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.