In 1993, Calderwood joined Tottenham Hotspur, where he spent four seasons and won the League Cup in 1999. After leaving Tottenham, he had spells at Aston Villa, Nottingham Forest, and Notts County before retiring as a player in 2001.
In 1993, Calderwood joined Tottenham Hotspur, where he spent four seasons and won the League Cup in 1999. After leaving Tottenham, he had spells at Aston Villa, Nottingham Forest, and Notts County before retiring as a player in 2001.