Years expressed as 1999 depict the 1998-99 season.
The traditional League Championship and FA Cup double is in RED.
European trophies are in BLUE.
| Season | Club | Trophies Won |
| 1889 | Preston North End | Championship FA Cup |
| 1897 | Aston Villa | Championship FA Cup |
| 1961 | Tottenham Hotspur | Championship FA Cup |
| 1968 | Leeds United | League Cup UEFA Cup |
| 1970 | Manchester City | League Cup Cup Winners Cup |
| 1971 | Arsenal | Championship FA Cup |
| 1973 | Liverpool | Championship UEFA Cup |
| 1976 | Liverpool | Championship UEFA Cup |
| 1977 | Liverpool | Championship European Cup |
| 1978 | Nottingham Forest | Championship League Cup |
| 1979 | Nottingham Forest | League Cup European Cup |
| 1981 | Liverpool | League Cup European Cup |
| 1982 | Liverpool | Championship League Cup |
| 1983 | Liverpool | Championship League Cup |
| 1984 | Liverpool | Championship League Cup European Cup |
| 1985 | Everton | Championship Cup Winners Cup |
| 1986 | Liverpool | Championship FA Cup |
| 1993 | Arsenal | FA Cup League Cup |
| 1994 | Manchester United | Championship FA Cup |
| 1996 | Manchester United | Championship FA Cup |
| 1998 | Chelsea | League Cup Cup Winners Cup |
| Arsenal | Championship FA Cup | |
| 1999 | Manchester United | Championship FA Cup European Cup |