The way the Coppa Italia is set up means Fiorentina's position in Serie A is now irrelevant. The winner of this cup is granted a Europa League berth.
On the other hand, the Rossoneri are desperately trying to salvage a lost season and go into the summer with any reason for optimism.
Clarence Seedorf is winless in his last four Serie A matches and will look to finally get three points after a draw last weekend against Lazio.
Every single member of Milan's organization has come under fire at different points of the season, and it's one of the darkest years in memories for a club that has such a storied past.
With that being said, let's take a look at some of the tactical battles and storylines that will shape this clash:
Matri to play against old team
After a lengthy layover, Mario Gomez has once again been injured. He has sustained damage to his collateral ligament in his knee and will miss the next three to four match days.
After a hyped summer move from Bayern Munich, the German striker hasn't been able to build any semblance of continuity.
This means that Milan's most expensive summer signing will play from the start against the Rossoneri. Alessandro Matri will spearhead a Viola attack that prioritizes possession and has the personnel to send plenty of quality balls into the box.
Seedorf to make other wholesale tactical changes
Seedorf is still trying to decipher which formation and groups of players will work best, and wholesale changes are expected around this Milan side.
It's been mysterious situation involving Taarabt, who certainly hasn't been benched because of his lack of effort. If anything, he has been Milan's best performer this calendar year since coming over from Fulham.
Robinho, on the other hand, has seldom been used for the past few seasons and really isn't part of the core of Milan's team anymore.
The ultimate possession battle
The most fascinating aspect of this match is that it involves two teams that want to play aesthetically pleasing possession football. Fiorentina have excelled at experimenting with their own version of tiki-taka, as the likes of Borja Valero, David Pizarro and Alberto Aquilani have formed a great partnership in the middle of the park.
Milan, on the other hand, have employed a sloppier version of the possession game, which often results in lackadaisical passes back to one of the central defenders, who then boots it up field.
Fiorentina should have no trouble dictating the play in their own stadium but could get caught out on the counter.
In the end, expect Fiorentina to have the upper hand throughout the match. Milan's defense often leaves gaps wider than the Panama canal, and the Viola have a wealth of midfielders who are able to pick out the perfect diagonal run into the box.