Nadal, an 18-time Grand Slam singles champion, could add another Masters footnote to his epic resume if he successfully defends his Canadian crown for the all-time trophy mark.
"It's a tough one", Shapovalov said.
Fabio Fognini is coming off a straight sets win over Adrian Mannarino that took 20 games to decide.
"He's having a great season, playing unbelievable, solid tennis every week".
Despite the disappointing result, he said his two matches in Montreal should serve as a confidence boost.
"If a couple of shots had went my way, I could have definitely won the match".
No. 6 seed Daniil Medvedev of Russian Federation defeated Great Britain's Kyle Edmund 6-3, 6-0, No. 10 seed Roberto Bautista Agut of Spain got past Argentina's Diego Schwartzman 6-2, 7-5, and No. 14 seed Marin Cilic of Croatia moved on with a 6-3, 6-4 win over Australia's John Millman. At the end I want to play well, I don't want to be disappointed.
Kyle Edmund, ranked 33, had come through a very tricky opener against the victor in Washington's ATP500 on Sunday, Nick Kyrgios 6-3, 6-4, but he now took on the newest addition to the top 10, Daniil Medvedev, victor of the most hardcourt match-wins this season, 21.
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After rain delays of six and 30 minutes, Nadal fought off two set points in the first-set tiebreaker before prevailing. He played a great match. The second seed Dominic Thiem had come five times to Canada and five times gone home without a win.
Zverev, the victor in 2017, was pushed to a final-set tie-break before edging past Nikoloz Basilashvili. Fognini won 61 percent of his total service points and converted on five of his 12 break points.
Basilashvili edged Zverev in a final-set tie-break in Hamburg last month.
The Russian sixth seed earned his spot by ousting Canadian Felix Auger-Aliassime on the youngster's 19th birthday - he shares one with Roger Federer, now 38.
Dominic Thiem of Austria serves to Marin Cilic of Croatia during round of sixteen play at the Rogers Cup tennis tournament Thursday August 8, 2019 in Montreal.
Khachanov administered a 6-7 (7/9), 7-5, 6-3 victory then apologized to the crowd after taking out the last Canadian, but said he thought he got a raw deal from Canadian partisans.
"I was happy that I was able to play so well, to beat him so easily", Medvedev said. I don't have anything against it when they cheer for Felix. "But still, not when I miss or not wishing me to miss, screaming during the points".
"I think I'm serving well". I just tried to tell him my experience.
The night session concludes with a battle of veterans when No. 10 seed Roberto Bautista Agut of Spain squares off with No. 16 seed Gael Monfils of France.