Third round singles action begins on Monday.
The top seeds and defending champions, Jannik Sinner and Aryna Sabalenka, both play the 30th seeds on Monday, and neither of those opponents are an easy draw. Sinner goes up against big-serving Canadian Gabriel Diallo, while Sabalenka faces fellow Major champion Emma Raducanu, in a rematch from a tight two-setter last month at Wimbledon.
Throughout the tournament, this preview will analyze the day’s two most prominent matches, while highlighting the other notable matches on the schedule. Monday’s play gets underway at 11:00am local time.
Aryna Sabalenka (1) vs. Emma Raducanu (30) – Second on Center Court
At Wimbledon, Sabalenka narrowly took the first set from Raducanu in an extended tiebreak, before taking the second set 6-4. In that contest, Emma returned extremely well, but her attackable second serve proved costly, as she only won 41% of her second serve points. Their only other encounter occurred last year at Indian Wells, where Aryna again claimed a tight two-setter.
Raducanu has earned 24 wins during 2025, the most she’s ever earned in a season at WTA level. And at the last WTA 1000 event in the United States, this past March in Miami, Emma reached her first-ever quarterfinal at this level. This is only her second career appearance in Cincinnati, and in her opening round, she overcame Olga Danilovic in straights.
In Sabalenka’s first match since losing in the Wimbledon semifinals to Amanda Anisimova, she defeated another Major champ, Marketa Vondrousova, by a score of 7-5, 6-1. That brought Aryna’s Cincinnati record to 19-6, as she vies to advance to the semifinals or better for the fourth consecutive year. And having yet to lose a set to Raducanu, I like Sabalenka’s chances of winning again on Monday.
Jannik Sinner (1) vs. Gabriel Diallo (30) – Not Before 7:00pm on Center Court
Sinner’s first match since Wimbledon also took place on Saturday, and he easily dispatched of Daniel Galan 6-1, 6-1. Jannik is now 27-3 on the year, and has won his last 22 matches on this surface. This is only his second Masters 1000 event of the season, after missing three months of action due to his suspension for failed drug tests, and skipping Canada to rest.
Diallo is a tall and powerful 23-year-old Canadian, but he’s not your typical big-server: he owns plenty of variety, and actually grew up playing a more defensive style before further developing his offense. He’s 23-16 this year at tour level, and won his first ATP title this past June on grass in ‘s-Hertogenbosch. Then at Wimbledon, he pushed Taylor Fritz to five sets in the second round. Gabriel’s best result at Masters level came a few months ago in Madrid, where he reached the quarterfinals.
In their first career meeting, Sinner is of course the favorite, especially on a hard court. But I’m interested to see how Diallo performs against the World No.1, and if the fast-playing conditions in Cincinnati embolden his game and enable him to pose a true threat to the Italian.
Other Notable Matches on Monday:
Alex Michelsen (28) vs. Holger Rune (7) – Michelsen achieved his first Masters 1000 quarterfinal this past week in Toronto, and won his opening round match on Saturday over Corentin Moutet in three sets. Rune is a modest 25-15 on the year, and has struggled since reaching the final of Indian Wells back in March. This will be their first career meeting.
Frances Tiafoe (10) vs. Ugo Humbert (20) – Tiafoe was the runner-up here a year ago, but is a subpar 23-17 this season, and it’s been a full year since Frances has reached a quarterfinal at Masters 1000 level. He leads the head-to-head against Humbert 2-1, which includes a victory four years ago in Cincinnati.
Anna Kalinskaya (28) vs. Amanda Anisimova (5) – Anisimova recently reached a career-high ranking of No.7, coming off her first Major final at The Championships. She received a walkover in her opening round here. Last summer in Canada, Amanda defeated Anna, though that match ended after the first set when Kalinskaya retired.
Monday’s full Order of Play is here.
