British number two Harriet Dart was braced for a sleepless night after she squandered a huge opportunity to break new ground at Wimbledon following a heartbreaking third-round defeat to Wang Xinyu.

Dart had failed to reach the last 16 of a grand slam since her main-draw debut at the All England Club six years ago, but she negotiated windy conditions and rain delays to move 5-4 up in the second before she sent a simple smash volley into the net at deuce.

It was the closest Dart would get to a match point, with further lapses of concentration in the third set after she raced into a three-game lead bringing her fine run at the Championships to an end with a 2-6 7-5 6-3 loss to Wang.

Harriet Dart shakes hands with Wang Xinyu
Harriet Dart shakes hands with Wang Xinyu (John Walton/PA)

“I don’t think I’m going to sleep very well tonight, that’s for sure,” Dart reflected.

“It’s something that I can try and learn from, for sure, make sure it doesn’t happen again.

“I mean, it was a huge opportunity today. I put myself in some situations where I was up and leading.

“Yeah, it was really tough. I mean, to be up in two sets and come away with a loss is pretty heartbreaking, to be honest.”

An emotionally charged victory over Katie Boulter on Thursday had booked Dart a place in round three at SW19 for the first time in five years.

China’s Wang stood in the way of potential history for the Briton, who had won their only other meeting in qualifying for the 2022 Gippsland Trophy in Melbourne, but rain pushed back the scheduled 11am start.

When play did begin two hours later, windy conditions contributed towards three breaks of serve in the first four games and Dart’s more solid play earned her an early 3-1 lead.

A further delay for wet weather occurred, but the Hampstead-born right-hander claimed the first set in 38 minutes on Court Two.

Breaks were exchanged in the fourth and fifth games of the second set before Dart dug deep in consecutive service games to establish a 5-4 lead and then squandered a golden chance for a first match point.

Dart slammed a simple smash volley into the net on deuce as Wang held and subsequently forced a decider when she broke her opponent straight after.

Harriet Dart leans on her racket
Harriet Dart missed her opportunities (John Walton/PA)

It was now a test of Dart’s mental resilience but a forehand arrowed down the line moved her 3-0 up before she relinquished her break with another sloppy shot into the net in the fifth game.

The momentum had firmly shifted as Wang broke again and frustration started to boil over for Dart, who sent down a double-fault during the final game before the world number 42 sealed victory with a volley at the net.

Dart admitted: “This one will definitely sting for a long time I think, especially because being here at such a big event and everything that comes with Wimbledon.

“Obviously, being a British player, you want to play well here.

“I feel like I’ve been playing some good tennis in the last few weeks and I’ve put myself in a position where I’ve been getting some good results. I really believed I could do some damage here.

“To lose today, being up twice, is going to sting for quite a while, but this is tennis. Every week you’re dealing with losses. Just have to find a way through it.”