Cameron Norrie lost to German fourth seed Alexander Zverev as Britain's interest in the Wimbledon men's singles ended for another year.
Norrie, 28, was beaten 6-4 6-3 7-6 (17-15) in the third round.
Zverev, who has never gone past the last 16 at the All England Club, battled through after sustaining a knee injury early in the second set.
The 27-year-old could not take his first five match points in a monumental tie-break, where Norrie also had five set points, before clinching victory at the sixth attempt.
Recently being deposed as the British men's number one was the result of a chastening few months for 42nd-ranked Norrie.