Stefanos Tsitsipas will need to come through qualifying to reach the main draw at the Montreal Masters, marking his first appearance in Masters qualifying since 2018.
The 27-year-old Greek is scheduled to face Canadian Keegan Rice, ranked No. 831 in the world, on Friday night.
A win would put Tsitsipas into the main draw, where his first-round opponent would come from a group including Hubert Hurkacz, Adrian Mannarino, Jenson Brooksby, Marin Cilic, Miomir Kecmanovic, Fabian Marozsan, Roman Andres Burruchaga, Thiago Tirante, Martin Landaluze, James Duckworth, Yannick Hanfmann, Gabriel Diallo, Daniel Altmaier, or Luca Van Assche.
Tsitsipas faces the same qualifying process at the Cincinnati tournament, which runs from August 13 to 23.
