By early 2014, it was clear that Milan were performing exceptionally poorly, prompting manager Massimiliano Allegri to be replaced by Clarence Seedorf in mid-January.

In the Champions League, Milan secured a place in the group stage after defeating PSV Eindhoven in the play-off round 4–1 on aggregate.

On 11 December 2013, Milan qualified for the knockout stage of the competition after playing to a 0–0 draw against Ajax, securing second place in the group behind leaders Barcelona.

They will play their first set of friendlies in Reggio Emilia in Città del Tricolore on 23 July to contest the TIM Trophy consisting of three games.

Milan started their 2013–14 UEFA Champions League campaign in the play-off round against Dutch runners-up PSV, winning over two legs to qualify for the group stage.

Jherson Vergara also arrived, having signed on before the transfer market, just after fellow Colombian defender Cristián Zapata was bought by Milan after a successful loan spell.

Another import transfer was midfielder Andrea Poli, purchased from Sampdoria.The main hits come in the final part of summer market, acquiring Alessandro Matri and welcoming back Brazilian star Kaká.

Other departures included Bojan (who returned to his main club Barcelona), Mathieu Flamini (who did not agree to a contract extension), Luca Antonini and, arguably most importantly, Kevin-Prince Boateng, who left just the day after scoring two goals in the 2013–14 UEFA Champions League play-off against PSV, assuring the team's progression to the tournament's group stage.