Cristiano Ronaldo grabbed the winner as Scotland suffered more late misery in their UEFA Nations League Group A2 encounter against Portugal in Lisbon.
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 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 match against Poland, there were elements of the performance to admire.
Clarke’s side forced some early corners and they took the lead after Andy Robertson teed up Kenny McLean to whip in a dangerous cross. McTominay timed his run to perfection as he sneaked round the back of the home defence to head home from six yards.
The half-time whistle was welcome relief but Scotland came back out to the sight of Ronaldo stripped for action and looking to add to the 900th career goal he netted against Croatia.
The equaliser came in the 54th minute when Leao set up Fernandes to sweep in a first-time strike from 20 yards which spun away from Gunn and into the corner of the net off the goalkeeper’s hands.
Ronaldo was firing shots from all angles but Scotland suddenly started to get the ball down and play and got their first efforts at goal since the opener. The hosts had already notched 20.
Joao Felix looked certain to score when Ronaldo set him up with a backheel but Gunn threw out a leg to block the Chelsea player’s shot.
Gunn pulled off an even better stop from Felix’s header before Ronaldo fired the rebound off the outside of the post before heading against the other upright moments later.
But the 39-year-old was soon on hand to net the winner and Scotland could not work the goalkeeper as they pressed for an equaliser.
In the same group, Luka Modric scored his 27th international goal on his 180th cap as Croatia beat Poland 1-0 in Osijek to hand his side their first points of their Nations League campaign.
Elsewhere in League A, Spain were 4-1 winners away in Switzerland despite playing for more than 70 minutes with 10 men, with Fabian Ruiz scoring twice for the European champions.
The Paris St Germain midfielder netted in the 13th minute, turning the ball home after Nico Williams' shot was saved, to double his side’s lead after Joselu’s early header had broken the deadlock in Geneva.
Robin Le Normand was then sent off before Zeki Amdouni pulled one back for the hosts before half-time.
Ruiz scored his second in the 77th minute, then Ferran Torres also netted late on to complete the rout.
Denmark maintained their perfect start to the competition thanks to a goal in each half from midfielder Albert Gronbaek and Yussuf Poulsen as they eased to a 2-0 win at home to Serbia.
In League C, Northern Ireland went down to a 1-0 loss in Plovdiv against Bulgaria, a mistake by goalkeeper Bailey Peacock-Farrell gifting the home side the winning goal in the second half.
A poor pass out intended for Daniel Ballard was intercepted by Bulgaria's Aleksandar Kolev who squared it for Kiril Despodov to tap in at the far post and condemn Michael O’Neill’s side to defeat.
Belarus were 1-0 winners away in Luxembourg in the same group thanks to Valery Gromyko’s second-half goal.
Newcastle’s Alexander Isak scored as Sweden ran out 3-0 winners at home to 10-man Estonia in C1, with Viktor Gyokeres scoring twice, whilst Slovakia defeated Azerbaijan 2-0.
Gibraltar were denied victory over Liechtenstein in League D by a goal scored in the 14th minute of stoppage time, Nicolas Hasler’s penalty snatching a 2-2 draw after Manchester United’s James Scanlon’s 97th-minute goal looked to have won it.
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