Having drawn their last two matches—a 2-2 tie to Livorno last weekend in league play and a scoreless draw against Ajax in the Champions League—Milan will hope to erase an early part of the season that hasn't quite gone as planned. They're at an uncharacteristic ninth place in the Serie A table.
Roma, however, have enjoyed a heap of success. Heading into their 16th game of the season they haven't lost once with 11 wins and four draws.
Will Roma's winning continue or will Milan get off the schneid and find a way to manufacture some success?
Here's a look at everything you need to know for the matchup.
Who will win?
When: Monday, December 16
Where: San Siro, Milan, Italy
Start Time: 2:45 p.m. ET, 7:45 p.m. GMT
TV: beIN Sport
Live Stream: beIN Sport Play
Top Storyline: Can Milan Start Season Turnaround With Big Win?
As one of the few traditional powerhouse clubs in Italy over the past century, Milan have built their success on winning year after year. Even when the organization hits a rough patch, it doesn't seem to last long.
Thus begs the question—how long will this woeful start last?
Heading into their 16th game of the season, Milan have all of 18 points to show—good for a depressing ninth place in the Serie A table. Torino, Genoa and Hellas Verona are just a few of the clubs ahead of them at this point as they trail leaders Juventus by 22 points, and that deficit could grow over the weekend.
With the season inching near its halfway point, time is running out for Milan to claw their way back into relevance. If they wait much longer, hopes and dreams of getting into the Champions League will soon evade them.
What better of a time to start than on Monday? Roma are in second place in the league and have proven to be one of the most impressive clubs.
However, it will be far from an easy task. Milan have scored 23 goals on the season, but offensive ineffectiveness has stricken them at times. Just as well, Roma have given up an incredible five goals all season long—five less than anyone else.
Despite Roma's recent successes they've only won the league championship three times. Milan, however, have racked up 18 titles and their last one was in 2010-11.
There certainly is no shortage of talent in Milan, but an attacking line of Mario Balotelli and Kaka has seemingly not come to life as much as was expected.
Perhaps winning a morale-boosting match at home against one of the league's best could begin a season turnaround for Milan.
Vying to not lose their favourable place in the league table, Roma will come out fired up to secure three points. Even when they aren't playing up to their standards, Milan are Milan, and seeing the name is all it takes for Italian league players to step it up a notch.
Playing at home should help Milan enough to secure a point for their squad. The attack is still a work in progress, but being on the San Siro pitch will inject enough life in them to threaten Roma's stellar defence at least once.
Milan 1, Roma 1