The Scotland boss admitted he looks back on his career with disappointment because the team never qualified for a big tournament.
However, he is urging his current crop of Scotland players to take full advantage of the opportunity they have in front of them in Belgrade on Thursday because there are no guarantees in football.
“I think it’s always been the dream, even for the years of failure to qualify,” Clarke said.
“It’s always there, that dream is always there when you start out every campaign you think ‘right, this is going to be the one’.
“The team at various times has been close to qualification but hasn’t quite managed to get it over the line.”
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Clarke’s recollections are ones Scotland fans know all too well in the years since they last qualified for a major tournament in 1998.
From the torment of defeats to the Netherlands and Italy in the mid-2000s to more recent woes, Scotland will be desperate to lay those shortcomings to rest, hold their nerve, and make history.
Last month’s Euros qualification semi-final against Israel was nerve-shredding enough, going all the way to spot-kicks before Scotland sealed a trip to Serbia for a winner-takes-all clash.
Now Clarke hopes his players can thrive on the big stage and do what he himself was not able to experience as a player.
“This squad, this team, this group of players is close again and this time hopefully we can get it over the line,” Clarke said.
“I had a good football career, I managed to win a few good trophies at the end of it. I played a lot of good matches at the highest level in both Scotland and England.
“But ultimately you’re always left with that little bit of disappointment that as a player I didn’t manage to play in a major tournament so for these lads, it’s the same.
“It’s not to think about (if) there’ll be another chance in two years’ time because maybe there won’t be.”
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