With Ivano Bonetti at the helm, bringing the might of Claudio Caniggia to the club opened a whole world of possibilities surrounding the footballing legend.
A Dundee strip made its way to Argentina, while the thought of Maradona, who died on Wednesday aged 60, making the return journey to the City of Discovery, sitting in the Main Stand and looking out to the Derry was a tantalising one.
Yet, it paled into insignificance to the reality.
The dark blue adorned by such luminaries as Bobby Fox, Alan Gilzean and John Duncan was being primed for the boulder-like figure many feel was the greatest to ever play the game.
Rumour and speculation didn't so much run free as rampage around the city. Maradona to line up alongside Caniggia, just as they did in the opening game of the 1990 World Cup in Italy. Could it actually happen?
Imagine the controversy and tempestuous nature of Diego combined with Dundee’s ability to conjure shenanigans.
It was thought Maradona would play for the club in Dubai during a winter break only for logistics to throw a spanner in the works.
Instead, at a time when money appeared to grow on Dens Road a “glamour friendly” was arranged for either February or March 2001. Not only would it involve Maradona sprinkling the city with star dust but he would do so in a game involving Napoli, the Italian side intertwined with the Argentine.
The club were reluctant to reveal the cost of tempting Diego to Scotland but it was reported to be £250,000 with the hope money would be made back through sponsorship and TV deals to show the match.
A club statement at the time read: "In relation to continuing speculation in the media, Dundee Football Club can confirm that there was recent correspondence between Diego Maradona, his representatives and Dundee Football Club that outlined both parties’ desire for Maradona to play for Dundee in a one-off glamour friendly.
"We hope that we are in a position to settle upon further details, such as a date, time and place for the game within the next few days. But it is looking increasingly likely that any match involving Maradona (and Dundee FC) will take place at Dens Park stadium."
The scandal which scuppered it all
It would have been Maradona’s return to the country where he scored his first goal for Argentina in a 3-1 win, the No.10 mesmerising the Scotland crowd that day.
Some things, as Dundee fans will know more than most, just were too good to actually come to fruition. However, it was no fault of the Dens Park side but that of a £16.6million tax fraud scandal being one of the "significant factors” which would prevent the game going ahead, as a Dundee spokesman put it.
Around that time, Dundee were talking about bringing Italian international Attilio Lombardo to the club from Lazio, but that merited a meer shrug of the shoulders compared to the Maradona news.
It is a mighty shame that the dream never came reality. But, at the very least, was another stroke in the colourful Bonetti-era at Dens Park.