Jack Draper's run at the BMW Open in Munich is over courtesy of a three-set defeat to the USA's Taylor Fritz in Friday's quarter-final.
The British number two took the opening set against the third seed, but he was again taken the distance and fell away during the third-set tie-breaker in a 4-6 6-3 7-6[1] defeat.
Fritz needed two hours and 15 minutes to overcome the 22-year-old, who had prevailed in their only previous meeting at the 2022 Queen's Club Championships, and the American will take on top seed Alexander Zverev or Cristian Garin in the semi-finals.
However, Fritz was pushed all the way by sixth seed Draper, who made the perfect start to Friday's quarter-final with a break in the opening game of the match and came agonisingly close to repeating the trick in the fifth game.
Fritz managed to save all four break points in that game to avoid going down a double break, but those wasted chances did not prove costly for Draper, who did not face a single break point on serve in the first set.
Draper responds emphatically to time violation
The 22-year-old was handed a time warning from the chair umpire while trying to serve out the set, but he kept his head magnificently, firing back-to-back aces and another venomous serve which Fritz could only return long on set point.
Both men opened the second set with love holds, but Fritz soon began to wear down Draper's defences, as the Briton let a 40-0 lead slip on serve in the fourth game and was broken for the first time.
A flurry of aces followed from both powerful hitters, but Fritz was unflappable behind his own racquet, losing just two points behind serve in the entire second set and levelling the match with a stunning hit down the T.
The third set began with a hold apiece before the heavens opened, sending down a barrage of hailstones onto the clay court as well as fierce winds - which sent Draper's protective umbrella into the crowd - but the storm passed within a few minutes.
An extremely tight third set of tennis saw love holds aplenty and not a single break point for either Draper or Fritz, the latter of whom fell 30-0 down in the 12th game while serving to stay in the match but kept his composure to fight back for the tie-breaker.
Clinical Fritz dominates serve against Draper
After displaying tremendous grit throughout the three-set encounter, Draper just could not maintain the intensity in the tie-breaker, handing Fritz his first mini-break on a double fault on the fourth point.
The 26-year-old remained unblemished on serve to bring up five match points, the first of which saw Draper go for broke on a forehand, but he undercooked his net-bound attempt to send Fritz through.
The British number two still put in a performance to be proud of - registering 10 aces and only allowing Fritz one chance to break in the entire match - but it was one that the American crucially took.
In contrast, the third seed saved six of the seven break points that Draper fashioned, while also bettering the Briton's aces tally with 18 and no double faults and landing 78% of his first serves, compared to Draper's 65%.
Fritz's first serve (80%) and second serve (62%) win rates were also marginally superior to Draper's 77% and 56%, as the world number 15 conquered his 22-year-old foe for the first time. body check tags ::
