Despite possessing a talented squad and reaching the semi-finals of both domestic cup competitions, Boro suffered in the league and when Justin Edinburgh's cross in the 72nd minute was headed back by Teddy Sheringham, Sinton got on the end of it to get to it first and force the ball past the keeper from close range for the only goal of the game.

Teams : 
Spurs -  , , , , Edinburgh, , , , Sinton, Sheringham (c)
Subs not used : 
Middlesbrough -   , , , Pearson, , , Juninho, Emerson, Ravenelli, .
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Attendance : -   29,940
Referee : -

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Middlesbrough -  .
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Middlesbrough -  .
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Spurs -  C. Armstrong
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Spurs - 
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Middlesbrough -  .
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Teams : 
Middlesbrough -  Otto.
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Spurs -  Hoddle, Villa, Falco
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Attendance : -  20,490

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Middlesbrough -  .
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Spurs - 
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Middlesbrough took the points with a three goal burst within 20 minutes to shock Spurs at White Hart Lane.

David Armstrong, Micky Burns and Bosco Jankovic put Boor into an unassailable lead, but Glenn Hoddle did pull one goal back with a classy finish.

Teams : 
Spurs -  Hoddle, 
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Middlesbrough -  Armstrong, Burns, Jankovic.
Sub. not used : 
Attendance : -  32,743

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Spurs - 
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Middlesbrough -  .
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Middlesbrough -  .
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In between, Tottenham had signed Ian Moores from Stoke City and 23 minutes into his debut, he hit the back of the net to give Tottenham the lead.  Boro equalised through Tony McAndrew before the half-time whistle, but it was Jimmy Neighbour who popped up to hit the second half winner for Spurs - his last goal for the club.

Teams : 
Middlesbrough -  Platt, Craggs, Boam, Cooper, Maddren, Souness, McAndrew, Mills, Boersma, Hedley (Hickton), Armstrong
Spurs -  Daines, Naylor, Young, Osgood, McAllister, Perryman (Pratt), Hoddle, Neighbour, Coates, Moores, Chris Jones
Attendance : -  19,042

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Spurs - 
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Middlesbrough -  .
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Ref. : -  

Pat Jennings showed his class in keeping out a shot from David Armstrong and the referee had a tough time with Terry Naylor and Graeme Souness having a running battle, which ended with them both in the book.

Teams : 
Spurs -  Jennings, Naylor, Perryman, Neighbour, Chris Jones
Subs not used : 
Middlesbrough -  Souness, Armstrong.
Subs not used : 
Attendance : -  25,502
Ref. : -  Roger Kirkpatrick

Jimmy Neighbour was the Spurs scorer, but goals from David Armstrong and David Mills sent Tottenham tumbling to 21st in the table.

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Spurs - 
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Middlesbrough -  .
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Attendance : -  23,282

In the 35th minute Malcolm Smith met a Craggs free-kick looped over Jennings after being deflected and then Tottenham went further behind two minutes before the break, when they conceded a goal by Mills after a four man move.

Tottenham made little impact on the Boro side and even Alfie Conn, making his debut, could not break through their defence.    Eight minutes into the second half, Beal made what looked like a fair tackle on MIlls, but the ref pointed to the spot and the penalty was tucked away by Hickton and all that was left was for Armstrong to round off the scoring on 73 minutes.

Teams : 
Spurs -  Jennings, Evans, Naylor, Beal, Osgood (Conn), Pratt, Neighbour, Perryman, Coates, McGrath, Chivers
Middlesbrough -  Platt, Craggs, Boam, Smith, Maddren, Taylor, Murdoch, Mills, Hickton, Armstrong, Foggon 
Attendance : - 15,216

Knowles, Pearce and Peters all had opportunities to score without taking them, but then Peters ghosted in to head home Perryman's free-kick at the far post to give Tottenham a 30th minute equaliser.  Jennings had to be alert to stop Mills and McMordie, while Plat stopped Knowles to take the game into extra time again.

Gilzean had replaced Pratt earlier, but his most telling contribution was in the 188th minute of the match, when he nipped across his marker and guided Coates' cross into the net to give Spurs a Fourth Round tie against Millwall.

Teams : 
Spurs -  Jennings, Evans, England, Dillon, Knowles, Pratt (Gilzean), Pearce, Perryman, Coates, Peters, Chivers 
Middlesbrough -  Platt, Craggs, Boam, Spraggon, Gates, Maddren, McMordie, Mills, Hickton, Armstrong, Jones
Attendance : -  19,287

Gordon Jones' cross-field pass picked out Bill Gates and his cross was headed tamely at Jennings, while Gilzean hit a fierce shot after starting the move himself, but it was turned round by Platt.  Craggs produced a save from Jennings with another header from a corner, but the game stayed scoreless at the break.

