Naomi Osaka crashed out of the Libema Open despite fighting to a tie-break in the final set, with Bianca Andreescu progressing to the semi-finals after a 6-4, 3-6, 7-6 (7-3) win.
Osaka's match was interrupted by rain early on with her in the lead, but Andreescu came back out in top form to take the first set.
The Japanese raced through the second though, taking a 5-0 lead before holding off Andreescu's fightback to go into a decider.
Despite an impressive comeback to force a tie-break in the final set, Osaka became sloppy, with her mistakes contributing to the Canadian's path into the semi-final, where she will face Dalma Galfi.
Elsewhere, Alex de Minaur is through to the semi-finals after a comfortable straight-sets victory over Milos Raonic.
Despite a long break due to bad weather, the Australian eased into the next round with a 7-5, 6-2 victory on Friday.
He will face either Ugo Humbert or Gijs Brouwer in the next round.
Data Debrief: Osaka not close enough, De Minaur in cruise control
Despite winning more points (98 compared to 94), and winning more games (16 to 15), Osaka could not hold her nerve in the tie-break to reach the semi-finals.
Competing as the top seed for the first time in his tour-level career, De Minaur felt no pressure as he rallied in the second set to ensure Raonic would not find a way back into the match, winning his last five games in a row on his way to victory.
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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