Andy Murray was beaten in three sets by Alex De Minaur in the first round of the China Open in Beijing.
A 2 hour, 53 minute back-and-fourth encounter eventually went the way of the Australian 6-3 5-7 7-6(6), despite Murray battling back from a set down and having three match points in the final set.
De Minaur wrapped up the first set in only 35 minutes, holding on his opening serve before breaking Murray at the fourth attempt in a topsy-turvy second game.
The Australian impressively held to love and moved 3-0 ahead and did not face a single break point to draw first blood and prevail 6-3.
The second set was much more closely contested, as the former world No. 1 took the first game and looked much stronger on his serve.
He did not give De Minaur a look in, as the first five games all went with serve before Murray broke the world No. 12 for the first time to move 4-2 ahead.
However, the 24-year-old showed his class and broke back immediately and claimed a successful hold to wipe out Murray’s second-set lead with another love hold.
The following three games all went by way of serve, before the Scot showed the resilience he has displayed time and time again in his career to break the De Minaur serve and take the second set 7-5.
A nervous start to the decider saw Murray save break point on his opening service game but the three-time Grand Slam winner was able to break in a lengthy fourth game to go 3-1 up.
At 5-2 Murray saw two match points come and go on De Minaur’s serve and a sloppy service game immediately afterwards opened the door for the Australian to bring the set back on serve.
Murray was able to stop the rot to edge 6-5 ahead but a love hold sent the match to a tie-break.
De Minaur secured the first mini-break to open up a gap and but Murray again refused to surrender setting up another match point.
The Brit was unable to convert yet again, however, and allowed his frustrations to get the batter of him as De Minaur finally saw out the win.
He now faces Tommy Paul or Daniil Medvedev in round two.