Patrik Schick's double either side of half-time, including an astonishing second from the halfway line, spoiled Scotland's Euro 2020 Group D opener as the Czech Republic ran out 2-0 winners at Hampden Park.
The Bayer Leverkusen striker's brilliant header put the visitors ahead three minutes before the break, albeit slightly against the run of play.
However, Schick doubled his side's lead with an outrageous effort seven minutes after the break - his 11th and 12th goals for his country - the forward somehow beating David Marshall with a shot from just inside Scotland's half after a counter-attack by the hosts broke down.
As a result, having waited 23 years to appear in the finals of a major tournament, Scotland will now have to wait a little longer to pick up their first points after this disappointing Group D loss.
How Schick brought Scotland back down to earth
Schick scored one of the greatest goals in the long history of Hampden as the Czech Republic dealt a huge blow to Scotland's hopes of qualifying for the Euro 2020 knockout stages.
His sensational shot from more than 45 yards looped over the back-pedalling Marshall early in the second half, and knocked the stuffing out of Steve Clarke's team on their long-awaited return to major tournament football.
Without the injured Kieran Tierney, Scotland played with poise for much of the first half, and came close through Andy Robertson and Lyndon Dykes, but fell behind after 41 minutes when they failed to deal with a Czech cross, which Schick classily headed past Marshall.
Schick's sensational second sandwiched a period of intense Scottish pressure, as Jack Hendry hit the crossbar and Dykes and Stuart Armstrong both came close, but ultimately they were outclassed in the key moments.
The Czechs should have scored more than just two; Schick could have had a hat-trick, and Marshall made a stunning save from Michael Krmencik late on, as they cruised comfortably to the top of Group D.
Scotland must now recover and prepare to travel to Wembley to face England on Friday, when the Czech Republic face Croatia at Hampden - but already it looks a difficult task for Clarke's side to qualify for the last 16.
The defeat proved to be a major let down after the raucous build-up, 23 years on from the men's national team's last game at a major tournament. This was the largest crowd to attend a match in Scotland since the suspension of football last March due to Covid-19, and those lucky enough to be present made the grand old stadium rock with noise from over an hour before kick-off.
The years of hurt following numerous failed qualification campaigns were forgotten as the Tartan Army roared their approval at the sight of their heroes during the warm-up, whilst the Czechs were roundly booed.
The national anthem was spine tingling - the main concern was whether the Scottish players could channel their emotions into producing a positive result.
Scotland suffered a huge blow before kick-with the news that Arsenal defender Tierney was ruled out, as Liam Cooper started in defence alongside Grant Hanley and Jack Hendry. Marshall started in goal ahead of Craig Gordon, while in midfield Callum McGregor missed out on his 28th birthday to Stuart Armstrong, with Ryan Christie preferred to Che Adams as the chief support for Dykes.
Tierney's absence was at first glance a massive deflation for Scottish hopes, given his form for Arsenal this season and his attacking drive from the back. Despite this setback, Scotland started brightly with some neat early link-up play between Christie and Robertson nearly fashioning a chance in the opening minutes.
Indeed it was all Scotland early on, as the Czechs struggled to get out of their own half. John McGinn burgled Tomas Kalas and had a sight of goal on the angle, but the defender recovered quickly to force a corner, which was easily cleared. Scotland looked crisp in possession and sharp to loose balls, while their opponents took time to settle.
When they did, they nearly scored. McGinn was bundled over but the referee waved play on, and Jakub Jankto cut the ball back for Schick whose powerful drive was smartly dealt with by Marshall at his near post. It was a major warning, but Scotland responded immediately. Armstrong fed Robertson on the left and his cross was poked wide by Dykes.
The sense of importance of this game to both sides hung in the Hampden breeze; after Croatia's defeat to England, this was a massive opportunity for each to take a giant step towards the knockout stages, and one could almost feel ripples of tension amongst the supporters as they fell quiet.
A pattern had been set; Scotland were seeking Dykes at every opportunity in the hope of finding runners around him, while the Czechs had become comfortable on the ball without really looking like cutting the Scots open. A stalemate had ensued.
The Scots needed a spark, and Robertson nearly provided it; Christie found him in acres of space, but the captain's curling shot was tipped over by Tomas Vaclik.
Scotland were finding increasing joy in the wide areas, and Robertson again threatened with a teasing cross that saw blue shirts queuing up, but Kalas headed it clear. Hanley raised the roof as he ran down Jankto like a rampaging buffalo, and the fans' spirits were lifted once more.
Czech pressure had been rare, but they forced three successive corners shortly before half-time, and the third yielded a goal. Vladimir Coufal was given space from the clearance to cross from the right, and Schick got himself between Hanley and Cooper to glance a beautiful header past Marshall into the far corner. It was barely deserved, but a striking masterclass from the Leverkusen forward.
Scott McTominay tried to respond, but his lung-bursting run was halted in the box by Jan Boril - judged fair after a VAR check - and Scotland's players went into the break with shoulders slumped. Clarke responded at the break by withdrawing Christie for Che Adams, in the hope of providing Dykes with more support.
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Forty-five seconds after the restart, Schick nearly had his second, but Marshall beat away his fierce drive as the Czechs swept through the midfield; Vladimir Darida then forced an even better save from the goalkeeper at his near post.
The game was in danger of getting away from Scotland, but in a frantic few moments, they suddenly became a threat again. Robertson's teasing cross was cleared to Hendry, who curled a delicious shot over Vaclik but against the crossbar.
The Czech 'keeper had to be at full stretch to tip away Kalas's miskick as it headed towards goal. It was a fabulous piece of athleticism, and well timed, as Schick then produced a moment of magic to crush Scottish hopes.
