Scotland's hopes of winning through to the knockout stages of a major tournament for the first time ended with a sobering 3-1 Euro 2020 defeat by Croatia at Hampden Park.
The Scots, playing in their first major tournament since the 1998 France World Cup, needed a victory in their final Group D fixture to reach the last 16 but despite a big effort fell short again.
Attacker Nikola Vlasic drove in the opener for Croatia in the 17th minute before Callum McGregor gave Steve Clarke's side encouragement with a leveller three minutes from the break, with his first international goal.
But just after the hour mark, captain Luka Modric restored Croatia's lead with a stunning strike from 20 metres.
Then Ivan Perisic headed in a third in the 77th minute to seal the win and take the Croats through, while Scotland finished bottom of the section with one point.
The Scots had not lost to Croatia in their previous five meetings and were hoping to make their own football history.
Clarke made one enforced change to his side.
Midfielder Stuart Armstrong came in for Billy Gilmour, 20, who was ruled out after testing positive for Covid-19 after his first start, against England at Wembley on Friday night.
Vlasic, Josip Juranovic, Bruno Petkovic and Marcelo Brozovic returned for Croatia.
The Scots roared into the game, winning their first corner within 10 seconds and their second on the back of it, trying not to let their opponents settle.
In the sixth minute attacker Che Adams just missed an in-swinging John McGinn cross by inches, with Croatia keeper Dominik Livakovic punching clear for another corner that was repelled.
Adams drove wide from long distance and it was all looking positive for the Scots until they fell behind.
Perisic climbed high above right-back Stephen O'Donnell at the back post to head a deep cross from Juranovic down to Vlasic and he took a touch 10 metres out before firing past defender Scott McTominay and keeper David Marshall.
Scotland suffered another blow in the 33rd minute when centre-back Grant Hanley went off injured to be replaced by Scott McKenna, who was booked seconds later for a foul on Petkovic.
Croatia were dominating the ball and dictating the play but with three minutes of the first half remaining they found themselves pegged back.
Captain Andy Robertson's cross was only half-cleared to the edge of the box by Domagoj Vida and McGregor took a touch and stepped on to it.
The national stadium held its breath for a moment before the Celtic midfielder drilled it low past the despairing Livakovic.
Croatia were first to threaten after the break and Marshall had to be quick out of his goal to foil defender Josko Gvardiol, who burst through the middle of the Scots rearguard.
Moments later, the Scotland keeper made another save from Perisic, who was then flagged offside, before McGinn failed to get a proper connection on an Armstrong cross just a yard from goal.
But in the 62nd minute, Scotland were back to square one and staring at the exit door.
As slick-moving Croatia penned the dark blue jerseys into their own box, Mateo Kovacic set up Modric who curled the ball from 20 metres with the outside of his right foot past Marshall, who had no chance.
Ryan Fraser replaced Armstrong in the 69th minute but there was more woe to follow when Perisic rose above Kieran Tierney to head Modric's corner in off the far post.
It was effectively over for the Scots and their fans, who will return to their armchairs to watch the rest of the tournament.