Che Adams had a last-gasp goal ruled out as luckless Scotland suffered a 2-1 Nations League defeat to Croatia in Zagreb.
Ryan Christie shot the disciplined visitors ahead in the 33rd minute from a tight angle before striker Igor Matanovic levelled three minutes later.
Steve Clarke's side came under increasing pressure after the break and eventually succumbed in the 70th minute of the League A Group 1 encounter at Stadion Maksimir when Andrej Kramaric headed the home side in front.
However, in a dramatic finale, Adams, who replaced Lyndon Dykes after the Scots fell behind, had the ball in the net in the fifth minute of added time, only for VAR to disallow the effort for offside, dealing another blow to the visitors.
The Scots have found the top level of the Nations League a tough task, with defeats to Poland and Portugal in their first two fixtures, and they go into Tuesday's game against the Portuguese at Hampden Park with just one win in 15 - and wondering if their luck will turn.
In mitigation Clarke was left with a depleted squad in Croatia, with over a dozen players unavailable through injury.
He gave a first start to Ben Doak, on loan at Middlesbrough from Liverpool, while 41-year-old goalkeeper Craig Gordon was between the sticks for the first time since November 2022, with Anthony Ralston, John Souttar, Grant Hanley and captain Andy Robertson making up the rest of the defence.
Kenny McLean partnered Billy Gilmour in the middle and Christie started on the left, with Scott McTominay behind lone striker Dykes, preferred to Adams who had struggled all week with illness.
Croatia's talismanic captain Luka Modric, 39, was in his usual midfield berth and there were familiar faces in the home side such as Ivan Perisic and Josko Gvardiol.
There was a bold attempt from Dykes early in the game.
In the sixth minute he robbed Borna Sosa just inside Croatia's half but his audacious long-range shot cleared the bar.
Moments later a Hanley slip allowed Matanovic to run in on goal and, in his quest to win back the ball, he fouled the striker just outside the box, earning himself a booking, with Luka Sucic's free-kick blocked by one of his own players.
There were suggestions that a goal was on its way.
On the half-hour mark Gordon made a good save from Sosa's angled drive before the Croatia attacker headed wide - and then Scotland took the lead.
The lively Doak crossed into the box from the right and a horror mistake by Sucic saw the ball fall back to Christie, who knocked it towards goal from a tight angle, with defender Duje Caleta-Car failing to keep it out.
The lead was short-lived as Matanovic, cleverly picked out by Perisic inside the box, turned and drilled a shot low across Gordon and into the far corner.
Gordon made crucial saves from Matanovic and Modric early in the second half as the home side turned the screw and Sucic thundered a shot past Gordon, but referee Istvan Kovacs had blown for a Scotland foul.
Modric curled a shot just wide in the 65th minute as the visitors were pressed back again and, when Gordon could only parry a powerful drive from Sosa high into the air, Kramaric was on hand to head in.
The goal had been coming and Scotland had to react.
Adams came on for Dykes and Ryan Gauld replaced Doak and moment later Christie raced clear but failed to hit the target.
In a late rally Adams also had an opportunity but lobbed it wide of the far post.
But when he had the ball in the net from close range with seconds remaining it looked like the Scots had salvaged a point, only for VAR to intervene.
Northern Ireland failed to make their chances pay as they were held to a frustrating 0-0 draw by Belarus in Zalaegerszeg, Hungary.
Michael O'Neill's side had two goals ruled out and hit the post, all in the first half, but could not find the goal that would have sent them top of League C3 as their familiar lack of cutting edge proved costly.
Conor Bradley, given the captain's armband, did as he usually does in another display of attacking verve, creating a string of opportunities for his team-mates - Jamie Reid in particular.
But there was to be no reward as Belarus - playing behind closed doors due to UEFA restrictions after Russia's invasion of Ukraine - made it seven clean sheets in their last nine competitive games.
At the other end, 19-year-old goalkeeper Pierce Charles enjoyed a quiet night on his debut, with he and midfielder Shea becoming the 23rd set of brothers to play for Northern Ireland or Ireland.
The group's other match between Bulgaria and Luxembourg also ended 0-0.
Elsewhere, Martin Zubimendi's first goal for Spain fired them to a 1-0 win over Denmark.
The Spanish paraded the Euro 2024 trophy before their first fixture back on home soil since beating England in Berlin this summer.
Zubimendi's 79th-minute strike ensured the Nations League holders then leapfrogged Denmark to top Group A4.
In the group's other match, Nico Elvedi scored an own goal and Aleksandar Mitrovic was also on target as Serbia beat Switzerland 2-0.
Cristiano Ronaldo scored his 11th goal of the season - and his third in three Nations League games - as Portugal won 3-1 in Poland to stay top of a Group A1 also containing Scotland and Croatia.
The 39-year-old put the visitors two up in the 37th minute, following up to convert after Rafael Leao burst forward and fired against the post, taking his record haul of international goals in the men's game to 133.
Ronaldo had earlier flicked an effort against the bar, before Bernardo Silva gave Portugal the lead with a 26th-minute finish.
After Piotr Zielinski pulled a goal back for Poland in the 78th minute, a late Jan Bednarek own goal gave the Portuguese their third.
Roberto Martinez's men extend their 100% start in Group A1 to three wins, while Poland stay third with three points, three behind Croatia.
In Group C2, Romania beat Cyprus 3-0 through goals from Dennis Man, Razvan Marin and Radu Dragusin, while Kosovo were 2-1 winners in Lithuania.
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