Gilzean almost converted Perryman's cross with a cheeky back-heel, but it went wide of the mark and Chivers suffered the same fate with a header.  An improvised save by Pat Jennings saved Spurs with eight minutes left, after Spraggon's effort flew off Perryman's head and the Spurs keeper managed to somehow get the ball over the bar with his feet !!  That took the game into extra time and there were only two decent opportunities, bith falling to Gilzean and both not converted.

Teams : 
Spurs -  Jennings, Kinnear, England, Knowles, Pratt (Pearce), Perryman, Naylor, Coates, Gilzean, Peters, Chivers 
Subs not used : 
Middlesbrough -  Platt, Craggs, Boam, Stiles (Brine), Spraggon, Maddren, McMordie, Gates, Mills, Hickton, Jones .
Attendance : -  19,256

A goal down in five minutes, Boro were not dispirited and fought back into the game after the break, when against the run of play, Beal made a short back-pass and Hickton nipped into make it 1-1.  Both sides pressed for the win in the later stages and Jennings thwarted Hickton twice and Mills, while England's header at the other end was hacked off the line by Craggs.

Teams : 
Middlesbrough -  Platt, Craggs, Boam, Stiles, Spraggon, Maddren, McMordie (Vincent), Gates, Mills, Hickton, Jones .
Spurs -  Jennings, Kinnear, England, Beal, Knowles, Pearce, Pratt, Perryman, Naylor, Coates, Chivers 
Subs not used : Peters
Attendance : -  23,822

Ted Ditchburn was in fine form to keep Boro at bay, with their forwards missing a shot of chances as the pressure grew on the Spurs goal and at the other end the visitor's goalkeeper Rolando Ugolini fouled Sonny Walters, but Alf Ramsey had his effort saved from the spot.

However, Tottenham did manage goals through Walters and Les Bennett before the half-time break, while George Robb scored a third into the second period.  Lindy Delapenha pulled a goal back for Boro straight away, but Len Duquemin got on the end of a Robb cross-ball and made it 4-1 to Tottenham.

Teams : 
Spurs - Ditchburn, Ramsey, Withers, Nicholson, Clarke, Burgess, Walters, Bennett, Duquemin, Baily, Robb
Middlesbrough -  Ugolini, Bilcliff, Cobbett, Bell, Dicks, Mulholland, Delapenha, Mannion, McPherson, Fitzsimons, Wlaker
Attendance : - 

Teams : 
Middlesbrough -  Bell
Spurs -   Ditchburn, Farley, Bennett
Attendance : -   44,004

Teams : 
Middlesbrough -  Spuhler
Spurs -   Ditchburn, , Murphy
Attendance : -  36,689

Boro's Jimmy Hartnett scored from an Alex McCrae cross on 13 minutes, only for Alf Ramsey to equalise from the spot after a penalty had been given to Spurs just a minute after.  Legendary striker Wilf Mannion put the visitors ahead again, but once more Tottenham came back to score through Len Duquemin, who knocked home a free-kick from Les Medley.

Another free-kick saw Middlesbrough take the lead for the third time as Lindy Delapenha made it 3-2 on 70 minutes, but Spurs showed they did not give up when Sonny Walters got his head to Medley's corner kick to make it 3-3 just three minutes later.

Teams : 
Spurs -  Ramsey, Medley, Walters, Duquemin
Middlesbrough -  , , , , McCrae, Hartnett, Mannion, Delapenha
Attendance : -  61,148

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Middlesbrough - 
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Spurs ran out winner courtesy of the three goals from Willie Evans, Les Howe and George Hunt, but Micky Fenton pulled one back for the visitors.

Teams : 
Spurs - W. Evans, Howe, G. Hunt
Middlesbrough - Fenton
Attendance : -  25,416

Teams : 
Spurs - 
Middlesbrough -  .
Attendance : - 36,077

Jimmy Cantrell hit four Spurs goals and Bert Bliss the other, but Spurs lost out to strikes from Carr, Storey, George Elliott two and a Tinsley hat-trick ensured a high-scoring home win. 

Teams : 
Middlesbrough -  .
Spurs - 
Attendance : - 6,000

Spurs scorers were Jimmy Cantrell, Ed Lightfoot and Fanny Walden, but they were pegged back by Boro's three goals from Jackie Carr (2) and Walter Tinsley.

Teams : 
Spurs - 
Middlesbrough -  .
Attendance : - 15,000

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