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Osaka beat Belgian Elise Mertens to reach the Western & Southern Open final after playing in a semifinal she had originally withdrawn from in a call for racial justice.
The Greek rallied from a set down to beat the 23-time Grand Slam champion 5-7, 7-6(5) 6-1 and reach the quarterfinals.
The third-seeded Briton needed medical attention just minutes into the first-round contest against Marie Bouzkova before she felt well enough to continue.
Former world No.1 Clijsters and 2017 US Open champion Sloane Stephens are among the headliners as World TeamTennis kicks off its three-week regular season on Sunday, at the Greenbrier resort in West Virginia.
Former world No.1 Kim Clijsters said she was looking forward to getting more matches under her belt and improving, after losing 6-3, 7-5 to Briton Johanna Konta in the opening round of the Monterrey Open.
Caroline Wozniacki said that the three-set grinder against Ons Jabeur was a fitting end to her career.
Svitolina, who broke the psychological barrier of reaching a Grand Slam semifinal at Wimbledon in July, became the first Ukrainian to make the last four of the US Open with a 6-4, 6-4 win over Britain's Johanna Konta.
Serena Williams claimed her 100th win at the US Open in style, dismantling her quarterfinal opponent Wang Qiang 6-1, 6-0 in a blistering 44-minute performance.
Djokovic, champion in four of the past five Slams and 16 overall, was less bothered by left shoulder pain that nagged him in the second round in defeating 111th-ranked American Denis Kudla 6-3, 6-4, 6-2.
The 37-year-old will become the oldest woman to contest a Grand Slam final in the professional era.