1. Roger Federer (7 Wins, 1 Runner-Up)
You knew he had to be #1. He’s Roger Federer. Nothing needs to be said about him because he is simply the greatest grass-courter in history.
Federer won 5 consecutive Wimbledon titles, and while going for his sixth, played the greatest match in all of history under fading lights, losing a match that defines this generation of tennis. Federer’s Edberg-esque style, combined with modern baseline smarts, is a perfect blend of artistry, genius, power and level-headedness. His whiplash forehand and fluid serve are the secret to his Wimbledon success, and his genius on the surface simply cannot be questioned.
Federer played three legendary finals in a row – 2007, 2008 and 2009. After losing early (for his standards) the following two years, he made a remarkable comeback to win Wimbledon for the seventh time in 2012. Federer, clad royally in his cream blazer, kissing the gold on a sunny summer afternoon is the very image of tennis of the 2000s.
Andy Roddick (3 Runner-Ups)
At least one American had won Wimbledon in the seventies, eighties and nineties. In fact, Americans had dominated Wimbledon with Sampras, McEnroe and Connors carving their legacies at South West 19. The burden of this voluminous history was transferred to Andy Roddick’s shoulders at the turn of the millennium.
Roddick came close, but fell at the final hurdle, not once, not twice, but thrice, each time to Roger Federer. His loss in the 2009 Wimbledon finals is one of the tournament’s most famous, with Roddick being broken only once the whole match – in the very final game, serving down 14-15 in the fifth set.
Goran Ivanisevic (1 Win, 3 Runner-Ups)
The story of this giant Croat is the stuff of legend. Arguably the true ‘People’s Champion’ on Centre Court, Ivanisevic’s monstrous serve got him to three finals in the nineties. Each time, he was beaten back by an American, including two heartbreaking five-set losses. Ranked 125th, Ivanisevic won the 2001 Wimbledon as a wildcard, defeating Pat Rafter in front of a noisy Monday crowd. His story is one of Wimbledon’s greatest.