Ranking the 10 Best Men's Tennis Matches in the 2016 Season

It was a tale of two halves for the 2016 season in men’s tennis. Novak Djokovic dominated the early year with historical acclaim as perhaps the most dominant No. 1 player of all time. Then he faded like old news print, while rival Andy Murray launched an iron-man streak of great play that spanned Wimbledon, the Olympic Games and the World Tour Finals.

The Djokovic-Murray rivalry was oddly not the centerpiece to important and memorable matches this year, though. There were other stars and significant moments that were more prominent in our annual list of the best 10 matches of the year.

Our countdown prioritizes the quality of big matches in late rounds of Grand Slams, but the Olympics, Davis Cup, World Tour Finals and Masters 1000 tournaments were all considered. The appeal of the superstars and the impact of the matches were also strong factors in determining the year’s best and most important matches.

Honorable Mention

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There were plenty of intriguing matches that miss our top 10. This year there were fewer Masters 1000 matches that made the list but more from Davis Cup and the Olympics competition that comes only once every four years.

Injuries plagued Roger Federer and Rafael Nadal, so there were fewer legendary clashes. Nevertheless, the following matches are good for honorable mention:

• Murray outlasted Milos Raonic in the Australian Open semifinals. Some of the greatness to the match was rubbed off when the Canadian was hampered by an abductor injury and a thigh problem. He was not the same as Murray took advantage for a five-set comeback and a trip to the final.
• Nadal defeated Gael Monfils in the Monte Carlo final for his biggest title since the 2014 French Open. It was an emotional moment for the Spaniard and his fans, and it would be his peak.
• In the Rome quarterfinals, Djokovic continued his dominance over Nadal and the ATP World Tour with a 7-5, 7-6(4) war in which both sets could have gone the Spaniard’s way. It might be the last real battle between the old rivals.
• Wimbledon featured some fine matches including Jo-Wilfried Tsonga’s 19-17 fifth-set victory over bullet-serving John Isner in the third round. The American has a way of causing marathon matches at Wimbledon.
• Rising star Lucas Pouille upended Bernard Tomic in Wimbledon’s fourth round. Perhaps it was a more accurate foreshadowing of who is the bona fide star of the future.
• Murray would go on to the Wimbledon final, but like 2013 he needed a five-set quarterfinal victory over a talented ball striker to move on. He survived Tsonga’s heartbreaking challenge. 

10. Rafael Nadal vs. Alexander Zverev, Indian Wells 4th Round

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Nadal and Alexander Zverev hooked up at the fourth round in Indian Wells for one of the most interesting intergenerational clashes of the year.

From the outset, the veteran Nadal had to fight from deep beyond the baseline to stay with the lanky Zverev, who hit serves and groundstrokes with an easy, powerful combination.

It came down to a few nerves in the third set. Zverev, then aged 18, had match point and what should have been a winning forehand volley, but he tightened up and the ball thunked into the net.

Given new life, Nadal didn’t give back an inch, ripping off 14 of the next 15 points and closing out the match, 6-7(8), 6-0, 7-5. 

"[It] is a great victory, as I said before,” Nadal said, per Tennis Now. “I'm very happy about it. I am especially happy about the mentality on court, the spirit of fight during the whole match, believing that I can win a match during the whole time even in the tougher situations.”

"On match point I sucked, so that was it," Zverev countered, per the same source. "I missed probably the easiest shot I had the whole match. That's what happened."

It was a catalyst for Nadal’s improved play in the spring, peaking with the Monte Carlo and Barcelona titles before he hurt his wrist and withdrew from the third round of the French Open.

Zverev generated plenty of good will from tennis observers, and we profiled this defeat with a look at the future. He’s ahead of schedule and perhaps can make his superstar breakout in 2017.

9. Novak Djokovic vs. Gilles Simon, Australian Open 4th Round

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The Australian Open did not have a memorable superstar match as Djokovic crushed Kei Nishikori, Federer and Murray in the final three matches to win his sixth championship in Melbourne.

