On 31 January 2011, after Juventus signed central defender Andrea Barzagli, the 34-year-old Legrottaglie – who made just eight appearances in all competitions comprised during the first half of the season, under new manager Luigi Delneri – left on a free transfer for fellow league side A.C. Milan, signing a six-month deal. However, he was only able to make one league appearance for the eventual champions due to a serious head injury suffered during a 0–0 draw with S.S. Lazio.