Denis Shapovalov defeated Frances Tiafoe 6-4, 6-2 at the Shanghai Masters on Monday, setting up a second-round encounter with defending champion Novak Djokovic.
The first game of the match stretched to 15 minutes before Tiafoe held serve, but Shapovalov eventually took control with a break in the first set and two more in the second.
"The start of the match was really important and I was trying to step up from the first game," Shapovalov said.
"I think the first game helped me find a rhythm on his serve."
The 36th-ranked Shapovalov played the top-ranked Djokovic on two previous occasions, with both matches taking place this year.
He took Djokovic to four sets in the third round of the Australian Open, but only won four games in the second round at the Rome Masters.
"He's beaten me twice so there's not much for me to lose, so I'll just go out there and enjoy myself," Shapovalov said. "I'll go out there and give it all I have.
"It's going to be a tough one, but I have a great game and I think I have a chance to beat him."
A Canadian citizen, Shapovalov was born in Israel and is currently a resident of the Bahamas. He said he hasn't been back home since Hurricane Dorian devastated the islands in August.
"Obviously it's terrible what has happened to the Bahamas," he said, adding his home didn't sustain much damage.
"I'm going to try to see what I can do to give back."
Fellow Canadian Vasek Pospisil upset 14th-seeded Diego Schwartzman of Argentina 7-6 (2), 6-2 in another first-round match.
The 10th-seeded Fabio Fognini of Italy faced little resistance from American Sam Querrey in a 6-4, 6-2 victory.
Andy Murray, playing on a wildcard, faces Argentine qualifier Juan Ignacio Londero in Monday's first night match.
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