The Canadian Open surprises continued on Wednesday as Daniil Medvedev became the latest big name to suffer an early exit, losing in straight sets to Botic van de Zandschulp.

Earlier in the day, Medvedev had seen both Alexander Zverev and Taylor Fritz crash out of the Montreal event, losing to Tallon Griekspoor and Thiago Tirante respectively, and the fourth seed suffered the same fate.

He was beaten 6-3 7-6 (7-5) in one hour and 39 minutes, having threatened to force a decider when he fought back to put Van de Zandschulp under pressure in the second set.

Medvedev found himself 3-0 down in the second and hurtling towards a comprehensive defeat, only to win the next four games to put himself back on top.

However, Van de Zandschulp broke back immediately to get the contest back on serve, which is how it stayed until the tie-break.

Medvedev made several uncharacteristic errors when it mattered most, and Van de Zandschulp caught the Russian out at the net with a wonderful passing shot on match point. 

"I managed to mix it up quite well," Van de Zandschulp said afterwards. "I had played him a couple of times already, and it has always been tough. 

"I never beat him before, but today I mixed it up very well… I had to change it up and go out of my comfort zone, and I think I did it quite well."

What. A. Finish. @Boticvdz claims his first Top 10 scalp of the season, getting the better of [4] Medvedev 6-3, 7-6(5).@OBNmontreal | #NBO26pic.twitter.com/aH7x52AyUk

— ATP Tour (@atptour) August 6, 2026

Two Americans, Tommy Paul and Learner Tien, will face off in the round of 32 after earning victories over French opponents. 

Seventeenth seed Paul overcame Valentin Royer 6-4 7-6 (7-5), while 12th seed Tien beat Gael Monfils 6-3 0-6 6-3.

But world number four Felix Auger-Aliassime had to withdraw from his home event ahead of his scheduled meeting with Titouan Droguet.

The Canadian was replaced in the draw by Portugal's Jaime Faria, who promptly lost in straight sets, after suffering a pain in his back that left him struggling to serve.

Men's draw wide open after more Montreal shocks

In Zverev, Auger-Aliassime, Medvedev and Fritz, four of the initial top six seeds for the Canadian Open have already been eliminated or withdrawn through injury.

And, when the absences of Jannik Sinner, Carlos Alcaraz and Novak Djokovic are added into the mix, the Montreal draw appears wide open. World number seven Alex de Minaur is now the highest-ranked player remaining.

Medvedev's defeat continued the theme of upsets and kept his difficult year going. The Russian has two titles this season, but they came way back in January (Brisbane, ATP 250) and February (Dubai, ATP 500).

He was aiming for his 100th ATP Masters 1000 win on hard courts, a figure only Djokovic, Monfils, Zverev, Grigor Dimitrov and Stan Wawrinka have achieved, but that century will have to wait – at least until the Cincinnati Open.