Last updated: 26/8/2019
Things look desperate for Bolton Wanderers, who face imminent liquidation this week after a deal to buy the club collapsed.
The Trotters who were a Premier League club as recently as 2012 have been given until 17:00 BST on Tuesday for a takeover to be completed or their Football League membership will be revoked and the club shut down as a company.
It's a desperately sad situation for a club that delighted fans for so long in the top tiers of English football and as recently as 11 years ago were mixing it with Europe's very best...
Beating Atletico Madrid
On 21 February 2008, a goalless draw at the Vicente Calderon was enough to secure passage to the last 16 of the UEFA Cup for Bolton Wanderers at the expense of Atletico Madrid.
Things get even more surreal sounding when you consider Bolton, managed by Gary Megson, beat Red Star Belgrade and earned a 2-2 draw at Bayern Munich (goals from Kevin Davies and Ricardo Gardner) in the group stages.
In fact, Megson was the last English manager to win a European knockout tie against Spanish opposition, until Craig Shakespeare led Leicester past Sevilla in the Champions League in 2017, while precious few Englishmen since have won European ties at all.
El-Hadji Diouf handed the Trotters a precious 1-0 lead to take to the Spanish capital with what can only be described as a poacher's effort, while the familiar name of Sergio Aguero was sent off just 12 minutes after getting subbed on...for spitting.
Megson's men then dug deep to grind out what the BBC report describes as a 'frustrating' 0-0 with 'few chances'.
Helmed by Javier Aguirre, Atleti boasted Diego Forlan, Maxi Rodriguez, Luis Garcia, Jose Reyes and Aguero among their ranks, but were unable to breach a resolute defence containing Andrew O'Brien and Jlloyd Samuel in 120 minutes of action.
More notable names on the Trotters teamsheet include Gary Cahill, Jussi Jaaskelainen, Kevins Nolan and Davies, as well as cult-Spaniard-in-England-before-it-was-cool Ivan Campo.
Bolton sadly fell at the next hurdle in a 2-1 aggregate loss to Sporting CP (who were in turn eliminated by Rangers), while Atletico's recent European history is a little more grandiose. The 2014 La Liga champions have reached Champions League finals in 2014 and 2016 and won the Europa League in 2010, 2012 and 2018.
While it might be little more than cold comfort right now, the Atletico result is one of many highs for Bolton fans in recent history that includes some of the Premier League's best-loved players.
Their story, though not quite yet over, is perhaps the most sobering cautionary tales yet for Premier League clubs about mismanagement and the ephemeral nature of stability.