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AC Milan Season Preview 20/21: Stability at Last

A project fans could wholeheartedly buy into.

Zlatan, Hakan, Kjaer and Saelemaekers celebrating against Shamrock Rovers
imago images/LaPresse

AC Milan’s 2019/20 season was a tale of two completely different halves. After a terrible start to the season, a change in coach and the addition of a legendary former Milan player, the season turned around, culminating in a 9 win 3 draw finish to the season. The Rossoneri’s run of form to end the season resulted in them finishing 6th and earning them entrance back into European competition via the Europa League. Let’s take a closer look at what we could expect from the Rossoneri during the upcoming season.

New AC Milan wonderkid, Sandro Tonali with Maldini and Massara


Incoming: Alexis Saelemaekers, Simon Kjaer, Zlatan Ibrahimovic, Brahim Diaz, Pierre Kalulu, Sandro Tonali, Ciprian Tatarusanu, Daniel Maldini (Primavera), Lorenzo Colombo (Primavera)............

Outgoing: Lucas Biglia, Pepe Reina, Asmir Begovic, Giacomo Bonaventura.............

During the shortened summer and transfer season, Milan management has continued their pursuit of slashing the wage bill and tending to their youth revolution with shrewed signings on team friendly wages, via club friendly formulas. With the transfer window in Serie A closing on October 5th, 2020, more sales and acquisitions can be expected as Paolo Maldini and company continue to shape the squad to be able to compete on three fronts. Regardless of further signings however, the strategic molding of the squad, albeit incomplete, sees significant improvement in key areas. The engine room of the squad has been significantly strengthened with the addition of Sandro Tonali, one of the most sought after youngsters in Italy, with Brescia president Massimo Cellino claiming that the player turned down advances from both FC Barcelona and Manchester United to join Il Diavolo. Where the midfield rotation last year included the likes of Lucas Biglia, the Rossoneri could now turn to a rotation trio of Ismael Bennacer, Franck Kessie and Sandro Tonali as they prepare to put forward a good showing in three competitions this year. Another highly touted youngster also arrived in the form of Brahim Diaz. The Spaniard’s ability to play either as an attacking midfielder or a winger will surely come in handy if Samu Castillejo and Alexis Saelemaekers fail to convince in the right wing positions (although reports suggest Milan might bring in a winger before the window closes). Although the player arrived on a dry loan from Real Madrid, reports claim that both clubs will meet back at the negotiation table to try to work out a deal involving either and option or obligation to buy.


One of the most important plot lines of the past season that has undoubtedly bled over into this season is the coaching situation at Milan. After intense and prolonged negotiations with Ralf Ragnick to take over from Stefano Pioli as coach, Milan made an about turn towards the end of last season, confirming and extending the current Milan coach by another year.

While it remains to be seen whether or not that decision would ultimately bear fruit for the Rossoneri, what is for certain is that stability within the club, something which has been lacking for the past decade, is now assured. Players could rest assured that the good relationships fostered, the formation, their roles and the requirements asked of them will continue into this new season. At the very least we could expect the same positive environment that was fostered at the end of the last campaign.

Pioli would look to employ the same 4-2-3-1 formation that served him so well last season. Look for the starting lineup to remain unchanged for the most part as well with the only change being Davide Calabria inserted instead of the oft-injured Andrea Conti. Again this is subject to change as well with the transfer window still being open. All in all the retention of Pioli represents a stability that bodes well for the club’s top 4 hopes.


There is one main objective for Milan at the moment: Champions League qualification. As stated earlier the club would be competing on three fronts this season: Serie A, Europa League and Coppa Italia. After a year of voluntary omission from European competition the Rossoneri are back in Europe, competing for the Europa League. Winning this tournament means automatic qualification for the Champions League. Top 4 in Serie A also guarantees qualification into the Champions League, although a 4th place finish would enter Milan into a Champions League playoff, where a victory would secure entrance into the group stage. Therefore in order for the club to achieve its primary objective it must either secure a top 4 finish in the league or win the Europa League.

Having squad depth to try to achieve both is imperative, but the Rossoneri must go all out for both. Placing all their ‘eggs in one basket’ could leave them with ‘egg on their face’ at the end of the season. The Rossoneri also have never lifted a Europa League trophy which if done, would represent a ‘feather in the cap’ of the Rossoneri. The Italian Cup represents less of a priority at this point of the rebuild, so expect Milan to focus their attention more on the league and Europa League than the Coppa Italia.


Most important player

With so many players having important functions in the squad its difficult to choose just one who stands out as more important than the rest. While Bennacer, Ibrahimovic, Ante Rebic, Theo Hernandez and Hakan Calhanoglu may be great shouts the person who the club is really counting on to stake their claim is Davide Calabria. Serge Aurier, Emerson and Denzel Dumfries have all been linked to the club over the past two months but Pioli has chosen to put his faith in the Italian fullback. Still only 23, Calabria is entering his 7th season with the Red and Black of Milan. The right side of defense had been the most problematic for Milan last season, but if Calabria could improve defensively while producing anything close to what Theo Hernandez did on the left last year, the club could benefit greatly.

Calabria vs Shamrock Rovers
Getty Images

Players to Watch

There’s really no other candidate for this than the mercurial Zlatan Ibrahimovic. The Swede’s inclusion in the squad last January, immediately coincided with the best run of football we’ve seen from Milan in eight years. Not only does produce tangible results on the pitch in the form of goals and assists, but he’s been able to effectively transmit his winning mentality to the other players. In one of his epic rants last season, Zlatan stated “If I was here from the beginning of the season, we would have won the Scudetto!” With the way Milan finished the season it’s hard to argue against that, but Ibra now has the chance to validate that claim this upcoming season.

Surprise Player

Various reports have stated that Milan will rely on two youngsters from the Primavera this upcoming season: Daniel Maldini and Lorenzo Colombo. While many fans have trepidation calling Daniel the next in a long line of great Maldinis to play for Milan, there is general consensus that Colombo may be the best Primavera striker we’ve seen in years. Couple that with his scorching form this preseason and his potential playing time, deputizing for Zlatan in a condensed season and the stars may be aligning for the hulking attacker. Blessed with a bulking physique, good mobility and a precise left foot, Colombo has all the tools to be a great modern attacker. If preseason is any indicator, look for him to continue to bag goals whenever the opportunity comes.


Serie A: 4th

Europa League: Semi finalists

Coppa Italia: Semi finalists

Top Scorer: Zlatan Ibrahimovic

Most Assists: Hakan Calhanoglu

Disappointment: Samu Castillejo