Britain's Kyle Edmund suffered a straight-sets defeat to Denis Shapovalov in the second round of the Western & Southern Open in Cincinnati.
Edmund, Britain's last hope of the tournament, was defeated 6-4 7-5 by his 19-year-old Canadian opponent in one hour, 53 minutes.
The 23-year-old held off five break points in the first set but failed to take advantage of his own break opportunities and eventually lost his serve in the final game.
Edmund failed to recover in the second set, falling below par on his first service game and handing his opponent an early 2-0 lead.
The Brit fought back and managed to level the score at 4-4, saving a match point at 5-5.
But Shapovalov dominated with a number of impressive backhands and despite needing four match points, ultimately broke Edmund's serve to advance to the third round on his tournament debut.
Sergio Ramos has taken a swipe at Jurgen Klopp's record in finals as the war of words over last season's Champions League final continuesRead the full story ›
Extreme sportsman Ross Edgley is aiming to become the first man to swim the coast of the British Isles.Read the full story ›
Gareth Bale's stunning overhead kick in the Champions League final has been overlooked in a goal of the season poll conducted by UEFARead the full story ›
Two-time Formula One World Champion Fernando Alonso has announced his retirement from the sport.Read the full story ›
Bath have no clear time frame on when England star Anthony Watson could return to action after he retore his Achilles tendon.
Watson suffered an initial Achilles injury playing for England against Ireland in the final game of last season's Six Nations Championship.
And Bath rugby director Todd Blackadder admitted on Tuesday that it is a "start again injury" as the countdown continues towards the start of the new season.
Speaking to reporters at Bath's training base in Farleigh Hungerford, Blackadder said: "The initial surgery did not quite take, and he has re-torn it.
"It is a start again injury, so we honestly don't know what the time-line is.
"It could come down to weeks or months, but it could be later in the season, we just don't know."
Watson, 24, has won 33 England caps and scored 15 tries for his country.
The prognosis from his first Achilles injury was a six-month absence, so the latest setback suggests that he might struggle to play again this year.
England kick off their autumn Test schedule against South Africa on November 3, with world champions New Zealand, Japan and Australia following on successive Saturdays.
Fabinho has stressed he knew there would be a battle for places in Liverpool's midfield when he joined this summerRead the full story ›
The all-rounder was charged after brawling with two nightclub revellers in Bristol city centre hours after he played for England.Read the full story ›
Chelsea midfielder Tiemoue Bakayoko has joined AC Milan on a season-long loan.
The Frenchman moved to Stamford Bridge from Monaco last summer for a reported £40million, but struggled to make the desired impact in the Premier League.
Chelsea said in a statement: "The 23-year-old now makes the temporary switch to the Serie A side who are managed by Gennaro Gattuso and are competing in the Europa League this season."
Milan said the deal includes an option to make the move permanent.
He will be presented to the media on Friday afternoon.
Manchester United are increasingly optimistic about agreeing new terms with goalkeeper David De Gea in the wake of Thibaut Courtois' move to Real Madrid, Press Association Sport understands.
The 27-year-old's future has been repeatedly questioned since he came close to joining Real Madrid three years ago and United are desperate to keep hold of the Spain international.
Courtois' move from Chelsea to the Bernabeu last week has taken his most obvious destination out of the equation, boosting United's hopes of agreeing a new contract with De Gea.
The Spaniard's current deal expires next summer with a further year existing as an option to be triggered by the club.
The market for keepers has spiralled considerably in the past year, with Jordan Pickford costing Everton £30million last summer when he was both uncapped by England and recently relegated, and the world record broken twice in the past month.
First Alisson Becker moved from Roma to Liverpool for around £66m, then Chelsea trumped that by replacing Courtois with Athletic Bilbao's Kepa Arrizabalaga for £72.1m.
That makes the £18.9m De Gea cost in 2011 look paltry by comparison but United's interest has long been in locking down a long-term stay rather than cashing in.