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Novak Djokovic defeats Roger Federer to win his fifth Wimbledon title.

The Best Grand Slam Matches Of 2019

ATP Tour Season In Review: Best Grand Slam Matches

Continuing our Season In Review series, ATPTour.com looks at the six best Grand Slam matches in 2019.

6. Milos Raonic d. Stan Wawrinka, Australian Open, R2 - 17 January 2019 (Match Stats)
Former World No. 3 Milos Raonic faced one of the toughest draws at this year’s Australian Open. The Canadian defeated the dangerous Nick Kyrgios in the first round, and then had to play three-time Grand Slam champion Stan Wawrinka in the second round.

Each man broke twice in the match, but with all four sets going to a tie-break, it came down to just a couple of points here and there to decide who would win and in how many sets. The roof was closed on Rod Laver Arena as rain suspended play for about 30 minutes towards the end of the third set. And the big-serving Canadian, who struck 39 aces to Wawrinka’s 29, captured the final two tie-breaks.

Both men brought a level reminiscent of their time in the Top 5, making this second-round match one that would have easily fit into the second week. And even with their big serving numbers, both acquitted themselves well in entertaining rallies throughout.

After four hours and one minute, Raonic defeated Wawrinka 7-6(4), 6-7(6), 7-6(11), 7-6(5) en route to the quarter-finals.

“I'm glad I passed sort of the test in that aspect. Obviously both matches considered, it's a very difficult way to start the tournament,” Raonic said. “I'm happy with the level I put forth.”

Read More: Raonic Roars Past Wawrinka

Raonic would only play 13 tournaments and Laver Cup in 2019. But a victory like this showed that he is still plenty capable of performing at a high level on the world’s biggest stages.

Despite the loss, Wawrinka would only get better from this match on in 2019. The Swiss later won an even more tense battle at Roland Garros against Stefanos Tsitsipas, and he’d return to the Top 20 after dropping as low as World No. 263 in June 2018.

Milos Raonic

5. Roger Federer def. Rafael Nadal, Wimbledon, Semi-finals- 12 July 2019 (Match Stats)
Eleven years ago, Nadal and Federer played what many consider to be the greatest match ever in the 2008 Wimbledon final, won under near darkness by the Spaniard in five epic sets. The match was so special that a book, Strokes Of Genius, was written about just that clash. The legends did not meet again at SW19 until this season, when they battled for a spot in the final, with Nadal trying to complete the Roland Garros-Wimbledon double for the third time.

But Federer spoiled the party, playing some of his very best tennis to triumph 7-6(3), 1-6, 6-3, 6-4.

“It's always very, very cool to play against Rafa here, especially haven't played in so long,” Federer said. “It lived up to the hype, especially from coming out of the gates, we were both playing very well. Then the climax at the end with the crazy last game, some tough rallies there. I mean, I don't know. It had everything at the end, which was great, I guess. I'm just relieved it's all over at this point.

“But it's definitely, definitely going to go down as one of my favourite matches to look back at, again, because it's Rafa, it's at Wimbledon, the crowds were into it, great weather. I felt like I played good also throughout the four sets. I can be very happy.”

Read More: Roger Beats Rafa, Sets Sights On Ninth Title At SW19

Federer moved forward on the grass whenever possible, winning 25 net points to just six for Nadal. And although he let slip his focus in the second set, at one point dropping 10 points in a row with a slew of errors, the righty recovered well. He returned aggressively and began to perform better in the longer rallies, winning after three hours and two minutes.

“The early break in the third set, I had a couple of mistakes in that moment. That was a tough moment I needed to resist. The beginning of the third set probably was one of the keys of the match,” said Nadal. “I started to play much better at the end of the match, but it was too late.”

The win gave Federer an opportunity to play for a ninth Wimbledon title against Novak Djokovic.

Federer, fourth set

4. Roberto Bautista Agut def. Andy Murray, Australian Open, R1 - 14 January 2019 (Match Stats)
Before the Australian Open began, former World No. 1 Andy Murray held an emotional press conference announcing that he would either push through pain in his hip to finish his career at Wimbledon, or undergo a second hip surgery that would put his playing future in jeopardy.

At the time, nobody truly knew what the future would hold for the Scot, so players, commentators and fans alike were in awe when he battled for four hours and nine minutes against the always-solid Roberto Bautista Agut. But the Spaniard had too much in the tank, reaching the second round with a 6-4, 6-4, 6-7(5), 6-7(4), 6-2 win.

