Five surprising upset victories in tennis in 2019

Everyone likes the story of David overcoming the challenge of the fearsome Goliath. And especially in sports, the victory of an underdog is celebrated like anything.

Here, we take a glance at five of the most surprising upset wins that happened in 2019.

5. Grigor Dimitrov vs Roger Federer

In an electric atmosphere with tennis worthy of a championship match, Roger Federer and Grigor Dimitrov battled through five riveting and dramatic sets to give a packed Arthur Ashe Stadium crowd all that they came for; and more, at the 2019 US Open.

Relentless in his shot-making and intensity, Dimitrov scored the biggest upset of his career by toppling the five-time Open champion, 3-6, 6-4, 3-6, 6-4, 6-2, in the quarterfinals.

Once ranked No. 3 in the world in 2017, Dimitrov reached his first Open semifinal and third Slam final four. 

“Only thing I kept thinking was to stay in the match, in the match,” he said after his first career win over the Swiss great in eight tries. “I’m just happy.”  

It was a big upset that left many an enthusiastic fan disappointed to have missed out on a potential Fedal final showdown.

4. Cori Gauff vs Venus Williams

Cori 'Coco' Gauff’s skill level has long been out of proportion to her age, a fact increasingly obvious in the world of tennis. 

But, she stunned one and all when she defeated five-time Wimbledon champion Venus Williams in the first round of the tournament, becoming the youngest woman to win a main-draw Wimbledon match since Jennifer Capriati beat defending champion Martina Navratilova in 1991.

Not only did Gauff upset her idol, who is more than twice her age, but she did so in spectacular fashion, eliminating Williams in straight sets, 6-4, 6-4.

“I don’t really know how to feel,” Gauff said. “This is the first time I’ve cried after a match, after winning.”

The tennis prodigy entered her Wimbledon debut ranked 313th by the Women’s Tennis Association, while Williams entered 44th. The 15-year-old prodigy had never played in a Grand Slam event before, while Williams had previously played in 16 Slam finals.

3. Daniil Medvedev vs Novak Djokovic

Russia’s Daniil Medvedev defeated the World Number 1 and defending champion Novak Djokovic in the Western and Southern Open semi-finals, and with that, he not only surprised the Serb, but also the multitude of people who would have bet their money on a Djoker triumph.

Medvedev dramatically stepped up his game after losing the first set in Cincinnati, eventually prevailing 3-6 6-3 6-3 to set up an unexpected final against David Goffin.

“I was so tired in the first set and playing Novak, I thought I’m not going to be able to keep the intensity, then there was one momentum change in the second, and I just started playing unbelievable,” Medvedev said.

The Russian never looked back and he was delighted to win a match he acknowledged would often have slipped away in the past. “Many matches like this I would go crazy and break the racket and lose 6-3 6-3,” he said.

2. Bianca Andreescu vs Serena Williams

It was as if Serena Williams was playing herself, the 17-year-old prodigy of 1999, when she won the first of her 23 grand slam titles, the first of six in front of her own fans; except the mirror answered back on that eventful night at the 2019 US Open final. 

The remarkable 19-year-old Bianca Andreescu won the title, beating the strongest of opponents in straight sets.

It was her first slam final, the first time in four attempts she had gone past the second round, and she became the first Canadian to win a major. 

After an hour and 40 minutes that seemed much longer, she brought the drama to a close with a forehand into empty space that validated the 6-3, 7-5 scoreline.

Last year she couldn’t get out of qualifying in all four slams, and finished the year ranked 178th in the world. When she left Flushing Meadows after winning in her fourth appearance in a main draw, Andreescu celebrated a remarkable season by breaking into the top ten.

1. Andy Murray vs Stanislas Wawrinka

Well, you might be wondering as to who the underdog is, in this one. But if you take the liberty of rewinding to the 2019 Australian Open, when a heartbroken Andy Murray contemplated retirement at a press conference, you should get context.

The Scot legend tearfully announced that he could have very well played his last game. The 31-year-old star said he had hoped to be able to get to Wimbledon in the middle of the year (where he planned to retire), but his body let him down.

Now nine months and a hip resurfacing surgery later, the three-time Grand Slam champion is now back in the winner’s circle, having defeated Stanislas Wawrinka 3-6, 6-4, 6-4 for the European Open crown.

It has also seen the former World Number 1 bounce back in the world rankings, rising 100 places to 127 in the world. He is the first player to win after the hip resurfacing surgery.

Murray has said he is a lot more optimistic about his future, after winning the title, which is his first ATP Tour singles title in more than two-and-a-half years.