TOTTENHAM held their nerve to come out on top of a tense penalty shoot-out as Nuno Esperito Santo made a second winning return to Molineux this season.
But he needed a huge helping hand from his former skipper Conor Coady, who crashed Wolves' fifth spot-kick off the crossbar to send Spurs through.
Last year's finalists rode their luck at times and Ruben Neves crashed a late shot off the crossbar, before the usually reliable Portuguese midfielder also missed from the spot as the game reached its thrilling climax.
Belgian international Leo Dendoncker who had scored earlier also fluffed his lines from the spot for Wolves.
And, although Pierre-Emile Hojberg missed Spurs fourth penalty, Harry Kane, Sergio Reguilon and Bryan Gil had already converted to leave Coady as Wolves' fall-guy.
The England man missed their fateful fifth spot kick to send Spurs through.
Wolves haven't made it past the fourth round of this competition for a decade.
And the Molineux faithful must have feared this wasn't to be their year again when their team – showing nine changes from the weekend – were rag-dolled from the start by a pumped-up Tottenham.
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Clearly still smarting from their 3-0 second-half surrender to Chelsea, Spurs came out fighting and were two goals to the good before Wolves knew what had hit them.
To be fair to Bruno Lage his plans were thrown into disarray within ten minutes when his Colombian defender Yerson Mosquera was stretchered off on his full debut.
The £4.5million summer buy from Atletico Nacional ominously dropped to the turf when there was no-one near him after five minutes.
Sadly for the 20-year-old his evening was over as the stretcher was called for and the kid was in tears as he was replaced by captain Coady.
However, Spurs were in no mood to take pity on their opponents and swiftly seized the initiative.
Oliver Skipp showed real determination to win a crunching 50-50 with Ruben Neves and the ball broke to Coady.
But the England defender's attempted clearance was charged down by Tanguy Ndombele who burst clear of Coady before calmly slamming the ball beyond John Ruddy to give Spurs the lead.
Wolves looked rattled and Fabio Silva was booked for a needless foul on Japhet Tanganga before Nuno's boys forged further in front.
Kane was on the receiving end of some amount of stick when he returned to action for Spurs at Molineux last month following his summer of uncertainty.
So it was payback time for the England striker when he put Spurs 2-0 up midway through the first half with his first club goal since August.
Dele Alli produced a brilliant defence splitting pass which sliced through Coady and Boly and Kane strode through to easily beat Ruddy.
As Wolves wobbled, Alli almost added as he danced around Ruddy, only to lose his footing at the crucial moment.
But to their credit Lage's Wolves unexpectedly bared their fangs as they hauled themselves back into this tie before the break.
Rayan Ait-Nouri's perfectly struck corner was met with a bullet header from Leo Dendoncker who gave Pierluigi Gollini no chance as the ball raged high into Spurs' net.
Suddenly Wolves' confidence surged back and Hee Chang Hwang almost snatched an equaliser on half-time with a header which flashed just over.
The last man Nuno wanted to see appear after the break, duly made his entrance as Adama Traore replaced Fabio Silva and he soon had Spurs' defence on the back-foot.
Hwang fired over from six yards under pressure from Ndombele and Neves was booked for protesting that the Spurs midfielder had fouled him in the process.
Ruddy then had an amazing let off when Ndombele thundered in a speculative effort which squirmed under the keeper but somehow the ball skidded off the turf and flew just over.
And this cracking tie took another twist as Wolves drew level just before the hour to wipe out Spurs two-goal lead.
Hwang seized possession and fed Dendoncker who clipped the ball beyond Spurs' advancing defence and Daniel Podence skipped through to beat Gollini.
Nuno sent Heung-Min Son on for Giovani Lo Celso and he almost made a rapid impact with a cross which Kane seemed sure to score with, until Ruddy somehow scooped his point blank header over.
However it was Wolves who now looked the more likely winners and Neves cursed his luck after 88 minutes when his dipping shot beat Gollini, only to crash to safety off the Spurs crossbar to set up a dramatic penalty shoot-out.
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