Milan may be about to turn their season around after beating rivals Inter in extra time in the Coppa Italia in midweek.
Despite spending nearly €175m in the summer, Milan find themselves in the bottom half, and below Saturday's opponents Fiorentina, who are going about their business nicely and sit eighth.
Here's all you need to know before Saturday's lunchtime clash.
The most memorable encounter between the two sides in recent years came at the back end of the 2012/13 season, where both teams were in direct battle for the third and final Champions League spot. Milan came to Florence narrowly ahead of their hosts, and took the lead when Ricardo Montolivo took full advantage of a David Pizarro slip.
Even worse for the hosts, they were reduced to 10 men following Nenad Tomovic's red card before half time. Ex-Arsenal man Mathieu Flamini was one hand to tuck away number two, and from there it looked like a crucial three points for Milan. However, Fiorentina were determined to keep the fight for third going and pulled two quick-fire goals back through Adem Ljajic and David Pizarro, both of which came from penalties.
Milan managed to hold on for the point but were frustrated as Mario Balotelli and co. threw away what would of been a huge win. It wasn't all bad in the end, as Milan did finish third and qualify for the Champions League whilst Fiorentina finished two points behind in fourth.
Hosts Fiorentina have a full squad to pick from, and could go with the same eleven that narrowly lost to Lazio in the Coppa Italia in midweek.
As for Milan, Antonio Donnarumma remains the team's only fit goalkeeper whilst full-back Andrea Conti is out until after the new year. Gennaro Gattuso could go with some of the players who played 120 minutes in the win over Inter on Wednesday but he may well mix it up after successive league defeats without scoring.
Potential Fiorentina Starting XI: Dragowski, Milenkovic, Vitor Hugo, Astori, Gaspar, Benassi, Sanchez, Veretout, Chiesa, Saponara, Babacar.
Potential AC Milan Starting XI: A Dommarumma, Abate, Bonucci, Ramagnoli, Rodriguez, Kessie, Biglia, Calhanoglu, Suso, Crutone, Bonaventura.
Whilst the Milan derby win was a step in the right direction, Gattuso still has a job to do in terms of getting the team together and building some consistency to helping them move up the table. Fiorentina are not to be messed with, and at home they will be a real force to beat as both teams will offer a relatively physical style.
Fiorentina are playing quite well at the moment, and for that reason they just have the edge here. Milan will still be fairly tired from Wednesday's efforts in the cup and the hosts should be able to take that as a major advantage here.
Prediction: Fiorentina 2-1 AC Milan