Tottenham 1 Middlesbrough 1 (Boro win on penalties)
Middlesbrough defender Frank Queudrue sealed a penalty shoot-out victory against Tottenham to set up a League Cup semi-final against Arsenal.
Penalties were needed to separate the two sides and while Kasey Keller saved from Gaizka Mendieta after Gus Poyet had missed, Mauricio Taricco then hit the post and left Queudrue to secure victory.
A late equaliser by Michael Rickets sent the tie into extra time just when it seemed that Darren Anderton's goal, after just a minute, would settle the tie.
Tottenham certainly had the edge against disjointed Middlesbrough, for whom only Danny Mills and Gareth Southgate could hold their heads high after 90 minutes.
Middlesbrough did not work goalkeeper Kasey Keller hard enough though just before they scored Juninho spurned a wonderful opportunity in the 81st minute when a lucky bounce sent him clear. But they did score when George Boateng put in Ricketts who beat Keller from close range. Then, in injury time, Ricketts had two more chances.
Spurs needed only 62 seconds to go into the lead. Stephen Carr's cross from the right was blocked by Colin Cooper but Anderton shot past Mark Schwarzer with the help of a deflection.
Spurs should have gone two up in the eighth minute when Anderton played the ball into Kanoute, who gave himself a shooting chance with a fine turn only to see Gareth Southgate make a fast recovery and block the effort. The same combination combined in the 13th minute when Anderton crossed from the right but just too high for Kanoute, who could get little power into his header.
It was an Anderton corner, however, that gave Spurs a wonderful opportunity to extend their advantage in the 18th minute. It was met by a powerful header by Ledley King from point-blank range and Schwarzer made a magnificent tip-over save.
Middlesbrough had two great chances in first half stoppage time. First Ricketts, sent clear by Mills, rounded keeper Keller but shot wide of the right post when he should have scored and then Maccarone decideded to make life complicated when a first-time shot would have been the wiser option.
Middlesbrough started the second half as they had ended the first. When Bodo Zenden crossed from the left Ricketts's neck muscles bulged as he put in a powerful header which Keller just managed to hold beneath the bar.
Middlesbrough appeared to be better balanced after Stewart Downing, a natural wide player, replaced the injured Maccarone at half-time.
Steve McClaren, Middlesbrough's manager, still looked a frustrated figure in the technical area, however, until Ricketts came to his late, late rescue.
TOTTENHAM: Keller; Carr, Richards (Doherty, 46min), Gardner, Taricco; Anderton (Poyet, 77), King, R Ricketts, Konchesky; Keane, Kanoute. Unused subs: Burch, Postiga, Dalmat.
MIDDLESBROUGH: Schwarzer; Mills, Cooper (Nemeth, 79), Southgate, Queudrue; Mendieta, Boateng, Zenden, Juninho; M Ricketts, Maccarone (Downing, 46min). Unused subs: Jones, Davies, Riggott, Booked: Mills
Referee: M Dean.