The 5 Best Tennis Matches Ever – Greatest Tennis Matches Of All Time

Roger Federer
LONDON, ENGLAND - JULY 05: Roger Federer of Switzerland celebrates victory during the men's singles final match against Andy Roddick of the USA on Day Thirteen of the Wimbledon Lawn Tennis Championships at the All England Lawn Tennis and Croquet Club on July 5, 2009 in London, England. Federer won 5-7, 7-6, 7-6, 3-6, 16-14. (Photo by Professional Sport/Popperfoto/Getty Images)

The first Tennis match is said to be played back in the 1860s. With over 150 years of history, there have been some matches which are considered the most memorable and will remain like that for the foreseeable future. From the most intense, longest and the most shocking tennis matches, here are our picks for 5 of the greatest Tennis matches of all time.

Roger Federer
LONDON, ENGLAND – JULY 05: Roger Federer of Switzerland celebrates victory during the men’s singles final match against Andy Roddick of the USA on Day Thirteen of the Wimbledon Lawn Tennis Championships at the All England Lawn Tennis and Croquet Club on July 5, 2009 in London, England. Federer won 5-7, 7-6, 7-6, 3-6, 16-14. (Photo by Professional Sport/Popperfoto/Getty Images)
  1. Roger Federer vs Andy Roddick, Wimbledon 2009

A year after losing the Wimbledon Finals against Nadal, Federer was once again playing in another classic against Roddick. The two tennis players knew each other very well, in fact too well. Some say Roddick was born a few years too late and had to play tennis at the same time as Federer, who managed to defeat the big-serving American 4 times in Slam Finals. However, no other defeat was as bad as the one in the 2009 Wimbledon finals. After 3 sets, Federer was leading 5-7, 7-6 (8), 7-6 (5), but Roddick held on in the 4th set, (3-6) which meant the 5th and the final set would be played. This would become the longest set in the history of the sport. The two tennis players went back and forth with the serve. Roddick at one point was not broken for 38 straight but of course, it had to be the 39th against Federer, who “snuck one in” at 15-14 in the final set. Federer then went on to win the Finals. This match was both the longest final in history and the longest 5th set in term of games. The finals lasted for 4 hours and 17 minutes, with a total of 77 games, which surpasses the previous record of 71 games set at 1927 Australian Open.

  1. Jimmy Connors vs Aaron Krickstein, U.S. Open 1991

Jimmy Connors, the Hall of Famer came into the match as 936th in the world. This alone makes this match that more interesting, but it was not only that, the chaos, arguing, fans and the fact that on the day of the match, Connors turned 39 years old, add to the excitement and make the match that much more memorable. It is most likely the most watched tennis match, as it showed us a picture of how Connors managed to win despite his age and all the odds that went against him.

Something is telling me this match alone made some of the players (like Federer, Agassi…) keep playing despite their old age.

The story and the message from Connors alone is far more important than the score alone, but for the sake of not skipping the results; 3-6, 7-6(8), 1-6, 6-3, 7-6(4). While the match was not the finals, but rather the 4th round, it still belongs to be ranked among the top 5 greatest matches ever played.

  1. John Isner vs Nicolas Mahut, Wimbledon 2010

I guess I can say this match that was so good it took 3 days to complete. Well, it was not “good” per se, but rather memorable due to the all the drama, history and its length. After the 4 sets, the match was tied but had to be suspended due to darkness. The next day when players once again met at the court not many people could have guessed the darkness would once again play a part. 7 hours after the match started on day 2, players were once again tied at 59 and with the day slowly turning into the night, the match was once again suspended due to darkness. Third’s a charm they say and it proved to be on that day. Isner finally managed to win 70-68, with the match lasting 11 hours and 5 minutes. The fifth set alone lasted 8 hours and 11 minutes. And no it was not even the finals, but rather the 1st round.

  1. Bjorn Borg vs. John McEnroe, Wimbledon 1980

For some unknown names, for others the legends of tennis. It was the year 1980 when two titans of their era played a spectacular match which ended after all 5 sets. On one side we had Borg who was looking for his 5th straight Wimbledon title, on the other side McEnroe who denied Borg his chance to finish the match 2 times during the 4 sets.

This match has a lot of factors which make it memorable. First, it was the 2 best players who played in the finals of Wimbledon. Second, it was one of the most interesting matches that also had a 22-minute 34-point 5th set tiebreaker which will be remembered forever.

There is not a lot written about this match, so you might ask yourself how did it get to our top 5 list? It does not have any record numbers, neither did it last for several days… Well to answer that question I have only 1 thing to say; Watch the replay of the whole match, come back and apologize for doubting its place in the top 5.

  1. Rafael Nadal vs. Roger Federer, Wimbledon 2008

There are books written about this match. Books. It’s only fair we get a movie as well. This was the match that saw 2 of the greatest of all-time going against each other to finally decide who was the best. Not only were Nadal and Federer the best tennis players of that time, but they were also the biggest rivals, and with their rivalry peaking in 2008, this match was to be the one to go down in history as the greatest tennis match of all time. The top 2 seeds in the tournament met each other in the finals for the 3rd straight year, with Federer looking to get his 6th straight Wimbledon title. However, things did not look too bright for Federer when Nadal went up 2 sets to 0. But Federer managed to win the tiebreaker in the 3rd and then 4th set, which forced the 5th set.

If that was not enough, rain added to the drama. Due to heavy rain, there were 2 delays, which resulted in about 2 hours of waiting. The match was in the end won by Nadal, who managed to end Federer’s winning streak.

While this match was not even remotely close in length to the John Isner vs Nicolas Mahut match, it still lasted 4 hours and 48 minutes, which is the longest final in Wimbledon history. While the length alone does not make this match the greatest of all time, the players who anticipated and their form at the time justifies the no.1 spot on our list.

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