Worst Serie A seasons in Milan’s history, how many difficult years

What are Milan’s worst seasons in Serie A over the past 40 years: the rossoneri’s top 10 worst finishes

Inzaghi (ANSA) – MilanLive.it

The 2024-2025 season risks becoming one of the worst ever (by Serie A placement) in the history of the Rossoneri club. A largely predictable failure considering that the choices made by Furlani, Ibrahimovic, Moncada and Cardinale last summer were blatantly wrong. It was clear to everyone but the managers. On the field then it is all a consequence: the performance of the Rossoneri perfectly reflects the historical moment of the club, which has fallen into a deep crisis from which it will not be so easy to rise again.

Maldini and Massara had managed to painstakingly bring Milan back to the top after the difficult years between last and post-Berlusconi; the current ownership and management has brought it all down, and with awareness. Such an ugly season, and one that threatens to take Milan out of Europe, has not been seen in a long time: it is the poster child for RedBird-branded failure. But what have been Milan’s worst Serie A seasons in the last 40 years? Let’s find out together the Rossoneri club’s lowest rankings.

2000-2001: la fine di un piccolo ciclo

La fine di un ciclo (ANSA) – MilanLive.it

Taking into consideration the final league standings of the last 40 years, Milan has finished outside the top five 11 times. Starting with the least worst, in the 2000/20001 season the Rossoneri finished in sixth place: they closed the season as coach Mauro Tassotti after Alberto Zaccheroni (who had won the title two years earlier) was exonerated.

2016-2017: il ritorno in Europa

Montella (ANSA) – MilanLive.it

To find AC Milan close the Serie A in sixth place, we have to go back 15 years: these were the last gasps of Galliani and Berlusconi just before a revolution, even a corporate one. Vincenzo Montella, with a team with major limitations from a technical point of view, managed to bring Milan back to the Europa League after years of absence in international contexts. The image of Montella carried in triumph by the players is one of the symbols of what fans call the Banter Era.

2017-2018: il fallimento cinese

Gattuso (ANSA) – MilanLive.it

It was April 2017 when Milan passed into the hands of the unknown Yonghong Lì, handpicked by Berlusconi to sell the club after 30 years. The Chinese entrepreneur presented himself in grand style: club in the hands of Fassone and Mirabelli and a stellar 200 million market. The enthusiasm, however, lasted very little: Montella exonerated after a few matches, Gattuso in his place and a very disappointing sixth place in the final standings.

2019-2020: un nuovo inizio

Giampaolo (ANSA) – MilanLive.it

Yonghong Lì was gone, the club was in the hands of Elliott and, after Leonardo’s departure, sports management had been entrusted to Maldini, Boban and Massara. The choice was made to bet on Giampaolo only to exonerate him after six games: in his place was Pioli, who was greeted with great skepticism but in fact was the beginning of a cycle that proved successful in the following years. In that season, historic for the stop caused by the Covid and the matches in the summer, Milan finished sixth but laid the foundations for the excellent future.

1985-1986: l’alba di una nuova era

Liedholm (ANSA) – MilanLive.it

In March 1986 the Silvio Berlusconi era began and Milan ended that season, with Liedholm on the bench, in seventh place in the standings. From those ashes began the revolution of the new ownership with Galliani and Braida managing the sports area: from that moment the history of the club changed.

2015-2016: un tentativo a vuoto

Mihajlovic (ANSA) – MilanLive.it

It can be seen as the latest attempt by Silvio Berlusconi and Adriano Galliani to raise their heads again in a very complicated period. The arrival of Mihajlovic in place of Filippo Inzaghi, a high-profile market with excellent graft (Luiz Adriano, Bacca, Romagnoli, Bertolacci, Balotelli) to bring Milan back to the top. This time, too, however, it ended in nothing: Mihajlovic’s exoneration in favor of Brocchi also served no purpose. Seventh place finish.

2013-2014: l’inizio della fine

Seedorf (LaPresse) – MilanLive.it

The 2011 Scudetto was the last major success of the Silvio Berlusconi era. In the following years the first difficulties, until the 2013-2014 season in which the team failed to qualify for the Champions League. The Allegri era ended, exonerated in January, and a long series of failed attempts on the bench began. Seedorf is the first: having just retired from playing soccer, Berlusconi wants him as coach. The results are also good, but the final standings say eighth place.

2014-2015: esperimento fallito

Inzaghi (ANSA) – MilanLive.it

The 2014-2015 season coincides with the beginning of Filippo Inzaghi’s Serie A coaching career. Coming off an excellent job with the Primavera team (complete with winning the Viareggio), Berlusconi and Galliani, following the fashion launched by Barcelona with Guardiola, decided to entrust him with a team that, in technical terms, had little to do with the Berlusconi era. Result? Tenth place in the standings, one of the worst Serie A results in the club’s history.

1997-1998: ancora in crisi

Capello (ANSA) – MilanLive.it

Fabio Capello returns to Milan after winning the championship with Real Madrid and Paolo Maldini is the new captain after Baresi retires. There is an air of a new beginning but instead it is the second year in a row of crisis after the previous one: 10th place in the standings.

1996-1997: la stagione peggiore

Sacchi (ANSA) – MilanLive.it

Milan’s absolute worst season in the last 40 years was 1996-1997. With the Capello era over, who went to Real Madrid, the Rossoneri chose to start again with Tabarez. Who, however, lasts eleven days: in his place comes back Sacchi, who has just resigned as Italy’s coach, who, however, fails to make an impact. The final placing is eleventh: it is the worst result in Serie A of the Berlusconi era.

The article The worst Serie A seasons in Milan’s history, how many difficult years was written and published in its original version on Milanlive.it.

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