Six key things that will define AC Milan’s 2019-20 season

By Oliver Fisher -

It is time for us to go unto the breach once more. The waiting is almost over, and Milan will get their 2019-20 campaign underway against Udinese on Sunday.

It has been a summer of radical overhaul for the Rossoneri and very familiar feeling in a way, with a new head coach and sporting director at the helm, plus a return for Boban and a bigger role for Paolo Maldini.

Five new signings have arrived for a total of €90million, namely Theo Hernandez, Rade Krunic, Rafael Leao, Ismael Bennacer and Leo Duarte, while fan favourite Patrick Cutrone has departed.

Preseason has seen mixed results. Good performances against Benfica and Manchester United were rewarded only with a defeat and a draw respectively. Last weekend’s win in Kosovo against Feronikeli was overshadowed by a mind-numbing stalemate in Cesena.

A return to the Champions League is essential, and for all the good things that this side has displayed under Marco Giampaolo thus far, there seem to be an equal number of doubts.

Here, we break down a few things that will define whether the Rossoneri can have a successful 2018-19.

1. The Pistolero must fire

There is cause for concern regarding the preseason that Krzysztof Piatek has had. The man who arrived from Genoa in a €35million deal back in January hit the ground running, scoring nine goals in his first nine starts, but has been on somewhat of a drought since then.

Giampaolo made a worrying admission regarding the Poland international’s physical state, but one thing is for sure: Piatek has to get back in the goals – and fast – for the team to win games consistently.

His relationship with new acquisition Rafa Leao will be interesting to watch and if the pairing can click, there’s no doubt that il Pistolero will find form again quickly.

2. Integrating the new signings

As mentioned above, there have been five new arrivals at San Siro this summer, all of which have generated varying degrees of excitement among supporters.

There is the feeling that Hernandez, once recovered, will become the new starting left-back, while Leao can currently be pencilled in as the support striker.

Ismael Bennacer will also start as the regista in time once he has had more opportunity to work with the group in training. Rade Krunic and Leo Duarte meanwhile look set to start the season as bench options.


Two things has been clear with the recruitment strategy in the current window: the vision has been to build a squad full of young players with huge potential, and Giampaolo has had a significant say in all the signings.

That seems to suggest that they will be an ideal fit for his 4-3-1-2 system, but it is important to see chemistry early to build confidence ahead of some tough stretches in the season.

3. Start as you mean to go on

Speaking of the fixture schedule, it is clear that Milan have a big opportunity to build up a head of steam ahead of a brutal stretch from matchdays 9-13.

As aforementioned, a trip to Udinese beckons to start the season, followed by games against newly-promoted sides Brescia (H) and Hellas Verona (A) respectively.


Without getting too carried away, nine points from nine would be the perfect preparation for the crucial derby against Inter which follows; a game which as recent history has dictated can set the tone for an entire season.

The gruelling stretch begins on October 27 with a trip to Roma, and a home game against SPAL is then followed by games against Lazio (H), Juventus (A) and Napoli (H). That, along with the reverse later in the season, could be indicative of where this side is.

4. Finding the captain’s deputy

In order to win games and have a successful campaign Milan must of course score goals, but they must keep them out too.

Giampaolo admitted after the Cesena game that at the moment a centre-back pairing of Alessio Romagnoli and Mateo Musacchio gives him ‘the most assurances’ due to their experience playing together.

However, one of the key areas that Milanisti have been calling on the team to strengthen is the centre of defence, with Musacchio guilty of a number of shaky performances last season.

Duarte’s arrival provides the potential for a player who could step into that role as Romagnoli’s partner in time, however he is at present viewed as Cristian Zapata’s replacement and thus more of a depth option.

The return of Mattia Caldara on the face of things will give Giampaolo an option and Musacchio serious competition; though it remains to be seen how his physical condition holds up after recovery.

5. The usual suspects

The new head coach appears to be willing to trust many of the existing squad members he inherited.

As mentioned, Caldara’s return to the fold has a potential to be season-changing too. He appears to be the man that the management are trusting to step up and partner Romagnoli.

Davide Calabria’s ability to be the complete full-back Giampaolo’s system requires will also be interesting to see, as will the question of how well Franck Kessie can adapt, plus the impact Hakan Calhanoglu and Lucas Biglia can make.

Giacomo Bonaventura made his comeback appearance against Manchester United in the International Champions Cup – his first game in a Milan shirt for 282 days.

Several reports in the Italian media have described him as the joker in the pack at Giampaolo’s disposal: a player who is a bit of an unknown quantity with regards to the 4-3-1-2 but one of proven quality.

Whether he is deployed more as a left-sided mezz’ala or as a back-up to Suso at trequartista remains to be seen, but if Jack can get back firing on all cylinders, it will feel like a new signing.

6. The Suso experiment

One of the more positive signs from preseason action has been Suso’s displays playing in behind the front two. The Spaniard netted goals against both Manchester United and Feronikeli and largely impressed in his new position.

There were several doubts about the 25-year-olds future given his more natural role as a winger, but what he has shown so far is enough reason for Giampaolo to apparently tell the club not to sell him.

If Suso can keep up those levels of performance and perhaps even improve, he will be Milan’s most creative player, just as he has been over the last two seasons.

The former Liverpool man has a combined 31 goals and assists over his last 70 Serie A appearances. The quality is there, both from open play and set pieces, so it is vital that he excels as a trequartista – especially given that Paqueta is seemingly type-cast as a mezz’ala.

Once the curtains raise on Sunday evening, we will embark on what will hopefully be a memorable season. The key is to support the team from the start, to show as much patience as possible and let the new boss put his stamp on the team.

It promises to be an exciting campaign, and hopefully one that shows the correct steps are being taken to lead the club back into Europe’s elite.

READ MORE: Player Ratings – Cesena 0-0 AC Milan

Tags AC Milan Franck Kessie Giacomo Bonaventura Ismaël Bennacer Krzysztof Piatek Marco Giampaolo Suso
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