Andy Murray of Britain plays a return to Jordan Thompson of Australia during day two of the Queen's Club tennis tournament in London, Tuesday, June 20, 2017.
Meanwhile in Birmingham, two-time Wimbledon champion Petra Kvitova made a winning return to grass with a 6-2, 6-3 victory over her fellow Czech Tereza Smitkova to move into the second round of Aegon Classic.
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. Showing no signs of being intimidated by Raonic's power game, Kokkinakis matched him blow for blow in the first set and held his nerve to win the tie-break.
As Murray struggled to get his shots to travel through the court and delivered a performance riddled with unforced errors world No.90 Thompson took out the match with an ace on his first match point.
This was the world number one's ninth defeat already in 2017 and sixth against an opponent ranked outside the top 20.
Kokkinakis' victory was perhaps the more surprising given that it was the 21-year-old's first ever against an opponent ranked inside the top 10 and came in only his fifth match this year, following a long lay-off with a shoulder injury.
But at Queen's Club on Tuesday, the likeable South Australian put all of that misery firmly behind him as he sent world No.6 Milos Raonic packing 7-6 (7-5) 7-6 (8-6) in the opening round just months after nearly hanging up his racquet.
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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 west London certainly was.
Trailing 6-3 in the second-set tie-break, he saved three set points and, on his third match point, finished off Raonic with a forehand victor.
"It's a big frustration", said Raonic, who failed to convert any of his nine break-point opportunities. Honestly, if this was three out of five [sets] today, it's a scenario I feel even more comfortable in because I really do believe a lot of my game can give me more time to figure out the situation and deal with it a little bit better.
Thompson, 23, reached the final of the Surbiton challenger event last week, but took the first set on a tiebreak and then raced through the second.
"That was 22 months out of the game", Kokkinakis said. "I've been out for so long".
Americans Sam Querrey and Stefan Kozlov, Frenchmen Julien Benneteau and Chardy, and Serbian player Viktor Troicki all advanced to the last 16.
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