For a time it seemed more akin to an old friend they would meet up with every few years for one heck of an occasion. This was mostly a good occasion (they won the FA Cup eight times between 1901 and 1991), but on occasion was bad (Coventry City's 1987 upset).
In recent times, though, the cup has belied its many years to transform itself into a most tantalising tease, providing some nice memories along the way for Spurs only to close the door just when things were about to get really fun.
The White Hart Lane club reached the competition's semifinals in 1993, 1995, 1999, 2001 and 2010, losing out on each occasion. No team really has the right to say any edition of the cup is "their year", but certainly in '95 and '10 there was a feeling Spurs were good enough to go all the way.
"We let ourselves down against Portsmouth two years ago [in the semifinal], we didn't play well and that was a tough defeat to take."
As it turned out, that disappointment at least had the effect of focusing the hurting Tottenham squad ahead of a daunting run-in, as they attempted to finish fourth and qualify for the Champions League.
This season, Spurs are once more a team capable of cup glory, again seeking fourth place with a different, but equally nerve-wracking, finish to the Premier League campaign awaiting. This time they will hope to approach it in different circumstances, having booked a place for the FA Cup final and the awaiting Liverpool.
Their opponents, Chelsea, present an intriguing challenge at Wembley on Sunday.
Still competing with Spurs for that Champions League place, they are a side on the wane in some respects. Yet they remain a club brimming with talent, and just as crucially, in the form of veterans like John Terry, Ashley Cole and Frank Lampard, they possess experience in these situations.
Having won the FA Cup three times since Roman Abramovich's 2003 takeover, their hope will be that they know what is needed to take that last step towards a final, whether it be the temperament to stay cool in the heated atmosphere of a London derby, or remaining composed and concentrated in what may be a long afternoon should the game extend beyond normal time.
This knowledge will stand them in good stead and may prove helpful in navigating past Spurs in the least harmful route possible, even if they are already looking towards their Champions League semifinal meeting with Barcelona on Wednesday.
Spurs have made it to two Carling Cup finals since 2008 (beating Chelsea in that year's final), with several of the players who got them there still representing them, so semifinals do not present an entirely new situation to them.
But how that 2010 defeat to Pompey, or even their erratic recent league form, will play on their minds remains to be seen.
That is for Harry Redknapp to deal with, and it is easy to imagine his pre-match rhetoric will at least in part make reference to a desire to make up for past disappointments.
The struggles of the past two months might be more troublesome, and how those league woes will affect their mindset is unclear. Will the FA Cup act as a revitalising breath of fresh air, or will it be a distraction that only further unnerves a team increasingly plagued with inconsistency?
The hope for Tottenham is certainly the former. It is a shame, then, that one player especially in need of a boost may miss out—Ledley King. Spurs' much-loved centre-back has suffered a loss of form of late.
As James Olley of the London Evening Standard pointed out this week, having performed impeccably throughout the first half of the season, his "concession of a last-gasp spot-kick in the 3-2 defeat at Manchester City in January appeared an isolated error rather than symptomatic of a wider malaise.
"But since then, substandard performances in the collapse at Arsenal, a disappointing home draw to Stoke and Norwich prompt fears of more deep-rooted problems."
King's persistent knee problems have not helped the matter and may see him miss the Chelsea match (with Younes Kaboul definitely out, Ryan Nelsen and William Gallas are ready to deputise).
But it is occasions such as this that often provide players the perfect opportunity to prove the doubters wrong, as shown by Liverpool's Andy Carroll grabbing the winner against Everton after a week in which he had been tagged as (outgoing director of football) Damien Comolli's folly.
The Tottenham skipper will realise the enormity of the occasion more than most, and if passed fit will be desperate to keep alive the chance of walking up those famous Wembley steps once more.
There really is nothing like seeing a guy realise he's not done yet, as it usually goes the other way. While that is certainly the hope for King, a more surprising candidate here may come in the form of David Bentley.
Though injury may have derailed his season thus far, it has meant the 15-million-pound man has remained at a club he might otherwise have left. With injuries depleting the Tottenham squad, Bentley may even be involved Sunday.
The midfielder will probably not see any game time, but should he find himself positively influencing proceedings for his team, let's just say it is typical of the FA Cup to create such storylines. Tottenham, however, will be hoping that a failure to get beyond the tournament's semifinal stage is one theme that does not go on any longer.