Spurs face table-toppers Monaco at the Stade Louis II on Tuesday night with their hopes of qualification from Group E of the Champions League hanging by a thread.
Though the north London outfit have looked better away from Wembley, where they have been woeful, they come up against an in-form French side hunting for a league title of their own.
It's a must-win but, just like a drunken gambler at a Monte Carlo casino who's spent all their money by 8pm, Spurs will be going home early. Away trips to FC Krasnodar, Konyaspor and Zorya FC beckon, and here's why...
1. Monaco are firing.
Monaco are unbeaten at home this season and second in Ligue 1. They have won three games on the trot, scoring 12 goals in the process.
The team are clinical, scoring twice with just two shots on target in their 2-1 win against Tottenham back in September.
Radamel Falcao, who looked past it in the Premier League, has caught fire and hit six goals in five games.
2. Igor Akinfeev last kept a clean sheet 10 years ago.
The hopes of Spurs fans will be in the buttery fingers of the Russian keeper. If Bayer Leverkusen beat CSKA Moscow, Spurs are in real trouble if they fail to win tonight.
The 30-year-old will have his goal peppered by the Bayer attack, and his chances of keeping them all out are slim.
His last Champions League clean sheet came in 2006 in a goalless draw with Arsenal. Since, he has conceded in his past 40 games.
In October the stopper came nail-bitingly close to ending the unwanted run before Monaco (who else?) scored in the 87th minute.
3. The Stade Louis II is a European fortress.
The hosts are excellent at home in the competition, last tasting defeat against Rangers in 2000.
Overall, they have only lost two of their past 19 Champions League home games and have kept five clean sheets in their past seven.
Tottenham, meanwhile, have won just one of their past seven elite-level European games.
For most of Tottenham's squad, it's the first time mixing Europe's top competition with the Premier League, and the cracks are showing.
The superior Manchester City struggled to produce in Europe in recent seasons and have only started to find form after maturing against top opposition for a few years.
And, after last season's spectacular defeat, some eyes will surely be at least half on Saturday's match with Chelsea.
5. Spurs have never beaten French opposition away from home.
The record is W0, D2, L1 and in those three games they put away just one goal.
Moreover, Monaco have only failed to reach the knockout stages once in their previous six Champions League campaigns.
Thursday nights in eastern Europe are on the way back.