Promotion in 1998 entered Dundee into the inaugural Scottish Premier League but it was a season that Dundee off the field were in a continual fight against adversity, expulsion, bankruptcy and takeover fears. The S.P.L. wanted to see Dens Park as a 10, 000 all seated stadium within twelve months and Dundee United attempted a takeover to merge the clubs but the players got on with it and turned in some terrific performances.
On the field, Dundee showed a gritty determination and fighting spirit to retain their top flight status and by the end of the season, The Dee finished in fifth place, their highest league position for twenty-five years and never bettered since they were Scottish champions in 1962.
Dundee had also failed to finish above their rivals Dundee United during the same period but now they managed to achieve this after a memorable derby victory on May 1st 1999 when goals from Brian Irvine and James Grady gave Dundee a famous 2-0 win.
The stands were built and named after the League Championship winning captain and manager Bobby Cox and Bob Shankly and despite being within a point of finishing fifth again that season, Jocky Scott was replaced in favour of Italian manager Ivano Bonetti.
Bonetti would bring excitement, stars and wonderful football and had no problem attracting players, most notably Argentine superstar Claudio Caniggia but the problem was that apart from Caniggia, they could not sell the stars in for a big profit. With costs spiralling out of control and no tangible league or cup success to match Dundee's stylish football Bonetti left in 2002 to be replaced by Jim Duffy who took over for the second time.
Dundee still had a fine squad and Duffy led them to the Scottish Cup Final in his first season, losing 1-0 to Rangers in a match which the Dark Blues could well have won and took Dundee back into premier European competition after a twenty-nine year absence. There they defeated KS Vllaznia 6-0 on aggregate in the preliminary round of the UEFA Cup before losing out 3-1 to Serie A side Perguia when over 2000 Dees had travelled to Umbria to watch the second leg.
However the following month, November 2003 brought a bombshell for the Dark Blue faithful as Dundee went into administration. The court appointed Tom Burton and Fiona Taylor from the accountants Ernst & Young as joint administrators and the following day the full extent of Dundee’s financial plight was revealed with debts reported to be close to a staggering £20 million.
Dundee fans feared the worst and it was a crucial time for the survival of Dundee FC with the supporters’ association launching its Dee4Life fundraising campaign which was crucial in helping save the Club.
Twenty-five members of staff had been immediately axed and manager Jim Duffy took it upon himself to inform the playing and coaching staff and almost immediately became a target for Partick Thistle to replace Gerry Collins who was sacked with the Maryhill club