Of all Fabrizio Ravanelli’s achievements in football – which included two Serie A titles, a Champions League win and 22 caps for Italy – it’s unlikely that a second half hat-trick in a Scottish League Cup tie for Dundee against Clyde ranks particularly highly.

Yet the Italian forward’s treble that Wednesday night in October 2003 marks the high point of his short spell in Scottish football; a period which suggested great promise but, six short weeks later, resulted in Ravanelli’s contract being terminated as Dundee entered administration.

Not long before he signed for Dundee, Ravanelli had been one of Europe’s leading strikers. His most notable spell was at Juventus, where he won his first Serie A title in 1995 and scored the Old Lady’s only goal in the Champions League final against Ajax in 1996. The Italian giants would eventually prevail on penalties. His four-year spell at the club also brought Coppa Italia and UEFA Cup glory for the man affectionately nicknamed ‘The White Feather’ owing to his distinctive white hair.

After leaving Juventus, Ravanelli helped Middlesbrough to two cup finals during the 1996/97 season but, despite a debut hat-trick against Liverpool on the opening day of the season, he was unable to stop the Teesiders dropping out of the Premier League. Spells at Marseille, Lazio – where he won his second league winners’ medal – and Derby followed before his improbable move to Tayside.

Or perhaps it wasn’t so improbable. This was a Dundee side who, under the managerial reign of Ivano Bonetti, had made headlines in 2000 by signing Argentine international forward Claudio Caniggia and followed it up with the acquisition of Temuri Ketsbaia a year later.

Although Bonetti had left in the summer of 2002, the transfer policy followed similar lines under the auspices of new club director, Giovanni di Stefano. The Italian lawyer – now a convicted fraudster – had previously represented Serbian warlord Arkan and later talked of his links to Saddam Hussein. Despite these somewhat dubious allegiances he was welcomed onto the Dundee board in the summer of 2003 and soon brokered the Ravanelli deal.

“Ravanelli seemed to be just another on the conveyor belt of stars we could get,” says Kenny Ross, club historian and chairman of the Dundee Supporters Association.

Gary Cocker, a Dundee fan and member of The Terrace Scottish Football Podcast, agrees: “When Ravanelli signed it seemed almost normal because of what had gone on before. Once Diego Maradona’s strike partner [Caniggia] signs for you, anything seems possible.”

Outside of the Old Firm, Scottish clubs are not renowned for paying big wages. But Dundee’s strategy – devised by chairman Peter Marr – was to bring in quality players and sell them off for a large profit a season or two later. Between transfers, television deals and merchandise, the Dundee board gambled on making their money back with a healthy profit.

In Caniggia’s case it worked. Not only did his signing convince ESPN to show Dundee games in South America, a stellar debut season at Dens Park saw Caniggia sold in the summer to Rangers for £1 million. “You could see what the Board were trying to do,” says Kenny. “With Caniggia they saw they could make money on this guy, so this is clearly what they tried to do with Ketsbaia and Ravanelli.”

Ravanelli signed at the same time as another high-profile player, Craig Burley, and both were paraded to the home crowd at half time during a UEFA Cup tie against Perugia which, as fate would have it, was Ravanelli’s hometown club.

The big striker certainly endeared himself to the Dundee supporters and before the away tie against Perugia was happy to meet fans, sign autographs and have his picture taken.

He made his debut against Partick Thistle and had an immediate impact, setting up the only goal of the game for strike partner Nacho Novo. Although he was 34 by this stage, his quality was still there for all to see. “He’d clearly lost his pace, but he still looked a player, absolutely…he was very intelligent, very clever,” says Kenny.

Ravanelli started in the Dundee derby away to neighbours United the following weekend, but was on the bench for the midweek League Cup tie at Clyde with Dundee expected to have enough quality to easily see off the First Division side.

At half time, the game was tied 1-1, and even though Lee Wilkie put Dundee ahead again on 66 minutes, Ravanelli was introduced shortly after. It took him only three minutes to bag his first goal in a dark blue shirt, slamming a left-footed shot past Clyde keeper Bryn Halliwell. Barely sixty seconds later, he grabbed his second after Halliwell spilled a Juan Sara shot.

Although Clyde pulled one back, Ravanelli got his third – and Dundee’s fifth of the evening – after a pass from Sara released the veteran striker in the penalty box. He had only been on the field for ten minutes, but could have had a fourth when another fierce drive rattled the post.

As the Clyde website’s match report put it: “In the end, class told in the shape of Mr. Ravanelli.”

“There wasn’t a huge crowd for that League Cup tie,” Kenny remembers. “But it was one of those moments where people would say ‘I was there when Ravanelli scored that hat-trick.’

“My recollection is that he was almost embarrassed because he did the whole shirt over the head thing for the first couple, but with the third one he was just having a laugh with the crowd. We were absolutely loving it though.”

After the game, Ravanelli was presented with the match ball, signed by the Clyde squad, and told the press that he’d be giving it to his children as a gift, having not seen them in almost a month. Quite what they’d think of a ball signed by the likes of Craig Bryson and Simon Mensing, no one can be quite sure.

Ravanelli’s performance amid the largely empty stands of Broadwood that night would turn out to be the highlight of his time at Dundee. He played three more games for the club, none of which they won, before the house of cards collapsed.

“I was over in Holland for the Scotland-Holland Euro playoff [which Scotland lost 6-0] and that night we were in the pub in Amsterdam,” Kenny explains. “I started getting texts saying that Dundee had gone into administration.

“I couldn’t believe it, but we arrived back in Scotland the next day and rumours were surfacing around town. Dundee made a statement the next day, we played Dunfermline on the Saturday, got beat and officially went into administration on the Monday. It was that quick.”

The high-risk financial gamble had spiralled out of control behind the scenes and, on November 24th, 2003, Dundee announced they had been placed into administration with debts amounting to £23 million.

Despite the sums involved, Gary Cocker believes the plan wasn’t necessarily doomed to fail. “The model itself makes sense in a way, but there was a perfect storm,” he says. “Had we pursued it five to ten years earlier it might have worked, but it happened at the time of the SPL television deal falling apart and the ramifications of the Bosman ruling – all of that made it a lot more dramatic.”

Sometimes I remember that Fabrizio Ravanelli and Claudio Caniggia both played for Dundee. It's still mental. pic.twitter.com/zeKLhA8qy3 — Gaby McKay (@GabyMcKay) December 20, 2016

Clubs embarking on a campaign to become the ‘third force’ in Scottish football have a history of ending in disaster; from Dundee, to Raith Rovers, to Gretna and Livingston. But back in 2003 this ambitious approach from the Taysiders didn’t elicit the same scepticism that it would now. “Hindsight’s a wonderful thing but I don’t think many Dundee fans were aware of the financial problems that the club were having,” Kenny admits.

Gary agrees that the steady stream of big-name signings made a risky approach seem normal. “It’s like the boiling frog anecdote. If you put a frog in boiling water it’ll jump out immediately, but if you slowly turn up the temperature it’ll stay in and die. That was what it was like being a Dundee fan at the time.”

Dundee barely survived the mismanagement of that period and, at the end of the 2004/05 season, they were relegated to the First Division. In 2010 they went into administration again, but finally returned to the Scottish Premiership for the 2012/13 season.

As for Ravanelli, his contract, along with 14 other players, was terminated the day after Dundee entered administration. After a few months out of the game he wound down his career at his hometown club Perugia. He clearly held his six-week spell in Scotland in high regard though – when Dundee entered administration again in 2010 he went on record to offer financial support. Perhaps, had it been necessary, he would even have auctioned his prized Clyde match ball to help save his former club.