Steve Clarke's Scotland fell to a 2-0 defeat against the Czech Republic in a disappointing return to tournament football.
The Tartan Army qualified for the UEFA European Championships in triumphant fashion by way of two penalty shoot-out victories over Israel and Serbia, but could not match their previous heroics in a game that they believed in large portions they could have got a result from.
Bayer Leverkusen striker Patrik Schick was at the double, netting either side of the interval with two wonderful strikes.
Scotland will have to recoup fast if they want to make it out of the group stage of the Euros for the first time, as they face the might of the 'Auld Enemy' in England down in the capital this Friday night.
Story of the match
John McGinn typified the bullish Scottish attitude to the match in the early phases by regaining possession twice in succession in the opposition box, stimulating an already electric 12,000 strong Hampden Park crowd.
The Czech's overcame the vivacious opening ten minutes from the hosts and grew in possession, but some initial smart press-beating passes from Grant Hanley were eventually found out as the ball found it's way into the feet of Patrik Schick, forcing a decent save from David Marshall.
Any fear of a weakened left flank in Kieran Tierney's absence appeared to be somewhat alleviated with nice link-up play between Stuart Armstrong and captain Andy Robertson, the latter of whom put it on a dime for Lyndon Dykes, who struck wide.
In such a fraught occasion, the Tartan Army's first appearance in a major tournament in 23 years, the likes of Liam Cooper and Scott McTominay remained collected in their defensive duties and forced turnovers.
Robertson put in a commanding defensive performance on his native left flank, but he had his side's best chance to break the deadlock fed through by Ryan Christie in space and firing straight at Tomas Vaclik.
As the first period drew to a close, Jaroslav Silhavy's team ramped up the pressure and camped out Scotland's defensive third with corner after corner.
It was indeed Schick who dealt the hammer blow five minutes from the break, towering over Cooper and Hanley to glance an underlapping Vladimir Coufal's cross into the far corner.
The Scots were typically unwavering in their determination to go in level, as McTominay's collision in the 18-yard area and consequential spot-kick appeals fell on deaf ears with man in the middle Daniel Siebert.
Marshall was forced into two crucial saves within the first sixty seconds of the restart, with strike force Schick and Vladimir Darida applying the early pressure.
Jack Hendry showcased his ability for a delicate finish in his side's impressive 2-2 draw with The Netherlands in preparation for the tournament, and almost levelled the score with a whipped side-footed attempt from the edge of the area, clamouring off Vaclik's crossbar.
Vaclik was called into action to prevent an own goal from his centre-back Tomas Kalas' botched clearance, almost looping over the man between the sticks with a lingering Dykes in the wings.
Schick bookended a frantic five minutes with a strike that could be described in no other terms than sublime.
Hendry's striking abilities this time aided in his team's undoing, attempting to steal the headlines with a rangy thunderbolt that left his back line exposed as the effort was blocked.
The Leverkusen star in Schick collected the ball and unleashed a pinpoint shot over a retreating Marshall, who had assumed a sweeper role as his teammates advanced up the pitch.
Substitute Che Adams looked to be the outlet for Steve Clarke and co. after replacing Ryan Christie, whose industrious slant tipped the game's momentum towards the chasing Scotsmen.
While Dutchman Denzel Dumfries stole the headlines last night, the man with Dumfries connections Lyndon Dykes could not etch his own name into the history books with his best chance of the afternoon.
Vaslik was able to deny Dykes with a strong right leg, the latter of whom had enough time and space at the back post to get off a better effort.
Cooper and McTominay's defensive acumen couldn't be matched further up the pitch, with the defender directing on a cross to the Manchester United midfielder that was blazed over in a harbinger of doom for the final 15 minutes.
With Schick squandering an opportunity for a hat-trick late on, Scotland's final substitutions in James Nesbit and James Forrest had chances of their own go begging as an initially positive showing from the boys in blue petered out in their first match in the European Championships for a quarter of a century.
Steve Clarke may be left with more questions than answers as to what more he can get from his side, but cameos from substitutes like Che Adams may aid in rediscovering the clinical edge required up top against the likes of England and Croatia in Group D.
Man of the Match- Patrik Schick
While honourable mentions should be awarded to both 'keepers for their valiant efforts throughout, only one man could be worthy of the acclaim for the Man of the Match award.
Schick's two goals would be the envy of any striker in the world, most notably his 50+ yard lob that caught out David Marshall in the second forty five minutes.
The 25-year-old put in a true number 9's performance with nifty movement and positional awareness as he notched his twelfth and thirteenth international goals for the Czech Republic.
The striker may just be a dark horse for the tournament Golden Boot should his nation go on to the similar heights of a final appearance in Euro 96.