In the following season, they managed a third-place finish behind champions Juventus and runners-up Internazionale, largely thanks to Oliver Bierhoff's 27 goals.
Zaccheroni's results at Udinese attracted the attention of Silvio Berlusconi, owner of Italian giants AC Milan, who appointed him as manager after the club had endured two miserable seasons, despite their expensive, star-studded squad featuring (George Weah, Leonardo, Paolo Maldini etc.).
Zaccheroni asked Berlusconi to sign two key players from Udinese to accompany him to Milan: German striker Oliver Bierhoff and Danish right wing-back Thomas Helveg.
[2] The following season was less successful for Zaccheroni as Milan crashed out of the Champions League early, and, despite finishing third in Serie A, were never really in the running for the title.
As manager of Milan, Zaccheroni was successful and prescient in some of his signings; Oliver Bierhoff, Kakha Kaladze, Gennaro Gattuso and, above all, Andriy Shevchenko would become key players for the club.
On the other hand, however, transfers like those of José Mari were expensive flops, and he was also criticised for letting top centre-back Roberto Ayala leave Milan and move to Valencia; Ayala was generally unhappy in his two seasons at Milan (making 13 appearances in 1998–99 and 22 in 1999–2000) as there was stiff competition in defence with established players like Paolo Maldini and Alessandro Costacurta.
However, despite a good start, Zaccheroni was not able to bring Torino to the top positions in the league table and even suffered a worrying sequence of six consecutive defeats, which led chairman Cairo to sack him on 26 February 2007, and reinstate De Biasi at the helm of the granata.
In his first game at European level with Juventus, his side defeated 2–1 Ajax in Amsterdam (the return leg then ended 0–0), and then went on to play English opponents Fulham.
The first leg ended in a 3–1 win, but in Craven Cottage his side suffered a 4–1 defeat, sending Juventus out of the competition on a 5–4 aggregate scoreline.
On 19 January 2016, Zaccheroni was appointed manager of Chinese Super League club Beijing Guoan on a two-year contract.
[12] Since April 2022 he is the technical commissioner of the "Italian Non Profit National Team", a Third Sector Entity (ETS) that promotes the values of solidarity through the sharing of a sporting experience involving non-profit associations.
His system made use of a back-three and wing-backs in lieu of wide midfielders, who would make attacking runs up the flank, looking to provide crosses to the team's centre-forward, rather than tracking back.
He made use of an attacking trident with inverted wingers who were known for their quick combination play, or ability to provide depth to the team with their runs off the ball, and cut inside either to score goals or create chances.