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Lucas Moura’s header ensured Tottenham Hotspur will have an FA Cup third-round replay with Championship side Middlesbrough.
Spurs named a full-strength team, bar the injured Harry Kane, but trailed when Ashley Fletcher ran on to George Saville’s ball and slotted home.
Moura saved the visitors with a fine header from Serge Aurier’s cross.
And the Brazilian twice went close to a winner, with goalkeeper Tomas Mejias stopping his long-range shots.
Aurier could have won the game for Jose Mourinho’s side in the closing minutes but fired an effort well over the bar.
Fletcher had an earlier chance to put Jonathan Woodgate’s Middlesbrough 2-1 up but shot straight at Paulo Gazzaniga.
No date for the replay at the Tottenham Hotspur Stadium has been set yet.
The fourth-round draw takes place on Monday at 19:35 GMT on BBC One and the iPlayer before Arsenal’s game against Leeds.
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Spurs’ strongest team was almost not enough
Mourinho said he would not forgive himself if he had named a weakened team against a side who had won their previous four Championship games. But even his first-choice XI – with Son Heung-min returning from suspension – was only enough for a draw.
Spurs have not won a trophy in over a decade. Middlesbrough manager Woodgate scored the winner that time, in the 2008 League Cup final against Chelsea, with Boro assistant Robbie Keane also playing in that game.
And in Mourinho, they have a manager who has won plenty of trophies, including the 2007 FA Cup with Chelsea, as well as domestic cups in Spain, Italy and Portugal.
However, they are suffering plenty of defensive problems – and have conceded first in eight of his 12 games in charge. Mourinho’s sides – including at the end of his spell at Manchester United – have only kept one clean sheet in their past 17 matches.
Spurs defenders appeared to switch off as Fletcher controlled Saville’s ball, before the midfielder ran through and finished. He was borderline offside, but there was no video assistant referee at the Riverside to try to dissect it down to the nearest millimetre or armpit.
They deserved their equaliser as Moura headed home, before the Brazilian was frustrated by Mejias on a couple of occasions.
Line-ups
Middlesbrough
Substitutes
Tottenham
Substitutes
Match Stats
Live Text
Match ends, Middlesbrough 1, Tottenham Hotspur 1.
Full Time
Second Half ends, Middlesbrough 1, Tottenham Hotspur 1.
Foul by Erik Lamela (Tottenham Hotspur).
Adam Clayton (Middlesbrough) wins a free kick in the attacking half.
Foul by Christian Eriksen (Tottenham Hotspur).
Lukas Nmecha (Middlesbrough) wins a free kick on the left wing.
Lucas Moura (Tottenham Hotspur) wins a free kick in the defensive half.
Foul by Djed Spence (Middlesbrough).
Corner, Tottenham Hotspur. Conceded by Marcus Tavernier.
Attempt missed. Serge Aurier (Tottenham Hotspur) right footed shot from the right side of the box is too high. Assisted by Erik Lamela.
Offside, Middlesbrough. Dael Fry tries a through ball, but Rudy Gestede is caught offside.
Booking
Erik Lamela (Tottenham Hotspur) is shown the yellow card.
Booking
George Saville (Middlesbrough) is shown the yellow card for a bad foul.
Giovani Lo Celso (Tottenham Hotspur) wins a free kick in the attacking half.
Foul by George Saville (Middlesbrough).
Corner, Tottenham Hotspur. Conceded by Tomás Mejías.
Attempt saved. Lucas Moura (Tottenham Hotspur) right footed shot from outside the box is saved in the top right corner. Assisted by Dele Alli.
Corner, Tottenham Hotspur. Conceded by Dael Fry.
Substitution
Substitution, Middlesbrough. Lukas Nmecha replaces Ashley Fletcher.
Corner, Tottenham Hotspur. Conceded by Patrick McNair.
Corner, Tottenham Hotspur. Conceded by Tomás Mejías.
Attempt saved. Erik Lamela (Tottenham Hotspur) left footed shot from outside the box is saved in the bottom right corner. Assisted by Serge Aurier.
Hand ball by Ashley Fletcher (Middlesbrough).
Foul by Erik Lamela (Tottenham Hotspur).
Marvin Johnson (Middlesbrough) wins a free kick in the defensive half.
Attempt blocked. Giovani Lo Celso (Tottenham Hotspur) left footed shot from outside the box is blocked. Assisted by Christian Eriksen.
Corner, Tottenham Hotspur. Conceded by Patrick McNair.
Attempt saved. Ashley Fletcher (Middlesbrough) right footed shot from outside the box is saved in the centre of the goal. Assisted by Rudy Gestede.
Substitution
Substitution, Middlesbrough. Rudy Gestede replaces Patrick Roberts.
Substitution
Substitution, Middlesbrough. Marvin Johnson replaces Hayden Coulson because of an injury.
Jan Vertonghen (Tottenham Hotspur) wins a free kick in the defensive half.
Foul by Djed Spence (Middlesbrough).
Offside, Tottenham Hotspur. Lucas Moura tries a through ball, but Son Heung-Min is caught offside.
Corner, Tottenham Hotspur. Conceded by Jonny Howson.
Attempt blocked. Erik Lamela (Tottenham Hotspur) right footed shot from outside the box is blocked. Assisted by Son Heung-Min.
Goal!
Goal! Middlesbrough 1, Tottenham Hotspur 1. Lucas Moura (Tottenham Hotspur) header from the centre of the box to the bottom right corner. Assisted by Serge Aurier with a cross.
Attempt blocked. Lucas Moura (Tottenham Hotspur) right footed shot from the centre of the box is blocked. Assisted by Son Heung-Min.
Attempt blocked. Lucas Moura (Tottenham Hotspur) right footed shot from outside the box is blocked.
Substitution
Substitution, Tottenham Hotspur. Giovani Lo Celso replaces Ryan Sessegnon.
Substitution
Substitution, Tottenham Hotspur. Erik Lamela replaces Harry Winks.
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