The world No. 1 was in the middle of an epic streak, and he almost always made his wins look effortless—except for his fourth-round battle against counter puncher Gilles Simon.

Djokovic was often torn between grinding against Simon or trying cheap, impatient winners. He attempted too many failed drop shots and had to fight himself as much as the Frenchman. But after four-and-a-half hours and 100 unforced errors, the Serb survived his only scare of the tournament.

It was a sloppy Djokovic performance, but a dramatic and unexpected 6-3, 6-7, 6-4, 4-6, 6-3 contest. Credit to Simon’s footwork and heart. He gave back every shot and took the right amount of risks for his big upset opportunity, but he came up a few games short of interrupting the Djokovic empire.

8. Stan Wawrinka vs. Novak Djokovic, US Open Final

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Most of Djokovic’s memorable matches revolved around his struggles in 2016. He crashed against Sam Querrey in the first week at Wimbledon, got ousted by Juan Martin del Potro at the Olympics and lost the U.S. Open final to Stan Wawrinka 6-7(1), 6-4, 7-5, 6-3.

The first takeaway was Djokovic’s injuries and lack of the form that had seen him capture the Grand Slam of tennis just a few months before. He generated negative attention for extended medical timeouts in the final set.

Wawrinka was the deserving winner, pounding his heavy groundstrokes against the wounded Serb. He powered his way to his third major title and reinforced his reputation as a big-match giant. He kept his nerve and like 2014 (defeated an ailing Nadal in the Australian Open final) and 2015 (used his blueprint to overpower Djokovic) he is experienced in standing up to beat his rival legends.

It was not a pretty match unless you like bruising sports like boxing. If it were a heavyweight contest, it would have been Wawrinka with an eighth-round TKO.

“You were the more courageous player in the decisive moments,” Djokovic said during the post-match ceremony, via the Guardian. “He’s a great champion. He deserves to win this title, well done.”

7. Roger Federer vs. Marin Cilic, Wimbledon Quarterfinals

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Although he only played 28 matches in 2016, Roger Federer can still create a flair for the dramatic.

The Swiss maestro was not in top form at Wimbledon after months of intermittent rest and play after February knee surgery. But there he was, a 34-year-old battling back from a two-sets deficit against a strong grass-court player in Marin Cilic to pull out an astounding 6-7(4), 4-6, 6-3, 7-6(9), 6-3 quarterfinal win.

Per ATP World Tour, Federer said:

"

Today was epic. Probably going to look back at this as being a great, great match that I played in my career, on Centre Court here at Wimbledon... This is huge for me, my season, my career. I'm very, very happy. To win a match like this, to test the body, to be out there again, fighting, being in a physical battle and winning, it is an unbelievable feeling.

"

Federer turned back three match points in the fourth set. He created the magic for one of the most compelling matches of the year. Unfortunately, it also left him at least somewhat fatigued for his semifinal match; more on that later in this countdown.

For Cilic it was a stunning blow, and it carried over a week later when he blew another two-sets lead, this time in the first Davis Cup rubber against American Jack Sock.

Although Cilic would go on for some giant success, including the Western & Southern Open title over Andy Murray, he would lose a third match up two sets. That will also be detailed with a later slide in this article.

6. (tie) Juan Martin del Potro vs. Andy Murray and Marin Cilic, Davis Cup

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Which match was better? They were equally important and impressive, so you make the call:

1) Last year, Murray carried Great Britain as they captured the Davis Cup against Belgium. This year, Juan Martin del Potro might have been an even bigger story, notwithstanding the suffocating media coverage from the UK who parlayed “Murray Mania” into Wimbledon glory and the dramatic chase for the world No. 1 spot.

Instead, there was Del Potro late in 2016 with one of the great injury comebacks of all time, defeating the likes of Dominic Thiem, Wawrinka, Djokovic, Nadal and, yes, Murray.

