Fresh off a 19th consecutive win at Masters 1000 level, Jannik Sinner faces Felix Auger-Aliassime in Friday's quarter-final in the Principality for a place in Saturday's semis.
Aware of the possibility of ending the week as world No. 1, three more wins at the Monte-Carlo Masters will guarantee the Italian supplants Carlos Alcaraz, but he must be wary ahead of facing the hard-hitting Canadian.
Match preview
Sinner was expected to get the better of Tomas Machac in two sets, and a smooth opener suggested another comfortable afternoon was in the offing.
However, the Czech player raced into a 5-2 lead in the second before fighting off the Italian player's resurgence to take the second-set tiebreak, ending the second seed's 37-set streak at ATP 1000 tournaments.
Tallon Griekspoor was the last man to take a set off Sinner at this level in Shanghai, where the four-time Grand Slam champion was forced to retire after severe cramping, only for the world No. 2 to take the titles in Paris, Indian Wells and Miami without dropping a set.
While that run is now over, the 24-year-old extended his winning run at this level to 19 with a 6-1, 6-7(3), 6-3 success, emulating Pete Sampras, Roger Federer, Rafael Nadal and Novak Djokovic to become the fifth player to achieve the feat since 1990.
Fourteen of those victories have been in 2026, and the latest triumph saw him join Sampras, Federer and Djokovic in starting the season with that many wins at Masters 1000s.
Now seeking a 15th, Sinner, who admitted to suffering physically during the second set against Machac, aims to avoid a shock exit to a player against whom he has won the last four meetings.
For Auger-Aliassime, this year's performance in the Principality counts as a win regardless of Friday's outcome against the Italian superstar.
The Canadian player had never progressed beyond the second round at this event in six previous main-draw appearances, only to break new ground by reaching the last eight this time.
Having reached the Shanghai Masters quarters last year, Auger-Aliassime had been involved in the final eight of all but one of the nine Masters 1000 events, with Monte-Carlo the only one to elude him.
However, he benefitted from Casper Ruud's unfortunate calf issue while ahead 7-5, 2-2 to advance from Thursday's third-round match, adding the victory to his second-round win over Marin Cilic.
Both wins have improved his previous 2-6 record in the Principality, where he now has four victories heading into Friday's contest with Sinner, against whom he aims to secure his first win in four years to reach the final four.
Tournament so far
Felix Auger-Aliassime:
First round: Bye
Second round: vs. Marin Cilic 7-6(4) 6-3
Third round: vs. Casper Ruud 7-5 2-2 ret.
Jannik Sinner:
First round: Bye
Second round: vs. Ugo Humbert 6-3 6-0
Third round: vs. Tomas Machac 6-1 6-7(3) 6-3
Head To Head
ATP Finals (2025) - Round Robin: Sinner 7-5 6-1
Paris Masters (2025) - Final: Sinner 6-4 7-6(4)
US Open (2025) - Semi-final: Sinner 6-1 3-6 6-3 6-4
Cincinnati Masters (2025) - Quarter-final: Sinner 6-0 6-2
Madrid Masters (2024) - Quarter-final: Auger-Aliassime walkover
Cincinnati Masters (2022) - Round of 16: Auger-Aliassime 2-6 7-6(1) 6-1
Madrid Masters (2022) - Round of 16: Auger-Aliassime 6-1 6-2
While Auger-Aliassime raced into a 2-0 lead in their head-to-head, Sinner has since reeled off four wins in a row to lead 4-2 ahead of their seventh meeting on the ATP Tour.
Friday would mark the pair's second meeting on clay, with the Canadian dropping just three games when they met four years ago in Madrid.
Much has changed for Sinner since, with the then-world No. 10 now among the leading players on the tour.
Sinner and Auger-Aliassime have split four meetings at Masters 1000 level, though the world No. 7 leads on clay 1-0.
We say: Sinner to win in two sets
While Auger-Aliassime will hope to take advantage of any lingering physical issues troubling Sinner, the Italian player is still expected to reach the semis.
The second seed has dropped just one of 10 sets in their past four meetings, and he ought to defeat the Canadian No. 1 in two to extend his winning run at Masters 1000 events.