Cam Norrie suffered an agonising defeat at the Australian Open as he was beaten in a fifth-set tie-break by Alexander Zverev after the British twice battled back in a brave display.
Norrie, who had not managed to win a set in their four previous meetings, lost the first and third sets before fighting back but it was Zverev who moved through to the quarter-finals after a 7-5 3-6 6-3 4-6 7-6 (10-3) victory.
Norrie will leave Australia, though, knowing that he can mix it with the best players in the world on the biggest stage and with confidence fully restored after a shaky second half of last season.
Stakes were high as both men bidded to reach the quarter-finals in Melbourne – which will now see Zverev take on World No 2 Carlos Alcaraz.
The match was briefly interrupted in the third set by a protester, who threw ‘Free Palestine’ flyers onto the court from the front row of Margaret Court Arena before being forcibly escorted away by two spectators.
Alexander Zverev dealt a crushing blow to British No 1 Cam Norrie as he edged him out in a tie-break after a five-set thriller
Norrie deserves huge credit for pushing Zverev all the way but missed the killer instinct as the game went to a tie-break
Zverev threw everything at the British star but was given a real battle as Norrie twice pegged him back to take him to a fifth set
The protester’s pamphlets were quickly swept up by on-court officials but it was left to two fans seated near the protest to escort them out of the Margaret Court Arena.
At the time, the British No 1 was on serve in the third set, and preparing to win his game with advantage to make it 4-2.
But both Zverev and Norrie were forced to stop and wait for the protest – which took place behind the German No 6 seed – to be cleared up at the back out of the court.
Those present in the arena claimed that security had been slow to intervene, with the Independent reporting that after the protester was ejected, the stadium burst into applause.
The leaflets appeared to highlight ‘war crimes and genocide’ and carried the slogan ‘Free Palestine’ in a bid to raise awareness to the roiling conflict between Israel and Hamas in Gaza.
‘While you’re watching tennis, bombs are dropping on Gaza,’ the pamphlet read.
‘Australia is a close ally of Israel. Australia is complicit in war crimes and genocide’.
Earlier on a protester hurled flyers in support of a ‘Free Palestine’ during Cameron Norrie’s match on Monday in Melbourne
Staff stooped to clear the leaflets off the court during a forced break in play on Margaret Court
The scenes were reminiscent of Wimbledon last summer, when Just Stop Oil protesters threw jigsaw pieces and confetti onto the court during two matches, although the leaflets were swiftly cleared here and play quickly resumed.
There were few rallies of any kind in the first set, with serve dominating until Norrie, who was trying to beat a top-10 opponent at a slam for the first time, was broken at 5-5.
Zverev immediately came under pressure on serve for the first time but saved a break point with a forehand onto the line, and looked to have taken control of the contest when he broke again to lead 3-2 in the second.
However, Norrie played what must be one of the best returning games of his career to hit straight back, finishing it off with a zinging backhand cross-court winner.
And Norrie was not finished there, the 28-year-old showing his new-found aggression and willingness to mix up his tactics to pile more pressure on Zverev in his next service game.
The German saved two break points but then mis-hit a forehand on the third and suddenly Norrie was serving for the set.
It was far from straightforward for the 19th seed but he saved four break points before taking it, fortuitously, when a forehand hit the top of the net and dropped over.
Norrie was the last remaining British player in the tournament and refused to go down without a fight in the longest match of his career
Norrie and Zverev put in an enthralling contest with tensions high as the German (R) made six double faults in total
A poor service game at 1-2 in the third set was enough for Zverev to take it and though Norrie pushed hard at the beginning of the fourth set, Zverev managed to save two break points in the second game.
However, the Olympic champion was powerless to stop Norrie forcing a decider, the 28-year-old creating two set points at 4-5 and taking the first with a delicate half-volley.
Norrie was managing to bully Zverev, one of the most powerful players on tour, at times from the baseline, while his drop shots and short angled slices kept the German guessing.
They exchanged breaks of serve at the start of the fifth set while Norrie survived a tense game at 3-3, saving three more break points.
Both men managed to hold serve through to a first-to-10-points tie-break but there Norrie’s resistance ran out, with Zverev clinching the win after four hours and five minutes to end British interest in the singles.