Nick Kyrgios’ return to tennis ended in defeat after he was beaten in straight sets by Wu Yibing at the Stuttgart Open.
The Australian was competing in his first singles tournament since October last year and has been sidelined since then following his recovery from knee surgery.
Kyrgios has previously reached the Stuttgart semi-final stages twice and he entered this year’s competition as eighth seed.
However, after appearing to be struggling physically throughout the match, he was beaten 7-5 6-3 by Wu in the first round on Tuesday.
“The last time I played on grass was juniors back in 2017, so six years,” Wu told the ATP website.
“I was really happy to play Nick in the first round. He’s one of the best players on grass and he served well.
“He aced me [so many] times. The key for me was to stay cool, stay patient in the game and find a way. I’m happy [with that result].”
A win means Wu will face qualifier Marton Fucsovics in the second round after the Hungarian came from behind to beat Denis Shapovalov 3-6 6-3 6-4.
Jan-Lennard Struff got off to a winning start with a 6-1 6-4 win against Zhizhen Zhang to set up a meeting against fifth seed Tommy Paul, who beat Benjamin Bonzi 6-3 6-4.
Gauff sets up Swiatek semi-final meeting after downing Zheng in Rome
Coco Gauff will have the chance to down world number one Iga Swiatek after progressing to the Italian Open semi-finals with Tuesday's victory over Qinwen Zheng.
The 20-year-old breezed into the last-four draw in Rome after her straight-sets victory over Zheng, winning 7-6 (7-4) 6-1.
Gauff faced just one break point throughout the match, failing to hold her serve at 5-3 up as seven-seed Zhen battled back in the first set.
Yet Gauff eased through the tie-break and never looked back from there on, teeing up a meeting with Swiatek, who overcame Madison Keys in straight sets in her quarter-final clash.
Data Debrief: Young Gauff powers on
No player has won more matches than Gauff (61) in WTA-1000 events before turning 21, since the introduction of the format in 2009, as the American moved past Caroline Wozniacki (60) with victory here.
Wozniacki (eight) is also the only player to manage more WTA-1000 semi-final appearances before her 21th birthday, with Gauff's last-four qualification here taking her onto six – one ahead of Swiatek.
Medvedev's Italian Open title defence ended by Paul in Rome
Tommy Paul stunned defending champion Daniil Medvedev at the Italian Open on Tuesday.
Paul needed just one hour and 13 minutes to down Medvedev 6-1 6-4 to secure his first victory over a top-20 opponent and reach the quarter-finals.
Medvedev could not get going from the start, and was broken in all three of his service games in the opening set as Paul cruised into the lead.
And even after a brief resurgence at the start of the second set, Medvedev could not prevent his opponent from reeling off four successive games to pave the way for a memorable win.
Paul, who is into his first ATP Masters 1000 quarter-final on clay, will face Hubert Hurkacz for a place in the last four.
Data Debrief: Zverev brings up 10th Masters QF
While Medvedev crashed out, Alexander Zverev had no such trouble, as he claimed a straight sets win over Nuno Borges.
Zverev has now equalled Michael Chang in 10th place for the most quarter-finals made (28) in ATP Masters 1000 events since the format's introduction in 1990.
Former US Open champion Thiem misses out on Roland Garros wild-card invitation
Former US Open champion Dominic Thiem will have to fight for his place at the French Open after missing out on Tuesday's wild-card invitations.
Thiem will retire later this year due to a persistent wrist injury that has derailed his career but will likely need to battle through the qualifying rounds to appear at Roland Garros for a final time.
The two-time French Open semi-finalist is currently six places away from a main-draw spot for the upcoming major, with Richard Gasquet among the eight male players to secure a wild-card invitation.
Frenchman Gasquet will equal Feliciano Lopez's 21 tournaments at Roland Garros, the joint-most appearances of any player in the Open Era.
In the women's tournament, world number 99 Alize Cornet was also invited on a wild-card pick and will appear in a women's singles grand slam main draw for the 72nd time in her career.
That is the third most in the Open Era for major appearances, behind only Venus Williams (93) and Serena Williams (81).
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