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When Roger Federer took the court Thursday night, he appeared in his 34th career Grand Slam semifinals and extended his all-time record.

His opponent, Gael Monfils, made his second semifinal in a Grand Slam event and his first since 2008. This is a time for tennis fans to reflect on the career Federer has and one has to wonder if this is his last shot at a Grand Slam title.

Federer, who turned 33 last month, is facing unlikely odds. No man at that advanced of an age has won a Grand Slam singles title in the last quarter century. American Andre Agassi won the 2003 Australian Open, four months shy of his 33rd birthday.

In fact, only two men in history have won a Grand Slam title past their 33rd birthday in the Open Era (since 1968).

Federer already has 17 Grand Slam singles titles, another record he holds on the men’s tour. Federer’s biggest rival, Rafael Nadal, did not play in this year’s U.S. Open because of injury. Andy Murray, the 2012 winner of the U.S. Open, was ousted by Novak Dkojovic. The opportunity is there for Federer, who CNN proclaimed as the greatest tennis player ever back in 2012. Federer and Dkojovic met in this year’s Wimbledon final and they are once again on the opposite side of the draw.

A rematch is possible if the higher seeds advance.

Not only is age a factor in Federer’s chances winding down. Several young guns have been emerging on the ATP that pose as future threats. Fourth-seeded Grigor Dimitrov, who Monfils defeated to make it to the quarterfinals, is 23. Milos Raonic is also 23 and was seeded fifth. Nadal, Murray, and Dkojovic aren’t going anywhere, either.

If this truly is Roger Federer’s best chance to win one last major, the sports world will look back and appreciate a legend one more time.

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