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  • Predicting winners, highlighting the must-watch matches, picking the players who will have a big breakthrough and more for Wimbledon.
By The SI Staff
June 28, 2019

With Wimbledon 2019 set to kick off Monday in London (6 a.m. ET), SI's tennis experts and writers Jon Wertheim, Stanley Kay, and Daniel Rapaport pick winners, discuss this year's top storylines, highlight must-watch matches and more.


Biggest takeaway from the albeit short grass-court season lead-up to Wimbledon?

Jon Wertheim: I’ll attack the premise (and try to answer in the process.) Is there even such a thing as a grass-court season? As far as playing strategy, the jury is sequestered. The list of the players taking a hard pass on the tune-ups grows each year. Serena—a mild surprise given her lack of match play in 2019—hasn’t played since Paris. Neither has Nadal, Djokovic, Dominic Thiem, even Fabio Fognini. Wimbledon will reveal whether this was wise or foolhardy.

 What else did we learn? Roger Federer and Ash Barty are really good, and real contenders. But we knew that already. Age is not especially relevant as Feliciano Lopez (age 37) impressed but so did 18-year-old Felix Auger Aliassime. We all, knew that, too. Andy Murray and tennis’ tragedienne Juan Martin del Potro are wildly popular irrespective of their physical condition? We all knew that as well.

Jamie Lisanti: Roger Federer won at Halle for the 10th time in his career, which has previously served as a solid starting point and a good omen for his performance at the All England Club. The takeaway: Fed’s got a green thumb and he arrives to the Wimbledon grass with the stinging memory of a quarterfinal, 13-11 final-set loss to Kevin Anderson last year. It’s not shocking news, but count him as a big favorite on the men’s side.

Another general lead-up note as we round the corner into the third Slam of the year: the Big Three is thriving. Federer, Rafael Nadal and Novak Djokovic have combined to win the past 10 Grand Slam tournaments, and their dominance at Wimbledon is even more obvious.

On the women’s side, Angelique Kerber deserves a mention. Deep into the tournament in Eastbourne with a win over Simona Halep, Kerber is the defending Wimbledon champion and although she’s been quiet elsewhere at the majors this year (including a first-round exit in Paris), consider her a threat to win another Wimbledon title.

I’m also excited to see American rising star Coco Gauff make her Wimbledon debut—the 15-year-old became the youngest Wimbledon qualifier in the Open Era this week and is one to watch in the years ahead. Fortunately or unfortunately, she’ll face Venus Williams in the first round.

Daniel Rapaport: What Jon said. The biggest takeaway is that there really is no grass-court “season,” for better or for worse. (And as we’ve discussed on this website, it’s for worse for Roger Federer’s win total). The second one: if watching Nadal on clay is the most awe-inspiring sight in tennis, watching Federer on grass is the most beautiful.

Which player do you see having a breakthrough tournament?

JW: Felix A-A on the men’s side. Part of that: he is really good at tennis and doesn’t turn 19 until August. Another part: despite his elevated status —he is currently the fifth choice with some oddsmakers to win the title— he has yet to win a main-draw singles match for his career. Remarkable. 

The women’s side is harder to mine for gems, simply because so many players have already shone through. Does Ash Barty winning the title and thereby putting up Hall of Fame credentials qualify as a breakthrough? Amanda Anisimova continuing her ascent?

JL: If healthy, 2016 finalist Milos Raonic and Borna Coric could be ones to watch on the men’s side. Despite her recent struggles, 39-year-old (!!) Venus Williams is always a threat, particularly at Wimbledon. Can Stefanos Tsitsipas make his Grand Slam breakthrough on the turf? The World No. 6 has all the tools and potential. We’ll also name check 23-year-old Russian Daniil Medvedev.

Let’s take this time to acknowledge a different type of breakthrough: it will be great to see Sir Andy Murray continue his comeback and return to the Wimbledon grass in doubles this week, as he teams up with Pierre-Hugues Herbert.

DR: FAA and Coco Gauff. If Gauff can beat Venus Williams in the first round, that would have a real changing-of-the-guard moment and could, in hinsight, become one of those matches that we see highlights of for years to come (think Fed d. Sampras, Wimbledon 2001).

