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John Gregory still carries the weight of Aston Villa’s defeat in the 2000 FA Cup Final against Chelsea. He blames himself for the loss and admits that he still feels guilty about it. As the ex-Villa boss, he led the team in the last-ever match at the old Wembley stadium where Roberto Di Matteo scored the winning goal for Chelsea. Despite David James’ error that led to the goal, Gregory takes full responsibility for the defeat.

In an interview with the Guardian, Gregory expressed his regrets, stating that he could have been more offensive in his tactics during the final. He acknowledged that he should have taken more risks, even if it meant potentially losing by a larger margin. The former manager believes that he could have done more to help the team secure victory in the prestigious cup final.

The memory of the FA Cup Final still haunts Gregory to this day. He vividly recalls the moment he walked out of the tunnel at the old Wembley stadium with 40,000 Villa fans cheering for their team. The sea of claret and blue colors in the stands was a beautiful sight for Gregory, but the disappointment of not winning the cup lingers in his mind.

Despite his successful career in football, Gregory feels that the FA Cup defeat stands out as a failure that he cannot shake off. He avoids talking about the final with others because of the pain of losing such a significant match. The longing to bring the FA Cup back to Birmingham for the first time since 1957 remains unfulfilled for Gregory, leaving a sense of regret and disappointment.

Reflecting on the final, Gregory acknowledges that he has achieved many great things in his life, but the missed opportunity to win the FA Cup continues to bother him. The feeling of coming so close to victory and falling short still resonates with him, impacting his thoughts and emotions even years after the event.

The 2000 FA Cup Final remains a significant moment in John Gregory’s career, serving as a reminder of the fine line between success and failure in football. Despite his accomplishments as a manager, the memory of that match continues to haunt him, reflecting the intense pressure and emotional toll that high-stakes games can have on those involved.