Since Serena Williams won the WTA Finals for the third straight year in 2014, we’ve had three first-time and surprising winners in Agnieszka Radwanska, Dominika Cibulkova, and Caroline Wozniacki. With world No.1 Simona Halep not participating, this year’s event feels as wide open as ever. This half of the round robin groupings includes some of the most compelling players to watch in 2018, making for some very intriguing matchups.
Naomi Osaka vs. Sloane Stephens
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This is a battle of the last two US Open winners, and is the opening round match I’m most excited for. Last year after her victory in New York, Sloane Stephens went on an eight-match losing streak over the next six months. She’s similarly struggled following her quarterfinal loss at this year’s US Open. After losing to Anastasija Sevastova in the quarterfinals on an extremely hot day in New York, Stephens went just 2-4 in Asia heading into this tournament. This though will be Sloane’s WTA Finals debut, and we’ve seen how she can step up on big stages in the past despite losses at smaller tournaments. This is also Naomi Osaka’s first time qualifying for the year-end championships. However unlike Stephens, Osaka has followed up nicely on her life-changing US Open title. Naomi went 7-2 after leaving New York, making the final in Tokyo and the semifinals in Beijing. While Stephens won their only previous meeting, that was nearly three years ago in Acapulco. Osaka is certainly the more in-form player right now. I give Naomi the slight edge in what will hopefully become a prolific rivalry in years to come between two of the games’ most talented players.
Angelique Kerber vs. Kiki Bertens
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2018 Wimbledon Champion Angelique Kerber is back in the WTA Finals for the fifth time. She was a finalist here two years ago, but failed to qualify last year after an extremely disappointing 2017 season. Kerber has struggled since winning her third Major in July, with a 6-5 record since that time. And she curiously split with her coach, Wim Fissette, just days before the start of this tournament. Kiki Bertens will be making her WTA Finals debut, and only due to Simona Halep’s withdrawal. But don’t discount Bertens’ chances in Singapore, as she’s arrives with plenty of momentum. Kiki has been one of the winningest players on tour over the past six months. Bertens was a surprise quarterfinalist at Wimbledon, and then went on to win the biggest title of her career at the Premier 5 event in Cincinnati. And just last month, she raised the trophy in Seoul as well. Bertens will likely play freely and feel little pressure in this tournament knowing she snuck in due to a withdrawal. And Kiki has just crushed top 10 opponents of late, winning her last eight matches over top 10 players. Of course she’ll face nothing but top 10 players over the next week, so she’s a real threat to advance out of the round robin stage. Kerber is 2-1 lifetime against Bertens, but all three matches have been tight. I’m picking Kiki to pull off another upset on Monday in Singapore.
