5 Key Remaining Fixtures in AC Milan's Season

The second half of the Serie A season has begun, and AC Milan started it well by avenging their opening-day loss to Fiorentina, beating La Viola by the same 2-0 score that went against them in Florence.

Going into the next round of games, Milan will be either sixth or seventh—depending on the results of Wednesday's match between Sassuolo and Torino, which had to be postponed several weeks ago due to fog—and only three points behind a freefalling Roma team for fifth.  

The San Siro team are also headed to the semi-finals of the Coppa Italia, where they will face third-division Cinderella team Alessandria.

There are 18 league games and at least two in the Coppa left to go, and some will be more important than others.  Several key matchups will go a long way toward deciding how their season will end.

What are the biggest games facing Sinisa Mihajlovic's men between now and May?  Today we take a good look at the fixture list and pick out the five biggest games remaining on Milan's schedule, in chronological order.

Alessandria, January 26/March 1

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Alessandria has become the first Lega Pro side to reach the semi-finals of since 1984.

We'll be counting the two-legged Coppa Italia semi-final against Alessandria as one fixture for the purposes of this list.

This looks like a massive mismatch on paper.  Milan, the 18-time Italian Champion and seven-time European champion, against Alessandria, a Lega Pro team that hasn't seen the top flight since 1960.

But Alessandria have proven a Cinderella team that refuses to let the clock strike 12.  They have been in the competition since the very first round in August, beating Altovicentino (2-), Pro Vercelli (2-1), Juve Stabia (1-0), Palermo (3-2), Genoa (2-1 in extra time) and Spezia (2-1).

Of those six teams, four play in a higher league than the Grigi and two of them were top-flight opponents.  And it isn't just that they've beaten higher-ranked opposition—it's that they've done it in style.  They never trailed in any game until Monday's quarterfinal against Spezia, and their reaction to going down was exemplary.  They could have equalized long before they finally did in the 83rd minute, and scored twice in nine minutes to advance.

Overall, they've played 210 minutes in the competition and trailed for only 63.

Their problem now is the two-legged nature of the semifinal.  This kind of tie tends to allow the team with the better talent come to the fore, and Milan certainly has the better team on paper.

This tie is also critical in the race for Europe.  On the other side of the bracket, it's likely that both semi-finalists will finish in the top five of the league.  Third-place Inter has already qualified for the last four, while second-place Juventus are favored to beat Lazio on Wednesday.  If one of them makes it to the final, that means simply qualifying for the showpiece will likely guarantee Milan a spot in the Europa League.

The target this year was a return to the Champions League, but qualifying for any European competition next will be a boon to Milan.  There will be some prize money involved, and it will give young players valuable experience on the continent.

Given the stakes, this tie could mean more for Milan than any league game.

Inter, January 31

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Carlos Bacca and Gary Medel battled in the first Derby della Madonnina in September.

Regardless of their position in the table, the Derby della Madonnina always brings the best out of Milan and Inter.

At least, usually.  In the second of the two matchups last year, the two teams played out a drab 0-0 draw.

Fortunately, this season's first encounter between the two rivals was far more entertaining.  There was end-to-end football, and the game was decided on an excellent goal by Inter's Fredy Guarin.  But Milan was by no means toothless.  They very nearly equalized, with a returning Mario Balotelli coming particularly close in with two shots, one that flashed past the post and another that was parried in stunning fashion by Samir Handanovic.

Even if a season ends without a trophy, there's always a silver lining if you win the derby.  Seeing Inter do the double would be unthinkable.  The fact that the Nerazzurri are ahead of them in the table takes this game to another level.  It's one thing to get one over on your rival, but it's another to draw closer to them in the table.

The result of this game could have multiple effects.  The result will set the tone for the rest of the season, and any disasters may cost the embattled Mihajlovic his job.

Napoli, February 22

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Napoli destroyed Milan at the San Siro in October.

October 22 was not a good day for AC Milan. That was the day Napoli came to visit the San Siro.  They meant business.

When the dust had settled, the Rossoneri had suffered their worst home defeat of the decade—a 4-0 mauling that marked the team's lowest point in the season.  Napoli soared, though, eventually becoming winter champions and romping through the Europa League.

Milan has managed to turn their season back upward, but this late-February fixture will be a major test—as well as a chance for revenge.

The San Paolo is an imposing place for a visiting team, but Napoli's defense can be penetrated if Mihajlovic pushes the right buttons.  The problem will be containing the deadly quartet of Marek Hamsik, Jose Callejon, Lorenzo Insigne and Gonzalo Higuain.  The last man in particular is the key.  According to WhoScored.com, Higuain has scored 20 of Napoli's 41 league goals—that's 49 percent.

If Higuain can be neutralized, Milan could manage a classic Serie A smash-and-grab.  If not, they'll have to score with the Partenopei—no easy feat.

This game could either provide a huge lift or totally deflate the team.  One way or the other, this result could set the tone for the next three months.

Sassuolo, March 6

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Domenico Berardi could haunt Milan yet again.

Sassuolo has been AC Milan's bogey team ever since they achieved promotion to the top flight three summers ago.  In two years, Milan has lost both of their visits to the Mapei Stadium.  Both games were shootouts—the aggregate score was 7-5.

The terror in this game will be Domenico Berardi, who scored all seven of the Neroverdi's goals.  The 21-year-old starlet added an eighth goal against Milan earlier this year in the Rossoneri's 2-1 October win at the San Siro.  Piling on even more, all but one of the goals came from open play.

April's home game against Juventus was a contender for this spot as well, but this game could have a much larger impact.  Another defeat to Sassuolo could be debilitating to morale, and—if the two teams are as close to each other in the table as they are now—it could provide a crucial difference in the table.

Roma, May 15

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Milan dominated Roma after a difficult start.

Milan hosts AS Roma on the last day of the season, and there could be quite a reward for winning.

If Roma manages to arrest its freefall and maintain its position in the table, there could well be a battle between multiple teams for the fifth and final European qualification spot, especially if Coppa Italia results mean sixth place isn't in play.

Earlier this month, Milan visited Roma and started in the worst possible way, conceding the opener within four minutes.  But by the half-hour mark, Milan found their footing and dominated the second half, managing to equalize but failing to find a winner.

That game cost Rudi Garcia his job in Rome, and there's no telling how Luciano Spalletti will have molded the team in five months' time.  But if the table stays relatively consistent until the end of the year, these two teams will likely be playing for something big when the end arrives.

In a battle of two heavyweights, European destinies could be on the line.