Weah joined A.C. Milan in 1995, with whom he immediately won the Italian league in 1996 under Fabio Capello, playing alongside Roberto Baggio and Dejan Savićević in Milan's attack, as well as Marco Simone, on occasion, and finishing the season as Milan's top goalscorer; he won the Serie A title once again in 1999.
In 1995, Ballack earned his first professional contract, thanks to his performances in the role of central midfielder. He was dubbed the "Little Kaiser", in reference to Franz Beckenbauer, who was nicknamed "Der Kaiser".