The former world No. 1 squandered a break advantage in the deciding set and bowed out to rising Chinese star at the Terra Wortmann Open.

Zhang Zhizhen clinched a dramatic victory over Daniil Medvedev, 6-3, 2-6, 7-6 (5) to reach the quarterfinals at the Terra Wortmann Open quarterfinals.

A former world No. 1, Medvedev had rallied from a set down to find himself up a break in the third, but ultimately lost five of the final six points as Zhang advanced in two hours and five minutes over the No. 3 seed on OWL Arena, booking a last-eight clash with American Christopher Eubanks.

After edging through his first grass-court match of the season against Nuno Borges, Medvedev found himself up against Zhang, a former academy training mate, for the first time in almost a decade. Though the pair never contested in an ATP main draw, the two did face off on clay in 2016, where Medvedev won a third-set tiebreaker to qualify for a 250 tournament in Nice.

While Zhang was largely absent from the ATP landscape for the next four years, he began to make in-roads in 2022 when he finished just outside the Top 100 thanks to four Challenger finals and one title in Cordenons. He made his first Masters 1000 quarterfinal the following year at the Mutua Madrid Open and repeated the result last month at the Internazionali BNL d’Italia.

While his best results have come on clay, grass remains relatively uncharted territory for the world No. 42, who earned his career-high ranking for the first time in May. Starting the 2024 grass swing with an 8-9 record, he earned his first grass win in over a year against Sebastian Ofner earlier this week to book the meeting with Medvedev.

The former world No. 1 enjoyed a strong start to his 2024 season, reaching a third Australian Open final and finishing runner-up at the BNP Paribas Open but saw his results somewhat recede on his least favorite surface, exiting before the quarterfinals of Roland Garros for the seventh time in eight appearances.

Back on grass, the 2023 Wimbledon semifinalist looked to make up ground gained by the likes of world No. 1 Jannik Sinner and No. 2 Carlos Alcaraz, who have split the first two major tournaments this season.

But Zhang proved a tough out as the match got underway, and Medvedev gave into early frustrations to net a backhand and fall behind 2-5. Zhang gamely served out the opening set but Medvedev threatened to run away with the contest after leveling at one set apiece, breaking for 2-0 in the decider.

Zhang broke back and held on through a dramatic tenth game that saw him two points from defeat, forcing a final-set tiebreaker.

Medvedev made the first move as the Sudden Death got underway, sending Zhang tumbling with a strong passing shot to score the first mini-break as the match hit the two-hour mark. Trailing 2-4 at the change of ends, Zhang served and volleyed his way to match point, winning four of the next five points. One last miss from Medvedev and Zhang had clinched his second career Top 5 victory.