Naomi Osaka in the US Open. Williams, 37, is in the same bracket as WTA No. 1 Simona Halep, so it'll be a long road for her.

Venus Williams could play Halep as early as the third round, whereas Serena would have her in the fourth if the bracket goes chalk.

Osaka is the No. 4 seed, and her side of the bracket is shared with Anastasija Sevastova. Osaka broke out at last year's Open with an incredible run that ultimately ended in her defeat of Williams. At just 21, Osaka is coming off a tough loss at Brisbane to Lesia Tsurenko, but her attitude after the match shows that she's refocusing.

"If I'm being really frank, I just feel like I had like the worst attitude today," she said afterform after a brutal Brisbane International loss to Yasutaka Uchiyama. A potential semifinal match with Federer looms if he's able to power through, but his quarterfinal section would include Kevin Anderson and John Isner. An Anderson-Isner rematch, of course, would evoke memories of last year's Wimbledon when the two played a marathon against each other.

Should things go chalk, Federer's quarterfinal matchup would be Marin Cilic, but in Cilic's section Karen Khachanov is looking to play spoiler.

Kei Nishikori and Djokovic could play in the quarterfinals after Djokovic swept Nishikori in the semifinals of the US Open. Djokovic has won the last two men's majors, and he's looking for No. 3. Andy Murray has a relatively favorable draw himself, ending up in Cilic and Khachanov's bracket, but he'll need to