Best and Worst: Tottenham’s FA Cup moments

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Tottenham have the perfect chance to put their recent league woes behind them by booking themselves a place in the F.A Cup quarter-finals when they go up against Stevenage in their fifth round replay at White Hart Lane tonight.


Back to back defeats have no only ended their title push but also endangered the third place finish as an in-form Arsenal side lurk behind them.


The F.A Cup has provided plenty of moments of joy and despair for Spurs over the years, and with another quarter-final beckoning GMF brings you their best and worst moments in the famous competition’s history.


The Best…..


Arsenal, semi-finals, 1991


A landmark moment in the club’s history, the 1991 semi-final against Arsenal also contained possibly the best free-kick ever scored at the old Wembley stadium.


Paul Gascoigne stunned the travelling Arsenal support with his fifth minute free-kick from 35 that left David Seaman stranded before Gary Lineker put the Lilywhites on cloud nine as he doubled their lead with just ten minutes gone.


Alan Smith pulled the Gunners, who would go on to win the league that year, back into the game when he headed past Erik Thorstvedt just before half-time, but Linekar put the game to bed with 12 minutes remaining.


Nottingham Forest, final, 1991


Off the back of their semi-final win over Arsenal, Spurs seemingly had their name on the cup even before they stepped onto the field against Nottingham Forest.


They needed a huge slice of luck to finally hold the famous trophy aloft but for a long time it seemed as though it wouldn’t be their day as Stuart Pearce’s early free-kick put Forest ahead and Gascoigne, playing his last game before moving to Lazio, sustained a serious knee injury in his horror tackle on Gary Charles.


When Mark Crossley saved Linekar’s spot kick their luck certainly seemed to be out but when Paul Stewart drew the side’s level the tides turned and Des Walker agonisigly turned into his own net with 94 minutes on the clock.


Leicester City, final, 1961


Almost certainly the finest era in the club’s history, the 1961 F.A Cup win helped Spurs win an historic double, making them the first club to achieve that feat since Aston Villa in 1897.


Another match fraught with frustration for Spurs in front of a crowd of 100,000 people, Cliff Jones saw his first half strike ruled out for offside in what was fast becoming a tense encounter.


The match continued in a similar vein until Bobby Smith broke the deadlock to relieve the tension in the 66th minute, and Terry Dyson sealed the deal nine minutes later.


…and the worst


Portsmouth, semi-finals, 2010


Tottenham were huge favourites going into their F.A Cup semi-final against a Portsmouth club plummeting down the Premier League and beset by financial trouble in 2010.


Harry Redknapp’s side were flying high and on course to secure Champions League football while Portsmouth would end the season rock bottom.


However the magic of the club prevailed at Wembley as their lowly opponents mustered a resolute defensive performance to keep Spurs at bay.


Former player Kevin Prince-Boateng rubbed salt in the wounds by finding the net from the penalty spot after Frederic Piquionne had taken advantage of a Michael Dawson slip to open the scoring.


Manchester City, fifth round, 2004


Described by observers at the time as ‘one of the best comebacks in F.A Cup history’, Tottenham’s tale of woe against Manchester City in the fifth round back in 2004 has entered both club’s folklore.


Spurs were cruising at home, racing into a 3-0 first half lead while Joey Barton’s seding off had put them on easy street.


City had other ideas however staged their dramatic comeback in the second half, with goals from Sylvain Distin, Paul Bosvelt, Shaun Wright-Philips pulling the scores level before Jonathan Macken earned himself a place in history by bagging the winner.


Leicester City, third round, 2006


Spurs were the victims of another early round dramatic comeback as Leicetser fought back from the dead to record a famous win, marking the last time the north London club exited the F.A Cup against lower league opposition.


Once again Tottenham were in control and had cruised into a comfortbale lead thanks to goals from Jermaine Jenas and Paul Stalteri in the first half.


Elvis Hammond pulled a goal back for the Foxes before half time before Stephen Hughes bought the sides level.


The momentum was with the home side but they were forced to wait until the 90th minute until they scored a dramatic winner, with Mark de Vries stoppage time strike sending the home crowd wild.

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Tottenham Hotspur
Premier League
Paul Gascoigne

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