Kieran Tierney was the surprise absentee from the Scotland line-up. The Arsenal left back was expected to be one of the Scots' key men, but there was no sign of him in the matchday squad, with Jack Hendry, Grant Hanley and Liam Cooper making up the back three. Callum McGregor paid the price for some low-key displays in last week's friendly clashes against Holland and Luxembourg as he dropped to the bench as Clarke opted for a cautious approach, also leaving out Nathan Patterson, Billy Gilmour and Che Adams from his starting line-up. Tried-and-trusted servants like Stephen O'Donnell, Stuart Armstrong and Lyndon Dykes got the nod to start.
With Scotland pressing high, they lost possession and Schick gathered just inside of his own half. He spotted Marshall off his line, and launched a magnificent left-footed shot that spiralled over the flailing goalkeeper and into the top corner, with Marshall helpless as he fell into the back of the net.
It was reminiscent of spectacular efforts of the past, from David Beckham and Charlie Adam and more recently Kemar Roofe - and perhaps even better than Zinedine Zidane's magnificent goal on this ground for Real Madrid in the 2002 Champions League Final.
Scotland now needed a miracle. Armstrong's low drive was deflected by Kalas and dipped agonisingly on to the roof of the net with Vaclik beaten.
Adams then headed it on for Dykes, who was denied at the near post by a smothering stop and the QPR striker also passed up a golden chance at the back post, as Vaclik stuck out a telescopic leg to divert the ball clear.
Ryan Fraser, McGregor, Kevin Nisbet and James Forrest were sent on as reinforcements as Scotland became increasingly desperate. Forrest nearly made an immediate impact as he jinked past two defenders, but once again the shot was deflected behind by last-ditch tackling.
Too often Scottish crosses failed to find their target, and indeed they nearly conceded a third as Krmencik was denied by Marshall, after another defensive mistake.
Boos rang out at full time, and Scotland's players sank to their knees as the sun finally made an appearance at Hampden - a desolate afternoon for the Tartan Army, and one that has given Clarke some serious thinking to do ahead of Friday's titanic game at Wembley.
- Czech Republic earned their first win against Scotland since October 2010, ending a run of one draw and three defeats against the Tartan Army in all competitions.
- Scotland have lost their opening match in five of their last six appearances at a major tournament (EUROs and World Cup), failing to score on five occasions in that run.
- Scotland have failed to score in five of their seven matches at the European Championship, with the exceptions being a 3-0 win vs CIS (1992) and a 1-0 win against Switzerland (1996).
- There were just 12 fouls conceded in this match (six each), the lowest total on record in a single match at the European Championship (since 1980).
- Czech Republic's Patrik Schick has been involved in 10 goals in his last nine international starts in all competitions (8 goals, 2 assists).
- Patrik Schick became the first player to score a brace for Czech Republic at a major tournament since Tomas Rosicky in the 2006 World Cup (vs USA). He's the first Czech player to score a brace at the European Championship since Milan Baros in 2004 (vs Denmark).
- At 49.7 yards, Patrik Schick's second goal for Czech Republic was the furthest distance from which a goal has been scored on record at the European Championship (since 1980).
- At 36 years and 101 days, goalkeeper David Marshall became the second oldest player to appear for Scotland at a major tournament (World Cup and EUROs), after 39-year-old Jim Leighton played in all three of their games at the 1998 World Cup.
Scotland boss Steve Clarke: "We came here to be competitive, I think we were competitive in the game. Sometimes a match doesn't go your way, today was that day," he said.
"I don't think there was much between the two sides, if I'm honest. If you look at our possession, our attempts at goal, we weren't quite clinical enough at the right time.
"The breaks went against us at the wrong time. Losing a goal five minutes before half-time from a set play was disappointing, we normally defend that quite well.
"We came out for the second half and started quite well. Jack hit the bar, and had another shot which got blocked, fell to their striker, and he produced a marvellous finish. From there it becomes a difficult afternoon.
"We showed good invention, chances to get back into the game and if we make it 2-1, it's a different afternoon. I'm disappointed, but ready for the next one."
The Bayer Leverkusen striker has long been held up as the future of Czech football and at Hampden Park on Monday, he showed exactly why with two eye-catching goals of differing quality.
His first, a clever glancing header into the far corner of the net broke the game open and gave the visitors a slightly undeserved half-time lead, while his second could already be the goal of the tournament.
Seeing goalkeeper David Marshall off his line as a Scotland attack broke down, the 25-year-old found the roof of the net from just inside the hosts' half, a breathtaking strike that Steve Clarke's team could not respond to.
And that brace takes Schick level with Belgium's Romelu Lukaku at the top of the Euro 2020 scoring charts.
What went wrong for Scotland - and what do they need to do to bounce back against England at Wembley?
After a 23-year wait, Scotland's first match back at a major international tournament ended in defeat, with Steve Clarke's side going down 2-0 to Czech Republic at Hampden Park.
We get reaction to the result and performance from former Scotland international James McFadden and Famous Tartan Army Magazine editor Iain Emerson, who joined Sky Sports News reporter Charles Paterson after the game for the latest Sky Sports Football Euros Podcast.
There's debate and discussion about the chances which came and went for Scotland, the mistakes at the back, the impact of "world class" Kieran Tierney's injury - and whether Scotland can bounce back in the mouth-watering match-up with England at Wembley on Friday.
And finally… was Patrik Schick's halfway-line strike better than Zinedine Zidane's volley at the same stadium? Or McFadden's goal in Paris?!
Both teams are next in action on June 18. Scotland face a huge Home Nations derby against England at Wembley (kick-off 8pm), while the Czech Republic take on Croatia at Hampden Park (kick-off 5pm).