Angelique Kerber (2018 record: 45-17; WTA Finals record: 6-8; Record vs. group: 6-6)
Kerber won two tournaments in 2018, but one of them was Wimbledon; hence her No. 3 ranking, and her top billing in the Red Group. Since then, she has been OK, but not good enough, apparently, to keep working with the coach who took her back to the top of the game, Wim Fissette—they broke up earlier this week. Kerber is 6-8 in WTA Finals, but she did reach the title match in Singapore in 2016, and the low-and-slow surface there should theoretically be to her liking. Kerber, more than most, is a momentum player and a confidence player; how she fares in her first match, against Kiki Bertens, should tell us a lot about how she’ll fare all week. But she has to like the fact that she’s the only player in this group who’s not a WTA Finals rookie.
Naomi Osaka (2018 record: 42-17; WTA Finals record: 0-0; Record vs. group: 2-4)
Like Kerber, Osaka won two tournaments this year. Also like Kerber, one of them was a big one, the US Open. The other, in Indian Wells, wasn’t too shabby, either. Unlike some players, Osaka hasn’t fallen off the face of the earth after her breakthrough win. Since the Open, she has reached the final in Tokyo and the semifinals in Beijing. How will she react to her first year-end championship, on an indoor surface that seems to be unlike any other, against all-quality opponents? It’s an interesting question; once she’s rolling, Osaka tends to keep rolling, over any opponent who happens to be in front of her.
Sloane Stephens (2018 record: 33-17; WTA Finals record: 0-0; Record vs. group: 6-1)
Despite winning just one event in 2018, the 25-year-old American will be making her first trip to Singapore. The late-year Asian swing hasn’t traditionally been Sloane’s time to shine, and that was true again this year. Since the US Open, she’s 2-3. But Stephens is 4-1 against the highest-ranked player in this group, Kerber, and 2-0 combined against Bertens and Osaka. If she can build a little early momentum, Sloane can beat anyone on any given day, on any given slow surface.
Kiki Bertens (2018 record: 43-19; WTA Finals record: 0-0; Record vs. group: 1-4)
Talk about wild cards. While Bertens is 26, she has never been in contention for the WTA Finals before, and only announced herself as a potential elite player over the second half of 2018. But with three titles, including one in Hong Kong late last month, Bertens should come to Singapore with confidence. No one is unbeatable in this group.
Semifinalist: Kerber, Osaka