I believe that Paolo Maldini (1989, 1990, 1994, 2003, 2007) and Alfredo di Stefano (1956, 1957, 1958, 1959, 1960) share that accolade, with 5 titles each I have just learnt i was mistaken - Francisco Gento won in 6 times (1956, 1957, 1958, 1959, 1960 and 1966)
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I believe that Paolo Maldini (1989, 1990, 1994, 2003, 2007) and Alfredo di Stefano (1956, 1957, 1958, 1959, 1960) share that accolade, with 5 titles each I have just learnt i was mistaken - Francisco Gento won it 6 times (1956, 1957, 1958, 1959, 1960 and 1966)
If you're talking just European Cup/Champions League, it's Real Madrid with 9. If you're talking all UEFA competitions, it's AC Milan with 17 (EC/CL 7; Cup Winners Cup 2; Super Cup 5; Intercontinental Cup 3).
Ex-Arsenal and current Chelsea player Ashley Cole has won the most FA Cup medals with six - with Arsenal (2002, 2003, 2005) and Chelsea (2007, 2009, 2010).