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With Scotland looking pretty likely to finish bottom of their WC qualifying group, I was trying to figure out if we would be the "best" team, or at least the highest ranked, to have suffered that rather embarrassing fate in the modern era.
By modern era I suppose I mean the last 20 years or so, the time since UEFA was flooded with new participants after the break up of the former communist countries, along with the admission of numerous other mickey mouse states. Prior to the early 90's, qualifying groups were much smaller and consisted almost entirely of credible teams, with the only easy games being against Luxembourg and Malta.
A look back through UEFA's WC and Euro qualifying tournaments reveals that the only nations with any real footballing pedigree to have finished bottom were Bulgaria and Wales.
I would say that Bulgaria finishing bottom is actually a much greater demise than Scotland, given that they have achieved far more in recent decades and were World Cup semi-finalists in the 1990's. What is interesting to note is how quickly they have turned things around - from finishing bottom just 2 years ago, they are currently 2nd in their group, ahead of Czech R and Denmark. I just can't imagine that we would bounce back like that.