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Jiri Vesely scored the biggest win of his career in upsetting Novak Djokovic in Monte-Carlo.

Biggest ATP World Tour Upsets Of 2016

ATP World Tour Season In Review: Biggest ATP Upsets

Continuing our Season In Review Series, ATPWorldTour.com revisits the biggest ATP World Tour upsets of 2016:

(5) Mischa Zverev d. Stan Wawrinka 6-2, 5-7, 6-1 – Basel quarter-finals
One of the brightest emerging talents on the ATP World Tour, #NextGen star Alexander Zverev made his presence known in 2016. Just weeks after notching his maiden title at the St. Petersburg Open, the 19 year old soared to a career-high World No. 20 in the Emirates ATP Rankings in mid-October. But Alexander wasn’t the only Zverev to enjoy a breakout run at season’s end.

Older brother Mischa turned back the clock with a slew of inspired performances of his own, employing his fast-paced lefty serve-and-volley brand of tennis with great success. One week after Alexander’s Top 20 milestone, Mischa reached his first ATP World Tour semi-final in six years behind a signature upset of World No. 3 and home favourite Stan Wawrinka at the Swiss Indoors Basel. The 29-year-old qualifier claimed his fifth match win in seven days, putting years of injury woes behind him with an impressive rise to year-end World No. 51 in the Emirates ATP Rankings. Zverev, who entered 2016 at No. 171, claimed just his second victory over a Top-5 opponent, breaking Wawrinka six times. It capped a strong finish to the season that also saw him push Novak Djokovic to the brink in the Shanghai Rolex Masters quarter-finals.

(4) Thiago Monteiro d. Jo-Wilfried Tsonga 6-3, 3-6, 6-4 – Rio de Janeiro first round
The 2016 Rio Open presented by Claro provided many intriguing storylines, with top seed Rafael Nadal and eventual champion Pablo Cuevas staging a late-night semi-final thriller and Argentina’s Guido Pella streaking to his first ATP World Tour final. But arguably the most remarkable performance was turned in by unseeded wild card Thiago Monteiro. To say that the 22-year-old Brazilian’s first tour-level match was a memorable one would be an understatement.

The Rio de Janeiro resident and World No. 338 shocked No. 9 Jo-Wilfried Tsonga to open the tournament, channeling the energy of the home fans to secure the biggest upset of the year over a Top 10 opponent. Monteiro entered the history books with the victory, becoming the first player to win his debut against a Top 10 player since Guido Pella (d. Tipsarevic) in Dusseldorf 2013 and the first ranked 300 or lower to beat a Top 10 player since Albano Olivetti (d. Fish) in Marseille 2012.

Monteiro would go on to enjoy a breakthrough 2016 campaign, becoming the only player to rise more than 300 spots to a year-end Top 100 position in the Emirates ATP Rankings. The World No. 82 reached a pair of ATP World Tour quarter-finals in Sao Paulo and Gstaad, in addition to claiming his maiden ATP Challenger Tour title in Aix-en-Provence, France.

(3) Federico Delbonis d. Andy Murray 6-4, 4-6, 7-6(3) – Indian Wells third round
Pressure? What pressure? With his nation on his shoulders, Federico Delbonis stepped up for Argentina, clinching the decisive fifth rubber in the Davis Cup final last month. But the 26 year old has proven he’s capable of big performances under pressure, turning in clutch displays throughout the year. Delbonis did not drop a set en route to the title in Marrakech after claiming one of the biggest wins of his career over World No. 2 Andy Murray at the BNP Paribas Open in March.

The Argentine survived a deciding tie-break against the eventual year-end No. 1 and Barclays ATP World Tour Finals champion in the third round, adding Murray to his list of Top 10 scalps that also includes Roger Federer (Hamburg 2013) and Stan Wawrinka (Geneva 2015). Murray was not at his best on a sun-kissed afternoon in Indian Wells, hitting 44 unforced errors, and World No. 53 Delbonis refused to shy away from the occasion, overcoming a break deficit in the third set to prevail after two hours and 45 minutes. The Round of 16 finish is Delbonis’ best result at an ATP World Tour Masters 1000 event.

"This was special," said Delbonis. "For this tournament, for the surface, for me it is my best win."

(2) Denis Shapovalov d. Nick Kyrgios 7-6(2), 3-6, 6-3 – Toronto first round
Making your tour-level debut on home soil is often a magical moment. Win it and you’re an instant hero. This year, Thiago Monteiro embraced the spotlight in Rio de Janeiro (see No. 4 above) and Marcus Willis thrilled the Wimbledon faithful (stay tuned for the best Grand Slam upsets on Tuesday). At age 17, it was akin to a fairytale for Denis Shapovalov at the Rogers Cup in Toronto. The Canadian teen stunned Nick Kyrgios in a dramatic first-round encounter under the lights at the ATP World Tour Masters 1000 event.

