Great Britain's Cameron Norrie has crashed out of the Estoril Open in the second round, losing to Spain's Roberto Carballes Baena by two sets to one.
The match, which lasted just over three hours, finished 5-7 6-2 7-6(1) to the world number 77.
British number three Norrie served for the match at 5-3 and had three match points on his opponent's serve, but the Spaniard proved dominant in the resulting tie-break.
Defeat sees the 22-year-old, who saw off Robin Haase in the previous round, miss out on the first ATP Tour quarter-final of his career.
Norrie will now turn his attention to the French Open, for which he will be included in the main draw on May 27.