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.
Calderwood cited the sale of several of De Graafschap's key players without adequate replacement as the reason for his resignation from the post.
[11] After two years with Willem II and a further six with Roda JC, Calderwood spent a short spell with Heracles Almelo before retiring in 1989.
That season the side also reached the 2004 Scottish Cup Final,[8] guaranteeing their return to European competition[8] for the first time in 35 years as opponents Celtic had already earned Champions League qualification.
In the summer of 2004 Willie Miller, returning to Pittodrie as director of football, brought Calderwood to Aberdeen to replace Steve Paterson as manager.
They narrowly missed out on qualifying for European competition in 2004–05 and 2005–06 but finished the 2006–07 league campaign in third place, ensuring UEFA Cup qualification.
[13][14] In December 2007, Calderwood led Aberdeen to the last 32 of European competition for the first time since 1986 with a surprising 4–0 demolition of FC Copenhagen at Pittodrie.
Calderwood signed a 3+1⁄2-year contract to end a month of speculation about his future, along with assistant manager Jimmy Nicholl and coach Sandy Clark.
Calderwood took Aberdeen to the 2007–08 Scottish Cup semi final, where they lost 4–3 to Dumfries First Division side, Queen of the South.
[8] Calderwood managed to secure Kilmarnock's SPL status for another season, but left the club in the summer after disagreeing with chairman Michael Johnston about the player and coaching budgets.