Top 5 Women’s Wimbledon First-Rounders—Trouble for Osaka, Kerber

View the entire women's bracket at our Wimbledon tournament page.

The draw ceremony took place at Wimbledon on Friday morning and some of the top women’s players definitely had better luck than others when it came to which first-round opponents they drew.

Here are five first-round women’s matches to watch for at Wimbledon this year:

Osaka was probably given the trickiest first-round match-up of all of the top women’s players in Yulia Putintseva. Not only did Putintseva beat Osaka in the only Wimbledon lead-up tournament she played—a 6-2, 6-3 upset in the second round of Birmingham last week—but the Kazakhstani has actually won both of their previous meetings in straight sets, having defeated the Japanese in the first round of the Australian Open lead-up tournament in Hobart last year, also in straight sets, 6-3, 6-3.

Osaka lost the No. 1 ranking to Ashleigh Barty this week after losing early in Birmingham and Barty going all the way to the title. The No. 2-ranked Japanese has a chance at taking No. 1 back this fortnight, along with No. 3 Karolina Pliskova, No. 4 Kiki Bertens and No. 6 Petra Kvitova.

In a generational match-up between a tennis legend and one of the sport’s brightest future prospects—as well as the youngest and oldest players in the women’s draw—39-year-old Venus will take on 15-year-old Gauff in the first round. The 24-year-age gap is the biggest age difference in a Grand Slam singles match in the Open Era since 2004. (At Wimbledon 2004, Martina Navratilova, 47 at the time, lost a second-round match to 19-year-old Gisela Dulko.)

Venus is a five-time champion at Wimbledon in 2000, 2001, 2005, 2007 and 2008, while Gauff—who wasn’t even born until 2004—made a little history herself here this year, becoming the youngest player to qualify for the main draw of Wimbledon in the Open Era.

Gauff is also the first 15-year-old to compete at Wimbledon since Laura Robson in 2009.

Before the draw was made, Gauff said it would be “amazing” to play a Williams in the first round.

Wimbledon is Kerber’s best Grand Slam—not only did she win the title in 2018, but it’s the only Grand Slam she’s been to more than one final at, having finished runner-up to Serena Williams in 2016. But the No. 5 seed hasn’t won a title since conquering SW19 a year ago, and her opponent Tatjana Maria, a fellow German, is quite the giant-killer with four career wins over Top 10 players. One of those Top 10 wins actually came in the first round of Wimbledon a year ago over Elina Svitolina.

Maria beat Kerber in their only career meeting, though it was 10 years ago on clay in Barcelona.

Like Kerber, Kvitova’s best Grand Slam is right here at Wimbledon—she’s a two-time champion in 2011 and 2014. But she hasn’t played since before the French Open, an arm injury keeping her out of Paris and the grass-court lead-up season.

To complicate the comeback, Jabeur’s on a roll—she’s fresh off making the semifinals of the Premier-level lead-up event in Eastbourne, beating Johanna Konta along the way, though she had to withdraw before her semifinal with an ankle injury. The Tunisian has three career Top 10 wins, as well.

A number of former No. 1s have been trying to work their way back up the rankings this year and Azarenka—a two-time Australian Open champion—is one of them. She broke back into the Top 50 in February, her first time since becoming a mom, and she was five points away from beating then-No. 1 Osaka at Roland Garros. She opens against Cornet, a former No. 11, and though the Belarusian has won all five of their previous meetings, three of their last four have gone three sets.