LONDON (AP) — Top-ranked Andy Murray headed a list of high-profile departures in the first round at Queen's on Tuesday, with the Wimbledon champion losing to a player who found out he was competing only on the morning of the match.

Murray put in a sloppy and error-prone display in losing to 90th-ranked Jordan Thompson 7-6 (4), 6-2, joining Stan Wawrinka and Milos Raonic in getting eliminated on a day of shocks at the Wimbledon warmup event. They were the top three seeds.

Thompson, who lost in the final round of qualifying on Sunday, stepped up to play Murray following the withdrawal early Tuesday of Aljaz Bedene because of a wrist injury. Thompson played the match of his life — but was given a helping hand by the erratic Murray, the defending and five-time champion in west London.

The Australian sealed victory with an ace down the middle.

"Definitely the biggest win of my career," Thompson said.

"Yesterday, I was sitting around, hoping to be able to get a game," he added, "but there weren't too many matches yesterday. I was always coming in, trying to sign in, and here I am in the draw. I'm so lucky."

It was Murray's first loss at Queen's since 2014, ended his 14-match winning run on grass dating to 2015, and is a setback to his preparation for Wimbledon, which starts on July 3.

"It's a big blow, for sure," said Murray, whose forehand was particularly errant and had a first-serve percentage of just 55. "It has happened in the past where guys haven't done well here and gone on to do well at Wimbledon.

"There is no guarantee that I won't do well at Wimbledon, but it certainly would have helped to have had more matches."

Both of Murray's titles at Wimbledon, in 2013 and '16, came after winning Queen's.

The second-seeded Wawrinka was beaten by big-serving Feliciano Lopez 7-6 (5), 7-5, with the Spanish player sealing victory off a net cord from a sliced backhand return.

Wawrinka, the runner-up to Rafael Nadal at the French Open, appeared to be struggling with a left knee injury in the second set.

While Wawrinka's exit wasn't too much of a surprise, given Lopez's recent form and liking for grass, the early departure of third-seeded Raonic in the first match on Centre Court certainly was.

Last year's runner-up at Queen's and Wimbledon — both times to Murray — lost 7-6 (5), 7-6 (8) to No. 698-ranked Thanasi Kokkinakis, who was playing only his sixth singles since November 2015 because of injury problems.

It was the first win over a top-10 opponent for the Australian, who trailed 6-3 in the second-set tiebreaker but won on his third match point with a backhand winner into the corner.

"It's a big frustration," said Raonic, who failed to convert any of his nine break-point opportunities. "Obviously it would have been a lot easier scheduling everything if I was to be here and have many more matches ahead of me."

Kokkinakis played only one match in 2016 because of a shoulder problem, and missed most of this year because of an abdominal injury. He returned to action in May and played three events before Queen's, with his ranking as low as No. 993 only last week.

"It's everything. It's huge for me," Kokkinakis said. "I've been out for so long."

Fourth-seeded Marin Cilic is the top player left in the field after beating John Isner 7-5, 6-3

Americans Sam Querrey and Stefan Kozlov, Frenchmen Julien Benneteau and Chardy, and Serbian player Viktor Troicki all advanced to the last 16.