Both teams have been involved in some of the greatest ever battles for the Serie A title, and now they both compete for the right to challenge Juventus' reign at the top of Serie A.
Vincenzo Montella and Luciano Spalletti have worked together before at Roma, Montella worked under Spalletti and now the two face off as managers of two of the top clubs in Italy hoping to rekindle old glories once again.
AC Milan in excellent form so far
Montella's AC Milan have been in very good form of late. They are unbeaten in their past five games, and while the race for Champions league places still looks like it will be very tight, the Rossoneri have proven themselves to be worthy competitors indeed.
It seems as though Milan have learned to grind out victories when necessary and also battle through to the very end. Their recent form in the Serie A is proof of their excellent work and is also a huge credit to the change Montella has brought to the team.
The clash with Roma will no doubt be a tough challenge for Milan, who have had tough luck against the Giallorossi in the past. They have won only one game in their past six meetings but Montella will hope things will be different this time around for his team.
Gianluca Lapadula has been in very good form and has been favoured by Montella up front for the Rossoneri as the Colombian hitman Carlos Bacca looks as though he is soon to be on his way out of the club.
The youthful exuberance of M'baye Niang, as well as that of Suso, will prove a challenge for a Roma defence which has looked shaky at times this season.
The industry of Giacomo Bonaventura will also be vital if Milan are to dominate the midfield battle against the likes of Radja Nainggolan and Kevin Strootman.
Roma looking to add to impressive home form
Spalletti's Roma have been excellent at the Stadio Olimpico so far this season and have won each of their last ten games at home. Their second-placed position in the table is because of the good football they've been playing this season.
History favours the Romans in this clash. They have emerged victorious against the Rossoneri on three of the past six clashes and are unbeaten against Milan in 11 of their past 12 games at the Stadio Olimpico, something they will look to maintain here.
Roma seem to have no problem with scoring goals this season. Edin Dzeko has been the spearhead of Spalletti's side, whose goalscoring burden has also been shared by the likes of Mohamed Salah and Diego Perotti. Both players have had a very productive season in terms of goals and assists.
The entire Roma midfield is full of battlers and the likes of Nainggolan, Strootman and Daniele De Rossi look as though they are going to give the Milan midfield trio a torrid time in the match.
If Bruno Peres is deployed on the right for Roma, his pace could cause a few problems for the Rossoneri too.
For Roma, the absence of Mohamed Salah as well as Alessandro Florenzi will be a concern. Peres will look to fill in for the pacy Egyptian international.
For Montella's Milan, Juraj Kucka and Riccardo Montolivo are still out through suspension and injury respectively. Montella will look to Manuel Locatelli to anchor the midfield and Bonaventura to dictate the game for the Rossoneri.
AS Roma Predicted XI: Szczesny, Rudiger, Manolas, Fazio, Emerson, Strootman, De Rossi, Peres, Nainggolan, Perotti, Dzeko.
AC Milan Predicted XI: Donnarumma, Abate, Paletta, Romagnoli, De Sciglio, Bonaventura, Locatelli, Pasalic, Suso, Lapadula, Niang.