The team started strongly in the league, with four wins on the bounce in their first four games, including a derby win against Inter. Meanwhile, the transfer market saw important arrivals such as Tonali, Díaz, Tătăruşanu and the renewals of Kjær and Saelemaekers' contracts. AC Milan remained unbeaten until the beginning of 2021 when Pioli's team fell to Juventus and Atalanta at home. Despite these defeats, AC Milan were the winter champions, collecting 43 points from 19 matches. The market opened again in January, and three players arrived at Milanello: although Meïté and Mandžukić's stays turned out to be brief, Fikayo Tomori's story in the Rossoneri shirt is still being written. February didn't quite see the same success: defeats against Spezia and Inter cost the team first place in the league, whilst the Nerazzurri also prevailed in the quarter-finals of the Coppa Italia. AC Milan collected important points on the road (Hellas Verona, Fiorentina and Parma) but suffered a heavy blow away to Lazio. The final five games saw an excellent Rossonero reaction: four victories (amongst them, two wins in three days against Juventus and Torino), one draw, zero goals conceded and a return to the Champions League after Kessie's brace in Bergamo on 23 May 2021.
An abnormal season in terms of both the calendar and the matches behind closed doors for Stefano Pioli's AC Milan, with the Europa League qualifiers kicking the season off. Having overcome Shamrock Rovers in Ireland and Bodø/Glimt at San Siro, only a play-off against Rio Ave in Portugal stood between Pioli's men and the group stage. And an epic play-off it was, decided on the 24th penalty after a 2-2 draw after 120 minutes. This experience forged Pioli's group, revealing their strong character. The Rossoneri carried this form into the Europa League, topping a very balanced Group H. AC Milan made it through the round of 16 in the Europa League, narrowly missing out on the quarter-finals to Manchester United, despite a proud draw at Old Trafford.