Andy Murray long-awaited return to competitive tennis ended in 6-2, 6-7 (4), 5-7 defeat to Nick Kyrgios at the Fever-Tree Championships on Tuesday.
Despite a fast start which saw Murray claim the first set 6-2 with relative ease, he was made to work for rest of the game which saw him lose a tie-breaker second.
The third set followed with more of the same from Murray, who despite playing with his usual intensity throughout the the entire game, couldn't cope with Kyrgios' forehands which were utlised with pinpoint accuracy.
Earlier in the day, Novak Djokovic set up a second-round match against Grigor Dimitrov at the Fever Tree Championships after beating John Millman 6-2 6-1.
Despite it being his first tournament at London's Queen's Club in eight years, Djokovic cruised to victory against the Australian in just 65 minutes.
He dominated the game from start to finish in one of his better performances since his return from injury earlier this year.
No. 2 seed Dimitrov is into the second round after beating Bosnia's Damir Dzumhur 6-3, 6-7 (4), 6-3.
The Bulgarian -- who won the Queen's title in 2014 -- had to work hard in the first-round match, finding himself a break down at the beginning of the third set after losing the second set tiebreak.
Returning to London for the first time since winning the ATP World Tour title at the O2 Arena in November, Dimitrov rallied and broke straight back to level up the set, and closed out the match in two hours, three minutes to book a place in the second round.
Former Wimbledon finalist Milos Raonic is also through after his opponent, India's Yuki Bhambri, retired with a knee injury in the second set with Raonic ahead 6-1, 3-1.
Elsewhere, No. 3 seed Kevin Anderson fell at the first hurdle, losing to Argentine Leonardo Mayer in three sets, while No. 4 seed David Goffin also lost to Feliciano López in three sets.
Kyle Edmund gave the British fans somethong to cheer about following Murray's defeat as he beat Ryan Harrison in two sets. He will now face Kyrgios in the next round.
However, fellow Brit Dan Evans lost 4-6, 6-0, 5-7 to Adrian Mannarino on court one.