Milan has sacked chief football officer Zvonimir Boban as CEO Ivan Gazidis begins what is expected to be a high-level clear-out of senior figures at San Siro.
Boban departs after just nine months in his role, with the Rossoneri having endured another difficult season in Italy.
Stefano Pioli was named head coach in October after Marco Giampaolo was sacked seven games into the Serie A campaign, yet Milan has won only 10 league matches and sit 12 points outside the top four.
Gazidis has been tipped to oversee significant changes behind the scenes, with Boban and sporting director Paolo Maldini long thought to be under threat of the sack.
It has been suggested Gazidis wants to bring in Ralf Rangnick, the head of sport and development for Red Bull, in a role that would see first-team head coach and sporting director duties combined.
Milan announced on Saturday that former Croatia star Boban has been relieved of his role with immediate effect, although the club made it clear they are supporting Pioli for the rest of the season.
"We thank Zvone for his efforts over the past nine months and wish him well in his future endeavours," Gazidis said.
"We must now turn our attention to football and the important games to come. Stefano Pioli and his staff are doing an exceptional job growing the performances of the team every week and will have our full support as they continue this work, in what is a difficult time for the country."
Milan face Genoa on Sunday in a match that was postponed due to the threat of the coronavirus in Italy.
The game, along with all others in the country before April 3, will be played behind closed doors to limit the risk of the virus spreading further.