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LIVE: Serena Williams loses 7-5 6-7 (4-7) 6-1 to Ajla Tomljanovic in US Open third round
Defeat is last match of 23-time Grand Slam single champion's career
Andy Murray loses 6-4 6-4 6-7 (1-7) 6-3 to Matteo Berrettini
Jack Draper retires injured in third set against Karen Khachanov
Top seeds Joe Salisbury & Rajeev Ram reach men's doubles third round but Jamie Murray & Bruno Soares lose
Day five of final Grand Slam of year at Flushing Meadows
Naomi Broady
British player on BBC Radio 5 Sports Extra
Berrettini's team are beside themselves. They're trying their best to keep their poker faces for when he looks up at them, but what a miss.
*Murray 4-6 4-6 5-5 Berrettini
Matteo Berrettini is definitely getting twitchy.
The ball sits up pretty for the Italian to thrash away a winner, but he dumps it long to allow Murray back to deuce...
*Khachanov 6-3 2-1 Draper
Jack Draper lets out a huge roar of frustration as he coughs up another break point, drawing some encouraging applause from the crowd.
It's not to be, though, as a horrible backhand skews over the tramlines from Draper and hands Khachanov the break. Draper covers his head with a towel at the changeover.
*Murray 4-6 4-6 5-5 Berrettini
Matteo Berrettini punishes a nothing-much mid-court backhand with a ripped forehand winner for 15-30 and then Murray is forced deep behind his baseline for 15-40.
Berrettini has his sixth and seventh break points of the third set. Can he make one of these stick?
Khachanov 6-3 1-1 Draper*
Danger for Jack Draper, as a missed swipe into the net hands Karen Khachanov an early break point.
Oh, and he's lucky that Khachanov works an ugly forehand long over the baseline.
Deuce.
*Murray 4-6 4-6 5-5 Berrettini
At the risk of sounding like an advert for a German executive car, the power comes with such ease for Matteo Berrettini.
The Italian clubs away a winner with a forehand swish before socking away a serve to wrap up the love game.
Sublime stuff.
Khachanov 6-3 1-1 Draper*
A nice, solid hold to start the second set from Jack Draper and he finds a nice drop shot to win a rare point on the Karen Khachanov serve.
No bother, though, as the Russian casually swings down a huge second serve to hold and put the pressure back on Draper.
Naomi Broady
British player on BBC Radio 5 Sports Extra
He's done well there has Murray to stay on the scoreboard because he was just starting to bubble over.
He managed to put it back in the box somewhat and get the hold.
Murray 4-6 4-6 5-4 *Berrettini
Andy Murray is still fighting a rearguard action, soaking up pressure but racking up games and keeping it on serve.
If he can just take a service game against the head in the next...well then.
Naomi Broady
British player on BBC Radio 5 Sports Extra
Andy is so annoyed because he knows he had the momentum in this game.
*Murray 4-6 4-6 4-4 Berrettini
Andy Murray with a chance to really crank up the pressure on Matteo Berrettini at 15-30.
But he hands the game giving any lip-readers of a delicate disposition the vapours with a fruity monologue on missed opportunities.
Two straightforward errors allowed Matteo Berrettini to wriggle back into the driving seat and then the Italian zoomed over the horizon via his trademark serve power.
Khachanov 6-3 Draper
Another dominant service game from Karen Khachanov, and a long Jack Draper forehand seals the first set for the Russian.
Dominant stuff.
*Khachanov 5-3 Draper
Jack Draper, after a lot of hustle and bustle, comes out on top in a point at the net, and an excellent second serve means Karen Khachanov will have to serve this one out.
Khachanov 5-2 Draper*
Trouble for Jack Draper...
After another speedy Karen Khachanov service game, the Brit finds himself dragged from 40-15 to deuce as he attempts to stay in this first set.
Naomi Broady
British player on BBC Radio 5 Sports Extra
He's still pumped out there is Andy. He needs a bit of this fire in his belly.
Murray 4-6 4-6 4-3 *Berrettini
Andy Murray hollers with frustration as a backhand slice swerves just outside the lines to give Matteo Berrettini a sniff of 30-30.
Can he keep the Italian at bay?
Yes, he can! Without even the usual detour via break points and deuce! Berrettini overcooks as he turns up the heat and Murray gets home in regulation time.
*Murray 4-6 4-6 3-3 Berrettini
Matteo Berrettini is flying at an altitude that Andy Murray just can't reach at the momentum.
The air is thin up there, the ball flies faster and everything seems a little easier.
*Khachanov 4-2 Draper
Jack Draper holds - by a very fine margin!
Karen Khachanov latches onto a second serve and sends his backhand inches over the baseline.
Draper keeps the deficit to just one break.
Khachanov 4-1 Draper*
A game point comes and goes for Jack Draper, before he larrups a backhand long to give Karen Khachanov another shot at breaking serve.
Oh, and a lovely big forehand into the corner wrongfoots Khachanov, and it's back to deuce!
Murray 4-6 4-6 3-2 Berrettini*
Andy Murray has saved five break points in the third set. Is Matteo Berrettini getting a little tight as the finishline looms?