There is regret - World Cup winner and two-time Champions League victor recalls greatest disappointment
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Andrea Pirlo missed a penalty in AC Milan's 2006 Champions League defeat by Liverpool (Credit: Imago)

There is regret - World Cup winner and two-time Champions League victor recalls greatest disappointment

Seye Omidiora 10:37 - 09.04.2025

One of the greatest midfielders of all time has shared some of the highs and lows of his extraordinary career.

Andrea Pirlo has reminisced about his decade-long tenure at AC Milan, which produced a surfeit of titles domestically and on the continent. 

Pirlo excelled in a regista role under coach Carlo Ancelotti, contributing to the club's success with two Serie A titles, two UEFA Champions League titles and several other trophies.

Andrea Pirlo
Former AC Milan midfielder Andrea Pirlo (Credit: Imago)

A World Cup winner in 2006, the former midfielder’s tenure ended controversially in 2011 when he left for Juventus on a free transfer, a move that still sparks debate among fans. 

Recently, he shared his memories during an interview with Milan TV, reflecting on both the highs and lows of his time in the iconic red and black jersey.

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Pirlo reveals biggest Milan regret

The 45-year-old shared that the Rossoneri could have won more than the eight titles they notched in those 10 years, pointing to the 2006 Champions League final loss to Liverpool in Istanbul. 

Andrea Pirlo
Andrea Pirlo missed a penalty in AC Milan's 2006 Champions League defeat by Liverpool (Credit: Imago)

“We could have won a few more championships. We lost another Champions League, we could have won others,” said Pirlo. 

“If we look at everything, there is the regret of having won perhaps a little too little compared to what we could have won. But in the end we won a lot and that’s not for everyone.”

Pirlo fondly remembers first Champions League success

Despite ruing the absence of more title victories in Milan, Pirlo also shared some of his memorable moments with the Italian giants, disclosing why the 2003 Champions League success remains special. 

Andrea Pirlo
Andrea Pirlo won the 2003 Champions League with AC Milan (Credit: Imago)

“Because it was the first, my first Champions League and for what it was. We came from a long journey, from the preliminaries,” continued Pirlo.

“Then getting to play the semi-final against Inter and the final against Juve, I think it was the culmination of an extraordinary year. I remember the emotion of arriving at Old Trafford. It was the most exciting match.”

Pirlo has transitioned into management after retiring, taking charge of  Juventus, Fatih Karagumruk and recently Sampdoria.