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.
9. Ryan Christie - 7
So industrious down the right, gave Scotland an outball on numerous occasions with mazy running carrying the ball deep into opposition territory. Only thing lacking was a final product although was unlucky to see a second half goalbound shot blocked. | AP
10. Scott McTominay - 8
Underlined his status as Scotland's most important player with a terrific headed opener for his 10th goal in his last 17 caps. A powerhouse in midfield, his driving runs were the platform for Scotland to turn defence into attack. Claims our star man award after Scott McKenna's late error. Where would we be without him? | AP
11. Lyndon Dykes - 6
Made life uncomfortable as he could for the Portugal defence with his work-rate and endeavour, and held the ball up well at times, but another cap goes by with little goal threat from the Birmingham City man. | Getty Images
12. Substitutes
Ryan Gauld and Tommy Conway were brought with 16 minutes remaining but did not manage to make notable contributions. Lewis Morgan and Ben Doak arrived on 87 and 90 minutes respectively but no time to make an impact. | AP