Britain’s former world number one Andy Murray broke down in tears after coming from a set down to beat Romanian Marius Copil and reach the last eight of the Washington Open.

The 31-year-old won 6-7 (5-7) 6-3 7-6 (7-4) in a match that finished at 03:02 local time.

Murray will play Alex de Minaur of Australia in the quarter-finals – his first since Wimbledon in 2017.

He is playing only his third tournament since hip surgery in January.

Three-time Grand Slam champion Murray – now ranked 832 in the world – lost the first set in one hour and six minutes, having taken a 5-0 lead in the tie-break before losing seven points in a row.

He broke Copil twice in the second set to take it in 45 minutes and looked set to take the third comfortably when he secured a break in the sixth game to move 4-2 up.

But the Romanian immediately broke back before holding serve to level the match, before Murray’s fitness prevailed in the deciding tie-break.

The tournament’s previous latest finish was 02:27 local time.

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Mischa Zverev said he had to “fight back tears” prior to his third-round defeat by younger brother and world number three Alexander Zverev at the Washington Open.

Defending champion Alexander, 21, won 6-3 7-5 in what was the first ATP Tour meeting between the German siblings.

They had previously met on two occasions: the last at the US Men’s Clay Court Championship in 2014.

“I needed a few seconds to actually bite my tongue and focus,” said Mischa.

“It was very emotional for me. It was just a great day.”

Alexander will play Kei Nishikori in the quarter-finals after the Japanese seventh seed defeated Canada’s Denis Shapovalov 7-6 (7-1) 6-3.

Speaking about his victory over his brother, Alexander said: “We played near our best. It was unbelievable.

“I just hope it happens again and I hope it happens at later stages of bigger tournaments. I hope we meet again someday in a final.”

Later on Thursday, the brothers teamed up to complete their rain-delayed first-round doubles match, in which they defeated top seeds Oliver Marach and Mate Pavic 6-1 6-4.

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British number three Heather Watson lost to seven-time Grand Slam champion Venus Williams in the last 16 of the Silicon Valley Classic in California.

American third seed Williams, 38, won 6-4 4-6 6-0 to reach the quarter-finals and is the highest remaining seed.

Defending champion Madison Keys withdrew on Thursday with a wrist injury, while top seed Garbine Muguruza pulled out earlier in the week.

World number 14 Williams will face Greece’s Maria Sakkari next.

Meanwhile, British number two Katie Boulter is out of the Citi Open in Washington after losing in three sets to qualifier Allie Kiick in the last 16.

Boulter, 22, who knocked out fifth seed Aleksandra Krunic in the first round, lost 4-6 7-5 1-6 to American Kiick.

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British number two Cameron Norrie reached his second successive semi-final by beating Adrian Mannarino at the Los Cabos Open in Mexico.

The 22-year-old won 6-4 6-4 against the French world number 25, who was seeded fourth.

It is Norrie’s third ATP World Tour semi-final, after reaching the last four at the Atlanta Open last week.

He will face 31-year-old Italian second seed and world number 15 Fabio Fognini on Saturday (not before 02:30 BST).

Argentine top seed and world number four Juan Martin del Potro will play Bosnia’s Damir Dzumhur in the other semi-final.

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France’s Benoit Paire has been fined $16,500 (£12,500) after smashing three racquets during an on-court tantrum.

Paire, 29, lost his temper after missing a shot as he trailed Cypriot Marcos Baghdatis 5-2 in the final set of his 6-3 3-6 6-2 first-round defeat at the Washington Open on Tuesday.

He was sanctioned for an audible obscenity, unsportsmanlike conduct and a lack of giving best effort.

“Yes, yes it’s true I got upset yesterday,” he wrote on Instagram.

“What I remember is that I’m on the right track and I’m progressing since the beginning of the year so for those who want to stay on it there’s no problem but I have already moved on.”

The ATP fine is more than double the appearance money he made at the tournament.

The world number 55 smashed his racquet on the ground several times after surrendering the chance to break Baghdatis, then hurled two more racquets across the court as his opponent attempted to calm him down.

He then walked to his chair and kicked it before smashing another racquet into the ground.

Paire next made no effort to return a Baghdatis serve then smashed another racquet before shaking hands.

He was booed off court by spectators – and blew kisses to the crowd as he headed to the dressing room.

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Former world number one Andy Murray took another big step in his comeback from hip surgery by beating fellow Briton Kyle Edmund in the second round of the Washington Open.

Three-time Grand Slam champion Murray beat British number one Edmund 7-6 (7-4) 1-6 6-4.

He will play Romania’s Marius Copil in the third round.

“It was much better, just in terms of the way I actually played the match,” said the Scot, 31.

“Regardless of the result, we wanted to at least be dictating more points, trying to use my forehand, be closer to the baseline.

“I think I did that, especially in some of the important moments in the third set. I was being more offensive.”

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Edmund beat Murray at Eastbourne in June – in the third match of his return during the grass-court season – before the world number 832 pulled out of Wimbledon.

Edmund, 23, said: “I gave my best of what I had on the day, it just didn’t work out. It would have been nice to hold serve and maybe even control what I can and take [the third set] to a tie-break but it didn’t happen.”

Elsewhere in Washington, defending champion and world number three Alex Zverev beat Tunisia’s Malek Jaziri 6-2 6-1 and will play his brother Mischa in the third round.

After five years together on the ATP Tour, this will be their first meeting on court.

“It’s going to be very interesting for me. It will be a special day,” said Alex Zverev. “Not many families can say they have two players playing at this level.”

Belgian third seed David Goffin survived a scare against France’s Pierre-Hugues Herbert to win 6-2 1-6 7-6 (7-5) while Japan’s Kei Nishikori beat American qualifier Donald Young for the second year in a row, winning 6-3 6-4.

He will face Canadian Denis Shapovalov in the next round, while Goffin plays American Frances Tiafoe.

Fifth seed Nick Kyrgios withdrew from the tournament with a hip injury, having retired during his Atlanta Open quarter-final last week.

Elsewhere, British number two Cameron Norrie is through to the quarter-finals of the Los Cabos Open in Mexico, following a 6-3 6-3 victory over Spanish eighth seed Feliciano Lopez.

Norrie, 22, will play Frenchman Adrian Mannarino in the last eight.