Denis Shapovalov suffered defeat at the hands of China's fast-rising Wu Yibing at the Dallas Open.
Wu landed a 7-6 (7-1) 6-4 win against the Canadian Davis Cup winner and former top-10 player in their second-round contest.
World number 97 Wu, who this week became China's second player to reach the ATP top 100, has surged from 1,869th on the ranking list last April and believes he can crack the top 30 by the end of the year.
Speaking after getting the better of Shapovalov, who stands at 27th in the rankings, Wu said: "I've been playing great tennis the past few months. Hopefully I can keep playing good."
Frances Tiafoe cruised into the quarter-finals with a 6-1 6-3 win over fellow American Mackenzie McDonald.
Second seed Tiafoe was playing for the first time since his third-round elimination to Karen Khachanov at the Australian Open last month.
He faced just one break point in the entire match and needed just 59 minutes to deal with the world number 59.
J.J. Wolf, seeded sixth, will face Tiafoe in the last eight after he saw off Romania's Radu Albot in a 6-3 7-6 (7-5) win.
At the Cordoba Open, fifth seed Pedro Cachin was the biggest casualty on Wednesday as he was beaten 6-3 6-4 by Bolivian qualifier Hugo Dellien.
Seventh seed Pedro Martinez was also ousted in the first round, while Bernabe Zapata Miralles was sent packing by Tomas Barrios Vera in the last 16, losing 5-7 6-4 6-3.
Fourth seed Sebastian Baez had no such issues with Italy's Luciano Darderi, however, reaching the quarter-finals as a 6-3 6-4 winner.
Murray's likely French Open swansong ended by wonderful Wawrinka
Andy Murray bowed out in the opening round of what is likely to be his final French Open appearance, following a straight-sets defeat by Stan Wawrinka.
The Swiss ran out a commanding 6-4 6-4 6-2 victor in two hours and 19 minutes on Court Philippe-Chatrier, and could play Murray's compatriot Cameron Norrie in round two.
Murray was facing Wawrinka for a third successive match at Roland Garros, having lost out to the latter in the 2020 first round and 2017 semi-finals.
The 2015 champion stole an early advantage this time around, too, breaking in the opening game and subsequently holding to win the first set.
A single break was also enough in the second set as Wawrinka doubled his lead.
Murray has repeatedly said he is approaching the end of his career, revealing in February that he does not "plan on playing much past this summer".
However, the 2016 runner-up's chances of extending what is potentially his French Open swansong were all but ended as Wawrinka broke twice in the third set for a 4-0 lead, before the 39-year-old rounded off a dominant win.
Data Debrief
Wawrinka (39) and Murray (37) locked horns in the second-oldest match-up at Roland Garros this century, behind the 2019 first-round showdown between Ivo Karlovic (40) and Feliciano Lopez (37).
And the Swiss was not to be denied, as he became the oldest man to win a match at the French Open since compatriot Roger Federer three years ago.
'It would be an honour to play Swiatek', Osaka admits ahead of potential French Open clash
Naomi Osaka admits it would be "a very big honour" to play Iga Swiatek at the French Open, ahead of a potential second-round showdown at Roland Garros.
After a 15-month maternity break, the four-time major winner marked her return to the French capital with a hard-earned three-set victory over Lucia Bronzetti in the opening round.
That potentially sets up a meeting with Swiatek in round two, should the reigning champion overcome Leolia Jeanjean on Monday.
And Osaka is thrilled by the prospect of facing the world number one, who has lifted Coupe Suzanne Lenglen three times in the past four years.
"I'm really excited," she told reporters during her post-match press conference.
"I watched her a lot when I was pregnant. I think it's an honour to play her in the French Open, because she's won more than once here. It's a very big honour and challenge for me."
After beating Bronzetti 6-1 4-6 7-5, Osaka (75.3 per cent, 58-19) now only trails Swiatek (81.4 per cent, 70-16) among active players, for the highest winning percentage in women’s singles matches at major events.
The Japanese was made to work hard for her victory. After a dominant opening set, Osaka was taken to a decider, in which she was pegged back from 4-0 up, but eventually got over the line.
"The match really was like a rollercoaster," she added. "I felt like I was extremely focused in the first set, and maybe I let it go a bit.
"I came back in the third, but then I let it go a bit, and I just got really tight from there. I'm really glad I was able to regroup and win."
Djokovic wants to 'lower expectations' after tough start to season
Novak Djokovic admits he needs to "lower the expectations" as he prepares to defend his French Open title.
The Serbian has failed to reach a final so far in 2024, having fallen at the semi-final hurdle in Australia, Monte-Carlo, and most recently Geneva with a defeat to Tomas Machac.
Djokovic also suffered shock defeats to Alejandro Tabilo in Rome and world number 123 Luca Nardi at Indian Wells in the round of 32.
Despite questions surrounding his recent form, the 24-time Grand Slam winner is looking to draw on his vast experience to end his trophy drought this season.
"I would say that I know what I'm capable of, and particularly in the Grand Slams I normally play the best tennis, at least I aim always to play the best tennis, and I was most of my career able to do that, so that's the goal," said Djokovic on his arrival in France.
"I have been saying, you know, for quite a while that in terms of clay, I want to peak here in Paris, in Roland Garros. Last year I had an amazing year, and particularly here in Roland Garros, and hopefully, I can have a great tournament.
"My hopes and goals are always the same, but I have to lower the expectations. When I say that I mean, you know, maybe not thinking too much ahead in advance in terms of the tournament and who I might face in the later rounds, but really taking it day by day, step by step, and really building my game.
"Because that's what I have really been struggling with, not really playing in a consistently good level."
Djokovic will play French wildcard Pierre-Hugues Herbert in the first round on Tuesday.
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