It all felt so inevitable as Scotland came within a whisker of a morale-boosting draw in Lisbon only for Cristiano Ronaldo to break their hearts with his 901st career goal.
Scott McTominay shocked the home fans at the Estadio do SL Benfica when he headed the opener in the seventh minute but the home side eventually made sustained pressure count when Bruno Fernandes netted from 20 yards early in the second half.
Scotland came back into the game but the tide turned again and substitute Ronaldo twice hit the post before knocking home a Nuno Mendes cross from close range in the 88th minute to seal a 2-1 win.
It was a third game in a row that Scotland had lost in the closing stages but, just like their opening Nations League A1 match against Poland, there were elements of the performance to admire.
However, with five defeats and three draws, Scotland are now without a victory in their last eight competitive fixtures which is the longest such winless run in their history.
Who were Scotland’s best and worst performers on the night? Here is how each player rated out of 10.
Scotland came back into the game but the tide turned again and substitute Ronaldo twice hit the post before knocking home a Nuno Mendes cross from close range in the 88th minute to seal a 2-1 win.