Andy Murray crashes OUT of the US Open after losing in straight sets to Grigor Dimitrov in the second round

The sense of generational change hung heavily in the air at the Flushing Meadows last night as Andy Murray sent down a valedictory double fault to exit the US Open second round.

The 2012 champion fell 6-3 6-4 6-1 to Grigor Dimitrov, barely an hour after Jack Draper had given another reminder of his startling talent by ousting seventeenth seed Hubert Hurkacz.

The formidable Pole had complained of feeling unwell, but there was no mistaking the quality of his 21 year-old British opponent, who has hardly been without issues himself, given the shoulder problems which have dogged him all summer.

Draper dished out the same treatment as he had done to Felix Auger-Aliassime at the same stage here a year ago, dismissing Hurkacz 6-2 6-4 7-5 to make the last 32. 

He now has the chance to go further as he will meet American wildcard Michael Mmoh, the world number 89, who brought the curtain down on John Isner’s career in a marathon five-setter.

Andy Murray has been knocked out of the US Open by Grigor Dimitrov in the second round

The 2012 champion lost in straight sets, with the match point coming through a double fault

The Scot appeared to grow frustrated as the match wore on, as he sarcastically applauded his support box in the final set

There were faint echoes of 2006-7 when the young Murray was emerging to replace Tim Henman as chief British standard bearer. It is a role Murray has performed with the utmost distinction, and if this is to prove his farewell to New York it was hardly a fitting one.

Chuntering to the end and sarcastically applauding his long-suffering support box, he served poorly and was well beaten by the talented Bulgarian, all the more painful because Dimitrov is coached by his former mentor Dani Vallverdu.

After a marathon opening seven games that took nearly an hour, Murray showed glimpses of what made him a great player in the past before resigning himself to a twelfth straight Major in which he has failed to make the second week.

Later he was forlorn after bowing out of another second round, just as he had done at Wimbledon: ‘It’s obviously disappointing not play how you would like. Maybe I need to accept that at these events the deep runs that I felt like I’m capable of, they might not be there.

‘I’m aware what I’m doing (with his metal hip), is unbelievably challenging to play at the highest level, some days it’s harder than others. Today is a really disappointing defeat and probably the manner of it as well.’

He admitted he did not know what his schedule would be for the rest of the year, and cast doubt on playing for GB in the Davis Cup finals qualifying group in Manchester the week after next: ‘If I’m being honest the other guys deserve to play ahead of me. Jack had quite a few injuries coming in, but if he’s fit and healthy he’s obviously playing very well. Cam (Norrie) and Evo (Dan Evans). We’ll see about Davis Cup and what happens there.’

Draper, who is playing with a small tear in an upper arm muscle, had again shown how quickly he can find form, reflected on how things have turned around for him since retiring from his ATP match at Winston Salem a week ago.

‘There was a strong chance I couldn’t play this week. I was with my coach and physio thinking about another bit of time off. We were almost in tears, like “what more can we do”?’ recalled Draper.

Dimitrov of Bulgaria will now advance to the third round after an impressive display against Murray

Murray admitted after the match it was ‘frustrating’ to be unable to perform at his best

Jack Draper has advanced to the third round after beating Hubert Kurkacz

‘There was maybe a 70/30 chance that I wouldn’t play so I’m very happy with the fact that I have been able to get out there and play, and actually my shoulder’s felt great.

‘It’s weird how this sport works. Sometimes you can be at your lowest point and then all of a sudden you get on a bit of form and you’re playing great and body feels good.

‘I’m kind of looking after it (the shoulder and arm) each day. It was a bit sore after my last match but when the adrenaline kicks in and it’s the US Open, I just put it out of my mind. 

Even though last year I was maybe a top-50 player, and my ranking has dropped I feel like I’m a much more complete and better player this year because of the work I’ve done, and like I’m playing better tennis as a whole. Maybe last year I was taking how well I was doing for granted. Maybe the time off has been a good thing, a reality check.’