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Will These Five Matches Define Milan’s Season?

Milan go in to the Serie A season with less expectation than last season, but seemingly in a far more stable position.

The Rossoneri spent over €200m on transfers last summer, with fans dreaming of a tilt at the Scudetto.

Owner Yonghong Li’s financial capacity soon came into question though, and he has been ousted by hedge fund Elliott Management.

The aim will still be to return to the Champions League under Gennaro Gattuso, and these are five games which could prove crucial in deciding whether or not that happens.

Napoli vs Milan – Week 2
It won’t be an easy start to the season for the Diavolo, as after debuting at home with Genoa they face a trip to the Stadio San Paolo.

The Rossoneri haven’t beaten Napoli since December 2014, and their winless run in Naples stretches back to October 25, 2010.

A clash with Roma at San Siro follows in Week 3, and with the spectre of Antonio Conte hanging over Gattuso, the Coach will want to ensure a fast start.

Milan vs Atalanta – Week 5
Milan successfully appeal to the Court of Arbitration for Sport after being barred from the Europa League by UEFA, and they get their European campaign underway on September 20.

If Atalanta come through the qualifying rounds they will also be in action that night, so the two would meet on Monday February 24.

Some fans suggested the Diavolo may be better off outside of the Europa League to really concentrate on reaching the top four, and that double-header of games will show where their priorities lie.

Inter vs Milan – Week 9
The first Derby della Madonnina is one to be marked on the calendar for all calcio fans.

Inter and Milan first square off at San Siro in late October, where the city’s bragging rights will be up for grabs.

The Nerazzurri appear to have strengthened well this summer, but of last season’s top-four they would appear to be the most realistic for their city rivals to overhaul.

A win in the first derby of the season would make a real statement to that effect.

Juventus vs Milan – Week 31
April brings a difficult double-header for Gattuso’s side, with a trip to Turin followed by the visit of Lazio.

Juve-Milan is a classic of Italian football, but the Rossoneri have lost all of their last five meetings and haven’t won at the Allianz Stadium since it was opened in 2011.

The Bianconeri could be in Champions League quarter-final action the following midweek though, so this could be a real chance to break that duck.

Fiorentina vs Milan – Week 36
Milan actually have a fairly comfortable looking run-in past Week 32, and if they’re in a good position by that point their destiny should very much be in their own hands.

One potential banana skin though is the trip to Fiorentina on the weekend of May 12.

The Stadio Artemio Franchi isn’t an easy place to go for anyone, and the Viola will hope to be very much in the Europa League mix by that point of the season.