What began as a contest of managerial wits between those two great allies George Graham and David O'Leary became, in the second half, a thrilling demonstration of Tottenham's ability to score outstanding goals, with Darren Anderton and David Ginola vying with each other for the most spectacular strike of the night.
The Englishman set Tottenham on their way and Ginola's volley, having earlier twice struck a post, secured his team a safe passage to the quarter-finals, where they will face first division Barnsley.
Afterwards Ginola promised to share his man-of-the-match champagne with Anderton. "I will share the champagne with Darren because he deserves it," said the Frenchman.
"The main thing is that we won the game 2-0. It was a great performance because Leeds are a tremendous team with tremendous young players.
"The first half was tough, but after the way we performed in the second, we deserved the win," he said.
Anderton added: "It was a good performance in a very difficult game. It was a great goal from David, and he deserved a couple more."
Tottenham lured Graham back to London from Leeds to replicate his success with Arsenal and this thrilling triumph strengthens the possibility that the League Cup finalists can match Arsenal's 1993 achievement in reaching two Wembley showpiece occasions in the same season.
With Jonathan Woodgate fit again after injury, O'Leary gave the teenager the task of shadowing Ginola. Lucas Radebe, who immediately after this game was booked on a flight to join the South Africa team, formed a central defensive partnership with David Wetherall, though a change of plan was demanded before half-way through the first period after a serious clash of heads.
When Wetherall and Les Ferdinand collided it was severe enough for neither player to take any further part in the contest, although the Tottenham man had clearly come off worse. Leeds adjusted by putting Gunnar Halle at right-back with Woodgate moving inside; Tottenham's replaced Ferdinand with Chris Armstrong.
The visitors' ability to spread play and strike accurate long passes continually had Spurs scrambling to cover, though as yet Ian Walker had not been sorely tested. He blocked one effort from Alf Inge Haaland from close in but it was not as close as Steffen Iversen had come 60 seconds earlier; on that occasion a fierce left-foot volley had been clawed away with some desperation by Nigel Martyn at his near post.
Ginola had posed only a sporadic threat so far but in the 55th minute he came to life spectacularly with a mesmerising run that took him from right to left, beyond four ineffective challenges. If he could have applied a decisive finish at the end of it then Tottenham fans would have been hailing the goal of the season but to his immense frustration he saw his shot bounce off the inside of the post and away to safety.
Nevertheless it was the harbinger of much joy for Tottenham, who took the lead five minutes later. Ginola, stepping up his involvement, had just been fouled for the second time in quick succession. Taking the free-kick himself, he rolled the ball square to Anderton, who unleashed a stunning first-time drive which rocketed into the top corner of the goal.
Ginola was determined to get on the score-sheet himself and six minutes later he struck the other post with Martyn again helpless. In the 67th minute the Frenchman finally got his reward when a Tim Sherwood centre was headed out to him just beyond the penalty area. A right-foot volley this time put Spurs well in command.
Leeds fought to the end. Harry Kewell twice extended Walker, and Jimmy Floyd Hasselbainkhit a post.
Tottenham Hotspurs: Walker, Carr, Vega (Young 78), Campbell, Edinburgh, Anderton, Sherwood, Freund, Ginola (Sinton 89), Ferdinand (Armstrong 24), Iversen. Subs Not Used: Baardsen, Nielsen. Booked: Edinburgh, Freund. Goals: Anderton 60, Ginola 68.
Leeds United: Martyn, Radebe, Wetherall (Halle 24), Woodgate, Harte, Haaland, Bowyer, Hopkin, Kewell, Hasselbaink, Korsten (Smith 71). Subs Not Used: Robinson, Granville, Jones. Booked: Radebe, Hopkin, Smith.
Referee: N Barry (Scunthorpe).