The Argentine took down Murray and Great Britain in the Davis Cup semifinals in a five-set victory that would ultimately be the difference in swinging the cup to the South American nation rather than Great Britain's chance at two in a row.

2) Of course, Croatia was a worthy contender, and they hosted the final, went up 2-1 and needed only for Cilic to finish off his two-sets lead over Del Potro.

Somehow, Del Potro keeps getting stronger as the season continues and the matches get bigger. He dealt Cilic his third two-sets collapse of 2016, which enabled teammate Federico Delbonis to win the fifth and decisive rubber. It’s Argentina’s first Davis Cup title and a storybook ending to 2016 for Del Potro.

The match was an instant classic, and nearly five hours of pure desire and a broken pinky finger. Del Potro might be the most dangerous player in tennis to the current Murray-Djokovic-Wawrinka triumvirate. He’s a legitimate major-title threat for 2017.

5. Andy Murray vs. Juan Martin del Potro, Olympics Final

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The Summer Olympics only come once every four years, and the men’s singles tennis final was a hard-fought showcase on the world’s stage. The Argentine fans traveled into Brazil and supported countryman Juan Martin del Potro’s fabulous comeback that included upsets over Djokovic and Nadal to get to the final.

Murray was the 2012 gold medalist, and the Scot came in as the Wimbledon champion and prohibitive favorite after Djokovic’s dismissal in the first round. What transpired would prove to be a pattern for Del Potro: grueling in-and-out forehands, a lengthy match and a lot of heart.

It was one of the best quality matches of the year, a crafty duel that saw Del Potro adjust with his softer backhand, slicing and creating the contrasting pace that made his forehand all the more explosive. He led 5-3 in the fourth set before Murray stormed back for the 7-5, 4-6, 6-2, 7-5 victory. It left both players emotionally and physically exhausted as they shook hands at the net.

Perhaps this effort cost Murray a better chance at winning Cincinnati and the U.S. Open, but he went on to scorch the tour in autumn and claim the No. 1 ranking.

Del Potro would get his revenge in the aforementioned Davis Cup semifinal clash, propelling Argentina to eventual victory. It was an epic match that will be remembered with some of the best of the Olympics games.

4. Novak Djokovic vs. Andy Murray, French Open Final

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Djokovic finally did it. His long-suffering ambition to win the French Open became a reality with his 3-6, 6-1, 6-2, 6-4 conquest of Murray. It was his crowning moment, his career peak, and he became the only player of the Open era to hold the Grand Slam with all four majors played on grass, clay and two kinds of hard courts.

It was the most significant historical accomplishment of the year even if the match seemed rather routine with Djokovic squeezing his lesser rival once again. He finally tracked down his white whale after years of watching Nadal rule the red clay.

The championship did not receive nearly the praise that it should have. If this were Federer or Nadal, there would have been much greater media acclaim, tennis-fan attention and sports awe. To top it off, Djokovic collapsed at Wimbledon and has not recovered his most dominant form. That became the story rather than the celebration of the Grand Slam—perhaps the greatest accomplishment of all time.

"This is something that is so rare in tennis," Murray said, per the Associated Press, via ESPN.com. "It's going to take a long time for it to happen again."

Well done, King Novak.

3. Kei Nishikori vs. Andy Murray, US Open Quarterfinals

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The drama see-sawed on every point late in the fifth set at the U.S. Open quarterfinal between favorite Andy Murray and 2014 finalist Kei Nishikori. What ensued was a classic upset for the Japanese player, 1-6, 6-4, 4-6, 6-1, 7-5.

It might have been the most compelling match of the year, given the quality of shots and emotional tests for both players. The difference proved to be Nishikori’s guts and perseverance.

Nishikori was more aggressive in mixing up serve-and-volley attempts, drop shots, slice and attacks on the Scot’s second serve, none bigger than the break he got in the 11th game to go up 6-5 in the fifth set. The successful aggression was more apparent after a rain delay and a talk from coach Michael Chang in the middle of the second set.

