A Kenny Miller goal just before half time saved Scotland's blushes, but left them with plenty of work to do in their qualifying group.
Scotland started their match against Macedonia knowing that, realistically, nothing but a win would suffice following a draw against Serbia on Saturday. It was the away side that started the brightest, however, Nikolce Noveski toe-poking an effort home after just 11 minutes.
Hope was handed the way of the frustrated Scotland fans shortly before half time, Kenny Miller bringing the stadium to its feet after connecting with a neat square ball from Jamie Mackie. Miller took one touch to slam the ball past Martin Bogatinov, and in the process changed the mood of the crowd drastically going into the break.
That hope wasn't to last, however, as Macedonia continued to edge possession and chances, both on and off target, in the early stages of the second half. Alan Hutton, for all his work and endeavour down the right for Scotland, simply couldn't find the final ball needed to create chances for the likes of Miller and Mackie.
Substitute Jordan Rhodes, who had scored 47 goals in 47 games for club and country prior to tonight's game, almost scored minutes after coming on with a diving header, but in the end Macedonia clung on, leaving Scotland's chances of qualifying for the 2014 World Cup hanging in the balance.