Pirlo: ‘Milan happiness and regret, I would’ve gladly stayed many more years’ | OneFootball

Andrea Pirlo looks back over his 10 years in the Milan jersey with pleasure, but also regrets, including his departure. ‘I would’ve gladly stayed, as it was not my decision to leave.’

The midfielder recently made his return to the pitch playing for the Milan Legends in a charity match against Tottenham Hotspur in London, where he scored a sensational free kick.

It brought back memories of his time in the Rossoneri jersey from 2001 to 2011, when he went on to more success at Juventus and NYCFC.

“I tried to make that role my own, with my particular characteristics, and it reflects the way I see football,” Pirlo told the official Milan channel.

He was in the squad that won the Champions League twice, but also lost an extraordinary Final on penalties to Liverpool in Istanbul in 2005, having fumbled a 3-0 lead in the space of six minutes.

“The first in Manchester was the most special, because it was the start of a golden age and for many of us it was our first Champions League trophy,” added Pirlo.

“There are also regrets, because we could’ve won more silverware, especially losing that Champions League Final. If we look at what we won, the regret is that we could’ve done more.”

As luck would have it, Milan were given the opportunity for revenge on Liverpool in 2007 when facing them again in Athens.

“Someone was watching us from up above and gave us this chance. I really think the 2005 Final was one of our best performances as a team, it was such a great game, and to lose like that… But we balanced it out a bit in 2007.”

Pirlo felt he could’ve done more at Milan

LONDON, ENGLAND – MARCH 23: Andrea Pirlo of AC Milan Glorie celebrates scoring his team’s second goal with teammates during the Legends Charity Match between Spurs Legends and AC Milan Glorie at Tottenham Hotspur Stadium on March 23, 2025 in London, England. (Photo by Andrew Redington/Getty Images)

Pirlo was a fan favourite at San Siro and spent a decade at Milan, but was released as a free agent when they did not offer him a new contract.

“I grew up there, I became a man, and frankly I would’ve gladly stayed for a few more years, but it was not possible. Perhaps they were my best years.

“I am still friends with many of those I met there, we even go on vacation together. That is what remained with me from Milan, the friendships.”

Pirlo never made a secret of the fact he felt himself pushed out of Milan by then-coach Max Allegri and director Adriano Galliani.

“It irritates me because many people still don’t realise it was not my choice. I wanted to stay on at Milan, but there weren’t the conditions to do that, so we had to take different paths.

“When I said goodbye to my teammates and told them I was leaving Milan, it was one of the most painful and sad moments of my life.”

Pirlo played 401 competitive matches for Milan, scoring 41 goals and providing 71 assists.

He won two Serie A titles, two editions of the Champions League, one Intercontinental Cup, two UEFA Super Cups, one Coppa Italia and one Supercoppa Italiana.