Jamie Carragher has experienced many challenging moments in Liverpool’s history, including one that remains significant to him.
The 2024/25 season has been largely positive for Liverpool, although there have been a few recent challenges. There are matches supporters would like to erase, including the Carabao Cup final loss and the defeat to PSG in the Champions League.
However, throughout the club’s history, several results have had a much heavier impact. Carragher has been part of many and recently mentioned which one he would change if given the opportunity.
Jamie Carragher reflects on his toughest moment with Liverpool
Photo by Robbie Jay Barratt – AMA/Getty Images
In a recent appearance on The Overlap, Carragher was clear about which result he would like to change. “Wembley (FA Cup semi-final),” he stated. “It felt like the entire club would rise to a new level if we won.”
The 2006/07 FA Cup semi-final loss to Chelsea was painful at the time and remains fresh in his mind.
Jamie Carragher wishes he could alter the AC Milan 2-1 Liverpool match
The early to mid-2000s were a tricky period for Liverpool, as the team had secured some trophies but was also experiencing a transition.
After their unexpected victory in the 2005 Champions League final, they reached another final two years later against AC Milan.
They lost that match 2-1, and this is the game Carragher wishes he could change, as he mentioned in a TikTok video for CBS.
Dirk Kuyt scored late in the game, but it wasn’t enough to equalize after Filippo Inzaghi scored twice, leading Milan to their seventh and most recent European Cup title.
Carragher played the full match and received a yellow card, with the team displaying a strong effort despite the disparity in skill on the field.
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