadian Touring Team | |
| 1951 | Tottenham Hotspur | 2 | v | 1 | Newcastle United | |
| 1952 | Manchester United | 4 | v | 2 | Newcastle United | |
| 1953 | Arsenal | 3 | v | 1 | Blackpool | |
| 1954 | Wolverhampton Wand's | 4 | v | 4 | West Bromwich Albion | (each held shield for 6 months) |
| 1955 | Chelsea | 3 | v | 0 | Newcastle United | |
| 1956 | Manchester United | 1 | v | 0 | Manchester City | |
| 1957 | Manchester United | 4 | v | 0 | Aston Villa | |
| 1958 | Bolton Wanderers | 4 | v | 1 | Wolverhampton Wand's | |
| 1959 | Wolverhampton Wands | 3 | v | 1 | Nottingham Forest | |
| 1960 | Burnley | 2 | v | 2 | Wolverhampton Wand's | (each held shield for 6 months) |
| 1961 | Tottenham Hotspur | 3 | v | 2 | FA XI | |
| 1962 | Tottenham Hotspur | 5 | v | 1 | Ipswich Town | |
| 1963 | Everton | 4 | v | 0 | Manchester United | |
| 1964 | Liverpool | 2 | v | 2 | West Ham United | (each held shield for 6 months) |
| 1965 | Manchester United | 2 | v | 2 | Liverpool | (each held shield for 6 months) |
| 1966 | Liverpool | 1 | v | 0 | Everton | |
| 1967 | Manchester United | 3 | v | 3 | Tottenham Hotspur | (each held shield for 6 months) |
| 1968 | Manchester City | 6 | v | 1 | West Bromwich | |
| 1969 | Leeds United | 2 | v | 1 | Manchester City | |
| 1970 | Everton | 2 | v | 1 | Chelsea | |
| 1971 | Leicester City | 1 | v | 0 | Liverpool | |
| 1972 | Manchester City | 1 | v | 0 | Aston Villa | |
| 1973 | Burnley | 1 | v | 0 | Manchester City | |
| 1974 | Liverpool | 1 | v | 1 | Leeds United | (Liverpool pens) |
| 1975 | Derby County | 2 | v | 0 | West Ham United | |
| 1976 | Liverpool | 1 | v | 0 | Southampton | |
| 1977 | Liverpool | 0 | v | 0 | Manchester United | (each held shield for 6 months) |
| 1978 | Nottingham Forest | 5 | v | 0 | Ipswich Town | |
| 1979 | Liverpool | 3 | v | 1 | Arsenal | |
| 1980 | Liverpool | 1 | v | 0 | West Ham United | |
| 1981 | Aston Villa | 2 | v | 2 | Tottenham Hotspur | (each held shield for 6 months) |
| 1982 | Liverpool | 1 | v | 0 | Tottenham Hotspur | |
| 1983 | Manchester United | 2 | v | 0 | Liverpool | |
| 1984 | Everton | 1 | v | 0 | Liverpool | |
| 1985 | Everton | 2 | v | 0 | Manchester United | |
| 1986 | Everton | 1 | v | 1 | Liverpool | (each held shield for 6 months) |
| 1987 | Everton | 1 | v | 0 | Coventry City | |
| 1988 | Liverpool | 2 | v | 1 | Wimbledon | |
| 1989 | Liverpool | 1 | v | 0 | Arsenal | |
| 1990 | Liverpool | 1 | v | 1 | Manchester United | (each held shield for 6 months) |
| 1991 | Arsenal | 0 | v | 0 | Tottenham Hotspur | (each held shield for 6 months) |
| 1992 | Leeds United | 4 | v | 3 | Liverpool | |
| 1993 | Manchester United | 1 | v | 1 | Arsenal | (Man United pens) |
| 1994 | Manchester United | 2 | v | 0 | Blackburn Rovers | |
| 1995 | Everton | 1 | v | 0 | Blackburn Rovers | |
| 1996 | Manchester United | 4 | v | 0 | Newcastle United | |
| 1997 | Manchester United | 1 | v | 1 | Chelsea | (Man United pens) |
| 1998 | Arsenal | 3 | v | 0 | Manchester United | |
| 1999 | Arsenal | 2 | v | 1 | Manchester United | |
| 2000 | Chelsea | 2 | v | 0 | Manchester United | |
| 2001 | Liverpool | 2 | v | 1 | Manchester United | |
| COMMUNITY SHIELD | ||||||
| 2002 | Arsenal | 1 | v | 0 | Liverpool | |
| 2003 | Manchester United | 1 | v | 1 | Arsenal | (Man United 4-3 pens) |
| 2004 | Arsenal | 3 | v | 1 | Manchester United | |