Liam Broady bowed out of Tokyo 2020 after falling in the third round to France’s Jeremy Chardy in an exhausting three-set encounter.
The Briton, a late call-up for the singles at the Olympics, fought back to take the match to a third set, but eventually lost 7-6(3) 4-6 6-1 in two hours and 39 minutes.
Broady, the lowest-ranked singles player in the tournament, was looking to produce another upset having knocked out number seven seed Hubert Hurkacz in the last 16.
GB’s Broady pulls off huge upset to knock out Hurkacz
And it was another battle for Broady as he was forced to fight back to level terms in the first set after seeing his serve broken in the fifth game.
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Chardy had the chance to serve for the first set, but Broady did brilliantly to engineer a break and then forced a tie-break two games later.
Broady was the first to drop serve in the breaker and Chardy repeated the trick in the ninth point to give himself a set point. The Frenchman took his chance and brought to a close a gruelling first set which lasted over an hour.
The second set proved equally as taxing with the pair sharing early breaks, but just as the match passed the two-hour mark Broady edged ahead with a second break.
A game later he then valiantly saved three break-back points before converting his second point and forcing a decider.
The pair took a lengthy break before the final set with the temperature above 30 degrees Celsius in Tokyo, and it was Chardy who kept his cool when breaking Broady before going 3-0 up.
Chardy took complete control when breaking again, and having sealed victory the 34-year-old now faces Alexander Zverev next for a place in the semis, with the German recording a 6-4 7-6 (7-5) victory over Nikoloz Basilashvili.
Tsitsipas out, Medvedev through
Elsewhere, Stefanos Tsitsipas’ Olympic dream is over for three years at least after the break fell in three sets to Ugo Humbert.
Tsitsipas raced to a 6-2 lead but was pegged back as France’s Hunbert pinched the tie-break 7-4 before winning the decider 6-2.
Daniil Medvedev is through to the quarter-finals after winning a three-set showdown against Fabio Fognini.
After comfortably winning the first in 38 minutes, Fognini staged a comeback in the second with the match dragging on for just under two-and-a-half hours.
Fognini drew level after a huge 56 minutes of action in the second set as each game was tightly contested.
Medvedev was finally broken in the eighth game after a 15-point exchange. It appeared the match had swung in the favour of the underdog and world number 15, but Medvedev dug deep in the third set.
The Russian grabbed an early break and raced into a 4-1 lead which proved insurmountable for a tiring Fognini.
Medvedev will face Spanish star Pablo Carreno Busta in the quarters and will fancy his chances of medalling.
KeiNishikori’s quest to win gold at his home Olympics goes on after he beat Ilya Ivashka 7-6(7) 6-0.
The world number 69 was made to dig deep in the first set with both men struggling to hold their serves. There were six breaks of serve in the first set before Nishikori just managed to edge the tie-breaker.
The second set was more straight forward for the home favourite as he won six games in a row to book his place in the quarter-finals.
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