The national team has never progressed beyond the initial phase of a senior mens’ tournament, whether it be the World Cup or two previous European Championship appearances.
Scotland have it all to play for at Hampden, with a win guaranteeing Steve Clarke’s side progression to the knock-out stage for the first time in history.
But on no less than SEVEN previous occasions it has all been in the balance going in to the pivotal last match.
Here’s a look back at each and how they panned out from the most recent 23 years ago, way back to the national team's World Cup debut in 1954.
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1. 1998 World Cup - lost 3-0 Morocco
Scotland needed a win over Morocco and Norway to lose to Brazil in the other group game - neither happened and Craig Burley was red carded in St Etienne as Craig Brown's side finished bottom of the section. Photo: SNS Group 0141 221 3602
2. Euro 96 - Won 1-0 vs Switzerland
Ally McCoist's drive had Scotland through until a late consolation for Holland in a 4-1 defeat to England at Wembley edged Craig Brown's team out on goal difference after amassing four points. Photo: SNS Group
3. 1992 European Championships - won 3-0 vs C.I.S.
The first European Championships campaign ended on a high with a comfortable win over C.I.S. through Paul McStay, Gary McAllister and Brian McClair - but earlier defeats to Germany and Holland were costly. Photo: SNS Group
4. 1990 World Cup - lost 1-0 vs Brazil
Scotland needed a draw and with ten minutes to play it was 0-0 in Turin against Brazil... but Mueller squeezed a late winner by Jim Leighton to send Andy Roxburgh's team home. Photo: SNS Group