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.
Medvedev pushed all the way to avoid third-round scare in Italian Open
Daniil Medvedev had to dig deep to overcome Hamad Medjedovic at the Italian Open on Monday and stay in with a chance of retaining his title.
Medvedev came out on top with a 7-6 (7-5), 2-6, 7-5 victory, but was made to work hard to avoid a third-round upset.
After enduring an up-and-down opening two sets in which he hit 10 double faults, Medvedev rallied into a lead before holding off Medjedovic’s fight-back.
The second seed remained composed to break in the match’s final game to advance after two hours and 50 minutes.
Medvedev will now play Tommy Paul in the next round on Tuesday, with the American seeing off Dominik Koepfer 6-4, 6-3.
Data Debrief: Reigning champion fights on
Medvedev has reached the last 16 at all 5 Masters 1000 events this season, with only Alexander Zverev able to match that distinction.
It was not an easy ride for him though, as Medjedovic wanted to prove a point against his first Top 10 opponent in what was his first Masters 1000 third round.
Swiatek passes Kerber test to reach Italian Open quarter-finals
Two-time Italian Open champion Iga Swiatek advanced to the quarter-finals of this year's tournament with an impressive 7-5 6-3 win over Angelique Kerber on Monday.
Three-time grand slam winner Kerber provided Swiatek with a real step up after routine victories over Bernarda Pera and Yulia Putintseva in the first two rounds on the clay in Rome.
Kerber responded to Swiatek's first break – which came in the eighth game – with one of her own, but the world number one then recaptured her composure to force a series of break points in Kerber's next two service games, finally converting at the eighth attempt to take the opener.
Kerber refused to go away, breaking straight back in the first game of the second set, but Swiatek upped her game to take the contest away from the 36-year-old.
Swiatek dropped just three further points on her own serve from there, adding three breaks of her own to set up a last-eight meeting with Madison Keys for Tuesday.
Data Debrief: Swiatek unmatched on clay
While Kerber rolled back the years to trouble Swiatek early on, she lacked the staying power to live with the world number one in longer rallies on a surface where she is truly unmatched.
Her win ratio at clay-court events at WTA 1000-level now stands at 88.2 per cent (30 wins, four defeats), the best of any player to have played a minimum of five matches since the format's 2009 introduction, ahead of Serena Williams at 88 per cent.
Osaka sees encouraging Italian Open run halted by Zheng in last 16
Naomi Osaka's promising Italian Open run was halted by Zheng Qinwen on Monday, as the seventh seed denied the four-time grand slam champion a quarter-final place.
Following Saturday's triumph over Daria Kasatkina – her second successive straight-sets win over a top-20 opponent in Rome – Osaka laughed off the "Clayomi" moniker given to her by some fans.
On Monday, her old troubles on the surface came back to the fore as Zheng dominated from the off to make the tournament's last eight for a second straight year, winning 6-2 6-4.
Osaka saw her serve broken in the very first game only to hit straight back, but Zheng assumed control by taking seven straight games to go from 2-1 down in the opener to 2-0 up in the second set.
The 21-year-old produced a clinical performance and converted all four of her break points, winning 78 per cent of first-serve points to Osaka's 68 per cent as she teed up a quarter-final clash with either Coco Gauff or Paula Badosa.
Data Debrief: 'Clayomi' no more as Zheng triumphs
Osaka impressed on a surface long regarded as her worst in Italy, but it was a bridge too far for her on Monday, Zheng reaching her fourth WTA 1000 quarter-final.
Since the format's introduction in 2009, she is just the second Asian player to reach multiple quarter-finals on both hardcourts and clay at that level before the age of 23, the other being Osaka.
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