Jimmy Calderwood 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 the Netherlands, where he spent almost 10 years playing for Sparta Rotterdam, Willem II Tilburg, Roda JC and Heracles Almelo 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 SPL position, finishing 4th in 2003/04. That season the side also reached the Scottish Cup final, guaranteeing their return to European competition 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.
Following his arrival in the Granite City, Calderwood oversaw an improvement in Aberdeen's fortunes on the playing field. 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 in 2007/08.
It was in that season that Calderwood led Aberdeen through to the group stages of the UEFA Cup for the first time. Aberdeen qualified from a tough section that included Lokomotiv Moscow, Atletico Madrid, Panathinaiokos and FC Copenhagen. A memorable 4-0 win over the Danes took Aberdeen through to a last 32 meeting with Bayern Munich, evoking memories of 1983.
Despite losing to Queen of the South in 2008 and again to Dunfermline a year later in the Scottish Cup at crucial stages, Calderwood guided Aberdeen to another 4th place finish and a coveted Europa league slot.
Jimmy left the club in May 2009.