Three-time Grand Slam champion Stanislas Wawrinka was knocked out of the second round of the Japan Open after defeat to Denis Shapovalov on Wednesday.
World No. 31 Shapovalov, 19, came from a set down to win 4-6, 6-1, 6-4 in what was his first meeting with the former world No. 3. The Canadian will now play Daniil Medvedev after he beat Martin Klizan 6-4, 6-3.
Kei Nishikori continued his good form as he advanced to the quarterfinals thanks to a 6-3, 7-5 victory over Benoit Paire.
No. 3 seed Nishikori, who is a previous winner in Tokyo having lifted the title in 2012 and 2014, battled from 0-3 down in the second set after he had comfortably secured the first in 31 minutes.
The world No. 12 won the next five games to lead 5-3, before holding serve in the 12th game of the set to seal the win.
Yoshihito Nishioka, Nishikori’s Japanese compatriot, was defeated by Nick Kyrgios in the opening match of the day.
Kyrgios fired 20 aces during the match as he won 7-5, 7-6(3) and will face Richard Gasquet in the next round.
No. 2 seed Kevin Anderson won his opening match of the tournament but required three sets as he defeated Matthew Ebden 4-6, 7-6(1), 6-2.
Milos Raonic defeated Yosuke Watanuki 6-3, 7-6(2) while Alex De Minaur knocked out Gilles Simon 6-7(1), 7-6(5), 6-2.