Cristiano Ronaldo’s late Nations League winner broke Scotland hearts in Portugal and ensured Steve Clarke’s side’s dreadful run of form continued.
The visitors took a shock seventh-minute lead thanks to a Scott McTominay header and performed admirably in repelling Portugal’s 16 shots before the break.
Another individual error robbed them of the lead though, when Angus Gunn allowed Bruno Fernandes’ long-range strike to creep into the net after the break.
Ronaldo was introduced at half-time and twice hit a post before finally breaking the barricades, forcing in a delicious Nuno Mendes cross for his 901st career goal.
The defeat – after losing to Poland on Thursday – means Scotland are now without a win in their last eight competitive games, the worst run in their history, and have won just one of the last 14 games.
However, Clarke can take some encouragement from the nature of the performances in the two games in this window, even if they are bottom of their section after Croatia beat Poland 1-0.
Scotland hold firm… but only for so long
With the exception of McTominay’s bullet header, it felt like the entirety of the first half was played in Scottish territory.
Rafael Leao terrorised the left-hand side, creating five fantastic chances either for himself or a team-mate.
Gunn made two fine saves – one from Leao and another from Liverpool forward Diogo Jota – while watching a few other shots fly inches wide.
Every Portuguese roar made Scotland fans wince but the defence somehow stood firm until the break – battered, bruised and punch-drunk but unbreached.
That was until Portugal’s first real chance of the second half.
A tame cutback was somewhat scuffed by Fernandes, but Gunn could only palm into his own net. Another individual error to add to a montage from Scotland’s recent performances.
Scotland responded well, though. There were penalty shouts from Billy Gilmour and Ryan Christie – both correctly not given – while McTominay thundered a shot into Diogo Costa’s midriff.
That was as good as it got for the visitors, though.
Portugal pushed again, led by Ronaldo. His backheel flick unlocked the Scottish defence and put Felix through on goal, but Gunn made amends with a superb save.
Three minutes later, Felix almost scored again with a diving header but Gunn was there again to deny him. Ronaldo hit a post on the follow-up, hitting the upright again in the next phase of play with a fantastic looping header.
Scotland did not heed the warning.
Mendes’ teasing cross evaded Jota at the front post, took out Gunn in the middle and was bundled home by a jubilant Ronaldo – his 132nd Portugal goal celebrated just like his first.
Ronaldo makes difference as numbers add up
From the outset, Scotland were up against it.
Penned back on the edge of their own box, they were forced into playing a back six at times as Bernardo Silva and Fernandes tried to pick holes in the defence.
The Scots stood strong in that low block though. Bodies were thrown on the line but extreme caution was used when tackling after two penalties were conceded on Thursday against Poland.
One problem was ball retention. When Scotland did win the ball, they rarely kept it for very long and struggled to hit either McTominay or Lyndon Dykes.
Occasionally though, they were able to string a passing move together and get it up the pitch.
Another issue for Clarke is the nagging, inevitable feeling they will eventually concede.
That’s now 33 goals shipped in 14 games. In the last six, they have been breached after the 85th minute on five occasions. There is a fragility that needs to be addressed.
There’s also the small matter of this winless run: they are now without a victory in their last eight competitive fixtures, the longest such run in their history.
With four tough fixtures to come in the Nations League – Croatia home and away, Portugal at Hampden plus a trip to Poland – it doesn’t look like ending soon.
As for Ronaldo, what can you say? Maligned after a poor Euros, he was influential here.
He has now scored against 48 different countries and stretched his lead at the top of the all-time international goalscorer chart in men’s football.
Surely no-one can catch him.