In the 1998-99 season, Associazione Calcio Milan competed in the Serie A for the 65th time, as well as in the Coppa Italia. It was their 16th consecutive season in the top flight of Italian football. It was the club's second season in a row in which they haven't participated in any UEFA competition, as they failed to qualify during the previous season, finishing in 10th place.
A.C. Milan returned to its previous glorious ways under the guidance of new coach Alberto Zaccheroni. The highly rated coach, hired from Udinese, brought lethal striker Oliver Bierhoff and the defensive right-winger Thomas Helveg with him. He introduced Milan to his unorthodox 3-4-3 formation, in which Bierhoff was a perfect centre forward, scoring 20 goals in the league.
Milan had a marvelous second half of the season, in which it kept pace with Serie A championship leaders Lazio, then passing the Romans when they had a couple of slips. In the end, a win in the final round was more than enough to clinch Milan's first league title for three years.