Scotland's first outing since ending a 28-year wait to qualify for the World Cup ended in defeat as Junya Ito's late strike earned Japan a 1-0 win at Hampden Park.
In a stark contrast to the jubilant scenes that accompanied a thrilling 4-2 victory over Denmark in November to secure the Tartan Army's trip to North America, a subdued atmosphere contributed to a tame encounter.
Japan had left a number of their key men, including Ito, on the bench in preparation for Tuesday's clash against England at Wembley.
But they continued their impressive form in friendlies since securing qualification a year ago, which includes a first ever win over Brazil in October, as Ito scored the only goal six minutes from time.
Scott McTominay had Scotland's best chance of the match inside the opening 10 minutes, but the Napoli midfielder's effort was brilliantly saved by Zion Suzuki.
Japan then slowly began to take control to extend Scotland's miserable record of not having won a home friendly for the past 10 years.
"To lose it on the goal that we lost is disappointing. The game at that stage looked like it was going to peter out to a 0-0 draw," said Scotland boss Steve Clarke.
"We played a lot of good stuff and I think we can be a bit more progressive to get to the top end of the pitch, but against top opposition sometimes that's difficult."
Angus Gunn made a fine save from Ito when the Genk forward ran clear on goal just after the hour mark.
Gunn faces a battle with 43-year-old Craig Gordon to be Clarke's No 1 for Scotland's opening game of the World Cup against Haiti on June 14.
The Nottingham Forest 'keeper did himself few favours in that debate for the winning goal, though, as he went to ground too early and allowed Ito's tame effort to trickle into the net.
Scotland are back in action on Tuesday when they face the Ivory Coast at Everton's Hill Dickinson Stadium and have one more outing at Hampden against Curacao in June before travelling across the Atlantic for the World Cup.