‘The 2007 Champions League Final was a missed opportunity for Liverpool. That Milan defeat still hurts me today’ Bolo Zenden on his huge Anfield regret

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Liverpool came up short against Milan in the 2007 Champions League final, two years after the Miracle of Istanbul

Boudewijn Zenden 2007
Bolo Zenden signed for Liverpool in 2005

Bolo Zenden enjoyed an 18-year top-flight career which saw him play at the highest level in the Netherlands, Spain, France and England.

The talented midfielder earned league titles with PSV and Barcelona before his 2001 move to the Premier League, where he enjoyed stints with Chelsea, Middlesbrough and Liverpool.

Bolo Zenden on his Chelsea and Liverpool regrets

Bolo Zenden is unveiled after signing for Chelsea from Barcelona, 2001

Bolo Zenden is unveiled after signing for Chelsea from Barcelona, 2001 (Image credit: Alamy)

Zenden was signed by Chelsea for £7.5million in the summer of 2001 and would score his first goal for the Blues just nine minutes into his debut against Newcastle United.

But he soon picked up his fair share of injuries, meaning his two-season stay at Stamford Bridge was often a stop-start affair.

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“I suffered a nasty thigh laceration, which is pretty rare, in a League Cup tie with Spurs – a tackle from Teddy Sheringham – and was out for four months,” the Dutchman recalls to FourFourTwo.

Zenden would spend the 2003/04 season on loan at Middlesbrough, where he would score the winner in Boro’s League Cup success over Bolton, before joining the team on a free transfer in 2004.

A year later, he would join Liverpool on a free, only to suffer more bad injury luck.

“Then in my first season at Liverpool [2005/06], I damaged my cruciate knee ligaments in a Champions League game against Real Betis,” he continues. “The day the squad flew to Japan for the Club World Cup, I was heading to the US to get my ACL done.”

His Reds team-mates were at the Club World Cup following the Miracle of Istanbul win over Milan, which came shortly before Zenden’s arrival.

The Liverpool football team prior to the UEFA Champions League Final match between Liverpool and AC Milan at the Olympic Stadium in Athens, Greece on May 23, 2007. AC Milan won 2-1. Left to right, back row: Pepe Reina, Dirk Kuyt, Xabi Alonso, Daniel Agger, Jamie Carragher and Javier Mascherano; front row: Steve Finnan, Boudewijn Zenden, Steven Gerrard, John Arne Riise and Jermaine Pennant. (Photo by Popperfoto via Getty Images/Getty Images)

Zenden and his Liverpool team-mates ahead of the 2007 Champions League final (Image credit: Getty Images)

The 54-time Netherlands international was then part of the side that faced Milan in a Champions League final rematch two years later, only for the Reds to come up short, handing Zenden another of his toughest career moments.

“Everyone recalls the win over them in Istanbul two years earlier, but this was the one I remember for all the wrong reasons,” he admits.

“People say semi-finals are the toughest losses to take, but I disagree – losing finals are the real sickeners because you’re really, really close. The greatest prizes of all are the World Cup, the Euros and the Champions League. All the top players set their sights on winning at least one and I came closest in the latter.

“I’m proud to have reached a final, but do you know something? That Milan defeat still hurts me today. It was a missed opportunity.”

Joe Mewis
Joe Mewis

For more than a decade, Joe Mewis has worked in football journalism as a reporter and editor. Mewis has had stints at Mirror Football and LeedsLive among others and worked at FourFourTwo throughout Euro 2024, reporting on the tournament. In addition to his journalist work, Mewis is also the author of four football history books that include times on Leeds United and the England national team. Now working as a digital marketing coordinator at Harrogate Town, too, Mewis counts some of his best career moments as being in the iconic Spygate press conference under Marcelo Bielsa and seeing his beloved Leeds lift the Championship trophy during lockdown.

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