“If today was my last match, look, it was a brilliant way to finish, as well. That's something that I'll probably take into consideration,” Murray said. “It was an amazing atmosphere. I literally gave everything that I had on the court, fought as best as I could, and performed a lot better than what I should have done without the amount I've been able to practise and train.”

Read More: RBA Overcomes Andy In Five-Set Thriller Down Under

For much of the match, Bautista Agut’s patience and point construction was too much to handle for Murray, but he maintained contact in the third and fourth sets, getting the crowd involved in a big way to urge him into a decider. Judy Murray and Jamie Murray were among the thousands urging Murray on from the stands, with fans flying Scottish flags in the stadium.

But while he fought until the end, Bautista Agut’s forehand aggression proved too much in the fifth set, as he won the match and eventually reached the quarter-finals.

This classic also set Bautista Agut on course for what would be the best season of his career. At 31, he broke into the Top 10 of the ATP Rankings for the first time, and served as an alternate at the Nitto ATP Finals.

Murray did end up undergoing hip surgery, making his comeback — on the doubles court — at the Fever-Tree Championships. He did not stop there, though, returning to singles action in Cincinnati and eventually rounding into enough form to win his first ATP Tour singles title since 2017 Dubai in October in Antwerp.

Bautista Agut Murray

3. Rafael Nadal def. Daniil Medvedev, US Open, Final - 8 September 2019 (Match Stats)
Nadal entered this match as the favourite. Not only was he trying to clinch his fourth title in Flushing Meadows, but the Spaniard also was trying to earn an additional 800 ATP Ranking points to give him breathing room in the battle for year-end No. 1 with Novak Djokovic.

His opponent, Medvedev, was a first-time major finalist who was trying to become the youngest Grand Slam champion since Juan Martin del Potro at the 2009 US Open. The Russian was riding the hottest streak of his career up until that point, fresh off finals in Washington and Montreal as well as his first ATP Masters 1000 title in Cincinnati.

In a tale of two matches that turned into a classic under the New York lights, Nadal outlasted Daniil Medvedev, battling past the Russian 7-5, 6-3, 5-7, 4-6, 6-4 for the US Open title after four hours and 49 minutes.

Nadal was on track when he led by two sets and a break. The Spaniard seemingly had all the answers for the 23-year-old, taking pace off his groundstrokes and not only changing the height of his ball, but using various spins to break Medvedev’s rhythm when he needed to. He’d then blast away with his penetrating forehand once he gained momentum.

Read More: Nadal Claims Trophy With Epic Five-Set Win Against Medvedev

But like he did in Cincinnati against Djokovic, Medvedev changed his tactics and rapidly upped his aggression, going for his shots to send the match to a fourth and then a fifth set. Nadal’s trademark grit showed as he led by two breaks in the decider. But again, Medvedev recovered and earned a point to get back on serve.

Nadal was relentless though, clinching his 19th major to move within one Slam of Federer’s record 20, meaning the Spaniard will have a chance to tie the Swiss for the first time at next year’s Australian Open. Nadal also took a 1,960-point lead in the ATP Race To London. And although Djokovic clawed closer to earn himself a chance at his sixth year-end No. 1 when the Nitto ATP Finals came around, it was Nadal who joined Djokovic, Federer and Jimmy Connors with five year-end No. 1 finishes apiece.

“The last three hours of the match have been very, very intense. Very tough mentally and physically, too,” Nadal said. “The crowd [was] as always amazing, all these facts that make the moment super special. [It was an] unforgettable moment. At the same time Daniil created this moment, too. The way that he fought, the way that he played, is a champion’s way. Just well done for him. I really believe that he will have many more chances.”

Medvedev showed that despite the loss, he is not far away from major glory.

"I definitely will remember tonight," Medvedev added. "I'm sure even talking about Rafa's 19 Grand Slams, I'm sure he remembers his first final, even though he won it and I lost it. It was an amazing match. It's an amazing story.”

Daniil Medvedev and Rafael Nadal helped the US Open set a new attendance record this year.

2. Stan Wawrinka def. Stefanos Tsitsipas, Roland Garros, R4 - 2 June 2019 (Match Stats)
Stan Wawrinka walked onto the court for his fourth round match at Roland Garros seeking his first trip to a major quarter-final since undergoing two left knee surgeries in August 2017. The Swiss star, a three-time Grand Slam champion, had been to the last eight at a major 15 times before, but a win over the rising Stefanos Tsitsipas, who had reached the Australian Open semi-finals after winning the 2018 Next Gen ATP Finals, would be the high point of his comeback.

