 Maldini went on to win the 1988 Supercoppa Italiana with Milan the following season, and followed up this trophy with back to back European Cup titles in 1988–89 and 1989–90, while Milan finished in third and in second place in Serie A during those respective seasons.On 19 February 1989, Maldini made his 100th appearance in Serie A.

Milan reached the final of the 1989–90 Coppa Italia, losing out to Juventus.Milan also managed to capture successive European Super Cup titles in 1989 and 1990, as well as successive Intercontinental Cup titles, once again 1989 and 1990.