Sorana Cirstea beat world number 12 Beatriz Haddad Maia in the longest WTA Tour match of the year so far at the Dubai Tennis Championships.
Liudmila Samsonova ousted Paula Badosa on Sunday in a three-set victory that lasted three hours and 22 minutes.
That record was exceeded by eight minutes a day later – Cirstea prevailing 4-6 7-6 (9-7) 7-5 in her first-round encounter with 11th seed Haddad Maia.
Cirstea, ranked 70th in the world, fended off two match points in the second-set tie-break and took that momentum into the decider.
Haddad Maia has lost four of her five meetings with Cirstea, though had defeated the Romanian in Adelaide in January.
"I fought really hard today. I really think I gave it all," Cirstea said.
"I have nothing left. Sometimes you just have to stay in there. Bia played amazing. You know, tennis is not fair sometimes. You play for three hours and a half, and it's a difference of a point.
"I wasn't planning to break the record! But Bia's been in great form, and I knew coming in she's a great fighter.
"I think this is what tennis is about, where all the work pays off. Sometimes it doesn't matter if it's a first round or a final, the joy is the same."
Another marathon encounter was played out between Veronika Kudermetova and Anhelina Kalinina, with the latter winning 6-3 5-7 7-5 in three hours and three minutes.
Karolina Muchova will face Cirstea in the next round after she saw off Bernarda Pera 6-1 6-4, with her victory including an early contender for shot of the tournament.
Muchova was scampering back towards the baseline as she looked set to lose a thrilling rally, only for the Czech to execute a perfect tweener lob.
Australian Open champion Aryna Sabalenka received a bye to round two, where she will face Lauren Davis after the American's victory over Jil Teichmann.
Jelena Ostapenko dispatched Katarina Zavatska 6-1 6-4 with the minimum of fuss, while Victoria Azarenka overcame Anastasia Pavlyuchenkova in straight sets.
Azarenka has won 135 WTA-1000 main-draw matches in straights sets, at least three more than any other player.
Karolina Pliskova defeated Marketa Vondrousova to set up a meeting with Yulia Putintseva, with Ana Bodgan, Aliaksandra Sasnovich and Shelby Rogers also victorious.
Sinner avoids O'Connell upset at US Open
Jannik Sinner beat Australia's Christopher O'Connell in straight sets to reach the fourth round of the US Open on Saturday, avoiding a similar fate to Carlos Alcaraz and Novak Djokovic.
The men's draw at Flushing Meadows has been blown wide open by early exits for Alcaraz and Djokovic, but the top seed remains in the hunt after a composed performance.
He reached the fourth round for a fourth consecutive year with a routine 6-1 6-4 6-2 victory, setting the tone with several huge groundstrokes in the opening set.
O'Connell never looked likely to fight back as Sinner smashed 46 winners in a ruthless performance, wrapping up his win in one hour and 56 minutes.
The Australian Open champion will face either Tommy Paul or Gabriel Diallo for a place in the last eight, and he was relieved to survive an opening week full of surprises.
"Everything can happen in this sport, so I try to stay on my side of the net and I'm trying to take the tournament day by day," Sinner said in his on-court interview after the win.
"Each opponent is a very tough challenge and [I am] also enjoying every moment on the court. There have been already a couple of upsets, so let's see what's coming.
"But I'm very happy to still be here and hopefully I can play as many matches as possible. But as I said, we go day by day and then we'll see how it goes."
Data Debrief: Sinner heating up
Sinner lost his first set of the tournament to Mackenzie McDonald but has been largely untouchable since then.
He has only lost 18 games across his last nine sets of tennis, an average of two per set.
The Italian's winning streak now stands at seven straight matches, meanwhile, following his triumphant Cincinnati Open run.
US Open: Sabalenka overcomes first set scare to progress in late start
Aryna Sabalenka came from a set down to keep her US Open dream alive as she beat Ekaterina Alexandrova in the early hours at Flushing Meadows.
Sabalenka emerged on court at the Arthur Ashe Stadium at seven minutes past midnight following Novak Djokovic's shock exit from the tournament, and consecutive upsets looked to be on the cards.
However, the Belarusian responded from a disappointing opening set as she looks to avenge her defeat in the showpiece match against Coco Gauff a year ago.
The world number two set up a meeting with Belgium's Elise Mertens as she emerged a 2-6 6-1 6-2 victor in one hour and 40 minutes in New York.
"I don't know what I did, I was just trying to stay low, put as many balls as I can back on that side," Sabalenka said.
"She played incredible tennis in the first set. It was really tough to change it."
"I'm really happy I was able to turn around this match and get this really difficult win. Thanks so much for staying that late."
Data Debrief: Sabalenka survives late, late show
Sabalenka's encounter with Alexandrova was the latest starting match at the US Open, beating Gabriela Sabatini and Beverley Bowes' meeting in 1987 that started at midnight.
The Belarusian, however, will be hoping for a much improved performance in the next round, having produced 27 unforced errors throughout the contest and serving four double faults.
US Open: Djokovic played 'worst tennis ever' in Popyrin loss
Defending US Open champion Novak Djokovic suffered a shock exit at Flushing Meadows as he lost in four sets to Alexei Popyrin.
Djokovic arrived at the tournament with confidence following his gold medal triumph at the Paris Olympics, and was tipped to lift a record-extending 25th grand slam title.
However, the Serbian's hopes of a fifth success in New York were dashed as he followed fellow favourite Carlos Alcaraz out of the competition in the third round.
Popyrin emerged victorious in three hours and 18 minutes, prevailing 6-4 6-4 2-6 6-4 to confirm Djokovic's earliest exit from the tournament in 18 years.
"I have played some of the worst tennis I have ever played," Djokovic said.
"Honestly, the way I felt and the way I played from the beginning of this tournament, third round is a success."
"I tried my best, I didn't have any physical issues. I just felt out of gas, and you could see that. From the first match, I just didn't find myself on this court.
"Life moves on. I'll try to recalibrate and look forward to what's next."
Data Debrief: Another one bites the dust
Djokovic was far from his clinical best, serving a career-high 14 double faults in a grand slam match and committing 49 unforced errors.
The Serbian will also end the year without winning a grand slam title, the first time he has done so since 2017.
But the day belonged to Popyrin, saving 12 of the 16 break points he faced against the world number two, finding particular success with his forehand as 31 of his 49 winners came from that shot.
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