With many of the stories leading up to this game surrounding the perilous state of the club's money problems, Paul Gascoigne took the game by the scruff of the neck and scored two goals to bring Spurs back from a goal behind against Second Division Portsmouth to go through to the quarter-finals.

A scuffed shot by Mark Chamberlain just before half-time gave Pompey the lead, but on the hour, Gascoigne played the ball wide to Paul Allen and then raced into the penalty area to rise and score a rare headed goal to pull Tottenham level.  Saving the best for last, his dribble past a number of players on a heavy, bobbly pitch, before hitting a low shot into the corner of the net, gave Spurs the lead they retained for the final six minutes.

Portsmouth -  Knight, Beresford, , , , , , , , , , Whittingham, M. Chamberlain.
Spurs -  Thorstvedt, Edinburgh, Mabbutt, Sedgley, van den Hauwe, M. Thomas, Gascoigne, Samways, P. Allen, Lineker, Nayim.
Unused sub. : - Gray
Crowd : - 26,049

Portsmouth were in the relegation zone on their arrival to play Spurs, but Horne's 35th minute strike gave Pompey the points, but it was not enough to save them from going down to Division Two at the end of the season.

Teams : 
Spurs -  Mimms; Statham, Fairclough, Mabbutt, Fenwick; Moncur (D. Howells),  P. Allen, Hodge (Moran), Samways; Walsh, Claesen
Portsmouth - Knight; Swain, Blake, Gilbert, Sandford; Dillon, Horne, Whitehead, Hilaire; Mariner, Quinn
Crowd : - 18,616

Portsmouth - .
Spurs -  .
Crowd : -  15,302

Portsmouth - .
Spurs -  .
Crowd : -  26,306 

Portsmouth - .
Spurs -  .
Crowd : -  28,100  
 

Spurs -  .
Portsmouth - .
Crowd : -  28,619 
 

After a three-match epic to overcome Hull City in the previous round, Pompey might have been drained and Tottenham took full advantage.  Pompey mascot (in full naval dress) Barry Harris got the 15,000 South Coast fans singing, but they were quietened by goals from Alan Gilzean (2) and Jimmy Greaves.  Ron Tindall netted a consolation goal for Portsmouth.

Spurs -  , , , , , , , , ,Gilzean, Greaves.
Portsmouth -  , , , , , , ,Tindall.
Crowd : -  57,910
 

.

Teams : -
Spurs : -
Portsmouth : -
Crowd : - 27,237
 

After 50 years with the club, Anderson resigned on health grounds and the point gained from this match was earned by a Alfie Stokes goal, which he netted from a Jeff Ireland cross after six minutes.  However, Ron Saunders equalised just three minutes later following a corner and the remaining 81 minutes saw Spurs under pressure.

Only a linesman's flag deprived Pompey of a win, when it signalled offside to wipe out the 86th minute "goal" the home side scored, much to the dislike of the majority of the 26,402 crowd.

Teams : 
Portsmouth -  Cutler, Saunders,
Spurs - Hollowbread, Baker, Hopkins, Hills, Ryden, Iley, Ireland, Stokes, B. Smith, Clayton, Robb
Crowd : - 
 

They were soon 3-0 up with goals from Peter Harris (12), Johnny Gordon (13) and Jackie Henderson (15).  Amazingly, Spurs were level by the break as they hit back with goals from Micky Dulin, Johnny Brooks and a Tommy Harmer penalty.

Former Spurs striker Sid McClellan put Pompey ahead again just after the break and Henderson won it with a fifth Portsmouth goal that left Tottenham bottom of the table after four matches.

Teams : 
Spurs -  , , , , , , Harmer, Brooks, Dulin, Bobby Smith, 
Portsmouth - Harris, Gordon, McClellan, Henderson
Crowd : -  35,813
Ref. : - 
 

Ray Crawford, new to the South Coast side, opened the scoring in the 26th minute, following up within a minute with his second.  Peter Harris then netted a brace in the 33rd and 37th minute as Spurs crumbled.  Harris completed his treble in the 56th minute with a penalty, before Spurs finally got a consolation goal from Bobby Smith on the hour.

Teams : 
Portsmouth - Harris, , Crawford, 
Spurs -  , , , , , , , , , Bobby Smith, 
Crowd : -  33,479
Ref. : - 
 

In the 42nd minute, Medwin linked up with Blanchflower to lay the ball into Bobby Smith's path and he hit a powerful right foot shot low into the net to make it 2-0.

Teams :  , , Mansell, 
Spurs -  , , , Blanchflower, , , Medwin, Harmer, B. Smith, , 
Portsmouth - 
Crowd : -   36,110
 

On 11 minutes, Jimmy Gordon got in between Harry Clarke and Ted Ditchburn to put Portsmouth ahead, but Spurs scored through Johnny Brooks in the 23rd minute, going past two defenders and hitting a left-foot shot to make it 1-1 at the break.

Marchi tried a back-pass on 56 minutes, but slipped it past his own goalie, while a deflected shot from Terry Medwin went in off Alec Wilson to get Spurs back level eleven minutes later.  It was left to Bobby Smith to wrap up a 3-2 win with a goal from a Medwin free-kick in the 69th minute.

