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Updated : 3 years, 7 months ago IST
World No.28 Kvitova of the Czech Republic took two hours and 18 minutes to outlast American Keys.
Tsitsipas registered a stunning win against Medvedev 7-6(6), 3-6, 6-3 in the semifinals to cruise into the final of the Cincinnati Masters.
The 26-year-old overwhelmed Canadian Shapovalov 7-5, 7-5 in one hour and 45 minutes clash to book a spot in the quarter-finals.
Keys registered a 6-3, 6-4 straight-set victory over Swiatek to enter the quarterfinals.
Kvitova defeated Jabeur 6-1, 4-6, 6-0 in a match that lasted for one hour and 47 minutes.
The Croatian fought for two hours, 51 minutes to secure his biggest win of the season by both opponent and stage.
Halep was set to face Veronika Kudermetova in the second round.
In a hard-fought match, Medvedev defeated Botic van de Zandschulp to secure a 6-4, 7-5 victory and advance to the third round in Cincinnati.
Zhang Shuai produced a stunning performance to advance to the second round of the tournament, defeating Osaka 6-4, 7-5 in a match that lasted for 75 minutes.
19-year-old Raducanu was dominant from the start of the match breaking Williams in the opening game before rolling to a 6-4, 6-0 win.
The Australian pair clinched the match by 6-0, 6-4 against Simone Bolelli and Fabio Fognini in 60 minutes.
Murray registered a hard-fought victory against Stan Wawrinka 7-6(3), 5-7, 7-5 to advance to the next round.