Scotland's dreams of making Qatar 2022 is over after a 3-1 loss to Ukraine in the World Cup play-off semi-final.
Steve Clarke's side weren't at the races and Andriy Yarmolenko punished them with a lovely lob before half-time.
A response was needed in the second period but Roman Yaremchuk's strike four minutes into was a hammer blow to the home side's hopes.
Celtic captain Callum McGregor almost gave the nation a bizarre way back into proceedings with goalkeeper George Buschan's clearance coming off him but it bounced painfully over the bar.
He did eventually get one back as he snuck a goal in to set up a dramatic finale but Artem Dovbyk scored with the game's final kick to seal Ukrainian joy.
The team in navy blue fell flat on an emotional night at Hampden, as Ukraine played on with passionate spirit amid their nation fighting off a Russian invasion of their land.
It was the away side who handled the occasion best, and they proceed to face Wales in Sunday's play-off final, with Craig Gordon having to deny Yaremchuk and Yarmolenko certain goals before their eventual opener.
Clarke's men headed into the match on a wave of momentum amid a positive 12 months that's included a return to major tournament football at last summer's Euro 2020.
This was a shattering journey back to earth for the Tartan Army, who sold out the national stadium in anticipation of another memorable night.
Those hopes were all but dashed in 49 minutes as despite a mini-revival in tempo, Scotland got nowhere near Oleksandr Petrakov's side for most of the night.
John McGinn's missed header from all of five yards out summed up a frustrating night of disappointment but McGregor's goal did provide hope when all appeared to be lost.
Not since 1998 has the country experienced itself at a World Cup and there were genuine hopes this could be the year that wait was ended.
Instead, it will extend to at least 28 years.
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