Sunday evening pits two heavyweights of Italian football together in what could be a crucial match so early on in the season.
Hosts Milan will be aiming to put the pain of a 2-0 defeat against Sampdoria firmly behind them with a victory over fifth placed Roma. It's been a slightly underwhelming start to Serie A for Vincenzo Montella's men. After a summer of huge squad investment, many expected Milan to storm Italy - but so far the Rossoneri sit in sixth with 12 points.
Meanwhile, Roma are hoping to build on a very strong start to their season. After an opening day defeat to Milan's fierce rivals Inter, they have gone on a four game winning streak, and will be planning on making it five as they bid to put some daylight between themselves and Milan in the league table.
Here's everything you need to know ahead of the clash at San Siro.
AC Milan: LWWWLW
While Milan have hugely impressed in the Europa League so far this season; of their last four Serie A games, the Rossoneri have lost two of them - including an unexpected defeat to Sampdoria last weekend. It seems as though Nikola Kalinic and Andre Silva are starting to come good in the striking department, but Montella will be hoping his defence can figure out how to stop leaking goals - having shipped ten in their last six matches.
Roma have begun their season on fire. Scoring ten goals and conceding only one in their last three Serie A matches proves just how impressive their performances have been, and will be hoping to exploit Milan's defensive issues come the weekend.
Classic Encounter: AC Milan 1-4 Roma (May 2017)
You only have to look back as far as May to find a five-goal thriller that put Milan to the sword at the back end of last season. Last term was a poor one by the Rossoneri's standards, and that is epitomised by how Roma outclassed the San Siro outfit the last time they visited AC at their home.
An early brace from Edin Dzeko set the pace of the game rather quickly. A ball into the box from Mohamed Salah found its way into the target man; Dzeko finding the top right corner from the middle of the box after eight minutes.
Donnarumma was picking the ball out of the back of the net once again 20 minutes later, after the same scorer found the top left corner with a close range header.
It took until the 76th minute for another goal to go in - this time offering the hosts a glimmer of hope when Mario Pasalic got onto the end of a Lucas Ocampos headed pass from a corner.
However, Milan's hope was short lived when Stephan El Shaarawy restored the two goal deficit not two minutes later from inside the box. Things went from bad to worse from there on out for the home team. Gabriel Paletta's foul on Mohamed Salah in the box proved to be a double edged sword in the 86th. After receiving his marching orders, Paletta had to watch as Daniele De Rossi put the game to bed from the spot.
The hosts are without five players heading into this weekend's tie. Muscle injuries to full backs Luca Antonelli and Davide Calabria kick-off Milan's injury list along with Riccardo Montolivo (hamstring), Andrea Conti (anterior cruciate ligamnet) and Hakan Calhanoglu (who is both suspended and injured with a contusion).
Roma, on the other hand, can go one better than Milan with six players missing for Sunday. Left-back Emerson is sidelined with a cruciate ligament injury, with Patrick Schick absent with a hamstring problem. Furthermore, Gregoire Defrel, Diego Perotti and Abdullahi Nura are all out with muscle injuries, and Rick Karsdorp is expected to be missing due to fatigue.
AC Milan (3-5-2): Donnarumma, Bonucci, Romagnoli, Musacchio, Abate, Kessie, Biglia, Bonaventura, Rodriguez, Kalinic, Andre Silva
Roma (4-3-3): Becker, Florenzi, Manolas, Fazio, Kolarov, Strootman, De Rossi, Nainggolan, Under, Dzeko, El Shaarawy
This is a very tough match to call. Roma have started the season strongly and look very capable of besting Milan (yet again - Milan have failed to beat this weekend's opponents at all in the last two years). With that said, this is a very different Milan team who are determined to grind out results, and have the players to do it.
In times like this, sitting on the fence is always a viable option - and it looks as though a draw is a real possibility here.
One thing that sways it in favour of the visitors is that they're scoring for fun, and Milan's defence has been sloppy of late. But at the end of the day, this is a couple of very good teams that both have the capability of taking three points. Regardless, it will be a highly entertaining match.
Score Prediction: AC Milan 2-2 Roma