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Andy Murray suffered arguably his most painful defeat of the season in a 7-6 (7-5) 4-6 7-5 loss to Alex de Minaur in the first round of the Paris Masters on Monday.

Murray, who won the title in the French capital in 2016, looked on course to finally end his drought against the Australian, leading 5-2 up in the deciding set, but he failed to take a match point chance at 5-4 before going on to lose to De Minaur for the sixth time in a row.

The Scot will now weigh up his options as to whether he will play at the Moselle Open in Metz or the Sofia Open in Bulgaria next week before Great Britain’s Davis Cup quarter-final against Serbia in Malaga on Thursday, November 23.

In September, De Minaur rallied from 2-5 down in the third set against the Scot to triumph in Beijing, saving three match points in the process and it was a case of déjà vu for Murray as De Minaur kept alive his slim ATP Finals qualification chances.

The former world No 1 had looked on course to end his run of defeats against his opponent in their first-round contest after recovering from losing the opening set tie-break to level and then forced two breaks to lead 5-2.

However, Murray failed to hold either of his own next two service games as the world No 13 rallied before turning the set around to close out another hard-earned victory.

A first match point went begging in the 10th game when Murray sent a return long and smashed his racket on the floor after handing De Minaur a break-point opportunity, which he took to level at 5-5.

After De Minaur then held, Murray’s temper boiled over again during the change of ends when he knocked the drinks bottles and towel off his bench.

De Minaur grew with the momentum and was given a match point of his own after the chair umpire over-ruled a call on the baseline, which was shown to be out.

There was to be no reprieve for Murray when he sent a return into the net, which sealed De Minaur’s victory in a three-hour epic.

Murray then again smashed his racket on the floor before trudging off court on the back of another gut-wrenching defeat.

In other action, Alejandro Davidovich Fokina earned his 30th ATP Masters 1000 match win, defeating American Ben Shelton 7-6 (7-4) 5-7 6-3.

Frances Tiafoe lost to Alexander Bublik 6-3 6-4 to earn his first Masters 1000 hard-court win since Miami in 2022.

Roberto Bautista Agut earned his first tour-level win since June, defeating Czech Jiri Lehecka 6-4 6-2 to reach the second round.

Norrie withdraws from Metz

British No 1 Cameron Norrie, who pulled out of this week’s Paris Masters due to a knee injury, has withdrawn from Metz next week and he now appears to be facing a race against time to be fit for next month’s Davis Cup finals.

With Dan Evans already ruled out of the crunch quarter-final tie with Serbia in Malaga, it leaves captain Leon Smith with Andy Murray, Jack Draper and doubles specialist Neal Skupski as his only fully fit players against a side containing world No 1 Novak Djokovic.

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