Three times an American nearly ended 25-year Wimbledon drought

Taylor Fritz is two wins away from becoming the first American man to win Wimbledon since Pete Sampras in 2000.

The 25-year drought for the prestigious grass-court major hasn't been for a lack of trying, as many came tantalizingly close to joining Sampras on the iconic honors board at the All England Tennis Club.

Here, we recap three times when the drought nearly came to an end.

John Isner (2018)

The 6-foot-10 giant with the booming serve was playing the best tennis of his career, dispatching three of his first four opponents in straight sets and beating Milos Raonic comfortably in the quarterfinal. 

In the semifinal, he met his match in Kevin Anderson, the lanky South African with a similar skill set, resulting in an instant classic. After four hours of grueling tennis, they battled in arguably the most riveting fifth set ever that lasted two hours and 50 minutes. 

Anderson would clinch the deciding set, 26-24, to win the third-longest match in the Open Era (six hours, 36 minutes). Isner later revealed he dealt with blisters on his foot during the never-ending fifth set. 

The American would have likely won if Wimbledon had a fifth-set tiebreaker, a rule change finally implemented in 2022. And if he did, Isner would have been favored to beat the lower-seeded Novak Djokovic in the final, given that the latter was fresh off elbow surgery and still finding his groove.

Andy Roddick (2009)

This was the "now or never" moment for a 27-year-old Roddick, who was nearing the end of his prime. After two previous Wimbledon finals losses (2004, 2005), it seemed like he'd never return to the grand stage at The Championships. 

Lady luck smiled upon him as defending champion Rafael Nadal withdrew due to injury. However, Roddick still had to take out top-ranked names such as Tomas Berdych, Lleyton Hewitt and Andy Murray to set up a finals showdown with Roger Federer. 

Roddick brought his A game, forcing Federer, the former five-time champion, into a fifth set that lasted a whopping 95 minutes. Federer would ultimately prevail, 16-14, in the longest fifth set in a major men's singles final (in terms of games). Roddick had two championship points, but failed to close the deal. The memories still haunt him. 

"Operation successful, but sometimes the patient dies. And that's the way it felt that day," Roddick told the New York Post of his heartbreaking loss. 

Andy Roddick (2004)

As much as the 2009 loss stung, Roddick was arguably a better player in 2004, fresh off his 2003 U.S. Open win and ascension to World No. 1 status. There was a realistic expectation that he had the game to take down Federer, the defending champion. 

The confidence in that sentiment grew stronger after he beat the Swiss star at an ATP 1000 event in Canada in the lead-up to Wimbledon. Roddick got off to a hot start, taking the first set and looking nearly invincible with his deadly service game. He even had the boisterous crowd behind him, given his expressive tendencies and ability to rack up aces. 

However, he made some untimely errors late in the second set and then in the third-set tiebreaker, giving Federer the opening to close him out in four. The match marked one of four times Roddick lost to Federer at The Championships, including the above-mentioned 2009 defeat and the subsequent 2005 finals, which Federer won in straight sets.  

Will Fritz be the one to end the 25-year drought? His tall task begins against Carlos Alcaraz in the semifinal on Friday.