Scotland conceded soft goals either side of the break to slip to a friendly defeat against Turkey in Diyarbakir.
It was a just third loss in 16 for Steve Clarke’s side, who looked shaky defensively in the first meeting of these nations in 62 years.
Ozan Kabak got between two defenders to head in a free-kick, before Cengiz Under finished a smart break after Stuart Armstrong coughed up possession.
Aston Villa midfielder John McGinn gave the Scots hope but his stunning strike was mere consolation.
Indeed, for all that the visitors rallied and might have had a penalty when Lyndon Dykes was wrestled in the box, the Turks could have been out of sight before then.
Ranked five places behind Scotland in 45th spot, they struck the frame of the goal and were denied on several occasions by Craig Gordon on his 700th senior appearance.
One bright spot for the Scots was a debut for Liverpool’s 19-year-old right-back Calvin Ramsay, who Clarke opted not to use from the start.
“A fantastic John McGinn goal as he normally gets for us and that changes the dynamic of the game,” said Clarke afterwards.
“Turkey had to be a little more cautious, we had some moments but we couldn’t get the equaliser.
“When you look at the penalty incident, it was a clear penalty and why it’s not given I do not know. On the flip side, when Stuart [Armstrong] went down on the edge of the box, I don’t think it was a foul and Turkey score from the counter-attack off that. I would have liked the penalty, to be honest!
“Young Calvin (Ramsay) gets his first cap, which is great for him and it was a tough night for him. He gave us a little bit more defensive stability. Lewis Ferguson came off the bench and was very good. There are positives to be taken from the game but the overriding feeling is disappointment that the four game unbeaten run comes to an end.”