Jimmy Calderwood is a former football player and is currently a football manager.

He started his professional career with Birmingham City in 1971, making his debut against Stoke City in 1972. He made 159 appearances for the Blues until switching to Cambridge United in 1979. He spent a short time in Cambridge before accepting the offer to move to Holland, where he spent almost 10 years playing for Sparta Rotterdam, Willem II Tilburg, Roda JC and SC Hercales before retiring in 1989.

After a few assistant coaching positions, Calderwood moved into management in his own right by taking over Dutch club NEC Nijmegen in 1997. After a two year spell there, Scottish Premier League side Dunfermline Athletic moved to make him their new manager. Calderwood spent five seasons at East End Park where he led the club to their highest ever league position, finishing 4th in 2003-04, guaranteeing their return to European competition for the first time in 35 years.

His achievements with Dunfermline didn't go unnoticed, and in the summer of 2004 Willie Miller, returning to Pittodrie as Director of Football, brought Calderwood to Aberdeen to replace Steve Paterson as manager.