5 Greatest Tennis Matches of All-Time

by Rob Joyce

“Manic Monday” at Wimbledon lived up to the hype once again, as the Round of 16 brought men’s tennis not only the upset of the year, but the match of the year. The 16-seed, Gilles Muller of Luxembourg, took Rafael Nadal to a five-set epic, eventually beating the 15-time Grand Slam winner 15-13 in that decisive set. It’s the second time ever that the 34-year-old has advanced that far in a Grand Slam event, with the last time coming in 2008.

It’s certainly the most important win of Muller’s career, and to date it is the most exciting match of the year. Though it’s not among the best of all-time, it’s nearly in the same breath as these five that do go down in history as the greatest matches ever played:

5) Jimmy Connors vs. Aaron Krickstein, 1991:

jimmy connors 5 Greatest Tennis Matches of All Time

Photo Credit Getty Images/Staff

The Hall of Famer Connors was ranked 936th in the world in 1990, making his run in the 1991 U.S. Open all the more improbable. On his 39th birthday he faced Krickstein in the fourth round, trailing two sets to one. He forced the fifth set, but in that decisive frame trailed 5-2 before storming all the way back, winning the set and, subsequently the match, 7-6 in front of a raucous New York City crowd. It was such a good match that, even to this day, rain delay filler at the Open is video of that fourth round.

4) Roger Federer vs. Andy Roddick, 2009:

roger federer 5 Greatest Tennis Matches of All Time

Photo by Clive Brunskill/Getty Images

A year after losing in heartbreaking fashion (we’ll get to that in a bit), Federer faced another instant classic, this time against Roddick. Federer led after three sets, 5-7 7-6 (8) 7-6 (5), but Roddick held in the fourth set to force a decisive fifth that would become the longest in history. The two went back-and-forth with the serve, with Roddick at one point not being broken for 38 straight games. However, he needed that to be 39, as Federer, up 15-14, finally broke serve and beat Roddick in a Grand Slam final for the fourth time.

3) John Isner vs. Nicolas Mahut, 2010:

john isner 5 Greatest Tennis Matches of All Time

Photo credit: GLYN KIRK/AFP/Getty Images

The first round Wimbledon match between Isner and Mahut was so good, it took three days to complete. Tied after four sets, the match was suspended on June 22 due to darkness. When they began the fifth set the next day at 2:05 in the afternoon, no one could have guessed darkness would again play a factor.

Seven hours later, with the final set tied at 59, darkness pushed the epic to a third day. Finally, on June 24, Isner won 70-68. The match took 11:05 to complete, with the fifth set lasting 8:11. Court 18 at Wimbledon now has a plaque to commemorate the three-day duel.

2) Bjorn Borg vs. John McEnroe, 1980:

bjorn borg 5 Greatest Tennis Matches of All Time

Photo by Rob Taggart/Central Press/Getty Images

The standard-bearer at Wimbledon for nearly three decades, two titans of the era played a masterful five-set affair. Borg, looking for his fifth straight Wimbledon title, had two chances during the fourth set to win the match, but McEnroe held strong and evened the set at 6-6. In the tiebreaker, McEnroe not only staved off five more championship points, but he had six set points of his own in the 34-point marathon, finally winning the set on his seventh try.

The fifth set saw Borg dominate with his serve, winning 19 consecutive points on his serve to take his fifth Wimbledon crown, winning the final frame 8-6.

1) Rafael Nadal vs. Roger Federer, 2008:

rafael nadal 5 Greatest Tennis Matches of All Time

Photo by Julian Finney/Getty Images

It’s only fitting that arguably the two greatest of all-time, in the peak of their rivalry, give us the greatest match ever played. The top two seeds in the tournament were meeting in the final for the third straight year, with Federer vying for a sixth straight Wimbledon title. Things looked bleak after Nadal went up two-sets-to-none, but Fed managed to win a tiebreaker in the third set, then again in the fourth (staving off two championship points in the process) to force a fifth set.

Adding to the drama was a pair of rain delays, combining for about two hours’ worth of waiting. Though it didn’t go nearly as long as Isner and Mahut, eventually Nadal was able to topple his rival on grass for the first time, taking the fifth set 9-7. At 4:48 it’s the longest final in Wimbledon history, and given the stakes and who was participating, it’s the greatest match in tennis history.

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