To get her fourth straight major title, Serena Williams will have to navigate a loaded top half of the Wimbledon draw featuring seven Slam winners. Her buddy Caroline Wozniacki, though, might have a path to a long-awaited breakthrough.
Nobody did Serena Williams any favors. The Wimbledon draw, announced on Friday, is complicated at best for the history-seeking five-time champion.
Williams, who is going for her fourth straight major and trying to keep alive her hopes of winning the first calendar-year Grand Slam since 1988, could get fellow five-time champion (not to mention sister) Venus Williams in the fourth round. It's the earliest the No. 1 seed and the No. 16 seed could meet.
To recap, Serena might have to make it past three former No. 1 players, including two former Wimbledon champions, just to make it to the final.
Up first for Williams will be Margarita Gasparyan of Russia, ranked 113th in the world. The two have never before played. The top half of the women's draw is full of danger for everyone. Of the nine major champions in the draw, seven are in the top half. There are a total of 41 major singles trophies floating around the Wimbledon draw, and 37 of them are in the top half. There are 16 American women in the draw, and 12 are in the top half.
Best first-round match
Venus Williams versus Madison Brengle. The only first-round match between Americans sure looks lopsided on paper. The 35-year-old Williams is the owner of 46 WTA singles titles, including seven Grand Slams and five Wimbledons. The 25-year-old Brengle is still looking for her first WTA title and has never even played in the main draw at Wimbledon, failing to qualify in six previous attempts. Williams has won 73 main-draw singles matches at the All England Club. Brengle has won zero. Williams has won nearly $31 million in prize money. Brengle is still looking to break the million-dollar mark. But focus in on 2015, and the numbers start to look a lot more similar. Brengle is 26-15 this season and ranked 36th in the world. Venus is 20-7 on the year and ranked 16th. Brengle made it to the Round of 16 at the Australian Open before losing to Madison Keys. Williams made it to the quarterfinals of the Australian Open before losing to Madison Keys. Both fell in the first round of the French Open. The two have never before played, but the edge certainly goes to the big-serving and grass-loving Williams. Honorable mention for best first-round match goes to Francesca Schiavone versus Sara Errani. The Italians are 1-1 head-to-head, and the grass won't bring out the best in either of them. But if you're looking for effort and noise, this is where you're going to find it.
Favorite most ripe for the picking
We all keep looking for opportunities for Victoria Azarenka to make another deep run at a major to give her ranking its rightful boost. Lady Luck keeps having alternate plans. Azarenka, a two-time Wimbledon semifinalist and former No. 1, was put in the Serena Williams quarter of the draw for the third time at a major this year. Things start out relatively routinely for Azarenka. First up is Anett Kontaveit, an Estonian ranked 143rd in the world. The second round would also be a very winnable match against either Annika Beck, who made it to the third round at the French, or Kirsten Flipkens. Things start to get a bit tricky in the third round, where, if seeds hold, Azarenka would play Carla Suarez Navarro, who is enjoying a career year but is certainly no grass guru. If Azarenka makes it to the fourth round, she could run into another former No. 1, Ana Ivanovic. In the quarters, it could be five-time Wimbledon champion Serena Williams. And, if she gets past Serena -- remember, she was oh-so-close at the French -- how does Maria Sharapova in the semis sound?
Favorite best positioned for sailing
Petra Kvitova. The No. 2 seed and two-time champion doesn't exactly have an easy draw. But it's not downright daunting, either. Kvitova opens her defense on Centre Court on Tuesday against 108th-ranked Kiki Bertens of the Netherlands. Her second-round match would be against either Kurumi Nara, ranked 57th, or Magda Linette, who is making her second appearance in a major. Former No. 1 Jelena Jankovic could be lurking in the third round, and 2012 finalist Agnieszka Radwanska is a potential fourth-round challenger. Madison Keys or last year's runner-up, Eugenie Bouchard, could be waiting in the quarterfinals before a matchup with potentially Caroline Wozniacki or Simona Halep in the semis.
Best Cinderella candidate
Say hello to Caroline Wozniacki. The former No. 1 has made it to the quarterfinals at every major except Wimbledon. This very well could be the year she makes the elusive elite eight. The No. 5 seed drew Saisai Zheng in the first round. She'll get a Czech in the second round -- either Katerina Siniakova or Denisa Allertova -- and neither has made it to the third round of a major. After that, would a possible matchup with Camila Giorgi make Woz shake in her slippers? Possibly. Wozniacki is just 1-2 against the 31st-seeded Italian, but Wozniacki won their only meeting on grass. Wozniacki's biggest hurdle to get to her first quarterfinals would be next and could be in the form of Angelique Kerber, a 2012 Wimbledon semifinalist and 2014 quarterfinalist who won the title on Birmingham's grass earlier this month. If the seeds hold, Wozniacki would play third-seeded Simona Halep in the quarters. Wozniacki is 2-2 in her career against Halep and won their only meeting this year.
American with the friendliest path
It isn't exactly pretty for any of the 16 Americans at the All England Club, but we're looking to Sloane Stephens to be wearing white for a while. The unseeded 22-year-old drew No. 27 Barbora Strycova in the first round, but it's a match the 43rd-ranked Stephens could/should win. The two have split their two career meetings, but the Stephens loss came back in 2011. In their most recent meeting, last summer in Cincinnati, Stephens posted a 7-5, 6-1 win. After that, Stephens could play either 81st-ranked Polona Hercog or 79th-ranked Lauren Davis. A win there would put Stephens in the third round against French Open finalist Lucie Safarova, the No. 6 seed. Stephens is 0-1 against Safarova.
The match we're hoping to see
Leave a Serena-Sharapova semifinal out of it for now. First things first. We're pointing to Eugenie Bouchard versus Madison Keys in the third round. For one thing, it means Bouchard, seeded 12th, has broken whatever evil spell has been cast over her this season and has won back-to-back matches for the first time since March. For another, it would be a matchup of two of the women tabbed for stardom when -- make that, if -- the Serena reign ends. Both women already have major success on their résumés. Not only is Bouchard the reigning runner-up at Wimbledon, but the 21-year-old Canadian also has been to the semifinals at the French Open and Australian Open. Keys, a 20-year-old American seeded 21st, advanced to the Australian Open semifinals this year before falling to Serena Williams. Keys leads the head-to-head 1-0, but that match was all the way back in 2012. The only downer to this dream? The winner would still be in the same quarter as Kvitova and just one more win away from a clash with the reigning champion.