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.
1. Angus Gunn - 7
A few social media comments aimed at the Norwich 'keeper after his poor attempt to keep out Bruno Fernandes' scuffed long-range equaliser may have been hastily deleted as he went on to make three stunning saves. Ensured his rating leapt from 5 to 7 but wasn't enough to earn Scotland a point. | AP
2. Anthony Ralston - 6
The Celtic right-back really had his work cut out against a quality winger as he struggled to handle the pace and trickery of AC Milan's Rafael Leao. Was exposed at times but avoided the type of costly errors that have blighted his recent international performances and mostly stuck to his task well. | AFP via Getty Images
3. Andy Robertson - 6
The Scotland captain was rarely found wanting defensively and drove the team forward down the left on occasions but his final ball could have been better with too many loose passes giving Portugal the chance to counter attack. | AP
4. Scott McKenna - 7
Was going to be Scotland's star man until dropping his crown in the 88th minute. Not the first defender to be outfoxed by Cristiano Ronaldo as he lost the Portugal icon in the box to spoil what had been a towering performance from the Las Palmas centre-back. Stood tallest when Scotland were under pressure with big blocks and clearances - just a pity he couldn't see it out as he was heading for an 8 or even a 9. | AFP via Getty Images