Two more World Cup appearances since in 1990 and 1998 are a paltry return for the passionate Scottish fans, whose side travel to Wales on Friday hoping for a win to boost hopes of a long-awaited return to the pinnacle of soccer in 2014.
Wales have faced harder times with no World Cup finals matches since 1958 and twice against Scotland, in 1977 and the fateful Stein match in 1985, they looked on aghast as referees awarded controversial penalties against them.
"Without doubt, Welsh football history is defined by three penalties, two given against us against Scotland and the one we missed against Romania in 1993," said former striker Ian Rush.
Then in 1985, Stein's last match in charge, Scotland trailed 1-0 at half-time before he introduced Davie Cooper on the hour and his expertly-taken penalty after 81 minutes sealed the team's place in a World Cup play-off.
"The devastation I felt in 1985 didn't compare to 1993," added Rush. "I remember sitting in the dressing room when [manager] Mike England told us what happened to Jock Stein, and all we thought about was one of the greatest managers ever had died."
With two draws from their opening two World Cup 2014 Group A qualifying matches and with Serbia, Belgium, Croatia, Macedonia and Wales in their way, the Scots would do well to recall Stein's spirit and enthusiasm for the game.
"Everyone knows it has been too long since we last qualified for a major finals," said Scotland striker Steven Fletcher, who has rediscovered his passion for the side having returned from a two-year hiatus after a fall-out with the management.
"They are not as bad as Pot Six - not anywhere near it," he said referring to Wales' position in the table. "And we've got this additional history and this British conflict."
"If you look through their team, with everyone fit, they are a formidable-looking side," said Levein. "Bale is just a top, top player who any club in the world would be happy to have - he's an impact player and one of the best in the world.
"But they've got other exceptionally good players in the team. The biggest difficulty with Wales,
