Jack Draper's maiden ATP Tour final ended in heartache as the British number four suffered a three-set defeat to French second seed Adrian Mannarino at the Sofia Open.
The 21-year-old had overcome top seed Lorenzo Musetti and third seed Jan-Lennard Struff en route to the championship match, becoming the youngest Briton to reach a top-level final since Andy Murray in 2009.
Draper blew Mannarino away in the second set after going down in a first-set tie-breaker, but the 35-year-old Frenchman harnessed his enviable experience to triumph 7-6[6] 2-6 6-3 in two hours and 17 minutes.
In their first-ever top-level meeting between, the pair exchanged breaks in the opening two games of the match before dominating on serve, which was also the theme in the tie-breaker before one error from Draper proved costly.
However, the Briton came out a different beast in the second set, roaring into a 5-1 lead with a double break and taking the match to a third set with a hold to love, but Mannarino drew first blood in the decider.
Draper ceded a break point with a double fault in the sixth game, and Mannarino capitalised before falling 40-15 down while attempting to serve for the championship, but the Frenchman crucially saved both break points to win his fifth ATP Tour title.
Three of those crowns have come in the past four months for Mannarino, who also prevailed at this year's Hall of Fame Open and Astana Open, and he has now triumphed in each of his last three top-level finals.