Mandatory Credit: Dan Hamilton-Imagn Images

Day of Surprises! Daniel Medvedev, Lorenzo Mussetti, Stefanos Tsitsipas Crash Out of the National Bank Open 2025

A shocking day in Toronto and Montreal as top seeds on both tours fall early, shaking up the draws.

Mandatory Credit: Dan Hamilton-Imagn Images

The National Bank Open in Toronto delivered a thunderous shake-up on Thursday, with three top ATP seeds, Daniil Medvedev, Lorenzo Musetti, and Stefanos Tsitsipas, crashing out in a string of upsets that turned the men’s draw on its head. But the surprises didn’t stop there.

Over on the WTA side in Montreal, big names like Mirra Andreeva, Elise Mertens, and Emma Navarro also fell early, making it a day of double trouble for the tournament’s seeded elite. While unpredictability is part of the sport, the magnitude and manner of these losses have raised eyebrows across the tennis world.

Pop off, Alexei 🎉

Alexei Popyrin fights back after dropping the first set and takes down Daniil Medvedev in three sets 🎾

The championship defence keeps rolling 🔥 @nationalbank pic.twitter.com/Muh5emdbSG
— National Bank Open (@NBOtoronto) August 1, 2025

Alexie Popyrin, Alex Michelsen, and Christopher O’Connell Deliver Major Blows In Toronto

Medvedev, seeded 10th, fell to defending champion and 18th seed Alexei Popyrin in three tight sets. Though it was their sixth career meeting, this win marked just Popyrin’s second over the Russian and his fourth Top 20 win this season. The Aussie, who also reached the Monte Carlo quarterfinals earlier this year, will next face fifth seed Holger Rune.

Musetti’s exit came at the hands of rising American Alex Michelsen. While struggling with nearly 50 unforced errors, the 20-year-old Michelsen held his nerve and capitalized on his seventh match point to close out a 3-6, 7-6(4), 6-4 win. This is his second career victory over a top-10 opponent and his first time reaching the Round of 16 at a Masters 1000.

20yo Alex Michelsen defeats #10 Lorenzo Musetti 3-6, 7-6(4), 6-4 to reach the last 16 of a Masters 1000 for the first time in his career.

From a break down in the 3rd set.

Quite a battle!

2nd career top 10 win as well! pic.twitter.com/7ZBAU8WXYi
— José Morgado (@josemorgado) July 31, 2025

Meanwhile, Tsitsipas’ early exit was perhaps the most stunning of all. The 23rd-seed Greek lost to unseeded Christopher O’Connell in three sets when he parted ways with Goran Ivanisevic (former Novak Djokovic’s coach). The fallout from that short-lived coaching stint was public, with Ivanisevic calling Tsitsipas “the most unprepared player I’ve ever seen.” Apostolos Tsitsipas, his father, is back in the coaching box, but the results haven’t bounced back yet.

Upset complete 👍

Christopher O'Connell takes out Stefanos Tsitsipas 6-4 4-6 6-2 to book his place in the last 32 🙌#NBO25 pic.twitter.com/EBxQaHPnCo
— Tennis TV (@TennisTV) July 31, 2025

Mirra Andreeva, Elise Mertens, Emma Navarro Face Upsets; Coco Gauff Survives In Montreal

The women’s draw saw its own share of shakeups, with several seeded players bowing out earlier than expected. Fourth seed Andreeva was stunned in straight sets by American McCartney Kessler, who now moves on to face Marta Kostyuk, herself a giant slayer after rallying past 15th seed Daria Kasatkina in three sets.

Kessler d. Mirra Andreeva 7-6(5) 6-4 in Montreal

McCartney gets one of the biggest wins of her career.

This is her 2nd top 5 win of the season.

When she’s on, she’s an incredible ball-striker.

✅2nd WTA 1000 R16

Challenging & beating some of the best in the world.

🇺🇸❤️ pic.twitter.com/QhF9k6kLr6
— The Tennis Letter (@TheTennisLetter) July 31, 2025

Meanwhile, 19th seed Mertens couldn’t withstand the comeback charge of Anna Kalinskaya, who recovered from a lopsided opening set to win in a second-set tiebreak. Also, Ukraine’s Dayana Yastremska added to the chaos, ousting eighth seed Navarro 7-5, 6-4 in a night-session upset.

Can never count out Coco 😤🦅 @CocoGauff roars back in Montreal to reach the last 16!#OBN25 pic.twitter.com/E1DRs8XMsg
— Tennis Channel (@TennisChannel) July 31, 2025

Gauff was the lone top seed to survive the carnage. Although battling 14 double faults, just days after recording 23 in a win over Danielle Collins, the American fought back from a set and break down to defeat Veronika Kudermetova 4-6, 7-5, 6-2.

Mandatory Image Credit: Dan Hamilton-Imagn Images

Coco Gauff

Daniil Medvedev

Lorenzo Musetti

Mirra Andreeva

Stefanos Tsitsipas

Rudra Dubey

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I’m an academic turned sports writer from Raipur, India, specializing in the NFL, MMA, and tennis at The Playoffs. I previously wrote for Sportskeeda and hold a B.A. and M.A. in History. My journey into sports media began far from the field, rooted in the arts and sciences. Funny enough, I didn’t grow up a sports fan; I used to see it all as just noise. But a fateful writing job introduced me to the world of sports, and what began as a gig quickly became a passion. I understood those voices aren’t noise; they’re emotions of true sports fans, and now I am one of them, writing with the same energy I once questioned.