His good form earned him a spot for the Summer Olympics in Beijing. As he sustained an injury while playing in the competition, he missed the first round of 2008–09 Serie A, against Juventus. He scored a crucial brace as Fiorentina defeated Udinese 4–2 after being down 0–1 in the first half. Montolivo scored two more goals against Sampdoria and Napoli and he ended the season with two goals, two more than his previous season. On 17 January 2009, he captained Fiorentina for the first time in a 1–0 defeat to AC Milan.