Capital One Cup heroes Brad Friedel, Harry Kane and Kyle Walker celebrate their penalty shootout defeat of Hull City.
The match went to spot-kicks following a captivating 2-2 draw that had seen both teams hold the lead.
Gylfi Sigurdsson put Tottenham in front with a brilliant long range strike in the first 20 minutes before a Brad Friedel own goal saw Hull equalise.
In extra time Paul McShane headed the Tigers in front before substitute Harry Kane leveled with a finely struck shot from the edge of the penalty box.
Aaron McClean and Erik Lamela both had penalties saved, forcing the shootout into sudden death. After Kyle Walker scored Spurs' eighth from the spot, Friedel dived right to deny Ahmed Elmohamady and send Spurs through.
Read on for some takeaways from Wednesday night's clash.
Gylfi Sigurdsson took his season's tally to four in stunning style (not counting his shootout striker), scoring a first-half goal that will rank among the very best of his career.
It summed up what the Iceland international is capable of when venturing inside. He has the skill to fashion himself an opening—as he did here with a wonderful drag-back—and the shooting ability to score from various ranges.
As welcome as this scoring threat is for Tottenham, the issue still is whether it is enough to justify Sigurdsson's selection on a regular basis.
Once again nominally operating as a left winger, besides his goal Sigurdsson was largely a peripheral figure. When he did get involved coming in off the flank, the lack of a presence out wide was noticeable until Jan Vertonghen was later switched to left-back following the more hesitant Kyle Naughton's injury.
A fit Danny Rose will help here, getting up and down that wing as he does. But at least in the full-back's absence, Sigurdsson's value mostly revolves around his ability to grab a goal.
His return so far this season shows that is no bad thing. But he will have to do more to convince Andre Villas-Boas he should start every game.
Christian Eriksen returned to the Tottenham team and again offered glimpses of his undeniable talent.
Shortly before the half hour mark he was involved in a wonderful exchange of passes with Jermain Defoe that almost had the striker through in the box before his touch failed him.
That vision occasionally threatened to unlock Hull on other occasions too, augmented by his aesthetically appealing running style as he floated into fleetingly dangerous openings.
Yet while it remains only glimpses, Villas-Boas will be reluctant to place his faith fully in Eriksen as his first choice attacking midfielder.
Eriksen's chief rival for the spot Lewis Holtby is not as creatively gifted. He is, however, good enough in this area that the addition of his movement and willingness to close down opposition players does go some way to compensating for any shortfall.
Holtby does have the advantage of having a few extra months experience in the Premier League. Considering Eriksen is playing catch up here, it may take him a little while to truly grasp what he needs to excel in England.
That does leaves Villas-Boas with the dilemma of what is best for his team right now, though.
Younes Kaboul's return from injury was a welcome sight for all concerned at Tottenham following his frustrating recent setback.
The game played out ideally for him in regards to getting back into the swing of things. A quiet start for him to get some touches on the ball and ease in was followed by Hull stepping up the pressure substantially, ultimately giving the Frenchman a testing night.
Kaboul responded well. He was alert to deny Danny Graham with a perfectly timed slide tackle when the striker looked poised to tuck away the rebound from Ahmed Elmohamady's long-range shot.
As the game progressed he remained assured and was one of Spurs' better competitors aerially. Neither goal was down to him, and he has the right to feel aggrieved at being left isolated in the six-yard box in the build-up to Curtis Davies' equaliser.
Kaboul undoubtedly needs further minutes for his return to fitness to fully take hold. It leaves Villas-Boas in an interesting predicament with four good centre backs to choose from.
For Kaboul, it might be a case of biding his time further with the trio of Vlad Chiriches, Michael Dawson and Jan Vertonghen all having performed well since the international break. Each will know they cannot afford to slip up with a worthy competitor looking to regain his place.
Villas-Boas spoke to Ben Pearce of the Tottenham & Wood Green Journal earlier this month about the possibility of Harry Kane going out on loan again.
The manager stated it would have to be one right for his progression, but regardless of that both he and the player were also happy for him "to continue to push for his place."
After his display against Hull tonight, the latter idea is one Villas-Boas should definitely go with.
Anyone who caught Kane's appearances in preseason and on youth international duty (as well as in a couple of first team cameos for Spurs) will have seen a player who has markedly developed. His mobility has increased and his confidence with the ball attacking the goal from across the width of the pitch has only enhanced his scoring threat.
That was fully on show versus Hull as he livened Spurs up after coming on in the 78th minute, almost snatching a dramatic normal time winner when he hit the cross bar from long range deep into stoppage time.
The goal he eventually scored was testament to his clear belief he could make a difference (as too was his penalty in the shootout). Pushing the ball in front of him and away from the defender, the subsequent finish was an impeccable take amid the pressures of extra time.
With Emmanuel Adebayor unable to yet convince Villas-Boas to restore him to first team contention, there is space for a striker to offer something different to that provided by the smaller pair of Defoe and Roberto Soldado.
Kane has responded well to almost every challenge posed to him in his fledgling career. Like Andros Townsend has been this season, the 20-year-old deserves his chance to push for a starting place.
Danny Graham might have thought he was catching a break with his selection to take on Tottenham. After being injured versus Everton just a couple of weekends ago, his return to fitness was a couple of weeks sooner than had been anticipated.
Unfortunately for the luckless striker, his goal drought continued as he was replaced at halftime following an unremarkable first half.
An offside call saved him from the embarrassment of what would have been regarded as a horrendous miss from close range. Later in the half he looked to have been provided with another golden chance but he had the ball stolen from the tips of his toes by Kaboul.
Graham proved at Swansea that he could score at this level. He will need to keep at it to regain that touch.
With other Tiger forwards Sone Aluko and Yannick Sagbo having found the back of the net though, it will have to be sooner rather than later if he does not want to be playing second fiddle to anyone else.
Steve Bruce will be extremely proud of the efforts of his Hull City side on Wednesday night.
One-nil down following Sigurdsson's stunner, injury to his son Alex saw them abandon their back five in favour of a more offensive setup.
It worked, and though Tottenham enjoyed the majority of the possession (67 percent by BBC Sport's count), Hull found ways to respond. So much so they led 2-1 midway through extra time.
Eventually losing on penalties though, at least part of Bruce will consider whether pushing so close to reaching their first ever League Cup quarterfinal was worth it.
The Tigers boss rested a number of first team players, but even with a number of changes still had to play some of his regular including Elmohamady and Curtis Davies.
In both their meetings with Spurs this past week, Hull showed in the quality of their performances they have good players beyond a main starting XI.
For a club looking to establish itself in the top-flight, though, such exciting but energy-sapping cup outings are not ideal. Without the resources of clubs like Spurs, it can be a coin toss between wanting to win every game and being realistic about where their priorities lie.