Seven years ago football pundits were amazed how a club who played on a "car park" in front of a few thousand fans could achieve such success but now the club face a similar heartbreak to the gambler who loses his chips in Monte Carlo's casinos.
What should be one of the most glamorous sides in Europe is lying third from bottom and Saturday's trip to mid-table Valenciennes is a key test of whether they can clamber out of the drop zone.
Only 13 games remain and after last weekend's soul-destroying 2-2 home draw with Caen, where the hosts had been 2-0 up and cruising, Monaco's plight is severe.
"The task is becoming more and more complicated," coach Laurent Banide (pictured), who replaced the sacked Guy Lacombe in January, told reporters.
"We no longer have a choice, there is nothing left to calculate. We just have to work really hard to find a way of moving forward."
The Stade Louis II, home to the European Super Cup thanks to UEFA's love of the partying principality, has also been home to some top players over the years such as Glenn Hoddle, George Weah and Fernando Morientes despite its tiny 18,500 capacity.
Opposing managers have always criticised the standard of the pitch given a car park lies directly beneath but now it is the standard of their playing staff under scrutiny.
The seven-times French champions boast much more modest talent than in the past with South Korea striker Park Chu-young among the bigger names as low crowds limit the club's reach.
Auxerre, a point above Monaco just outside the drop zone, were third in Ligue 1 last season but the club which helped produce the likes of Eric Cantona have suffered this term.
Last weekend's opponents Girondins Bordeaux came into the game in crisis but ran out 3-0 winners and Saturday's visit of in-form title challengers Paris Saint-Germain hardly appeals.
"Psychologically, the team is lacking confidence," president Alain Dujon told the Journal du Centre newspaper.
"We are in a downward spiral. We need a boost to restart."
While Monaco and Auxerre fret at the bottom, leaders Lille go to champions and third-placed Olympique Marseille on Sunday bidding to end a streak of two league games without a win in one of the most tightly-contested title run-ins in decades.
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