Stefanos Tsitsipas had to come through qualifying to earn a spot in the main draw of the Montreal Masters 1000, a situation the Greek had not faced at a tournament of this caliber since the Rome Masters in 2018. At 28, the former world No. 3 is enduring a rough stretch that has sent shockwaves through the tennis world.
From Roland-Garros to qualifying
Three years ago, Tsitsipas was contesting Roland-Garros semifinals and occupying the top 5 with clockwork consistency. The reality of 2026 tells a very different story. Having plummeted to as low as 88th in the world this season, the Greek has watched his ranking collapse under the combined weight of recurring injuries and disappointing results at major events. Since the start of 2025, he has not advanced past the second round of a Grand Slam and has reached just one Masters 1000 quarterfinal.
The 2026 season has been particularly harsh. Successive injury comebacks prevented Tsitsipas from building any momentum. Each attempt at a revival was cut short by a new physical setback or an early loss to a lower-ranked opponent. The Greek, once considered a natural heir to the Big 3, found himself looking at the top 50 from the outside.
Gstaad as a ray of light
A glimmer of hope emerged in July, when Tsitsipas captured the title in Gstaad on clay. This victory, his first in many months, propelled him roughly 30 places up the rankings to settle around world No. 51. An encouraging result, but not enough to secure direct entry into Masters 1000 main draws, where the cutoff typically sits around the top 40.
That is how Tsitsipas found himself as the top seed in Montreal qualifying. He fulfilled expectations by dispatching American Keegan Rice 6-3, 6-4, showing no visible frustration at a situation unusual for a player of his pedigree.
What has changed in his game
Tsitsipas' decline cannot be attributed to a single factor. His attacking game, built around an elegant one-handed backhand and a sharp net approach, has lost none of its inherent quality. The issue lies more in physical consistency and the ability to string together matches at the highest level. Injuries have fragmented his season, preventing him from building the momentum needed to climb in a ranking system where points are lost as quickly as they are earned.
Adapting to the power game that dominates the men's tour presents another challenge. Against big servers like Ben Shelton or Jack Draper, Tsitsipas' style, more technical than physical, struggles to find answers when the pace intensifies.
Montreal as a test of character
The Greek faces Martin Damm Jr. in the main-draw first round. A winnable match on paper, but one that takes on added significance in the current context. Every victory matters for Tsitsipas, who needs to accumulate points ahead of the American swing and the US Open. At 28, time is still on his side, but the window to reclaim a top-20 ranking narrows with each week without a meaningful result.
Tsitsipas by the numbers in 2026: lowest ranking reached, world No. 88. One title won at Gstaad. No third-round appearance at a Grand Slam since early 2025. Current ranking around No. 51. Last time qualifying at a Masters 1000, Rome 2018, eight years ago.
