MONTREAL - Canadian teenager Denis Shapovalov didn't bend an inch against tennis superstar Rafael Nadal.

Shapovalov upset Nadal 3-6, 6-4,7-6 (4) in the Rogers Cup third round on Thursday Night at a sold out Uniprix Stadium, where crowds roared with every point scored by the 18-year-old from Richmond Hill, Ont.

He advanced to a quarter-final meeting Friday night with France's Adrian Mannarino, who defeated Hyeon Chung of South Korea 6-3, 6-3.

Shapovalov has taken major strides this week to reach his goal of cracking the world's top 100 with wins over Rogerio Dutra Silva and 2009 U.S. Open champion Juan Martin Del Potro. He also halted Nadal's bid to regain the No.1 ranking, which the Spaniard could have achieved by reaching the semifinals.

Shapovalov looked unfazed in facing the biggest opponent of his young career. After Nadal cruised through the first set, Shapovalov kept battling, breaking service while taking a 3-0 lead in the second. When Nadal would start taking a control of a game, the younger of the two lefthanders would respond with big serves or impressive forehands down the lines.

Nadal fought off two break points to hold serve at 4-2, then earned his own break to win back the momentum from the 2016 Wimbledon junior boys champion, only to see Shapovalov snatch it back and clinch the second set.