A quarter of a century has now passed since Jimmy Calderwood arrived at Dunfermline Athletic to kick-start a celebrated era for the East End Park club.
Appointed as the new manager on November 30, the Glaswegian – who was at that point virtually unknown in his homeland after two decades in the Netherlands – presided over a remarkable spell for the Pars.
He won his first game in charge against Ayr United on December 4 and went on to clinch promotion back to the Premier League just months later, before making a huge impact on the top-flight.
The Fifers finished ninth, sixth, fifth and fourth in Calderwood’s four full seasons in charge before he angered some fans by departing for Aberdeen in the wake of the 2004 Scottish Cup final, which was lost to Celtic.
Wage cuts to players and staff, including himself and assistant Jimmy Nicholl, as well as the scrapping of appearance and win bonuses, due to financial troubles, helped make the Dons an even more attractive proposition.
Calderwood, now 69, insisted it had been a ‘wrench’ to leave Dunfermline.
But that did not wash with some supporters and they were slow in forgiving the former Willem II and NEC Nijmegen boss, who sadly announced in 2017 that he was suffering from early onset Alzheimer’s disease.
Twenty-five years on from his first match as Pars manager, Courier Sport has taken a look back at some of Calderwood’s most significant games at the helm.
1. Ayr United 0-3 Dunfermline, Dec 4 1999
Dunfermline had won their previous three matches under interim head coach Jimmy Nicholl, who stayed on as assistant to Calderwood, and they would go on to form a strong partnership.
With just one loss in their previous seven, there was not much wrong with the East End Park outfit.
On-loan Hibernian striker Stevie Crawford, who signed permanently the following summer, got the ball rolling for the Calderwood reign with the opener in the 40th minute.
And a double from Hamish French sealed a comfortable victory.
The Pars went on to win seven of their last 10 outings to finish second and seal promotion with champions St Mirren.
2. Dunfermline 0-0 Aberdeen, July 29 2000
Dunfermline announced their return to the top-flight with a goalless draw at home to Calderwood’s future club, Aberdeen.
The Dutch influence was already apparent in the line-up for that first Premier fixture, with goalkeeper Marco Ruitenbeek, Michel Doesburg and Rob Matthei all in the squad along with Lithuanian defender Andrius Skerla, who had arrived from PSV.
A goalless draw was no hint of some of the attacking football to be seen under Calderwood in the coming years.
But it was a solid start in a season that finished with the Pars in ninth place and safe from relegation.
3. Dunfermline 2-0 Dundee, March 22 2002
Having narrowly missed out on the top-six in the previous season on goal difference, Dunfermline sealed a top-half finish with a comfortable victory over Dundee.
Goals either side of the break from Barry Nicholson and Stevie Crawford earned the three points they needed to leapfrog over Kilmarnock.
Kick-off was held up for nine minutes due to the large home support in the crowd of 7,299.
Although they failed to win any of their subsequent top-six fixtures, it was an indication of the steady progress during Calderwood’s tutelage.
4. Dunfermline 2-0 Rangers, Dec 14 2003
Calderwood presided over an era for Scottish football dominated by strong Celtic and Rangers teams.
Stars such as Henrik Larsson, Lubo Moravcik, Stiliyan Petrov, Chris Sutton, Stefan Klos, Giovanni van Bronckhorst, Ronald de Boer and Artur Numan made the Old Firm extremely tough opponents.
So, the 2-0 win against Rangers in December 2003 was a significant milestone.
Calderwood managed just one win against the Ibrox side he supported as a boy and the same against Celtic.
His first success came against the reigning champions on East End Park’s controversial synthetic surface.
Crawford snatched an early opener for the Fifers and a bizarre late own goal from Paolo Vanoli sealed a long-overdue victory.
5. Dunfermline 1-3 Celtic, May 22 2004
Dunfermline had sneaked a surprise first win against Celtic under Calderwood just three weeks before the Scottish Cup final.
Barry Nicholson and Gary Dempsey scored either side of a Larsson strike to rain on the Hoops’ parade as they were presented with the SPL trophy.
And Andrius Skerla sparked dreams of a repeat in the final with his 40th-minute opener.
However, Larsson struck with a second-half double in his last appearance for Celtic, before Petrov ensured there was no way back for the Pars.
Just six days later, Calderwood was unveiled as the new Aberdeen boss, with Dunfermline chairman John Yorkston upset at the Dons’ approach in the wake of the Hampden disappointment.
It meant Calderwood did not stick around to lead the Fifers into European competition for the first time in 34 years.
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