Two players from the Netherlands eliminated a pair of the sport’s biggest names within hours of each other at the Canadian Open on Wednesday, and when a third top-ten seed fell in the same session, the tournament’s projected hierarchy collapsed almost entirely. The double Dutch shock, delivered against world number three Alexander Zverev and fourth seed Daniil Medvedev, arrived three weeks before the US Open and left the Montreal draw looking nothing like the one that had been seeded days earlier.
Three Upsets That Reshaped the Draw in a Single Session
The day’s most striking result came when Tallon Griekspoor, ranked 69th in the world, dismissed Zverev 6-7(3), 6-2, 6-4 in the second round, per Reuters. Griekspoor had arrived in Canada with just one win from his previous eight tour-level matches, a stretch bleak enough that he admitted afterward he had considered stepping away.
“I’ve been very close to throwing in the towel a couple of times,” Griekspoor said. The win, his third in as many career meetings with Zverev, carried particular weight given the German’s status as reigning French Open champion. “I felt like it was just a matter of time,” Griekspoor added. “This one is special, especially against a player like Sascha.”
It was Zverev’s first competitive match since losing to Jannik Sinner in the Wimbledon final the previous month. The return lasted one round.
Medvedev’s exit was equally abrupt. Botic van de Zandschulp, the second Dutchman to make headlines Wednesday, defeated the 2021 US Open champion 6-3, 7-6(5) in what was their first meeting to go van de Zandschulp’s way.
“I played him a couple of times, and it has always been tough,” van de Zandschulp said. “I never beat him before, but today… I had to change it up, go out of my comfort zone and I think I did it well.”
The third blow fell on Taylor Fritz. The American seventh seed, who had taken the Washington Open title the previous week for his biggest trophy in nearly four years, lost 7-5, 6-3 to Argentine Thiago Agustin Tirante. Three top-ten seeds, gone in an afternoon.
Crypto Betting Markets Repriced the Field Almost in Real Time
Dalius Mikalauskas, a crypto and sports betting analyst with more than two decades of experience tracking outright markets, observed that the speed of repricing after the trio of exits was notable even by the volatile standards of ATP 1000 events. Once Zverev, Medvedev, and Fritz fell within the same session, the Canadian Open outright market looked almost unrecognizable within hours, with the remaining contenders suddenly carrying odds that reflected a field far more open than anyone had anticipated at the draw.
Mikalauskas noted that bitcoin sports betting sites saw a surge of activity as bettors scrambled to reassess who could realistically run through such a depleted draw, with crypto-based books adjusting outright prices on the survivors nearly in real time.
“Three top-ten exits in one session is exactly the kind of volatility that forces a full recalibration of the outright market. When the draw thins out that fast, nobody has a clean read on who holds the best path to the final, and you see the numbers move accordingly.”
The combination of the Dutch results and Fritz’s loss to Tirante produced precisely that kind of moment, where the field opened and the market had to catch up quickly.
A Bracket Already Stripped of Its Biggest Names
The Wednesday exits compounded damage that had already been building before Griekspoor and van de Zandschulp reached the court. Sixth seed Flavio Cobolli and tenth seed Andrey Rublev had both lost their opening matches. Fifth seed Felix Auger-Aliassime withdrew with a back injury before his campaign began.
Those departures, stacked onto Wednesday’s results, left just four of the original top-ten seeds alive in the draw. The field had already been shaped by two high-profile absences before a ball was struck. World number one Jannik Sinner chose not to enter the tournament, and Novak Djokovic, 24 times a Grand Slam champion, also skipped Montreal. World number two Carlos Alcaraz was ruled out by a wrist injury, an absence extending to both the Canadian Open and the Cincinnati Open that follows.
The result is a draw that has lost most of the players a neutral observer would have expected to contest the title, with the survivors facing a bracket that offers far more opportunity than resistance.
What the Montreal Losses Mean With the US Open Approaching
The timing compounds the stakes for the three biggest losers. Zverev was returning to competition after a month away following Wimbledon, and the loss to Griekspoor leaves him without a match win heading into the hardcourt swing. Montreal was meant to sharpen his preparation. It did not.
Medvedev, a former champion at Flushing Meadows, has similarly lost the chance to build form and confidence on the surface where the year’s final major will be played. Fritz, who arrived in Montreal carrying genuine momentum after Washington, watched that momentum stop in a single afternoon against Tirante.
Alcaraz, meanwhile, remains an uncertain presence over the coming weeks. His wrist injury has already cost him both North American Masters events, and how close to full fitness he arrives in New York remains an open question.
The US Open begins on August 30. Which contenders step onto the hardcourts there with form, fitness, and a sense of momentum is, at this moment, far from settled.
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