Queudrue decides it for Boro in penalty shoot-out

Tottenham 1 Middlesbrough 1

Darren Anderton became the first player to score against Boro in more than 11 hours’ play but then Michael Ricketts, whom Spurs spurned the chance to sign in January, struck a late equaliser to force extra-time.

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.