Dick Advocaat, nicknamed the Little General, succeeded Walter Smith at the start of season 1998-99. Advocaat, former manager of PSV Eindhoven, was only Rangers' tenth manager and the first non-Scot to hold the position.
His appointment was viewed by some as reflecting a desire to begin to challenge Europe's elite clubs. David Murray, the club's owner and chairman, had long proclaimed that Rangers ought to be judged not just in relation to success in Scotland, but on performance in Europe, and especially in the increasingly high-profile (and financially lucrative) Champions' League. But despite being given resources on a scale never before handed to a Rangers manager, success on a larger stage failed to materialise, and the costly legacy of Advocaat's time at Ibrox was a debt that would cripple the club for years.
The scale of these resources made available to Advocaat initially confirmed that the Rangers management was thinking in bold, European terms. Confronted with a rump of players remaining after Smith's departure, Advocaat was furnished with an unprecedented transfer budget over the coming seasons. In total Advocaat spent over £36 million on new players in his debut season. Some - the Dutch internationals Arthur Numan and Giovanni van Bronckhorst - were successful; others - for example Andrei Kanchelskis - proved ineffectual.
But while Advocaat's record in transfer dealings remained mixed throughout his time at Ibrox, at first the club appeared to be beginning to deliver in playing terms, both in Scotland and (less predictably) Europe. Advocaat's first season saw another domestic treble secured. Performance in Europe was promising, with Bayer Leverkusen defeated in a solid, if unspectacular, UEFA Cup run. In the following season, Advocaat continued to spend big, bringing the likes of Michael Mols and Claudio Reyna to Ibrox. A domestic double was secured in Advocaat's second season. In Europe, too, there were signs of greatly improved performance in the Champions League, as Parma were defeated en route to qualification for the group stages of the competition.
Rangers entered Advocaat's third season emboldened by the capture of five of the six domestic trophies available in his first two years. However, while the club again qualified for the Champions League group stage, performances in the league began rapidly to disintegrate. Further high-profile signings - Tore André Flo for a club record £12 million, and the Dutch internationalist Ronald de Boer on a lavish contract - could not reverse the decline. Morale amongst players and supporters plummeted amidst credible rumours of players unrest and dressing room divides. A worsening financial position exacerbated the gathering gloom. The club failed to win a major competition in the 2000-01 season, as Celtic swept the domestic board. Having continued in similar fashion in 2001-02, and with Martin O'Neill's Celtic side once more running away with the championship, Advocaat resigned as manager and took up a general manager position, which he would leave after only 11 months. Alex McLeish was the surprising appointment as the new Rangers manager in December 2001.
Advocaat's tenure at Ibrox had been a paradoxical one. On one hand, Advocaat spearheaded the building of Murray Park - a £14m training complex at Auchenhowie which was viewed as essential if the club was to compete with its European peers in nurturing home-gown talent and developing players. On the other hand, Advocaat's man-management was subject to criticism, and some argued that he had squandered a real opportunity to establish Rangers as consistent European competitors. With the club deep in financial difficulty, there was no realistic prospect of boosting its fortunes through further expensive player acquisitions. The challenge of restoring the club to supremacy in Scotland looked to be an unenviable one for Alex McLeish.