World No. 370 Shapovalov was unflappable in trading baseline blows with the 11th-seeded Aussie, taking an aggressive approach with his one-handed backhand and refusing to acquiesce to the pressure after dropping the second set. A #NextGen star in the making, he was the youngest player to win an ATP World Tour match this year. Despite falling to Grigor Dimitrov in the second round, Shapovalov says it was a memorable experience.

“I might be dreaming still. It’s still hitting me,” said Shapovalov after defeating Kyrgios. "I didn't expect to win. I'm just going to go fight for every point. That's what I did. The outcome was very good today."

“He's coming off one of the best results of his career. He has a great future,” Kyrgios said. “I'm really looking forward to seeing how he's going to progress... He's a top player.”

(1) Jiri Vesely d. Novak Djokovic 6-4, 2-6, 6-4 – Monte-Carlo second round
Novak Djokovic was an indomitable force to open the 2016 season. The champion in Doha, Melbourne Park, Indian Wells and Miami, the Serbian was 28-1 through the first three months of the year and entered the Monte-Carlo Rolex Masters as the heavy favourite to retain the title. But his clay-court opener did not go as planned, as World No. 55 Jiri Vesely made a massive statement on one of the game’s biggest stages.

The Czech earned the biggest win of his young career, halting Djokovic’s run of 106 consecutive matches won against players ranked outside the Top 50. It was also his earliest defeat at an ATP World Tour event in three years, since suffering a second-round loss to Grigor Dimitrov in Madrid in 2013. The inaugural Star of Tomorrow presented by Emirates in 2013, Vesely held his nerve for a stunning victory in two hours and six minutes, maintaining his steely resolve in a tense third set. Djokovic had seemed poised to stage a fightback after reeling off four straight games from 2-2 in the second to level the match. But Vesely regrouped in the decider to claim the memorable victory.

"I'm just very, very happy," Vesely said. "When I went on court, I had completely different thinking, like, 'I hope to win a game,' or 'I really hope to do well.' But I really had no idea that I really would be able to beat Novak today."

Biggest ATP World Tour Upsets By Emirates ATP Ranking

Player

Opponent
Tournament
Ranking Difference
No. 1042 Juan Martin del Potro
No. 30 Jeremy Chardy
Delray Beach
1012 spots
No. 1042 Juan Martin del Potro
No. 65 Denis Kudla
Delray Beach
977 spots
No. 1045 Dmitry Tursunov No. 75 Sam Groth
Acapulco
970 spots
No. 1042 Juan Martin del Potro
No. 135 John-Patrick Smith
Delray Beach
907 spots
No. 837 Reilly Opelka No. 28 Kevin Anderson
Atlanta
809 spots
No. 837 Reilly Opelka No. 53 Donald Young
Atlanta
784 spots
No. 761 Nikola Cacic No. 69 Aljaz Bedene
Umag
692 spots

Honourable Mentions
•    In just his third ATP World Tour event, American teen Reilly Opelka made a splash in reaching the BB&T Atlanta Open semi-finals. At 18, the World No. 837 stunned third seed Kevin Anderson and seventh seed Donald Young, before falling to John Isner in three sets. Later in August, the 6’11” Opelka would save two match points in also upsetting Jeremy Chardy 11-9 in a deciding tie-break at the Western & Southern Open.

•    #NextGen star Alexander Zverev became the first teenager to win an ATP World Tour crown since 2008 with a title run at the St. Petersburg Open. He earned consecutive Top 10 upsets of Tomas Berdych and Stan Wawrinka in the semis and final.

•    After nearly a year on the sidelines with a hip injury, 18-year-old Swede Mikael Ymer impressed the home faithful at the If Stockholm Open, routing former World No. 7 Fernando Verdasco 6-2, 6-1 in the first round. The World No. 549 was contesting just his second ATP World Tour event.

•    Di Wu put China on the map in 2016, becoming the first from his country to win an ATP Challenger Tour title (in Maui, U.S.A.) and the first to win a match at an ATP World Tour Masters 1000 event. At No. 182 in the Emirates ATP Rankings, he upset No. 22 Pablo Cuevas in a deciding tie-break at the Shanghai Rolex Masters.

Coming Tuesday: The biggest Grand Slam upsets of 2016