And eight years later Craig Brown unlocked that same pain all over again.
Now it's Steve Clarke's turn to be the bad guy as the clock ticks down towards Scotland's next big tournament, with only limited seats left available for the charter flight to Germany.
In five months' time the national boss will have to submit his final 23-man squad list for the Euros to UEFA.
And he knows from bitter personal experience the extent of the devastation this will cause for those not lucky enough to make the cut.
Clarke was one of three players chopped at the last minute by Roxburgh after he had fallen out of favour at Chelsea at the worst possible moment.
Then, at a time when he was back riding on the crest of a wave while enjoying an Indian summer at Stamford Bridge, Brown decided to leave him out of his squad for France 98.
This, then, is the brutal side of the management business.
And it's enough to make the man in charge visibly wince at the thought of how it will feel to be on the end of the one call none of his players will want to receive.
"I didn't even get that phone call in 1998, said Clarke with another grimace.
"But I was also very close to being selected for Italia 90 with Andy Roxburgh.
"We took a 26-man squad to Genoa in February for a pre-camp and I was in it.
"I didn't go in the summer because, at the time, I was having issues at Chelsea. I wasn't playing regularly.
"Andy just phoned me up and said, 'Listen, if you are not playing with Chelsea, then I can't pick you'.
"I even fell out with Bobby Campbell, who was my manager at Chelsea at that time, because he wouldn't pick me!
Diese Geschichte stammt aus der January 10, 2024-Ausgabe von Daily Record.
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Diese Geschichte stammt aus der January 10, 2024-Ausgabe von Daily Record.
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