Continuing our Season In Review series, ATPTour.com looks at the five biggest ATP Tour match upsets in 2019. (The biggest Grand Slam upsets will be featured Thursday.)

5) Jannik Sinner d. Gael Monfils, European Open, Antwerp Second Round, 17 October 2019 (Match Stats)
Those in Italian circles will tell you that it’s no surprise Jannik Sinner’s has surged up the ATP Rankings over the past 12 months, from No. 778 to a 2019 year-end No. 78. They’ll describe how Riccardo Piatti first unearthed a gem and that it was only a matter of time before the 18-year-old made an impact. But you have to back it up on the court.

Sinner heralded his arrival on the ATP Tour in mid-October with a 6-3, 6-2 victory over Nitto ATP Finals contender Gael Monfils for a place in the European Open quarter-finals. Having previously beaten No. 59 Steve Johnson in May at the Internazionali BNL d’Italia in Rome, Sinner saved the only break point he faced to overcome World No. 13 Monfils in 61 minutes. Sinner misfired on a return on his first match point, but if he had any nerves, he did not show them, forcing an error off Monfils’ backhand slice to finish off the sixth tour-level win of his career.

Three weeks later, Sinner ran through the Next Gen ATP Finals field for the 21-and-under title (d. de Minaur) and the following week, in his final tournament of the year, he didn’t drop a set to capture his third ATP Challenger Tour title at the Sparkasse Challenger in Ortisei (d. Ofner). A 700-place rise in 13 months means that the Italian will be one to watch in 2020.

Read Sinner-Monfils Match Report

4) Laslo Djere d. Dominic Thiem, Rio Open presented by Claro, Rio de Janeiro First Round, 20 February 2019 (Match Stats)
Laslo Djere had yet to win a clay-court match in 2019 or beat a Top 10 star in his career, yet the Serbian saw the ball big to beat one of the standout red-dirt performers in recent years, Dominic Thiem, the then-World No. 8 and 2017 champion, 6-3, 6-3 at the Rio Open presented by Claro. Djere, who lost his serve in the opening game, broke Thiem five times and benefitted from five double faults from the Austrian.

“It was a great day,” said World No. 90 Djere. “The biggest win in my career so I’m really happy right now… I hit the ball really well. He played a bit worse than normally I think, to be honest. But I had a great day. I felt the ball really well, hitting well from the baseline and then attacking well when it was time for that. This is my favourite surface. So I know that I can play great tennis on clay.”

Four days later, the 23-year-old dedicated his first ATP Tour title to his late parents, Caba and Hajnalka, after beating Felix Auger-Aliassime in the title match.

Read Match Report | Read Feature: Djere – My Point

<a href='https://www.atptour.com/en/players/laslo-djere/db63/overview'>Laslo Djere</a>

3) Jeremy Chardy d. Daniil Medvedev, Rolex Paris Masters, Paris Second Round, 29 October 2019 (Match Stats)
In the final throes of the regular 2019 ATP Tour season, one of the sport’s brightest new stars, Daniil Medvedev, who had reached six consecutive finals dating back to the Citi Open in early August, found Jeremy Chardy too hard to crack. Chardy, on home soil, fought off nerves and saved 14 of 15 break points to record one of the biggest upsets of his career, 4-6, 6-2, 6-4 in the Rolex Paris Masters second round. Fourth seed Medvedev, who had won his past 11 ATP Masters 1000 matches, including title runs at the Western & Southern Open in Cincinnati and the Rolex Shanghai Masters, had been riding a nine-match winning streak dating back to the US Open final (l. to Nadal).

“It’s a beautiful victory,” said Chardy, who broke during a 13-point seventh game in the third set. “When you play a match like this on the central court in France and you win it, it’s a wonderful feeling. All the efforts that are deployed every day are aimed at achieving a goal like this one. When you play players like that, that are of such a high level, you need to have a perfect game level. And all my break points, I played them well, so it’s frustrating when you’re the opponent. This has happened to me the other way round, and it was great to be on the right side of the court this time.”

Chardy had previously lost 10 matches against Top 10 opponents since beating then No. 4-ranked Thiem in March 2018 at the Miami Open presented by Itau.

Read Match Report & Watch Highlights

Djokovic, Kohlschreiber

2) Philipp Kohlschreiber d. Novak Djokovic, BNP Paribas Open, Indian Wells Third Round, 12 March 2019 (Match Stats)
Aged 35, Philipp Kohlschreiber had long proven to be a master on home soil, winning seven of his eight ATP Tour titles in Germany. But when it came to beating World No. 1s, he had an 0-11 record. So when he squared off against five-time champion Novak Djokovic, who held an 8-1 FedEx ATP Head2Head record, at the BNP Paribas Open in Indian Wells, chances of a Kohlschreiber victory were slim. He hadn’t won a set in their past four meetings.

In a match suspended by rain from the previous day, World No. 39 Kohlschreiber got the better of a sluggish Djokovic, who sparked into life for the first time at 2-5 in the second set. But Kohlschreiber held his nerve for a 6-4, 6-4 victory over one hour and 38 minutes for the 25th Top 10 match win of his career.

“It’s a very special win today,” Kohlschreiber said. “I had a great strategy to play against him. I had two good wins [entering the match]. So everything came together. [It’s] very special to beat the No. 1. Unfortunately, the tournament is not over. I have to get back tomorrow with a great mindset. Today I want to take the moment, celebrate with my coach. I’ve got a lot of messages. I know it’s a very special victory today.”

Read Match Report 

1) Andrey Rublev d. Roger Federer, Western & Southern Open, Cincinnati Third Round, 15 August 2019 (Match Stats)
Roger Federer isn’t accustomed to losing early at the Linden Family Tennis Center, the scene of seven crowns at the Western & Southern Open, let alone in the time it took Andrey Rublev to dismantle his game. In mid-August, having won 15 of his past 16 matches at the Masters 1000 event, Federer came unstuck against the Russian qualifier in just 62 minutes — Federer’s fastest defeat in more than 16 years.

Rublev, then No. 70 in the ATP Rankings, had initially forgotten to sign up for the tournament, but got an alternate spot and found his way into the qualifying competition. By the time he met Federer for the first time, Rublev had played four matches in Cincinnati and took his power game to the Swiss superstar on Stadium Court with a barrage of forehands to earn three breaks of serve.

Federer tried bringing Rublev forward but the Russian delivered volleys with newfound touch. “It’s my biggest and the most emotional win,” said Rublev, after beating Federer 6-3, 6-4 in the third round.

It was Federer’s earliest loss in Cincinnati since 2008 (l. to Karlovic in 3R) and his quickest defeat since a 54-minute loss to Italian Franco Squillari in the 2003 Sydney first round.

“He was super clean,” said Federer, contesting his second match since the Wimbledon final on 14 July, of Rublev. “Defence, offence, serving well. Didn’t give me anything. He was everywhere. So it was tough for me, but excellent match by him. I was impressed.”

Read Match Report & Watch Highlights

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