Another youngster who has fallen a bit under the radar, given the success of FAA and Tsisipas: how about Denis Shapovalov? He plays aggressive. He has variety and flair. The serve is improving. Sounds to me like a recipe for success on grass. 

Which high seed is in danger of losing early?

JW: He’s a lovely guy. But Dominic Thiem’s game is just not made for grass, as his first-round Wimbledon loss in 2018 confirmed. And while No. 11 might not even qualify her as a “high seed,” I worry about Serena. Health concerns, motherhood, outside obligations and, above all, no match play since Paris. Say this: if she DOES win title— at age 37, with so little momentum—it might mark her most impressive major campaign ever. Which is saying quite something.

JL: Although she has two grass-court titles in her career, World No. 3 Karolina Pliskova has not been able to find success on the grass courts at the AELTC. Last year was the first time in seven appearances that she made it past the second round at Wimbledon, so while she is trending upward, I’d be wary of the Czech making a deep run.

Because of the Wimbledon seeding rules and last year’s runner-up finish, Kevin Anderson earned a No. 4 seed. But the towering South African missed the clay season this year to extend his recovery from an elbow injury and before playing Queen’s Club last week, he’s only played two other tournaments this year: Miami in March and the Australian Open in January. Despite his success here last year, I’d definitely classify him as a top-five seed in the danger zone.

DR: Serena Williams, for one, but she could also just as well win the whole tournament. It is virtually impossible to predict how she will fare. And Jamie’s points re/Kevin Anderson are valid, but I think the big serve bails him out. So I’ll go with Jon and say Thiem. I do have some of my own thoughts, I promise.

One offbeat storyline to follow during the event

JW: You wish Andy Murray were competing to win his third singles title. But as a doubles player and front-facing figure he will singlehandedly own the rest of the tournament….Has GEMS life—the outré Gael Monfils/Elina Svitolina multi-platform partnership—returned? The usual tennis politics will be a story (the players side of the ATP Board should be set; the ITF elections heat up’ the jockeying for the big USTA job continues.) 

JL: I’m always fascinated by long-standing traditions at the All England Club (Pimms cups! Strawberries and cream! Henman Hill!) but the implementation of the strict rules on clothing is always interesting to see. Who will be the first break the Wimbledon dress code and how?

One more: I’m always here for the Nick Kyrgios show. After skipping the French Open last month, Kyrgios ought to have a lot to say this week at Wimbledon.

DR: If Murray has any sort of success, that is going to explode in the best way possible. And if Serena Williams loses early, could we start to hear some retirement rumblings?

Who will win the women’s title?

JW: Boring pick, but I like Ash Barty, the top seed, to pull of the Channel Double. If she can win on clay, she can sure as hell win in grass. And her measured disposition and quintessential Aussie equanimity make it so her winning a major will not be a destabilizing life event.

JL: Gosh, this is hard. No. 1 seed Ash Barty’s quarter of the draw is absolutely brutal: Kerber, Serena Williams, Garbine Muguruza, Belinda Bencic…..the list goes on. Whoever makes it out of there is going to win the title. While Ash Barty is certainly the favorite of the summer, I’m going to pick someone who’s very familiar with winning at Wimbledon: Serena Williams. 

DR: Kerber. Defending champ, playing well in the grass leadup. 

Who will win the men’s title?

JW: Short answer: someone among the Big Three, the juggernaut which shows few signs of downshifting. As if they weren’t good enough, the best-of-five format helps immensely. Among the Big Three—and I write this prior to seeing the draw—I guess I go with Djokovic, despite (or maybe because of) his light lifting since Paris. The defending champ until proven otherwise.

JL: Roger Federer played the clay season for the first time in a long time this year, and while he ran into the King in Paris, something tells me the extra match play and overall confidence he gained will be a big boost over the next two weeks. Roger Federer wins Wimbledon title No. 9 in 2019. 

DR: Djokovic d. Federer, who is gassed from outlasting Nadal in an epic semi final.

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