The record for most winner's medals for a manager is held jointly by George Ramsay, who won six with Aston Villa (1887, 1895, 1897, 1905, 1913, 1920) and Arsène Wenger, who has won that many with Arsenal (1998, 2002, 2003, 2005, 2014, 2015) [REF].
Seven clubs have won the FA Cup as part of a League and Cup double, namely Preston North End (1889), Aston Villa (1897), Tottenham Hotspur (1961), Arsenal (1971, 1998, 2002), Liverpool (1986), Manchester United (1994, 1996, 1999) and Chelsea (2010).