Daniil Medvedev and Stefanos Tsitsipas lost to lowly ranked players at the ongoing ATP Masters 1000 level at the Omnium Banque National présenté par Rogers in Montreal on Thursday.
Tsitsipas fell 6-4, 6-4 to 576 ranked Kei Nishikori.
Nishikori’s victory earned him his first Top 20 win since 2021.
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He advanced to the third round at ATP Masters 1000 level for the first time in three years.
The Japanese became the third lowest-ranked player to reach the last 16 at an ATP Masters 1000 event since the series began in 1990.
Nishikori described the victory as a testament to his hard work.
“It means a lot,” Nishikori said after reaching the third round.
“I am playing well and feel I am back on track again, so I am really happy with the way I played today.
“Beating Stef is not easy and for me it is a great win.
“I stayed aggressive and was not missing too many balls today. It was much better than the first round.”
He will face 12th-seeded Frenchman Ugo Humbert or Portugal’s Nuno Borges in the next round.
Also World No. 5 Daniil Medvedev lost 6-4, 1-6, 6-2 to Alejandro Davidovich Fokina.
Fokina, who reached the semi-finals at the Canadian ATP Masters 1000 event last year in Toronto, will next play Karen Khachanov or Matteo Arnaldi.
Medvedev was competing in his first hard-court match since reaching the semi-finals in Miami in March.
He is still seeking his first title since May 2023 when he won in Rome.
By Dotun Omisakin