Teams : 
Portsmouth -  Drinkwater, McGhee, Alec Wilson, Pickett, Gunter, Dickinson, Harris, Gordon, Dale, Rees, Peak
Spurs -  Ditchburn, Hopkins, Baker, Clarke, Blanchflower, Marchi, Robb, Medwin, B. Smith, Brooks, Harmer
Crowd : -   31,903
 

Len Duquemin started the move for the first goal after 64 minutes.  He got in the way of a pass out of the home defence, then put Eddie Baily in on the right wing.  He crossed to Johnny Gavin, whose header flashed into the net.  Gavin also scored Tottenham's second, again from Baily's pass, this time with a shot in the 69th minute.  

Alf Ramsey needed to produce a well-timed tackle to prevent Jackie Henderson getting in on goal and Reynolds denied Peter Harris with a timely save.

Len Duquemin scored from a Gavin corner with five minutes remaining to secure the points for Tottenham.

Teams : 
Portsmouth -  Uprichard, McGhee, Mansell, Phillips, Reid, Gunter, Harris, Gordon, Henderson, Rafferty, Dale
Spurs -  Reynolds, Ramsey, Hopkins, Blanchflower, Clarke, Marchi, Gavin, Baily, Duquemin, Brooks, Robb
Crowd : -   27,539
 

A fine display of goalkeeping from Ted Ditchburn held Portsmouth goal-less until the 42nd minute, when Peter Harris scored for the home side with a 20 yard finish and Duggie Reid made it 2-0 ten minutes into the second half.  However, late on, Dennis Uphill hit a shot that debutant goalie Norman Uprichard fumbled and then knocked the ball into his own goal to make it 2-1, although Tottenham could not grab an equaliser before the end.

Teams : 
Portsmouth -  Uprichard, Gunter, Stephen, Scoular, Froggatt, Dickinson, Peter Harris, Munday, Duggie Reid, Phillips, Gaillard
Spurs -  Ditchburn, Ramsey, Willis, Nicholson, Clarke, Burgess, Walters, Uphill, Duquemin, Baily, Medley
Crowd : -   40,462
 

It was the visitors who went ahead, shocking Spurs in the fifth minute, as Jackie Henderson's low cross was touched out by Ditchburn to the edge of the six yard box, where Len Philips ran in to force home from close range.

Len Duquemin's fired home in the 12th minute with a left footer after Alf Ramsey has put him through and he had held off a number of challenges, while the Spurs striker then squared the ball from the left wing for Eddie Baily to give Tottenham the lead, after Charlie Withers and Les Medley had opened the Portsmouth defence up to play Duquemin into space.

Right on half-time, Baily scored his second when he converted the rebound when Charlie Dore stopped Medley's shot, but was helpless to prevent the goal that saw Spurs finish 3-1 victors.

The second half failed to live up to the high points of the first forty five minutes although Les Medley hit the post with a shot in a move that started with Ted Ditchburn and went through Ramsey and Sony Walters before reaching Medley.
 

Teams : 
Spurs -  Ditchburn, Ramsey, Withers, Nicholson, Clarke, Burgess, Walters, Bennett, Duquemin, Baily, Medley
Portsmouth -  Charlie Dore, Stephen, Ferrier, Beale, Froggatt, Jimmy Dickinson, Harris, Reid, Jackie Henderson, Len Philips, Gaillard
Crowd : -   67,088
 

Ted Ditchburn was the man of the match for Tottenham, with a good save to stop Reid's header from Dickinson's free-kick, but Reid bested the keeper with another header in the sixth minute to give the home side the lead after Marcel Gaillard crossed from the left wing.   Pompey were hampered by Reid having to move out to the touchline after knocking himself out in a collision with the post.

Ditchburn kept out Gaillard and Albert Mundy, but coming up to half time, Ronnie Burgess floated a free-kick in for Sonny Walters to head on to Dennis Uphill and the 19 year old steered the ball past Ernie Butler for the equaliser.  The goal earned Spurs a draw in an entertaining match played out in gale force winds.

Teams : 
Portsmouth -  Butler, , Stephen, Dickinson, Mundy, Gaillard, Frogatt, Harris, Reid
Spurs -  Ditchburn, Ramsey, , Burgess, , , , , Baily, Uphill, Walters
Crowd : -   49,716

Teams : 
Spurs -  Ditchburn, Ramsey, Willis, Nicholson, Clarke, Brittan, Walters, Bennett, Duquemin, Baily, Medley
Portsmouth -  , 
Crowd : -   66,402

Portsmouth -  .
Spurs -  .
Crowd : -   15,000 

A George Ludford hat-trick along with goals from Jackie Gibbons and Pat Beasley netted for Spurs, with the visitors scoring through Bert Barlow and Billy Bushby.

Portsmouth -  .
Spurs -  .
Crowd : -   7,146 

Spurs -  G. Hunt, Bolan, Howe.
Portsmouth -  Weddle.
Crowd : -   33,461