Above all, Nishikori was the more composed player, keeping his head while Murray often ranted with the frustrations of playing a dogged match against a less-favored player. Perhaps the pressure of playing as a slight favorite to win the tournament was also a factor, but he simply wasn't as good as his opponent when it mattered most.

Murray would bounce back and sweep his way to the world No. 1 ranking by November, and he would survive another tough marathon test by Nishikori at the World Tour Finals.

2. Andy Murray vs. Milos Raonic, WTF Semifinals

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One of the sneaky, budding rivalries could be that of Andy Murray and Milos Raonic; now if the big Canadian could just finish off one of those big matches...

He lost a fifth-set semifinal at the Australian Open, lost the Queen’s Club final after being up a set and a break, and he lost one of the great matches of the year in the World Tour Finals.

There was plenty at stake for Murray who had to win this semifinal match in order to set up his WTF title and keep the No. 1 ranking into 2017. After more than three-and-a-half hours and after saving one match point, Murray squeaked through with the monumental 5-7, 7-6(5), 7-6(9) victory. That, not the next day’s door slam on Djokovic, turned out to be the real test.

Raonic moved up to No. 3 in the ATP Rankings and might be the most likely player to get his first major title in 2017. He’s becoming much better than just a bullet-serving giant. He’s worked hard on his net game, stays steady with his groundstrokes and has continued to play better under pressure. If he can stay healthy for a year without interruption, he could very well get over the Murray hump by Wimbledon.

Murray? What else can we say except that he continues to fight his way to the top despite his three legendary career rivals and in spite of the naysayers who thought his game didn’t have enough clout to be so dominant.

“I fought hard," Murray said, per ATP World Tour. "I fought very hard this week. I have also the last few months, too. It would have been easy today when I was behind to have gone away a little bit, but I didn't... Even after serving for the match twice, having a bunch of match points in the tie-break, still stayed tough, chased balls down, fought as best as I could."

Murray has proved himself 10 times over. From here out, it’s all icing on the cake—or maybe the quests for the Australian and French Open titles have only just begun.

1. Milos Raonic vs. Roger Federer, Wimbledon Semifinals

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Every serve and each precious break were filled with breathtaking tension and fine skill. Of course this is Roger Federer on the biggest stage in tennis—Centre Court Wimbledon. He willed his aging, injured body to a thrilling but monumental loss to new serve king Milos Raonic with a 6-3, 6-7(3), 4-6, 7-5, 6-3 defeat that had it all.

Unfortunately for Federer, one fatal slip on the grass would spell the end of his year, and that—perhaps more than any other image—will be remembered in a year that was dominated by Djokovic’s Grand Slam and Murray’s furious charge to the No. 1 ranking.

Raonic got the biggest win of his career, forcing his way to win the fourth set after trailing 40-0.

“I can't believe I served a double fault twice," Federer said, per BBC Sport. "Unexplainable for me really. Very sad about that and angry at myself because never should I allow him to get out of that set that easily.”

Until then, Federer had gained the upper hand with his superior defense and variety, weathering some big serves and fine net closes by Raonic. After the fourth-set glitch, though, it was the Canadian who stepped up his game.

Federer got behind in the fifth set and never could rise up. There was the tragic fall on the grass and treatment from the trainer. Raonic never gave him an opening and finally got his ticket to a major final. Two days later, he got swept by Murray.

The net effect for Federer was further damage to the knee injury that had plagued him since February’s surgery and subsequent attempts to play matches and get in shape. How he competed so well despite not being in top shape is another wonder for the Swiss. That he came back to win a five-setter against Cilic in the quarterfinals and play five more against Raonic is a courageous effort.

Unfortunately, 18 days later Federer announced he would not be able to play in the Olympics, the U.S. Open or the rest of the ATP Tour in 2016. His ranking would fall to No. 16, but most of all he was missed by tennis fans from all over the world.

At least he and Raonic left a gift of the most dramatic match of the year.