Despite not being part of Tottenham's squad for the 1999 Football League Cup Final he made four appearances during their victorious League Cup campaign. Two days after the final Calderwood moved on from Tottenham in March 1999, signing for Aston Villa. He then had brief spells with Nottingham Forest and Notts County before retiring. Calderwood's career was brought to an end by a broken leg suffered while with Nottingham Forest.