It was a day of top 10 upsets in the men’s draw at the ATP Cincinnati Masters on Wednesday.

Fifth seed Stefanos Tsitsipas saved three match points but lost to Germany’s Jan-Lennard Struff 6-4, 6-7 (5/7), 7-6 (8/6) while sixth seed Kei Nishikori went out to fellow Japanese Yoshihito Nishioka 7-6 (7/2), 6-4.

Alexander Zverev, seeded seventh, remained winless in his Cincinnati career after losing 6-7 (4/7), 6-2, 6-4 to 19-year-old Serb Miomir Kecmanovic. The German struck an unbelievable 20 double-faults in defeat.

However, ninth seed Daniil Medvedev, losing finalist to Rafael Nadal in Montreal last weekend, eased past Benoit Paire 7-6 (7/2), 6-1 and will next face Struff.

France’s Richard Gasquet, who ended Andy Murray’s comeback singles tournament in the first round, saw off Argentinian Federico Delbonis 7-5, 7-6 (7/1).

For Nishioka, it was a dream result as he defeated longtime idol and Japanese countryman Kei Nishikori.

Sixth-seeded Nishikori, Asia’s top-ranked player, went down to his 77th-ranked compatriot, who came through qualifying, in just over 90 minutes. For the winner, the second-round success was legendary.

“I was so excited to play with him, because he’s the hero of the Japanese tennis, Asian tennis,” Nishioka said.

“I couldn’t sleep yesterday, I know him very well. I was watching him when I was junior. I was learning many things from him.

“I tried to go his weakness, I just wanted to be my best against my hero.

“This was a very important experience for me. Today I learned many things from him. The most important thing was to play with him.”

Nishikori, a 2014 US Open finalist, has never been past the third round in Cincinnati while Nishioka is making his first appearance.

Nishioka will aim for the quarter-finals on Thursday against Australian Alex de Minaur who defeated American Reilly Opelka 7-6 (7/3), 6-4.

Results

Men

2nd rd

Lucas Pouille (FRA) bt Denis Shapovalov (CAN) 6-4, 6-4

Andrey Rublev (RUS) bt Stan Wawrinka (SUI) 6-4, 6-4

Daniil Medvedev (RUS x9) bt Benoît Paire (FRA) 7-6 (7/2), 6-1

Jan-Lennard Struff (GER) bt Stefanos Tsitsipas (GRE x5) 6-4, 6-7 (5/7), 7-6 (8/6)

Miomir Kecmanovic (SRB) bt Alexander Zverev (GER x7) 6-7 (4/7), 6-2, 6-4

Diego Schwartzman (ARG) bt Radu Albot (MDA) 6-4, 6-2

Richard Gasquet (FRA) bt Federico Del Bonis (ARG) 7-5, 7-6 (7/1)

Yoshihito Nishioka (JPN) bt Kei Nishikori (JPN x6) 7-6 (7/2), 6-4

Alex De Minaur (AUS) bt Reilly Opelka (USA) 7-6 (7/3), 6-4

David Goffin (BEL x16) bt Guido Pella (ARG) 6-1, 7-5

Adrian Mannarino (FRA) bt Mikhail Kukushkin (KAZ) 6-1, 6-3

Roberto Bautista Agut (ESP x11) bt Frances Tiafoe (USA) 6-3, 3-6, 6-1

Karen Khachanov (RUS x6) bt Nick Kyrgios (AUS) 6-7 (3/7), 7-6 (7/4), 6-2

With AFP inputs