Scotland under-21s 0-1 Macedonia under 21s
Scotland Under-21s suffered another night of frustration as they went down 1-0 to their FYR Macedonia counterparts in their European Under-21 Championship qualifier at Tynecastle.
Ricky Sbragia's side started the game confidently but were stunned in the 17th minute when striker Kire Markoski fired the visitors ahead.
The home side wrestled back control of the game and pressed even harder after Egzon Bejtulai was sent off by referee Sebastian Coltescu in the 69th minute after picking up two quick yellow cards for fouls on Ryan Fraser and then Liam Henderson.
However, despite their best efforts and some late drama against the 10 men the Scots could not breach the visiting defence and were left in fourth place with three remaining.
Scotland began the night in positive mode and dominated the early stages.
After midfielder Fraser had driven wide in the second minute from 20 yards, Swansea left-back Stephen Kingsley's powerful 30-yard drive was tipped over the crossbar by visiting keeper Igor Aleksovski.
Macedonia were content to contain but it took a last-gasp tackle by defender John Souttar to prevent striker Marjan Radeski latching on to Enis Bardi's searching pass.
That should have been a warning, but in the 17th minute Radeski took possession outside the box and slipped the ball to Markoski who swivelled before drilling his shot from 16 yards low past debutant keeper Liam Kelly.
Scotland struggled to get back on top but should have levelled in the 34th minute when midfielder Ryan Christie picked out striker Jason Cummings with a pin-point cross from the right but the unmarked Hibernian striker headed weakly into the arms of Aleksovski, who then made a fine save from Cummings' close-range hook shot moments later.
The Scots finished the half strongly and Ryan Gauld's curling shot from 20 yards in the 39th minute escaped the far post before another drive from the midfielder was parried by Aleksovski.
The keeper pulled off another fine save from skipper Jordan McGhee's close-range header from a Gauld cross early in the second-half as Sbragia's side went all out for a leveller.
Scotland continued to huff and puff but the visitors were organised and resolute, offering little encouragement although that came when Bejtulai was dismissed.
In the 76th minute a swirling cross from wide on the right by McGhee fooled Aleksovski but rebounded off the post, moments before centre-back Darko Velkoski headed against his own cross bar.
When Henderson had the ball in the net in the seven minutes of added time only to have it ruled off for a foul on the keeper before a penalty was awarded for a handball then rescinded on the advice of the linesman, it confirmed yet another depressing result for the home side.