Darren Jackson believes the Scottish FA “were confident” the national team would progress from their World Cup group under Steve Clarke, who has stepped down after Scotland missed out on the round of 32.
Clarke sealed Scotland men’s first appearance at a World Cup since 1998, having also overseen qualifications to two European Championships.
However, in all three major tournaments, Scotland lost two of their three group games and the recent 1-0 win over Haiti was the only victory at a finals for Clarke’s side.
Both Clarke and Jackson were capped by Scotland manager Craig Brown in the 1990s but the pair were never international team-mates.
“Is it a surprise? Probably not for the way they performed and probably the disappointment for Steve,” Jackson told BBC Radio Scotland’s Sportsound.
Clarke, 62, was given a new contract before the World Cup, which would have kept him in the job until 2030.
And Jackson said: “Giving his new contract beforehand, I think that was to give everybody a boost, the country a boost. I don’t know if that’s backfired. It’s really disappointing.
“I think they were confident they were going to go through.”
Jackson won 28 Scotland caps, scoring four goals, was part of the squad that went to Euro 96 and started two of the games at the 1998 World Cup in France.
And he believes one injured player was sorely absent for Scotland at this year’s event in the United States.
“Billy Gilmour was a huge miss,” said Jackson. “Huge miss because Billy does things that other players can’t. They definitely missed Billy Gilmour.”
On the future, Jackson commented: “There’s always going to be a turnover, possibly after tournaments.
“I don’t think we should worry to a massive extent because it happens at every level, it happens in every country that there’s got to be a new breed come through, it’s just how many are ready?”