Andy Murray's shot at a first grass-court title since Wimbledon 2016 went begging as he lost in the final of the Stuttgart Open to Italy's Matteo Berrettini in three sets on Sunday.
Murray also struggled with an apparent hip injury during the latter stages of the contest and needed on-court medical attention, which has raised fears over his condition for Queen's and Wimbledon.
A spate of early double faults allowed Berrettini to break in the third game of the match, although Murray failed to take four break points to level the contest in the next game.
Murray remarkably managed to save three break points of his own soon after but could not find a way past the big-serving Berrettini, who took the first set courtesy of a cross-court forehand.
The Brit was forced to keep his emotions in check in the second but was handed three set points at 6-5 in Berrettini's service game, and Murray forced a third set with a resilient showing.
However, Berrettini broke immediately in the third as Murray received attention on his physical problem, and he ultimately needed two timeouts before battling on.
It would be a step too far for the 35-year-old, though, as Berrettini - just back from surgery himself - took his second match point to condemn Murray to defeat in his 70th ATP singles final.
While Murray's afternoon ended in disappointment, a ruthless Dan Evans stormed to the Nottingham Challenger title with a straight-sets victory over Australia's Jordan Thompson in front of the home crowd.
Evans made it through to the final without a dropping a single set and continued that theme right to the death, securing a 6-4 6-4 success over the 28-year-old on Sunday.
Thompson had five opportunities to break Evans on the day but was only able to take two of them, with the home favourite producing an eye-catching performance to kickstart the grass season.
Evans has now won a total of 22 ATP Challenger titles after also coming up trumps in Nottingham three years ago and is now looking ahead to Queen's, where he will meet Murray's Stuttgart conqueror Berrettini in round one.
Murray is due to open against Lorenzo Sonego at Queen's before a potential second-round clash with Evans, but fans will eagerly await an update on the 35-year-old's condition following his latest injury woes.