Carlos Alcaraz, Stefanos Tsitsipas, and Holger Rune were all drawn in the top half of the National Bank Open Presented by Rogers draw Friday.

Wimbledon champion Alcaraz, who is looking for his first match win at the ATP Masters 1000 in Canada in his second appearance, could add another chapter in his budding rivalry with Rune in the quarter-finals, the same round that Tsitsipas may meet seventh seed Jannik Sinner.

Boasting a season-leading 47-4 match record, the World No. 1 Alcaraz will open against #NextGenATP star Ben Shelton or countryman Bernabe Zapata Miralles.

In the bottom half of the draw, Daniil Medvedev, who triumphed in Toronto in 2021, is seeded to meet Taylor Fritz for just the second time in the last eight. Andrey Rublev and Casper Ruud could clash in the quarters.

Gael Monfils and Christopher Eubanks will light up Toronto with their shotmaking during an exciting first-round clash, the winner earning a second-round contest against Tsitsipas. Playing in Canada for the fifth time, Tsitsipas is aiming to go one step further than his run to the 2018 final and capture his first ATP Masters 1000 crown away from Monte-Carlo.

In other opening-round action, 15th seed Hubert Hurkacz, who was a finalist last year in Canada, will open against Alexander Bublik and 11th seed Cameron Norrie drew World No. 19 Alex de Minaur.

10th seed Felix Auger-Aliassime will look for a season turnaround on home soil, where he starts against a qualifier and should he advance, he will face Lorenzo Sonego or three-time major champion Andy Murray.

Former World No. 3 Milos Raonic will make his first appearance at the Canadian Masters since 2019. Playing in just his third tournament since returning from injury in June, the 32-year-old Raonic will play ninth seed Frances Tiafoe in the opening round.

Potential second-round matches include an all-Italian battle between Sinner and Matteo Berrettini and a third tour-level meeting between Britons Norrie and Daniel Evans.