Andy Murray’s quest for a sixth Queen’s title is over after shock defeat. 

It’s been an extraordinary day at Queen’s Club.  Here’s a round up of all the matches that took place on Centre Court:

Thanasi Kokkinakis bt. Milos Raonic (7-6, 7-6)

Last year’s runner-up at both Queen’s and Wimbledon Milos Raonic was beaten in straight sets by wildcard Thanasi Kokkinakis.

The number three seed struggled to take control of the game, and failed to claim a single break against the Australian.

Kokkinakis, who is ranked 698th in the world, took the first set after winning the tie-break 7-5.

The second set was just as gruelling, with temperatures reaching up to 40 degrees on court.

Raonic dropped three set points to rub salt into the wound, with Kokkinakis winning the second set tie-break 10-8.

This defeat will be difficult for the world number six to shrug off ahead of Wimbledon, but for the 21-year old Aussie, this was a massive win after 18 weeks out through injury.

Feliciano Lopez bt. Stan Wawrinka (7-6, 7-5)

Three-time major winner Stan Wawrinka suffered a shock straight sets defeat at the hands of tour veteran Feliciano Lopez.

Once again, it proved difficult for the player returning the serve, with no breaks in the opening set.

Lopez, who came out on top 7-4 in the tiebreak, won the first set with a superb forehand across court that caught second seed Wawrinka.

The first break of the day came in the final game of the second set, with the Spaniard winning 7-5.

Wawrinka, who lost the French Open final against Rafael Nadal less than 2 weeks ago, has now lost in the first round at Queen’s for the second year running.

Jordan Thompson bt. Andy Murray (7-6, 6-2)

The biggest shock of the day saw defending champion Andy Murray crash out to Australian Jordan Thompson in straight sets.

The world number one became the latest top seed to struggle returning the serve, but seemed to have an off-day in all departments. His serve wasn’t as quick as it has been and his forehand let him down on numerous occasions.

Thompson, who replaced the injured Aljaz Bedene, won the first set by winning the tie-break 7-4.

The world number 90 then double-broke the five-time Queen’s champion, and won the second set 6-2.

Murray’s preparation ahead of his Wimbledon defence has taken a major setback with his early exit, but for Thompson it was the biggest win of his career.

Marin Cilic bt. John Isner (7-5, 6-3)

Number four seed Marin Cilic is now the favourite for the Queen’s title after he beat John Isner in straight sets.

The Croatian won this tournament back in 2012, and was very sharp on the court. He crucially broke Isner in the opening set and win it 7-5.

Cilic, who is currently ranking in at world number 7 ahead of Wimbledon, then made light work of the second set, winning it 6-3.