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Former referee Howard Webb has revealed that the decision he regrets most in career was awarding Manchester United a controversial penalty during a Premier League game against Tottenham in the 2008/2009 campaign.

Two months on from their penalty shoot-out defeat to Sir Alex Ferguson’s men in the League Cup final at Wembley, Spurs found themselves in a surprising 2-0 lead at Old Trafford, thanks to first-half goals from Darren Bent and Luka Modric.

Harry Redknapp’s side, who were chasing a European place despite a poor start to the campaign under Juande Ramos, looked comfortable at the beginning of the second period, too, and were on course to earn their first victory in that part of Manchester since 1989.

However, just before the hour-mark, Webb inexplicably awarded United a penalty after he adjudged Spurs goalkeeper Heurelho Gomes to have fouled ex-midfielder Michael Carrick.

Replays showed that the Brazilian had clearly taken a large chunk of the ball and was extremely unfortunate to have conceded a spot-kick.

Cristiano Ronaldo sent Gomes the wrong way from 12-yards, and less than 25 minutes later Tottenham found themselves 5-2 down and their hopes of earning a first ever Premier League victory at Old Trafford were in tatters.

Webb explains the story and admitted that after quickly noticing that he’d got the decision wrong, he hoped that Ronaldo missed the resulting penalty.

“The one that stands out is one where in the game I knew I got it wrong,” Webb told the Athletic. “It was a Premier League game at Old Trafford – Manchester United versus Tottenham Hotspur in 2009.

“I could see Carrick got there first and then the goalkeeper clattered into him. It was really an easy penalty award. I was expecting the usual cursory appeal that you get from the players, not the huge look of absolute astonishment and amazement and incredulousness on the look of Gomes. It was obvious within seconds I’d got the decision wrong. There was something more to this.

“I was left with the decision I had taken with no independent evidence that I’d got it wrong other than a gut feeling, and I was just hoping that Ronaldo would miss the penalty, but he didn’t.”

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