A trivia question for you to start with: name the nine cities to have produced more than one club to reach the European Cup (or Champions League) semi-finals. The full list is at the bottom, but I’ll give you a head start by telling you which is the smallest such city – it’s Dundee, each of the city’s senior clubs having lost at that stage on one occasion. For Dundee United, it came in their 1980s heyday, losing 3-0 in a famously bad-tempered game at Roma in 1984 having taken a 2-0 lead from the first leg.

In Dundee’s case you have to go a bit further back, to 1963, when Bob Shankley’s side lost to AC Milan: the damage was done in a 5-1 defeat in Milan, before Alan Gilzean scored the only goal in the return game at Dens Park. Dundee were traditionally the bigger side in the city, then and for a long time, until Jim McLean turned United into one half of the New Firm who – with Alex Ferguson’s Aberdeen – mounted a genuine challenge to the Glasgow clubs for a while.

That challenge might not have lasted, but it did change the balance of power within Dundee – since then it’s been United who have remained the more successful club, overshadowing their neighbours from over the road. (Quite literally – the two stadia are opposite one another on the same street.) And so it’s been this season – while United celebrate Scottish Cup success, Dundee have been left to pick up the pieces of another failed campaign in the first division, and to face the financial realities that they cannot continue to spend money as they have been doing. Chairman Bob Brannan recently published this open letter on the club’s website, which among other things stressed the importance of fans continuing and increasing their fundraising efforts.

This letter, and subsequent media interviews, were a little over-dramatised by some sections of the press, which made out that the club were again on the brink of going bust. The situation is not that serious, but perhaps it has been jumped on with some elements of glee because there are many in Scottish football who remain to be convinced that Dundee have learned the lessons of their previous spell in administration.

A bit of background on their earlier bout of rainbow-chasing a decade ago: Jocky Scott had established the side in the SPL following promotion in 1998, but a couple of years later he was cast unceremoniously aside for a more glamourous manager in Ivano Bonetti. Under the ownership of the Marr brothers, and with backing from “controversial” Italian lawyer (and convicted fraudster) Geovanni di Stefano, Bonetti was given the backing to put together a team containing Julian Speroni, Nacho Novo, Juan Caballero, Georgi Nemsadze, and then bigger money again to bring in star names in Fabrizio Ravanelli, Craig Burley, Temuri Ketsbaia and Claudio Caniggia.

They were great to watch on their day, but produced nothing more than a couple of mid-table finishes and defeat to Rangers in the Scottish Cup final of 2003. By November of that year, it was obvious that the spending had not paid off and despite di Stefano’s pleas that he still had everything under control, the Marrs placed the club in administration, with a debt reported to be something over £20 million. The big names were sold or sent packing and the supporters Trust set about raising funds to save the club. Those involved are due a lot of credit for this: Dee4Life has been the largest and most successful Trust movement in the Scottish leagues and within months they’d raised a six figure sum – not even enough to pay the administrators, as it happens, but a big help to the running costs and anyway that wasn’t really the point. It had been a galvanising campaign, they had their club back and – in due course – a 26% stake and members on the board. New chairman Bob Brannan set about agreeing a CVA (at 2.5 pence in the pound), separated the ownership of the ground from the bank debt, and for a time at least the club adjusted themselves to their reduced circumstances. It meant relegation to the first division, in 2005, and some disappointing seasons thereafter. They had some good youngsters – Scott Robertson and Paul Dixon, who have since moved on (to United) and forced their way into the Scotland squad, and Kevin McDonald who was sold on to Burnley and recently attracted headlines for a ill-timed trip to the pub – but it wasn’t enough to get them back up.

Managers came and went – Jim Duffy, Alan Kernaghan, Alex Rae – and then, in 2008 Jocky Scott returned to the club for this third spell in charge. By then, the finances had been largely sorted out. The bank debt was wiped out by last summer, and if the club still didn’t own the ground they had it rent free. All good and well, but then things started getting silly again, thanks in part to the appearance on the scene of Aberdeen businessman Calum Melville.

Melville answered a newspaper advert looking for new investors, he had money to burn, and last summer Scott started burning it. The promises to buy back the ground came to nothing, but six figure transfer fees were splashed out for Leigh Griffiths and Gary Harkins, making Dundee the second biggest-spenders in the Scottish game after Celtic. The wage bill went through the roof too, as Brannan’s letter has admitted, far outstripping anything else in the division. All that was left was for the team to do their bit and win promotion back to the SPL.

It didn’t work. Dundee were top for most of the season but without ever looking convincing, and by the time Jocky Scott was sacked in March they had already lost any form they’d had. I’m still not sure what went wrong: they started the season with talk of how they’d rotate their impressive battery of strikers – Griffiths, Higgins, McMenamin, Antoine-Curier, Clarke – but ended it playing mediocre Celtic loanee Ben Hutchinson on his own up front. Inverness coasted past them and ended up winning the league (and only promotion spot) comfortably.

Hence the current soul-searching. To repeat, Dundee are not on the brink; Melville is no di Stefano and has not saddled the club with commitments that he does not appear (at present, anyway) to be willing and able to subsidise. And such debt as exists is mostly in the form of soft loans – to Brannan and John Bennett (who owns the ground). In the accounts up to July 2009 no money was owed to Melville, but there have been conflicting signals as to whether any of the money he has put in since then has been in the form of loans rather than gifts, and the accounts for this season may make interesting reading. It might all work out yet – promotion is more or less essential if it’s to do so, and the mooted SPL expansion for next season might make that a little easier. But as one of four SPL clubs to go into administration during the noughties, Dundee ought to be as aware as anyone that the higher league does not provide a pot of gold rich enough to justify any cost in getting there.

Most worringly, to see a club who have so recently been bailed out by supporters – and unpaid creditors – splashing the cash again, failing, and then turning back to the Trust to insist on the importance of their continued fundraising is, at best, on the unedifying side of legitimate business practice. Of course, with the Trust now having a say in the running of the club they have to bear their share of responsibility for it too, and it was hard to find many dissenting fans a year ago when the money was being spent. But Brannan was right about at least one thing – it’s important now for the Trust to be as active as ever. Not to provide money for him to waste, but to make sure the club is sensibly run from hereon and does not suffer once again at the hands of businessmen playing fantasy football.

The cities to have produced multiple European Cup semi-finalists are: London (Tottenham, Chelsea, Arsenal), Milan (AC Milan, Inter), Madrid (Real, Atletico), Glasgow (Celtic, Rangers), Dundee (Dundee, Dundee Utd), Vienna (Rapid Vienna, Austria Vienna), Budapest (Vasas, Ujpest), Bucharest (Steaua, Dinamo) and Belgrade (Red Star, Partizan). London is actually the most recent city to be added to this list, doing so in 2004 when Chelsea reached their first semi-final, but then became the first and only city to boast three clubs with Arsenal in 2006. Scotland remains, rather surprisingly, the only country to boast two such cities. Some sources also give Prague (Dukla, Sparta) and Moscow (Spartak, CSKA) as answers to the question – in each case it relies on the participation of the second-named side in the group stages during 93 or 94 when there were no semi-finals. Note that Glasgow’s inclusion, however, does not rely on this since Rangers were in an actual semi-final in 1960.