While Milan certainly have a chance to advance past Barcelona, it's tough to see it happening.
AC Milan aren't quite as formidable of a side as they have been over the last two seasons, but they've improved significantly as a team in recent months, and could end up hitting their stride just in time for their UEFA Champions League clash with FC Barcelona. The two sides were placed together in the Round of 16 during Thursday's draw, and will get a chance to play a rematch of last season's group stage fixtures.
Barcelona vs. AC Milan
Riccardo Montolivo - Who was I going to pick, Lionel Messi? It's obvious that the little magician is the tie's best and most important player, so much so that it's hardly worthwhile to write about. The biggest difference between Milan getting steamrolled and pulling off an upset could potentially be Montolivo, the versatile central midfielder who has played advanced and deep-lying roles for Milan and Italy over the last year. His defensive positioning will be key against Milan, and his incredibly precise long balls will be Milan's best way to create chances.
Matchup to watch
Stephan El Shaarawy vs. the right side of Barca's defense - He's just 20-years-old, but Stephan El Shaarawy is already Milan's best attacking threat, and arguably the best Italian forward in the game today. He lines up on the left side of Milan's 4-3-3 and does plenty of both drifting wide and cutting in onto his right foot for shots. Between Javier Mascherano's inconsistency, Carles Puyol's age and Dani Alves' tendency to get caught up the pitch, there should be plenty of space for El Shaarawy to exploit. If Milan can get the ball to him -- which is no easy task in and of itself -- he should be able to capitalize on the space he's granted.
Barcelona through by two goals - Milan will set out to deny Barcelona an away goal at the San Siro, as futile of a goal as that may sound on the surface. Ultimately, they're unlikely to pull off that feat, but it wouldn't be the least bit surprising to see them snag a 1-1 draw in the home leg. That will give them a faint bit of hope heading to the Camp Nou, where the Blaugrana will simply be too good for Milan to handle in a 2-0 or 3-1 loss.
It's not impossible for AC Milan to nick a goal or two on the counter, keep compact in midfield, dodge some bullets and walk away with an aggregate victory, but it's tough to see it happening. This is not your father's Milan. They're simply not one of the world's best defensive sides anymore.