In a way, both Wawrinka and Tsitsipas came out winners on the terre battue. But it was Wawrinka who advanced to the quarter-finals with a thrilling 7-6(6), 5-7, 6-4, 3-6, 8-6 victory after five hours and nine minutes, making their battle the longest in the clay-court Grand Slam’s history.

“Playing in front of such a crowd, such a big atmosphere, five-set match in Grand Slam, that's the reason why I came back from the surgery in the first time, is because I love and enjoy to play in front of people, to play in the biggest tournaments you can play,” Wawrinka said. “Today was something really special.”

Read More: After Five Hours, Stan Escapes Stefanos

This classic was a bruising, physical encounter full of jaw-dropping baseline rallies that saw each man hammer away at their strokes ball after ball, with the down-the-line backhand proving a key shot for each. Wawrinka, a three-time major champion, was No. 28 in the ATP Rankings, still pushing for a return to top form at a major.

Wawrinka saved 22 of the 27 break points he faced, including eight in the final set. And Tsitsipas made a crucial mistake on match point, letting a slice backhand pass go, allowing it to land on the line.

“I feel exhausted. I don't know. Never experienced something like this in my life. I feel very disappointed at the end,” Tsitsipas said. “[It’s been a] long time since I cried after a match, so emotionally wasn't easy to handle. I will try to learn from it as much as I can.”

Tsitsipas’ momentum slowed after this match, reaching just one semi-final until the China Open in October. But from there, the Greek, reinvigorated, found his best level again and won the biggest title of his career at the Nitto ATP Finals.

Stan Wawrinka beats Stefanos Tsitsipas

1. Novak Djokovic def. Roger Federer, Wimbledon, Final - 14 July 2019 (Match Stats)
Wimbledon is momentous in and of itself. But this year's final had even more importance with the Big Three battling for the most Grand Slam titles.

Federer was a point from taking a three-major lead over Nadal, who had 18 at the time. It would have been a massive victory for the Swiss, who was pursuing his first Slam crown since the 2018 Australian Open. Djokovic, then the World No. 1, was playing for his fifth trophy at SW19, and his 16th major overall.

In a match of extraordinary shotmaking and drama, Federer served for his ninth Wimbledon title at 8-7 in the fifth set against Djokovic on the hallowed lawns. Throughout the match, Federer used controlled aggression to his advantage, winning 78 per cent of his trips to the net (51/65) and striking 94 winners to only 62 unforced errors.

But the Serbian rallied to triumph in a historic 7-6(5), 1-6, 7-6(4), 4-6, 13-12(3) victory after four hours and 57 minutes, the longest championship clash in tournament history (since 1877).

“It was probably the most demanding, mentally most demanding, match I was ever part of. I had the most physically demanding match against Nadal in the finals of Australia that went almost six hours. But mentally this was different level,” Djokovic said. “I'm just obviously thrilled and overjoyed with emotions to be sitting here in front of you as a winner. I was one shot away from losing the match, as well. This match had everything. It could have gone easily his way. He was serving extremely well, I thought, the entire match.”

Djokovic scratched and clawed to stick with the Swiss, winning the match’s first two tie-breaks to hang around, despite Federer claiming 14 more points than him (218-204) in the match.

Read More: Novak Saves Two MPs, Beats Roger In Historic Final

Djokovic appeared to have seized control, taking a 4-2 lead in the decider, but Federer found his best to get back on even terms and later serve for the title at 8-7 40/15. Federer first missed a forehand wide and then Djokovic crushed a forehand pass to stave off those chances, and the Serbian went on to win the first final-set tie-break in singles play at Wimbledon. This was the first year that there was a tie-break at 12-12 in the fifth set.

Two months later, Nadal triumphed at the US Open, putting him within one of Federer’s record 20.

“I will look back at it and think, ‘Well, it's not that bad after all.’ For now it hurts, and it should, like every loss does here at Wimbledon,” Federer said. “I think it's a mindset. I'm very strong at being able to move on because I don't want to be depressed about [what was] actually an amazing tennis match.

"It's such an incredible opportunity missed."

Novak Djokovic celebrates winning his fifth Wimbledon title on Sunday.