Great Britain’s Jay Clarke and James Ward suffered defeats in the first qualifying round of the French Open.
GB number four Clarke served for the match before 19-year-old Alejandro Davidovich Fokina, ranked 26 places higher at 133, won 2-6 7-6 (7-5) 6-1.
Fifth-ranked Briton Ward, 169th in the world, lost 6-1 6-2 to German Oscar Otte, who is rated 24 places higher.
It leaves Kyle Edmund, Cameron Norrie and Dan Evans as the British men in the main competition.
Englishman Clarke, 20, made a fine start as he broke his opponent’s serve in both of his first two service games to dominate the opening set.
After fighting back from 4-1 down in the second, Clarke was serving for the match with a 6-5 second-set lead, but the Spaniard broke back and then won the tie-break to take it to a deciding set.
Davidovich Fokina, a winner of the Wimbledon juniors event in 2017, broke immediately in the third set and two further breaks saw him move into the next phase, needing to win two more matches to qualify for the tournament.
Meanwhile, Jamaican-German Dustin Brown, who famously beat Rafael Nadal at Wimbledon in 2015, progressed into the second qualifying round with a 7-6 (7-5) 6-1 victory over Denis Istomin, the second seed in the qualifying tournament.
The 34-year-old will now face Ecuadorian Emilio Gomez.
Former world number five Tommy Robredo, at 37 the second oldest player in the event and a five-time Roland Garros quarter-finalist, lost 7-6 (7-5) 6-3 to German 18-year-old Rudolf Molleker.
A total of 128 qualifiers began on Monday battling for 16 places in the main draw.