Tomas Berdych punished a wayward performance from Andy Murray to reach the semi-finals of the Monte Carlo Masters on Friday.

The Czech won 6-7 (4-7) 6-2 6-3.

The third-seeded Murray was struggling for most of the match, saving seven break points – including four set points – to edge a tight first set that Berdych let slip.

Murray varied his game to try to stem the Czech’s momentum but overused the drop shot, and sixth-seeded Berdych came back strongly to break Murray’s serve twice in the second set and another three times in the third.

Berdych clinched victory on his first match point with another forehand pass.

The former Wimbledon finalist took his chances and profited from a Murray miscue in a struggle lasting for just over two-and-three-quarter hours.

“I had to stay in the fight after the first set,” Berdych said.

“I had some bad luck in the tiebreaker but my game started getting stronger.

“I hope to keep playing my best tennis on clay,” said the Monte Carlo semi-finalist from 2007 who leads Murray 4-2 in their career meetings.

He next faces top-ranked Novak Djokovic or unseeded Robin Haase.

Djokovic buried his grief to advance to the quarter-finals, just hours after learning of the death in Serbia of his beloved grandfather.

His match, interrupted by rain at the Monte Carlo Country Club, eventually ended with a 2-6 6-1 6-4 win over 16th seeded Alexandr Dolgopolov of Ukraine.

Djokovic was said to be close to grandfather Vladimir and sheltered with him and other family members during the NATO bombing of Belgrade in 1999.

He left the court in silence prompting ATP officials to release a statement which read: “Novak Djokovic would like to ask for your understanding.

“As you know, he lost his grandfather today just before the match, and it was very hard for him to play. After he won, he just felt totally exhausted physically, mentally and emotionally.”

Second seed Rafael Nadal continued the quest for an eighth straight title at the tournament as he dispatched Mikhail Kukushkin of Kazakhstan 6-1 6-1 in exactly one hour.

Nadal will next face Stanislas Wawrinka of Switzerland for a place in the semi-finals.

Fourth seed Jo-Wilfried Tsonga saved nine break points to beat Fernando Verdasco of Spain, the 13th seed, 7-6 (9-7) 6-2.

He was joined by compatriot Gilles Simon, who upset seventh seed Janko Tipsarevic of Serbia 6-0 4-6 6-1.