Main draw action begins on Monday in Canada, with the women playing in Montreal this year, and the men in Toronto. With the US Open just three weeks away, who will gain momentum going into the last Major of the year?
Nine of the top 10 male and female singles players in the world are present in both cities, with only the Wimbledon runners-up absent (Djokovic, Jabeur). Reigning French and US Open champion Iga Swiatek is the top seed in the WTA singles draw, while newly-crowned Wimbledon champion Carlos Alcaraz headlines the ATP singles draw.
Monday’s schedule in Montreal features four Major singles champions, and three other Major singles finalists. The highest profile WTA match of the day is an all-American battle between Madison Keys and Venus Williams.
Men’s first round action on Monday is highlighted by two tour veterans coming back from long injury layoffs, Milos Raonic and Gael Monfils, respectively facing two top Americans, Frances Tiafoe and Christopher Eubanks.
Throughout the tournament, this preview will analyze the day’s most prominent match in both Montreal and Toronto, while highlighting the other notable matches on the schedule in each city. Monday’s play begins at 11:00am local time in both cities.
Venus Williams (WC) vs. Madison Keys (13) – Not Before 7:00pm on Court Central in Montreal
Venus has only played 10 matches across the past two seasons, with a record of 2-8. The 43-year-old has struggled to remain healthy the last few years, yet six weeks ago on the grass of Birmingham, she reminded us of what she’s still capable of. Despite suffering a knee injury in the first set, she went on to defeat Camila Giorgi in an over three-hour affair, and then pushed Jelena Ostapenko to three sets in the next round.
Keys is 27-10 this season, and won a grass court title at Eastbourne. She went on to reach the quarterfinals of Wimbledon, and has now won 11 of her last 13 matches. Madison has an odd history in Canada: she was a finalist in 2016, but is 1-4 outside of that run.
Madison is 3-2 against Venus, and took their most recent meeting, four years ago in Cincinnati. They also played seven years ago in Canada, with Keys winning that contest as well. And based on recent form, Madison should comfortably prevail, though any chance to see Venus Williams on a tennis court feels special at this point of her career.
Milos Raonic (WC) vs. Frances Tiafoe (9) – Not Before 7:00pm on Center Court in Toronto
This is only Raonic’s third tournament since July of 2021, after missing nearly a full two years due to injury. He went 2-2 on grass this season, and will now play for his first hard court victory since Miami 2021. Milos is appearing in his country’s biggest event for the first time in four years, and while he reached a final in 2013, he’s just 12-10 here lifetime.
Tiafoe is 32-12 in 2023, with two ATP titles (Houston, Stuttgart). And a year ago, he made a huge breakthrough in his career, with a thrilling run to the US Open semifinals. But it’s been a disappointing summer thus far for Frances: he got thumped in the third round of Wimbledon by Grigor Dimitrov, and lost to Dan Evans this past week in Washington, in an event not far from where Tiafoe grew up.
Their only prior encounter occurred at this same tournament five years ago, with Tiafoe prevailing in three sets. Despite Milos having the home court advantage, Frances is a considerable favorite to prevail again on Monday night in Toronto.
Other Notable Matches on Monday:
Jennifer Brady (PR) vs. Jelena Ostapenko – Just a few days ago in Washington, Brady, a 2021 Australian Open finalist, played her first match in nearly two years due to a knee injury. Ostapenko is 27-14 on the year, having won a grass court title in Birmingham. They have split four previous matchups.
Gael Monfils (PR) vs. Christopher Eubanks – After retiring from this same event a year ago with a knee injury, Monfils missed seven months of action. He’s just 3-6 this season at tour level, though two of those victories came this past week in Washington. Meanwhile, 27-year-old Eubanks is having a career-year, winning his first ATP title in Mallorca, and advancing to the Wimbledon quarterfinals, where he was just a set away from defeating Daniil Medvedev.
Monday’s full Order of Play for the WTA is here, and the ATP is here.
