With owner Silvio Berlusconi seemingly overseeing a cost-cutting exercise over recent years, Milan have now gone three seasons without a trophy. Maybe the penny has finally dropped for Berlusconi, as Milan look set to be active in the transfer market this summer, and have already swooped to snap up Paris Saint-Germain duo Alex and Jeremy Menez.
Long gone are the days of Champions League glory, and Milan fans will be hoping for a vast improvement in the coming season having finished eighth in the last campaign. In order to do that, the club must bring in some new talent - and two names have been strongly linked with moves to the San Siro.
The first player is right back Sime Vrsajlko from Genoa. The Croatian international featured for Niko Kovac's men at the World Cup in Brazil this summer, and has continued to build on a strong reputation that he established during his time with Dinamo Zagreb as a youngster.
The 22-year-old was recently linked with Arsenal as a potential replacement for Manchester City-bound Bacary Sagna, but Milan are reportedly on the verge of completing a swap deal, with striker Alessandro Matri heading to Genoa in exchange. It will enable the Rossoneri to form a promising full back duo of Vrsajlko and Italian international Mattia De Sciglio as they look to get younger in defence.
The second name is a bigger one, and one that Arsenal fans would surely have wanted to see turning out at the Emirates Stadium. French winger Antoine Griezmann has been starring in Spain for Real Sociedad, and is one of the most coveted wingers in football right now having hit 16 goals last season and impressed at the World Cup.
However, the 23-year-old is reportedly a backup option if Milan can't tie up the signature of Verona's Argentine winger Juan Iturbe, who has been labelled 'the next Lionel Messi'. If they can sign the 21-year-old, then Griezmann could be available to sign once again - which should alert Arsenal as Arsene Wenger looks to add a spark to his front line.