Top seed Felix Auger-Aliassime crashed out of the Grand Prix Hassan II after he was beaten 6-4 2-6 7-6 (9-7) by world number 65 Alex Molcan.
Making his debut in Marrakech, Auger-Aliassime arrived off the back of an impressive start to 2022.
Indeed, the world number nine had already triumphed in Rotterdam and been runner-up to Andrey Rublev in Marseille.
But he came unstuck at the hands of the player ranked 56 places lower, with Molcan securing his first career win over a top-10 player.
The Slovakian crucially broke in game nine on the way to taking the opening set. Auger-Aliassime, who hit 10 double faults during the contest, responded by dominating the second, while the players exchanged breaks in a decider that went to a tie-break.
The top seed forced match point at 7-6 up, but Molcan held on by reeling off the next three to secure a dramatic victory.
David Goffin, meanwhile, claimed his 300th tour-level win as he came from behind to defeat three-time champion Pablo Andujar.
Andujar had seen off second seed Dan Evans in the first round but, despite making a fast start against Goffin, it was the Belgian who triumphed 5-7 7-6 (7-4) 6-3.
Federico Coria overcame Mirza Basic in straight sets, while Roberto Carballes Baena defeated Portugal's Joao Sousa 6-2 7-6 (7-4) and Richard Gasquet saw off Pavel Kotov.
Swiatek soars into Madrid Open last 16 after dropping just two games against Cirstea
Iga Swiatek stormed through to the Madrid Open last 16 following a dominant straight-sets victory over Sorana Cirstea.
The world number one dropped just two games as she inflicted a comprehensive 6-1 6-1 rout on her Romanian opponent in the Spanish capital.
Swiatek, who was runner-up to Aryna Sabalenka in last year's event, will play Sara Sorribes Tormo in the round of 16 after the Spaniard defeated two-time Australian Open champion Victoria Azarenka.
The Pole is now 26-4 for the season, in which she has already triumphed at the Qatar Open and Indian Wells Open, as she eyes the ninth WTA 1000 singles title of her career.
Data debrief
Swiatek is through to her sixth round of 16 from seven main-draw appearances in WTA 1000 events on clay (85.7 per cent) - the highest percentage rate among players with at least five such appearances since the format's introduction in 2009.
The three-time French Open champion also boasts the best WTA match win rate of any player since 2000 on clay (87 per cent). Overall, only Chris Evert (94.5 per cent), Margaret Court (89.5 per cent) and Steffi Graf (89.2 per cent) boast a higher percentage in the Open Era.
Alcaraz begins Madrid Open campaign with emphatic win
Carlos Alcaraz continued his fine record at the Madrid Open with an emphatic 6-2 6-1 victory over Alexander Shevchenko on Friday.
The two-time defending champion made it 12 straight wins at his home tournament to ensure he will face Brazilian Thiago Seyboth Wild in the last 32.
Alcaraz was playing his first match on the ATP Tour since March 28 after being unable to compete in the Monte-Carlo Masters and Barcelona Open due to an arm injury.
But he was still able to make a fine start to his clay-court season, breaking serve in the first game and racing to victory in only one hour and eight minutes.
Data Debrief
Sometimes the scoreline can be harsh on a beaten player, but on this occasion Alcaraz was clearly dominant, breaking the Kazakh seven times in the match and forcing 11 break-point opportunities while conceding only three for his opponent.
That allowed the Spaniard to claim a dominant victory despite being broken once in each set. He will now turn his attention to a clash with Seyboth Wild, who battled past Lorenzo Musetti with a 6-4 6-4 win.
Reigning champion Sabalenka pushed by Linette at Madrid Open
Aryna Sabalenka got her Madrid Open campaign started with a 6-4 3-6 6-3 win over Magda Linette on Friday.
Sabalenka could not quite hit her peak form against Linette, but the world number two nevertheless got the job done after going the distance.
The Belarusian is hunting a record-equalling third title in Madrid, where she is the reigning champion, though she has not won back-to-back matches at a tournament since winning the Australian Open.
"It's not about being confident," Sabalenka said. "It's about how much you're ready to do to get it. It's about the hard work and to be ready, be ready for the big fights. I feel like confidence is not going to help you in those big matches. It's about staying there and fighting for it."
Data Debrief
Sabalenka (70 per cent, 56-24) is now one of five active players since 2020 to hold a winning percentage of 70 per cent or higher at WTA-1000 events.
Iga Swiatek, Simona Halep, Elena Rybakina and Jessica Pegula are the other players to feature on that list.
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