Scotland Under-21s hopes of reaching their first European Championship finals in 24 years suffered a major blow as 10-man Greece snatched a last-gasp 1-0 win at Tynecastle.
Scot Gemmill's men were hoping to breath fresh impetus into their Under-21 Euro 2021 bid following back-to-back blanks against Lithuania and the Czech Republic.
With Ryan Porteous called-up for Steve Clarke's A squad, Gemmill had to shuffle his defensive options.
But it was up front where they suffered most, as again they failed to take their chances and paid the price as Dimitris Nikolaou tucked home a stoppage-time penalty after Daniel Harvie had handled in the box.
The defeat will sting all the more given the visitors had played out the final 27 minutes a man light after seeing Bayer Leverkusen youngster Panagiotis Retsos dismissed.
Gemmill's team started the night leading Group D but dropped to third, two points behind the Greeks who took over at the top.
Nikolaou held his nerve at the death but Scotland should have put the game to bed long before that.
A sublime Billy Gilmour flick set Jamie Brandon surging forward four minutes in before the Hearts youngster slipped a reverse pass to Allan Campbell.
The skipper, however, wasted the opening as he pushed wide.
Lewis Ferguson rolled a quick free-kick down the side for Jordan Holsgrove but his cross flashed across the box with no takers.
It was Holsgrove's turn to try something different with a set-piece as he shaped to flight the ball into the box from out wide only to tee up Gilmour for a strike which zipped just over Marios Siampanis' bar.
Campbell did steer the ball into the net eight minutes before the break from Stephen Kelly's cross but saw his effort ruled offside, while there was also time for Holsgrove to fizz another strike just off target before the interval.
Greece had barely threatened during the first half and the odds looked to be mounting against them in the 63rd minute as Retsos got his marching orders.
Already on a booking after a late tackle on Gilmour, the Greek captain clattered into the Chelsea midfielder again as he collected his second yellow.
But with Scotland failing to make the most of their man advantage, they left themselves open to a sucker punch which duly arrived as Harvie inexplicably threw an arm out at the ball with the 90 minutes almost up.
Nikolaou did not blink as he rolled the ball past Ross Doohan to leave the Scots dejected.
