After his second move to local rivals Milan in 1991, Serena's reputation as an Inter legend was somewhat tarnished, however; this was shown recently when Serena's name was booed by some of Inter's Ultras supporters when it was announced that he was to be part of an Inter Legends gathering after the final game of the 2006–07 league trophy presentation. Although Serena's first spell with Milan saw him help the team win the Serie B title and achieve Serie A promotion in 1983, as he scored 8 goals in 20 appearances, his second spell with Milan was less successful; despite winning another Supercoppa Italiana in 1992, and another two Serie A titles in 1992 and 1993 under manager Fabio Capello, he was used with less frequency due to several injury struggles, only making 10 appearances over his two final seasons, and he failed to score in Serie A during his second spell with the club, ultimately retiring from professional football in 1993.