John Terry’s biggest regret at Chelsea: “I still wake up in the middle of the night”

In the 2008 Champions League final, John Terry was on the brink of making history with his boyhood club.

The Chelsea captain was the heartbeat of the team that had made it to the final in Moscow, and he had the decisive spot kick in the penalty shootout. Terry stepped up confidently but slipped at the moment of contact with the ball and tumbled to the ground as he watched his kick strike the post. The chance was squandered and Manchester United went on to lift the trophy.

As Terry explained in an appearance on the Mennie Talks podcast, digesting that slip was difficult. In fact, he confessed that even today, 17 years later, that penalty is still etched in his memory: “It’s softened over the years, but when you’re playing you can compartmentalize it a bit, and put it to the back.”

“But it’s now that I’m retired and I don’t have that focus of playing every week... It still really gets me. I still wake up in the middle of the night and think, ‘Oh yeah, that happened,’ but I don’t think it’ll ever go away.”

“I remember after the game we all went back to the hotel, I think I was on the 25th floor. And I’m just looking out of the window, thinking ‘Why, why?’ And I’m not saying that I would have jumped, but things just go through your head at that particularly time. Then the boys came up and took me downstairs.”

In the conversation Terry paid particular tribute to Ray Wilkins, a Chelsea legend as both a player and later a coach. He revealed that Wilkins had been a big part of helping him through that difficult period in his life. He explained: “You discover very quickly who your friends are and who the people are who really care about you and look out for you.”

Terry had been denied the chance to lift the Champions League in 2008 but he would finally taste European glory four years later. In 2012 Chelsea won the Champions League after defeating Bayern Munich on penalties. Terry, who was sent off in the semi-final against Barcelona, was suspended for the final but he was able to make up for that slip-up and lift his first and only Champions League trophy.

John Terry left Chelsea in 2017, nearly two decades after he made his professional debut for the club. He won five Premier League titles with the Blues and was named UEFA Club Defender of the Year on three occasions. But for all his successes, that night in Moscow will remain a sliding doors moment for Terry.

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