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DUBAI: Former champion Andy Murray dug deep to edge out Canada’s Denis Shapovalov 4-6, 7-6, 6-3 in front of a jubilant center court crowd at the Dubai Duty Free Tennis Championships on Monday night.

The come-from-behind victory saw Murray — who claimed a solitary Dubai title in 2017 — register a landmark 500th career win on hard courts. He becomes only the fifth player to achieve the feat, joining luminaries of the game Roger Federer, Rafael Nadal, Novak Djokovic and Andre Agassi.

“It’s not bad, is it?” Murray said after reaching the milestone. “Hard courts have been a great surface for me over the years, and getting to 500 is a lot of matches. I am very proud of that, not a lot of players have done it, so it’s great to do it before I’m done.”

In challenging winds, the twilight ATP 500 round of 32 match started with eight consecutive service holds as both players found early rhythm. The first break points arrived in game nine, as Shapovalov found the outer corners of center court with a pair of dazzling one-handed backhand winners. After squandering the first chance, the 24-year-old grabbed the second to move 5-4 up, then held serve to claim the first set.

With both players holding serve for the first three games of the second set, Murray finally broke the big-serving Shapovalov in game four. The Brit’s ecstasy, however, immediately turned to agony as Shapovalov instantly broke back, then held, to make it 3-3.

As Murray, 12 years his opponent’s senior, increasingly threatened the Shapovalov serve, the Canadian’s monstrous first service cannons got him out of jail on numerous occasions. Murray, receiving, regularly stood some way behind the Dubai signage adorning the hardcourt beyond the baseline. The tactic proved fruitless, as Shapovalov unleashed 215-km serves time after time with pinpoint accuracy.

Battle-worn and grimacing repeatedly after several points near the end of the second set, Murray found emergency reserves of energy to force a tiebreak, which he won 7-5 to level the match — much to the delight of an adoring crowd.

Murray then broke Shapovalov in the opening game of the third set, which progressed on serve until 5-3 when Shapovalov suddenly found himself serving to stay in the match. With unforced errors now littering the Canadian’s game, Murray unleashed a glorious backhand winner at 30-30 to set up match point. It proved to be the only opportunity the British veteran needed, as Shapovalov volleyed Murray’s return of serve into the net.

In the ATP 500 event’s opening match on center court, the Netherlands’ Botic Van de Zandschulp upset sixth seed Adrian Mannarino, the world No. 19, in straight sets. With both players holding serve and almost politely swapping breaks enroute to a 6-6 stalemate, Van de Zandschulp, the world No. 75, managed to pull clear in the tiebreak to seal it 7-3.

After the umpire handed Mannarino a conduct warning between sets for smashing his racquet in frustration, the second set remained a tight affair. Eleven consecutive holds of serve suggested another tiebreak lay in wait, but Van de Zandschulp got the better of his French opponent’s service game at exactly the right time to triumph 7-6, 7-5 in just under two hours.

In the evening games under the lights, world No. 5 Andrey Rublev safely negotiated his route to the round of 16, defeating Zhizhen Zhang 6-7, 6-2, 6-4. The former Dubai champion was made to fight by his opponent, however, with the serve of the world No. 46 looking particularly formidable as he claimed the first set.

“It was a really tough match,” said Rublev. “I started well, but he was serving unreal. I don’t know how high his percentage was on the first serve, but it feels like some games lasted only one second, and serves were around 220 and super tough to return.”

A center court surprise came even closer in the following match as world No. 8 Hubert Hurkacz came within two match points of crashing out in the first round. His tie with German Jan-Lennard Struff went the distance as both men held their thumping serves for three straight sets, before the Pole squeezed through on the decisive set tiebreak to claim a 7-6, 4-7, 7-6 win.

“He’s such a great guy and great opponent,” said Hurkacz, who will face either Christopher O’Connell or Maximilian Marterer in the round of 16. “In the end, I got a little bit lucky, but I tried to compete until the last point and that is what I always try to do. It could have gone either way.”