James "Jimmy" Calderwood (born 28 February 1955) is a Scottish football player and manager. Calderwood played for Birmingham City and Dutch clubs Sparta Rotterdam, Willem II Tilburg, Roda JC and Heracles Almelo. After retiring as a player, Calderwood stayed in the Netherlands and became a coach, becoming a manager of Willem II Tilburg and NEC Nijmegen.
He returned to his native Scotland in 1999 to become manager of Dunfermline Athletic, guiding them to the 2004 Scottish Cup Final. Calderwood left Dunfermline that summer to become manager of Aberdeen, a position he held for five seasons. Aberdeen performed relatively well in the SPL under Calderwood and reached the last 32 of the 2007–08 UEFA Cup, but suffered a number of domestic cup defeats by lower league opponents. He then had brief stints with Kilmarnock and Ross County, helping each club retain their league status. Calderwood returned to the Netherlands in March 2012, with Go Ahead Eagles.
In January 2014, Calderwood spent just under a month as manager of De Graafschap before resigning. Calderwood cited the sale of several of De Graafschap's key players without adequate replacement as the reason for his resignation from the post. In July 2016, Calderwood was appointed to the board of directors at Cowdenbeath.Close