Calderwood, a midfielder, won an apprentice contract with Birmingham City in 1971 and played over 150 senior games.
He joined Sparta Rotterdam in 1979, where he played alongside Dutch football giants and future coaching luminaries such as former Rangers boss Dick Advocaat, Danny Blind and Louis van Gaal.
Calderwood would end his playing days in Holland, playing for Willem II, Roda JC and Hercales, where he retired in 1989 and became a coach.
His first managerial appointment came in 1996, when he was promoted from his assistant position at Willem II, before moving to NEC Nijmegen a year later.
In 1999, Dunfermline brought him to Scotland and Calderwood repaid their faith by winning the second division title in his first season.
In the top flight, Calderwood’s team finished ninth, sixth and then fifth, qualifying for the UEFA Cup, before achieving a club-best fourth place finish in 2004, while losing the Scottish Cup final to Celtic.
Dunfermline say they are “very saddened” by his death.
After five years at East End Park, Calderwood moved north to Aberdeen and spent another five years at Pittodrie.
Their best domestic season came in 2006-07, when the Dons finished third in the league (their highest position in 21 years) and conquered European football.
That sparked an improbable run in the UEFA Cup the following campaign, when Dnipro were eliminated in the qualifying round, FC Copenhagen thrashed in the group stage and secured qualification for the round of 16.
Aberdeen drew with Bayern Munich and battled to a historic 2-2 draw at Pittodrie before being eliminated in the second leg.
Calderwood left Aberdeen in 2009 and kept Kilmarnock in the top flight after taking charge of Rugby Park in January 2010.
He oversaw Ross County’s Challenge Cup victory a year later, before returning to the Netherlands with Go Ahead Eagles.
He revealed his dementia diagnosis in August 2017 in a bid to raise awareness about the disease.