Britain’s Dan Evans continued his poor record at the Italian Open after a marathon three-set second-round defeat by Spain’s Roberto Carballes Baena.
The British number two was beaten 7-6 (7-5) 5-7 6-4 in three hours and 48 minutes – the longest best-of-three-set match of the season so far.
Evans, the 20th seed, had a bye in round one and has never won a main draw match in the Rome event.
He is also yet to win a Masters Series match this year.
Evans had led 5-2 in the first set and served for it but Carballes Baena, who won in three sets when they met in Marrakech last month, rallied to take a 6-5 lead before a rain interruption.
On the resumption, Evans managed to break his opponent and force a tie-break but the world number 51 always had that bit extra with the rain constantly threatening.
The second set proved tight until Carballes Baena, the world number 51, played a loose service game at 5-5, enabling Evans to break and then eventually serve out the set and level the match.
The deciding set was as close but playing after three solid service games in a row, it was Evans whose nerve failed first and a couple of unforced errors and a double fault on match point handed the win to his opponent.
Earlier, world number two Carlos Alcaraz had a slow start before beating unseeded Spaniard Albert Ramos-Vinolas 6-4 6-1 on his Rome debut to ensure he will take over as world number one from Novak Djokovic on 22 May.
Alcaraz, who won in Barcelona and Madrid, is aiming for his fifth title of 2023 and fourth on clay before the French Open.
The 20-year-old was broken early but levelled it up at 2-2 before earning another chance to break Ramos-Vinolas in an intense 10th game and took the advantage in the match when his compatriot finally cracked under the pressure and sent a forehand long.
“The first round of every tournament is really tough and, of course, Ramos-Vinolas is a specialist on clay,” said Alcaraz. “I had to adapt my game quickly to be able to go through.
“The conditions weren’t easy, the rain and the waiting all day to know if I’m going to be able to play but I’m really happy with my performance in the end.”