Save for a frantic corner of away supporters, the sense of anti-climax was enormous at White Hart Lane last night as Spurs finally succeeded in giving away a match they appeared to have well won, losing as they did so the opportunity of meeting their North London rivals Arsenal in the Carling Cup semi-final.
Penalty misses by Gustavo Poyet and, ultimately, Mauricio Taricco saw Steve McLaren's compact team achieve the result their efforts deserved.
But there was no hiding the desolation on the faces of a Tottenham team that had had their noses ahead in this quarter-final from the second minute, when Darren Anderton made the most of a poor Boro clearance, until five minutes from time, when Michael Ricketts, reviled in these parts for snubbing a move to Tottenham from his previous club, Bolton, brought the visitors back into the tie.
But if there was one man who was entitled to feel more aggrieved than anyone on the night it was the Tottenham goalkeeper, Kasey Keller. The American international spoke up this week about his discomfort at Tottenham's public efforts to find a new goalkeeper. Clearly he wanted to do his talking on the pitch and he proceeded to offer a display of expertise that was hard not to credit.
Keller's high point in the match came in the 82nd minute when a close-range save from Juninho appeared to have denied Boro what looked like their last chance of a late equaliser. That was all for nothing, though, as he had no chance with the Ricketts goal.
It arrived from a break after Taricco had lost possession from a throw-in deep in the Boro half, the ball being swiftly transferred to George Boateng, whose near-post cross was turned home by Boro's burly forward.
Keller then gave Tottenham an extra half-hour with an instinctive save from Ricketts' point-blank header in the last minute of time added on. Once the tie had gone to penalties, natural justice dictated that this should continue to be Keller's night, a thought doubtless shared by the crowd as they chanted "U-S-A, U-S-A'' while he walked to the goal.
For a few tantalising moments it seemed as if Keller's night would end in triumph as, with Gaizka Mendieta only needing to score to secure the match following Poyet's miss, Keller saved low to his right.
But no sooner had Tottenham's hopes risen than they sank again as Taricco's drive bounced away off the inside of the post and Franck Queudrue subsequently succeeded where Mendieta had failed.
"If it had not been for Keller, we would have won the match before the penalties," McLaren said. "He was outstanding for them." The Tottenham caretaker manager, David Pleat, put on a stoical front after his traumatic night. "When it comes to penalties, you are in the lap of the gods," he said. "I have to take the positives from this match."
There were plenty of those in a first-half in which the home side dominated proceedings, lifted by Anderton's early opportunism. The scorer himself, who has often looked out of touch in midfield this season, was clearly exerting maximum effort to maintain his side's progress in a competition that appeared to offer their best opportunity of glory this season.
But as the former England man began to fade - he was eventually replaced by Poyet after 77 minutes - so, too, did Spurs who began to give the ball away with increasing profligacy as the match went on.
First the ball, then the tie.
Tottenham Hotspur (4-4-2): Keller; Carr, Gardner, Richards (Doherty, h-t), Taricco; Anderton (Poyet, 77), King, R Ricketts (Dalmat, 85), Konchesky; Kanouté, Keane. Substitutes not used: Burch (gk), Postiga.
Middlesbrough (4-4-2): Schwarzer; Mills, Cooper (Nemeth, 79), Southgate, Queudrue; Mendieta, Boateng, Juninho, Zenden; M Ricketts, Maccarone (Downing, h-t). Substitutes not used: Jones (gk), Davies, Riggott.
Referee: M Dean (The Wirral).
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