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.
5. Grant Hanley - 6
Backed by Steve Clarke after his costly error against Poland, the Norwich centre-back can be happy with the way he recovered from a difficult week. No rash challenges in the box this time around and a solid enough display, although not as commanding as his centre-back partner. | AP
6. Billy Gilmour - 7
Another fine display from the Napoli man who showed composure on the ball and an assertiveness to win it back. Protected the back four well and really came into his own during a 15-minute spell of Scotland domination after Portugal equalised. | AP
7. Kenny McLean - 7
Sensational cross for Scotland's opening goal, the Norwich midfielder drifted out of the game for a long spell in the first half before becoming more influential after the break. Seemed to pick up an injury and was replaced with 16 minutes remaining. | Getty Images
8. John McGinn - 5
Battled hard and won a number of crucial free-kicks for Scotland but still not producing the X-factor that he used to bring so regularly for the national side. Not enough quality on the ball or telling contributions in the final third and seemed to be on a different wavelength from his team-mates at times. | SNS Group