Britain’s Andy Murray missed three match points as he suffered a first-round defeat by Alex de Minaur at the China Open.
The former world number one lost 6-3 5-7 7-6 (8-6) in a tightly contested match in Beijing.
Murray led 5-2 in the third set and had two match points on De Minaur’s serve, before the Australian broke back as Murray served for the match.
The Scot missed another match point in the tie-break as De Minaur prevailed.
It is the 36-year-old’s fifth successive loss to De Minaur, who is number 12 in the world rankings.
Murray committed just 13 unforced errors compared with the 16 of De Minaur, who will play either Tommy Paul or second seed Daniil Medvedev in the second round.
The 24-year-old becomes the fourth player to beat Murray in five consecutive matches, as well as Rafael Nadal, Roger Federer and Novak Djokovic.
Thursday’s defeat is the third time this year Murray has been knocked out of a tournament in the opening round by De Minaur.
The Australian ended Murray’s chances of being seeded at Wimbledon with victory at Queen’s in July, before a further win at the Monte Carlo Masters.
On Friday, British number one Cameron Norrie faces fifth seed Andrey Rublev, while fellow Briton Dan Evans plays Italian sixth seed Jannik Sinner.