If he fulfills his contract until 2025 and then extends it again, the 57-year-old could catch up with Carlo Ancelotti. As ‘(Site notre équipe d’expert)’ portal reports, today’s real manager was in charge for more than 2700 days between 2001 and 2009. Pioli would be Milan’s head coach for 2091 days at the end of his term. new contract.