Top seed Jessica Pegula bowed out of the Libema Open following a three-set defeat by Aleksandra Krunic in s'Hertogenbosch.
The world number five was ousted 7-6 (7-3) 6-7 (3-7) 6-4 by the 2018 winner of this event, who claimed the fifth top-10 victory of her career and advanced to the quarter-finals.
Now ranked 400th in the world, Krunic recovered from an earlier break in the opening set to force a tie-break, in which she won five straight points to draw first blood.
The Serbian also cancelled out a break before heading into another tie-break, but Pegula reeled off five points on the spin this time to level.
The American was appearing in her first tournament since April, having missed the European clay-court season with a rib injury.
However, she saw two break-point opportunities go begging in the opening game of the deciding set, and Krunic crucially broke in game three before holding out for an impressive victory.
Later on, Alex de Minaur booked his place in the quarter-finals of the competition after a straight-sets victory over Zizou Bergs.
The world number nine had to work for his victory over the Belgian, overcoming his opponent 7-5 6-4 to earn his first triumph on a grass court this year.
Bergs matched his opponent in the opening exchanges, but the Australian would eventually prevail, winning a break-point and following up without dropping a point in the final game.
De Minaur would again endure a difficult set to confirm the victory as Bergs threatened to level the encounter, but the number one seed again showed his class, finishing the contest in style.
De Minaur will face either Roberto Bautista Agut or Milos Raonic in the next round.
Data Debrief: Krunic rekindles special memories as de Minaur earns maiden grass win
Krunic will forever have an affinity with s-Hertogenbosch, where she won her only career WTA title six years ago.
And the 31-year-old claimed an impressive scalp here to reach her first WTA quarter-final since 2022 - and first on grass since that 2018 triumph.
De Minaur impressed once again, winning 86 per cent of his first serve points against the Belgian.
Their meeting in s-Hertogenbosch was the first between the pair, with De Minaur able to overcome his quarter-final defeat to Alexander Zverev at the French Open.
Defending champion Alcaraz stunned by Draper at Queen's
Jack Draper earned the biggest win of his career, upsetting defending Queen's Club champion Carlos Alcaraz in straight sets on Thursday.
He followed up his first ATP tour title in Stuttgart with a statement win, beating the French Open winner 7-6 (7-3) 6-3.
He did not lose a service game in a dominant display, though Alcaraz did not lose one in the opening set either, forcing a tie-break before his sloppiness allowed Draper to edge in front.
Despite Alcaraz bringing his usual threat, Draper got a vital break to make it 4-2 in the second set, rallying to see out a third victory against top-10 opposition.
Draper will play fifth seed Tommy Paul in the quarter-finals.
Data Debrief: Alcaraz sees streak snapped
Alcaraz had won eight consecutive matches coming into this meeting thanks to his victory at Roland Garros, but could not find a way past Draper.
The British number one impressed, especially in his serves, winning 76 per cent of his service points during the one hour 39 minute contest.
Sinner rallies to reach Halle Open quarter-finals
Jannik Sinner survived a scare to reach the quarter-finals of the Halle Open after beating Fabian Marozsan on Thursday.
After having to go all the way in the opening round, Sinner was once again forced into a decider but eventually came out on top 6-4 6-7 (4-7) 6-3.
It looked like it might be an easier match for Sinner after he took the first set, but Marozsan rallied in the second. The world number one was able to force a tie-break, but he could not get the better of the Hungarian's aggressive play.
Sinner did get a decisive break in the decider though, lunging to the net to get a vital point as he rushed into a 4-0 lead before holding out to reach the next round.
Data Debrief: Sinner stays in the hunt
Sinner is still chasing his first grass-court title, and looks like he will be pushed all the way to get one in Germany.
He has improved his record for the season to 35-3 after beating Marozsan in their first ATP meeting.
Murray hopeful that latest injury will not affect Wimbledon participation
Andy Murray hopes his latest injury will not rule him out of his Wimbledon swansong next month after withdrawing from the Queen's Club Championships on Wednesday.
The former world number one was forced to retire against Jordan Thompson five games into their second-round encounter due to a back injury and pain in his right leg.
It was a sad end for Murray, who has won the tournament a record five times. However, attention will immediately turn to being fit for Wimbledon, which starts on July 1.
"Let's hope it will be OK with some rest and treatment, and I'll still be able to play [at Wimbledon]," said Murray, who won two Wimbledon titles in 2013 and 2016.
The three-time grand slam champion was set to play an exhibition event in Hurlingham next week before Wimbledon but looks likely to miss the event.
Murray had said earlier this week he felt ending his illustrious career at Wimbledon or the Olympics would be a fitting stage to retire from the sport.
The Scot is set to undergo a scan on Thursday to clarify his potential participation at the tournament next month, where he is also due to play in the doubles alongside his older brother, Jamie.
"I don't know exactly what the problem is. I hadn't experienced that before," said Murray. "I have no idea how long it will take to get better and what the treatment options are."
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