The 56-year-old played 36 times for Scotland and represented his country in both Euro 96 and the 1998 World Cup. He was only a matter of yards away when Paul Gascoigne scored his famous goal at Wembley in 1996.
Scotland, who were beaten by Czech Republic in their opening group game, return to the capital this evening, and Calderwood believes Steve Clarke's team are capable of causing a major upset.
In a recent interview with the Daily Record, Calderwood said: “Scotland should fear nobody.
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“Everyone in that squad competing against England - or whoever - are exactly at that level.
“They have the ability. They deserve to be there and they have the quality to be there.
“It’s a game of football and they have a chance of winning at Wembley. No doubts about it.
“Scotland have a very talented group. You look at Andy Robertson, Kieran Tierney, John McGinn to name just a few.
“More and more players are playing at a higher level in the Premier League just like we had in ’96.
“We came so, so close then. It was the finest of margins but hopefully this group can go one better.”
Calderwood was speaking before Scotland's defeat Czech Republic, and that result means they will likely need to take something from tonight's fixture to give themselves a realistic chance of qualifying for the knockout stages.
“Results in the first games will dictate what may transpire or at least the feeling going into that Wembley fixture because you can put yourself under pressure with a poor result," Calderwood added.
“If you can win one of the first two games then you have an unbelievable chance of qualifying.
“This Scotland side has the ability to do that. No doubts about it.”