[1] Cudicini is mostly remembered for his highly successful and dominant stint with A.C. Milan, and he is one of the most celebrated goalkeepers in the club's history, helping them win the 1969 European Cup Final in particular, among other domestic, European, and international titles.

After two seasons as the team's back-up goalkeeper behind Luciano Panetti, he was promoted to the team's starting goalkeeper in 1960, and retained the position for the next six seasons, collecting 166 league appearances, and winning the Inter-Cities Fairs Cup in 1960–61 and a Coppa Italia in 1964.

[1][2][5] He is Milan's seventh-most capped keeper of all time, behind only Christian Abbiati (380), Sebastiano Rossi (330), Dida (302), Lorenzo Buffon (300), Enrico Albertosi (233), and Dario Compiani (221).

[6] Despite his reputation and club achievements, Cudicini never played for the Italian senior national team, mainly because of the contemporary presence of several other notable players in his role throughout his career, such as Lorenzo Buffon, Giorgio Ghezzi, Dino Zoff, and Enrico Albertosi.

Although he often stood out throughout his career for his athleticism in goal and ability to produce acrobatic dives and decisive saves, he was also known to be an extremely efficient rather than flamboyant goalkeeper, who possessed an excellent positional sense.