Richard Gasquet sent French Open champion Stan Wawrinka flying out of Wimbledon on Wednesday, winning the battle of the slingshot backhands 6-4 4-6 3-6 6-4 11-9 to reach the Wimbledon semi-finals for the second time.

Wawrinka, bidding for a rare French Open and Wimbledon double, looked out of sorts from the first set, spraying his groundstrokes uncharacteristically long and wide on a breezy Court One and failing to tame the stinging backhand of the 21st-seeded Gasquet.

The Frenchman served two double faults to gift Wawrinka the second set after which the powerful Swiss rediscovered some range and began spraying winners off both sides of the court.

He broke Gasquet’s serve in the fourth game of the third set, found his own booming serving rhythm and fearsome backhand bullet and wrapped up the set with a forehand winner.

But Gasquet, no slouch on grass after reaching the semi-finals here in 2007 and twice winning Nottingham, hung on with consistent shot-making and waited for more errors. They came at 4-5 on Wawrinka’s serve and the Swiss produced his first double fault to send the match into a fifth set.

They were the first sets Wawrinka had dropped in the tournament so far and it was a battle of nerves and scintillating tennis that took the pair deep to an 83 minute fifth set.

Gasquet had the advantage of serving first and Wawrinka saved two match points before sending his famed backhand long and bowing out.

Gasquet will meet No 1 seed Novak Djokovic in Friday's semi-finals after the defending champion beat Marin Cilic on a comfortable 6-4 6-4 6-4 scoreline on Centre Court.

Djokovic had not lost a match to the Croat and his unbeaten record never looked in danger against the US Open champion who failed to master the Serb’s precise groundstrokes.

The holder made it into his 27th Grand Slam semi with his 50th win at Wimbledon, only the seventh man to reach that number of victories, and was surely relieved to have an easy time of it.

The Serb had to recover from two sets down in the last 16 against South African Kevin Anderson but his crisp passing shots ensured big-serving ninth seed Cilic never got a look in.

Djokovic broke in the third game of the first set, the ninth game of the second set and the seventh game of the final set to wrap up victory inside two hours on a cool London evening.

Andy Murray stayed on course for the title but was made to work hard for a 6-4 7-5 6-4 defeat of Canada's Vasek Pospisil.

A match that started under grey skies and finished under Centre Court’s roof because of rain showers was never straightforward for the third seed but his Grand Slam pedigree told in the important moments.

Cheered on by a full house, Murray broke serve in the third game of the match and was leading 3-1 when light rain forced a suspension of play.

On the resumption Murray resisted some eye-catching tennis from the quarter-final debutant but moved a set ahead when 25-year-old Pospisil netted a forehand.

Another rain break in the second set with Murray down 4-3, which this time prompted the roof to close, seemed to unsettle Pospisil and he dropped serve at 5-5 when he was left floundering at the net by a dipping Murray backhand.

Murray pressed hard in the third set but Pospisil did not crack and even when Murray served for the match at 5-4 Pospisil earned his first break point of the match.

He could not take it though and Murray secured the win with a rasping forehand on his second match point to reach his sixth Wimbledon semi-final where he will face seven-times champion Roger Federer who thrashed Frenchman Gilles Simon.

“I thought I played some good stuff but he served very well,” Murray said moments after securing his 150th Grand Slam match win. “I hope I can get to another final but it’s going to be another tough one on Friday.”

Federer was at his regal best as he floated into the last four with a silky 6-3 7-5 6-2 win over Simon.

Federer was broken for the first time at this year‘s championships but apart from that blip he did not put a foot wrong as he reached his 37th Grand Slam semi-final, and 10th at Wimbledon.

Federer beat Murray to win the 2012 title, the last of his 17 Grand Slam titles.

Such was the seven-times champion’s command of the match that the only thing that could halt the Swiss second seed’s charge was two separate 40-minute rain breaks on No 1 Court.

Simon did earn some bragging rights for finally breaking the Federer serve after 116 successive holds, stretching back to the first round of last month’s Halle Open.

Otherwise, he could only watch in wonder at the winners flying off the Swiss maestro’s strings.

“(My) reaction was always going to be important once the streak ended and the serve was broken,” said Federer.

“I was able to do that because Gilles is a quality return player. The game I got broken, he was too good so no problem to accept that,” added the Swiss, who fired down 11 aces and 36 winners during the dazzling 95-minute exhibition.

The world number two broke Simon once in the first set, twice in the second and twice more in the third as he rolled on towards a sixth successive win over the luckless Frenchman.

A high backhand volley dinked away at the net ended Simon’s hopes of reaching his first Grand Slam semi-final.

“The stop-and-goes are tough as you never know how you are going to come back from them but I used them to my advantage,” said Federer of the rain delays.

“The breaks actually helped me rather than hindered me, I am very happy to have managed the conditions.”