Andy Murray suffered a 4-6, 7-5, 6-2 defeat to second-seed Grigor Dimitrov in the first round of the Brisbane International on Monday, beginning what could be his final season on a sour note.
The three-time Grand Slam champion told the BBC ahead of the match -- his first singles contest since October -- that he would likely retire if he is "not enjoying" tennis this season, having won just two matches in his final five events last year as he struggled with shoulder and knee injuries, as well as an illness.
Murray won a tight first set that saw both players hold serve in the opening nine games of the match until an error-strewn service game from Dimitrov allowed the Brit to take the lead.
However, Dimitrov wrestled back control toward the end of the second set, breaking Murray twice to edge the set 7-5. The final set was more straightforward for Dimitrov as he broke Murray twice in the first three games and raced to victory.
The result ends any chance that Murray, ranked world No. 42, would be seeded for the upcoming Australian Open, which begins on Jan. 14.
Murray won his first Grand Slam title at the US Open in 2012 before becoming the first British man since Fred Perry in 1936 to win Wimbledon when he lifted the trophy in 2013. He won the Wimbledon men's singles championship again in 2016. He also has two men's singles Olympic gold medals.