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It will be an emotional night for Stefano Pioli on Sunday, as he returns to take on AC Milan, a club that he made history with.
The 2021-22 Scudetto-winning coach returns to San Siro with a Fiorentina side that are struggling. With Milan, he experienced the pinnacle of his sporting career, turning doubters into believers and awakening a sleeping giant. La Gazzetta dello Sport recall his 10 symbolic moments.
Proving everyone wrong
On 9 October 2019, Stefano Pioli was named Milan’s new manager, amidst a climate of intense skepticism from the Rossoneri crowd. The likes of Luciano Spalletti and Gennaro Gattuso were linked as replacements for Marco Giampaolo, but Pioli was chosen.
Not many approved of the hire and there was a viral online protest. Yet, in the space of five seasons, Pioli took over a team that were 11th in the table, qualifying for the Champions League, lifting the Scudetto and getting to the final four in Europe’s top competition.
That night in Portugal
Who knows what would have happened if, five years ago, those penalties against Rio Ave hadn’t gone the way they did. On 1 October 2020, a dramatic Europa League play-off encounter went to penalties thanks to Hakan Calhanoglu’s late equaliser.
The score: 11-10 after 24 penalties. Pioli, post-match, limited himself to a ‘yes, they can do better than tonight’. He was right: the Rossoneri went 13 consecutive games unbeaten in the league, finishing second in Serie A and getting to the round of 16 in Europe.
Back in the big time
On 22 December 2019, Milan hit one of the lowest points in their recent history, a 5-0 defeat to Atalanta. It was to be a forgettable campaign, but a tactical reshuffle came with Zlatan Ibrahimovic’s arrival, and by the end of the 2020-21 season the Rossoneri were in a top four race.
After two consecutive defeats against Sassuolo and Lazio, Pioli made a change: in Turin against Juventus, he opted for a double attacking midfielder, with Brahim in the middle and Calhanoglu on the left. It was a turning point.
The Rossoneri won 3-0 at the Allianz Stadium, followed by a historic 7-0 victory over Torino. Kessié’s penalty brace on the final round against Atalanta closed the circle: Milan returned to the Champions League after seven years.
The Giroud derby
Back on 5 February 2022, Milan came from behind to win 2-1 in the derby against Inter thanks to an extraordinary brace from Olivier Giroud. Inter dominated the first half, taking the lead through Perisic, but Pioli said at half-time: “The obstacles are insurmountable for those who don’t believe.”
Milan got the message, turned the game around, and, essentially, the fate of the league. That victory took Milan within one point of Inter, who in the following weeks lost more ground, and we know how the rest went.
Tonali in the capital
Another huge sliding door in the season leading to the Scudetto, after the February derby, came on April 24th against Lazio. Milan arrived at the Olimpico fresh from a heavy 3-0 defeat in the Coppa Italia semi-final against Inter, a tough pill to swallow.
The pressure was on: the Nerazzurri had won the previous day against Roma, temporarily regaining the lead while awaiting the postponed match in Bologna. Immobile scored after just four minutes, Giroud equalised, and Sandro Tonali’s strike in the 92nd minute sealed a crucial victory.
Two pieces of news surrounded that evening. The first: Milan mathematically qualified for the Champions League. The second: Acerbi’s chuckle after falling over during Tonali’s goal was a gesture that filled the internet for weeks.
Crowning moments
Milan secured their 19th Scudetto in just over half an hour. It was 22 May 2022: against Sassuolo, Giroud scored a brace and Kessié scored the third goal all in the first 36 minutes. It was all orchestrated by the future league MVP, Rafael Leao, who got all three assists.
Reggio Emilia was tinged with red and black, and the Rossoneri returned to the top of Italy eleven years after the last time, after changes in ownership, coaches, and players. In February, Pioli confessed: “No one believes we can win the title, there’s a strange atmosphere.”
Three months later, he let it out: “My players are phenomenal.” A team that overcame injuries and difficulties, pushing each individual beyond their limits, as if every obstacle were a springboard.
Some vivid images of that triumph remain: Ibrahimovic with a megaphone leading the chants, the banner mocking Inter on the open-top bus, thousands of fans chanting ‘Pioli is on fire’ and Giroud waving the flag like a victory banner. It was Pioli’s first trophy, after 311 games in charge.
Summer fever
The summer of 2022 was unlike any other for Pioli. He got a tattoo of the Scudetto, and people recognised him on the beaches while on vacation. He told DAZN: “I saw lots of kids wearing AC Milan jerseys asking me for a photo, it was all really beautiful and exciting. I was happy with this enthusiasm; we involved all the Rossoneri fans who needed to experience a moment like this.”
That summer, Pioli was probably the most viral person on social media, thanks to the soundtrack dedicated to him: ‘Pioli is on fire’, which became a hit in clubs across Italy. The chant, inspired by Gala’s song ‘Freed from Desire’, became a pop icon, so much so that even DJ Bob Sinclar turned up his nose when he heard it blaring during his sets.
Disastrous derby run
Pioli has a heavy burden on his conscience: six consecutive derbies lost. The last – on 22 April 2024 – was the most painful: Inter won 2-1 and secured the Scudetto, and their second star. His derby record wasn’t good: 10 defeats, three wins and two draws.
Pioli explained to La Gazzetta how this negative streak influenced his departure from Milan: “It was a natural conclusion, the derbies accelerated it. Losing six in a row hurt, of course. Especially the two in the Champions League, also because they took away from a great achievement: returning to the semi-finals after 16 years. It was written that Milan would win the derbies without me.”
The final four
After eliminating Tottenham and Napoli, Milan would return to the Champions League final four after 16 years in April 2023. It was a derby, Pioli’s Achilles heel. The result is well known: a 3-0 aggregate win for the Nerazzurri. The damage was done in the first part of the first leg, with Inter scoring twice.
Pioli was blamed for once again failing to contain Simone Inzaghi tactically, as he admitted: “Inter deserved it; we were lacking in the first 15 minutes of the first leg.” A painful defeat, following the 3-0 defeat in the Supercoppa Italiana in January, also against the Nerazzurri.
Beginning of the end
On 18 April 2024, Pioli’s Milan adventure virtually ended. That day, they were eliminated in the Europa League quarter-finals by Roma, who had beaten them in both legs. After a 1-0 defeat at San Siro, the Giallorossi prevailed 2-1 at the Olimpico thanks to goals from Dybala and Mancini.
It was an unrecognisable Milan side for the full 180 minutes: exhausted, lacking in ideas and the mental strength needed to withstand a two-legged tie. Pioli even admitted to Gazzetta that he knew his time was up.
“When did I realise it was over at Milan? The second leg of the Europa League quarter-finals, Roma-Milan, at the Olimpico. In the dressing room before the match, I gave a speech that gave me goosebumps, one of my most heartfelt ever.
“I was sure I would advance. Instead, nothing came of it for the team, and he did little on the pitch. There, I realised that what I was giving was no longer enough. My empathy had deteriorated,” he reflected. Tonight, there will be room for some more reflections.
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