Whether it's bashing one's head off a brick wall as a 13-point lead over your nearest rivals suddenly becomes a one-point deficit or watching your former goalie doing his best (or should that be worst?) to ensure that said bitter rivals reach the Champions League qualifying stages by assuming the guise of a stringless Marionette, no team in football manages to screw things up quite like Tottenham Hotspur.
It's peculiar primarily because this haplessness is in the DNA of the club, even when it isn't quite their fault. Three times in recent seasons, Spurs have been the victims of goal-line decisions that have gone the way of opponents, whether it is Tottenham doing the scoring (Pedro Mendes versus Manchester United) or the apparent conceding (Chelsea in Premier League action last season and in the FA Cup this).
Six years ago, Spurs had the opportunity to qualify for the Champions League and missed out due – depending on whether you are a tabloid headline writer or merely just someone who accepts the truth – to a dodgy batch of lasagne or a bout of gastroenteritis that worked its way through the entire squad 24 hours before a match at West Ham United that Tottenham needed to win in order to pip – you've guessed it – Arsenal.
Now Tottenham face further agony when Chelsea play Bayern Munich in the Champions League final. Only in the world of the Spurs fan can a fourth-placed finish not mean qualification for Europe's elite competition. It has happened once before, in 2005, when UEFA decreed that Everton (fourth) and Liverpool (Champions League winners) could compete in the following season's competition. Not this time. Liverpool made such a fuss that the rules were changed (no doubt to safeguard against Spurs qualifying) to prevent five clubs from the same jurisdiction from competing in the tournament.
Which brings us to this week's bet. Writing this as a Spurs fan, there can be but one outcome and that is that Chelsea defeat Bayern in Munich's Allianz Arena. The big worry from the partisan's point of view is that Bayern have a number of injuries and suspensions. Chelsea do, too, but it would seem the Germans' missing personnel – David Alaba, Daniel Van Buyten, Luiz Gustavo and Holger Badstuber – are a greater loss than John Terry, Ramires and Branislav Ivanovic are to Chelsea.
The bigger fear is that Didier Drogba is up against Anatoliy Tymoschuk. The Ukrainian holding midfielder will likely deputise at centre-half for Badstuber and one would fancy the Ivorian to have plenty of joy.
That said, this has draw written all over it, especially given Bayern's parsimony on their own patch and Chelsea's resilience in previous rounds, which bordered on outrageous good fortune.
Should it end all square after 90 minutes, you'll find me on the roof of the house, ignoring Mrs Tenner Bet's gentle coaxings 'to act my age'.
Selections Chelsea-Bayern Munich to draw (3/1, general); Didier Drogba to score anytime (3/1, betvictor)
Season's total -£82.13