Canada's top two men's singles players take the court Friday morning as Denis Shapovalov and Milos Raonic each get set to play quarter-final matches at the St. Petersburg Open.

Shapovalov -- the tournament's second seed and the 12th-ranked player in the world -- is up first as he battles Stan Wawrinka of Switzerland.

Watch LIVE at approximately 7:45 a.m. ET/4:45 a.m. PT on TSN3, TSN.ca, the TSN App and on TSN Direct.

Shapovalov is 1-1 lifetime against his counterpart and is expecting a battle, calling Wawrinka a "tough opponent."

"It is especially difficult to play against him when he feels confident. I think tomorrow will be a difficult match, but I think that I am also in good shape, and I also played very well in two matches here," he said Thursday after taking down Ilya Ivashka of Belarus 6-1, 6-4 in the Round of 32.

Shapovalov has won 11 of his last 14 matches dating back to his run at the US Open in September, which ended in a quarter-final loss to Pablo Carreno Busta. He is the highest seed remaining in St. Petersburg after Russian Daniil Medvedev lost 2-6, 7-5, 6-4 to American Reilly Opelka in Round 2.

Meanwhile, Raonic won the St. Petersburg Open in 2015 and comes into Friday off of straight-set victories over Jeffrey Wolf and Alexander Bublik. The 29-year-old is set to face fourth-seeded Russian Karen Khachanov at around noon ET/9:00 a.m. PT on TSN3.

After his run to the Western and Southern Open final, Raonic was ousted in the second round in each of his past two tournaments.

With a victory, Raonic would take on the winner of Opelka and Borna Coric, while Shapovalov would be up against either Cameron Norrie or Andrey Rublev.

Full Round of 16 coverage gets underway LIVE at 6:00 a.m. ET/3:00 p.m. PT on TSN3, TSN.ca, the TSN App and on TSN Direct.