Andy Murray was beaten by fellow veteran Fabio Fognini to suffer a disappointing first-round exit at the Italian Open.
Murray, fresh from claiming success at an ATP Challenger event in Aix-en-Provence on Sunday, had hoped to extend his five-match winning streak but instead saw his time in Rome end early to the 35-year-old home favourite.
A 6-4 4-6 6-4 defeat to the world number 130 halts the momentum of the Briton, who will now turn his attention to the French Open later this month.
Three-time grand slam winner Murray made the worst possible start in Italy with Fognini able to break him in his opening service game.
While the Scot did force a number of opportunities to break back at 3-2, he failed to seize the moment and his frustration boiled over later in the set with a debate occurring with umpire Mohamed Lahyani over a tight line call that saw Fognini go 5-3 up.
Fognini went on to clinch a 69-minute opener but quickly found himself 4-0 down in the second with Murray hitting his straps, albeit helped by a string of double-faults from his opponent.
A second-set wobble saw the veterans exchange breaks before Murray did force a decider with the encounter by that point edging past the two-hour mark.
Despite Fognini seemingly struggling physically during the second set, he found a new lease of life and took the initiative with an early break in the third.
Murray tried to keep pace with the Italian, who was mixing an array of baseline winners with unforced errors but a concern for the two-time Wimbledon winner occurred when he held his back during the seventh game of the third.
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It was not enough to stop the new world number 42 from continuing, and yet there would be no big fightback on this occasion with Fognini earning a fifth victory in nine meetings thanks to an ace after two hours and 55 minutes.
This latest first-round exit at an ATP 1000 event on clay, after similar losses in Madrid and Monto-Carlo, will give Murray around 10 days preparation before Roland Garros begins on May 22 where he is now unlikely to be seeded.
Elsewhere, fellow Briton Kyle Edmund was also knocked out in the Italian Open first round after he suffered a 6-1 6-3 defeat to Alexandre Muller.
World number 473 Edmund saw his struggles continue against a French player who broke into the top 100 last month.
Muller managed to wrap up the first set in 23 minutes in Rome and, while Edmund was able to push his opponent more in the second, the former Australian Open semi-finalist was consigned to a third consecutive loss.
Djokovic relieved to pass Michelsen test in Shanghai
Novak Djokovic was relieved to edge past Alex Michelsen at the Shanghai Masters as his quest for a 100th career title got up and running.
Djokovic, who has won the tournament in China on four occasions, needed almost two hours to overcome his American opponent on Saturday, eventually doing so 7-6 (7-3) 7-6 (11-9).
The Serbian's slow start was punished by Michelsen, who raced into a 4-1 lead in the opening set, with Djokovic managing just three points from the first three games.
But the 24-time grand slam champion rallied to take the first set to win his 11th tie-break from the 15 he has played this season.
"It was the first match against Alex and I also hadn't played in a while, so it took me a little time to get the rust off," said Djokovic after his first match sine the US Open.
“He started off terrifically; big serves and an aggressive style of tennis, he's not afraid to step it up and take it to his opponent."
Djokovic then led 4-1 in the second, only to allow Michelsen back into the contest, but the Serbian held his nerve in the decisive tie-break, saving two set points to advance.
The 37-year-old has now won 35 of the 40 matches he has contested at the ATP Masters 1000 event in Shanghai - more than any other player.
Djokovic is also the only player in history (since 1990) to win all nine ATP Masters 1000 titles, a feat he has achieved twice on his way to a record 40 titles at this level.
He is yet to reach a final in the series this year, with the Serbian acknowledging the difficulties he faced against his American opponent.
"I was 4-1 up, 15/40, and he hit the net-cord that went over. It could easily have been 6-1 for me in the second,” Djokovic said.
"But at this level, things can change very quickly.
"It was a very close encounter and I thought a high level of tennis in both sets. I'm just glad to keep calm when it mattered in the second-set tie-break.
"I'm glad to really be challenged by a young player, and I'm looking forward to the next one."
Up next for Djokovic is either Italian Flavio Cobolli or wildcard Stan Wawrinka.
Djokovic recovers from slow start to move past Michelsen on Shanghai return
Novak Djokovic marked his Shanghai Masters return with a hard-fought straight-sets win over Alex Michelsen.
The four-time champion, who is appearing in this event for the first time since 2019, required two tie-breaks before prevailing 7-6 (7-3) 7-6 (11-9) in just under two hours.
Djokovic, still donning a protective sleeve over his right knee, made a slow start in only his second match since losing to Alexei Popyrin in the US Open third round, winning just four points in the first three games as he fell 4-1 behind.
However, the 24-time major winner broke back in the seventh game before dominating the tie-break for first blood.
Roles were reversed in the second set as Michelsen cancelled out an earlier break in game seven.
However, the American squandered two set points to level and was eventually punished by Djokovic, who will play either 28th seed Flavio Cobolli or three-time major winner Stan Wawrinka in the next round.
Data Debrief: Djokovic continues American dominance
Djokovic was given an early scare, but his experience eventually showed as he came through.
Including team events, the Serb has now won his last 33 ATP-level matches against American opponents, with his last such defeat coming against Sam Querrey at Wimbledon in 2016.
The 24-time major winner also demonstrated his determination when the pressure intensified, and he has now come through 12 of his 16 tie-breaks played this season.
Gauff fights back to beat Badosa in China Open semi-finals
Coco Gauff recovered from a set and a break down to reach the China Open final with a 4-6 6-4 6-2 victory over Paula Badosa on Saturday.
Having given up an early break in the opener, Gauff got one of her own by converting her eighth break point in a mammoth eighth game featuring 10 deuces, only for Badosa to hit back immediately to go a set up.
Gauff lost serve immediately in the second set to go on the back foot, only to level the match with back-to-back breaks, the second of them to love.
The decider began with a series of breaks, Gauff taking two of them as the momentum swung her way, then she protected her lead all the way to reach her first final since winning January's Auckland Open.
The 20-year-old is the youngest player to reach the women's singles final at the China Open since Caroline Wozniacki in 2010.
She has fought from a set down to win in each of her last three matches, the first time she has done so in her career. She is the first player to do so in WTA-1000 events since Iga Swiatek at Indian Wells 2022.
Data Debrief: Gauff brings up century
Saturday's match was Gauff's 100th at WTA 1000-level events, and her 67th such victory.
Among American players, only Serena Williams (87), Venus Williams and Jessica Pegula (70) have bettered her 67 wins through their first 100 matches at such events.
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