Andy Murray saved match points before taking a 6-2, 6-4 loss to Illya Marchenka on Sunday at the Biella Challenger in Italy.
The minor-league event staged in the home city of the Fila clothing empire was the Scot’s only alternative after missing special player flights to Australia a month ago.
Murray came up with a positive COVID-19 test and was barred from heading to the Australian Open.
Biella will hold a second Challenger next week in which the three-time Grand Slam winner is also entered.
Murray was top seed this week on a wild card entry.
He saved a match point in the penultimate game against Marchenko and another a game later before the No. 212 finally prevailed in 90 minutes.
Marchenkoa hit nine aces to three for Murray and broke the Scot three times while never facing a challenge to his own serve.
Murray’s appearance was his first tournament since October during a COVID-hit season in which the 33-year-old still finding it tough going after his two hip surgeries played only seven official Tour matches.
He defeated Marchenko in both of their previous Tour matches, played at the Australian Open in 2011 and 2017.
Murray benefitted from a special Italian COVID-19 entry dispensation for athletes coming from outside the EU.
Brexit border problems will now dodge him for the rest of his career as a result of the controversial 2016 exit vote which is already starting to have serious consequences for go-it-alone Britain.