10 Greatest Men’s Tennis Matches in Wimbledon History (Ranked)

Ranking factors include:

• Legacy – the relevance and landmark quality of the result of the match.
• Quality / Jeopardy – the standard of tennis played and what was at stake.
• Grit – Wimbledon is a best-of-five-set competition, so endurance and determination are key.

11Boris Becker vs Kevin Curren

1985 final

Boris Becker had a special relationship with Wimbledon, reaching the final seven times and winning it on three occasions. The first victory came in 1985 when the German was just 17. There is a strong argument that some of Becker’s other appearances at Wimbledon are deserving of the rankings. His five-set thrilling semi-final win over Ivan Lendl in 1989 was also a memorable match.

However, Becker’s first win in 1985 was a landmark. He made a statement win on the grass at Queen’s Club in the lead up to Wimbledon, where he was not seeded at the tournament. Victory saw him become the youngest ever Wimbledon winner, making him one of the greatest teenagers in sports history.

10John Isner vs Nicolas Mahut

2010 First Round

John Isner reached the 2018 Wimbledon semi-finals, yet his career was defined by his efforts in the first round in 2010. Incredibly, the fifth and final set alone lasted a mammoth eight hours and 11 minutes. Before that, the contest had ebbed and flowed, with the third and fourth sets going to a tiebreaker.

What came after that was unprecedented. The rules then meant the winner needed to be two games clear, instead of having a tiebreaker. In the end, Isner needed to win 70 games in the deciding set. That alone is the equivalent of 11 sets.

You can only imagine how the tournament organisers felt when the two were drawn against one another the following year. This time, Isner won in straight sets. New rules are now in place so that a tie-break would take place in the deciding set if the competitors are tied 12 games all.

9Roger Federer vs Pete Sampras

2001 Fourth round

Pete Sampras came into this match as a seven-time Wimbledon champion and defending champion. While Roger Federer had shown promise during this early time of his career, and was seeded fifteenth, Sampras was dominant on grass and expected to win. Yet he did not.

Incredibly, Federer’s win was the only time he played Sampras. The five-set thriller was seen as the passing of the baton from one great to the next. Federer went on to lose that year in the quarter-finals to Tim Henman. Yet the win over Sampras was the start of an incredible career on grass.

8Pete Sampras vs Andre Agassi

1999 final

Pete Sampras dominated Wimbledon during the 1990s. That he was largely without a rival on the surface explains why he isn’t talked about enough as a tennis legend. His performance against Andre Agassi in the 1999 final was as good an example as any of his power and domination at Wimbledon.

Armed with a powerful serve, Sampras was a master of coming into the net to smash any returns into oblivion. Agassi came to Wimbledon having won the French Open. As great a competitor as Agassi was, he was unable to prevent Sampras from winning in straight sets on Centre Court.

7Jimmy Connors vs Mikael Pernfors

1987 fourth round

Jimmy Connors won Wimbledon in 1974 and 1982. Yet it’s his performance in the earlier stages of the 1987 competition against Mikael Pernfors that makes the rankings. Conners was a dogged personified. He never gave up, and this was clear to see during this epic comeback. Known for his exciting rallies, Connors was something of a warrior on court.

At one stage, Connors was two sets down and four-one down in the third. Somehow, he managed to drag his way back to win that third set. It brought the crowd to their feet. With the momentum shifted, Connors began a remarkable comeback. In the final set, he had a thigh injury, but was never going to let up. “I was always going to finish the match, even if I had to crawl,” he said.

6Novak Djokovic vs Roger Federer

2019 final

This would be Djokovic’s fifth Wimbledon title. It would also be the last time Federer reached the tournament final, having been there 12 times. So not only a memorable game, but the end of an era. By now, Federer was 37, but Djokovic, at 32, still had some years left. This was the final gift from both of them.

5Andy Murray vs Novak Djokovic

2013 final

That Murray had come close, losing in four sets the year before to Federer, made this victory all the more special. Naturally, Murray is considered one of the best British tennis players of all time. Given that Djokovic had beaten Murray in that year’s final of the Australian Open showed the quality of this win.

3Roger Federer vs Andy Roddick

2009 final

Roger Federer’s win was his fifteenth career Grand Slam title. Federer was as absorbed in the contest as the spectators: “It was a crazy match and my head is still spinning,” said Federer. Roddick had played perhaps the best game of his career and still fallen short. This game lives long in the memory of many tennis fans.

2Bjorn Borg vs John McEnroe

1980 final

McEnroe would famously beat Borg in the final the following year, but the 1980 final has gained legendary status. It helped propel interest in the game. Looking back at the highlights, playing with the smaller-headed rackets, you have to marvel at the quality of the play. Two titans of the game who needed each other as much as tennis needed them.