Whilst at Tottenham Hotspur for five years Calderwood played with a succession of defenders including Gary Mabbutt and Ramon Vega. While at Tottenham he gained many of his Scotland caps, making his debut against Russia in the UEFA Euro 1996 qualifying Group 8 section. Calderwood represented his country at UEFA Euro 1996 and the 1998 FIFA World Cup, playing in all three matches at the first tournament and two matches at the second. He was a regular under Scotland manager Craig Brown.