On 25 January 2011, Van Bommel signed a six-month contract with Milan on a free transfer after terminating his contract with Bayern. He was given the number 4 shirt, and the day after, he made his debut in a 2–1 victory against Sampdoria in the Coppa Italia quarter-final. On 29 January 2011, Van Bommel made his Serie A debut against Catania but was sent off after receiving a second yellow card early in the second half. Soon after, however, he adapted to Italian football and became a regular in Massimiliano Allegri’s squad, contributing greatly in convincing 3–0 wins against Napoli and city rivals Internazionale. He was a starter in the match against Roma on 7 May 2011 that brought Milan their 18th Scudetto. On 17 May 2011, Milan announced that Van Bommel had extended his contract for one more year. In the second season of his stint at Milan, he continued to be a starter and occupied the defensive midfielder position throughout the season. He decided not to stay with Milan for another season, despite being offered a new contract.