With our Final against Leicester City level at 0-0 and with the match seemingly destined for extra time, Danish international midfielder Allan Nielsen popped up with a late diving header to secure a famous 1-0 win at the old Wembley Stadium.
It was a result that yielded our first piece of silverware since the 1991 FA Cup success – and Allan still remembers it well...
FINAL COUNTDOWN – ALLAN NIELSEN – LEAGUE CUP WINNER 1999
It was his most famous moment in a Spurs shirt.
The image of Allan Nielsen diving in to head home our winning goal in the 1999 League Cup Final remains one of the most iconic of that era.
And the fact that we lifted the trophy having been reduced to 10 men – Justin Edinburgh harshly seeing red after an incident involving Robbie Savage – made it an even more magnificent achievement.
As the now 43-year-old recalls, that victory came at a time when our domestic form wasn’t exactly hitting the heights of bygone days.
“It was a fantastic moment to win the League Cup in that manner,” said the former midfielder, who joined us from Danish side Brondby IF in 1996 and went on to make 115 appearances in our colours.
“It came at a time where every year we were pushing for consistency, but couldn’t really find it. Because of that, I remember there being a feeling of great relief as well as enjoyment that we had won a cup final.
“For myself, it was obviously great in regards to scoring the winning goal and, even after we went down to 10 men, just the way the whole thing happened was superb.”
Casting his mind back to the build-up to that day at Wembley, Allan said he always felt confident of getting the right result against the Foxes.
“To be honest, a few days before the final I was going over the whole thing in my mind; from our arrivals at the stadium, to going through the game and then to everything afterwards where the fans were all celebrating. So actually, for me during the game, I never had any doubts whatsoever that we were going to come out as winners.
“There was one particular moment just after Justin saw red where I distinctly remember running past David Ginola and I could see from his face and his mannerisms that he was disheartened. I remember just patting him on the shoulder and saying ‘cheer up, we’re going to be okay’ and later in the game we scored the goal. The rest, we all know!”
Allan left us for Watford in 2000, having earlier had a loan spell at Wolves.
But fast-forward to the here and now and we have another Danish maestro who has a habit of scoring late goals!
Christian Eriksen has popped up with his fair share of crucial strikes this season – none more so than his brace at Sheffield United that rubber-stamped our place in the forthcoming Final.
“Christian is one of the best Danish players there is at the moment,” beamed Allan. “He’s a fantastic young talent and for me it’s a pleasure to see him doing so well for Tottenham, where I had four happy years.
“He’s definitely improved his scoring ability lately and he’s finishing moves off now. He’s always been a very good box-to-box player, setting up goals and scoring from free-kicks, but now he’s been getting into the box as well.
“When I see him happy and smiling in all his goal celebrations, it gives me good memories of my own time at White Hart Lane.”