5 Great Tottenham Moments Against Arsenal in Cup Competitions
In 18 FA and League Cup meetings, Arsenal have won 10 to Tottenham Hotspur's five with three draws coming in the latter competition.
Tottenham will be hoping to pull one closer in the record books when they host the Gunners in Wednesday's League Cup third round.
If things go well for the home team, the game may produce a moment or two that will find itself worthy of being recognised among the following highlights from Spurs' past.
In truth, there is not a whole lot to pick from in terms of great Tottenham cup moments against their capital rivals (as somewhat demonstrated by the fifth entry on the list and the absence of any honourable mentions).
However, the selections chosen here are notable not only for the club getting one over on Arsenal. They also led to some of the greatest occasions in the club's history.
Indeed, given the importance of the north London derby in any format, it is perhaps no surprise that success would follow Spurs defeating the men in red.
First up, we head back to the early 1980s and a moment that was not so much something in a game as the result itself.
Third-Round Win Sets Spurs on Their Way to More FA Cup Glory
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Tottenham were the FA Cup holders heading into 1982. A year earlier they had won at Highbury to book their place in the final. It had not been against Arsenal (Wolverhampton Wanderers were the victims in the semi-final replay), but winning on their ground was an enjoyable bonus, one typified by the fans' pitch invasion at the final whistle.
After a season in Division Two in 1977-78, Spurs' cup success confirmed their rejuvenation. Understandably, Keith Burkinshaw's side were keen for more in the club's centenary year.
A promising campaign in which Spurs competed hopefully on four fronts at home and in Europe ultimately suffered from an overwhelming schedule.
The one strand they did follow to a happy conclusion was in defending their FA Cup. An achievement that began with a third-round defeat of Arsenal at White Hart Lane.
The two teams had only met once previously in the FA Cup, back in the same round in 1949 when the Gunners won 3-0.
Almost 43 years to the day they were drawn together again, this time at White Hart Lane. "The Centenary Year, 1982, could not have got off to a more dramatic start," wrote Phil Soar in his book commemorating Spurs' first 100 years, And The Spurs Go Marching On.
A Garth Crooks goal would secure a 1-0 win in what Soar described as "a one-sided game." Having received an Ossie Ardiles pass, the striker's tame shot was uncharacteristically let through by former Spurs goalkeeper, Pat Jennings.
Seeing arguably the club's greatest goalkeeper—who joined Arsenal in less-vitriolic circumstances than Sol Campbell decades later—suffer was an unfortunate byproduct.
But in securing the first result of an unbeaten treble over the Gunners that season (Crooks would score a further brace in a 3-1 win in April) that set the team on their way to a victorious return to Wembley, it deserves its place here.
Gazza's Free-Kick in 1991
2 of 5The importance of Paul Gascogine to Tottenham Hotspur in the late-1980s/early-1990s is typified by how often his exploits in just a three-year spell continue to be recalled.
In the matchday programme for their recent win over Crystal Palace, he was prominent in Andy Greeves' feature interviewing former Eagles midfielder Geoff Thomas about the period. "Everyone involved in English football during Gazza's era seems to have their own tales to tell about the Gateshead-born player's individual talent and personality."
Chief among those tales from a Spurs perspective is his FA Cup semi-final free-kick against Arsenal at Wembley in 1991. The piece de resistance of an inspirational, influential run through the competition that had already seen the midfielder score five times in the previous three rounds.
The match was only a few minutes old when Spurs won a free-kick around 30 yards from the Gunners' goal. "It was an impossible position to score from," wrote Bob Goodwin in Tottenham Hotspur: The Complete Record. "Only Gascoigne would have had the audacity to try, but he hit the ball with such venom that it flashed past David Seaman into the net."
"I hit the ball as hard as I could, managed to make it swerve and poor old Dave Seaman got beaten all ends up," remembered Gascoigne in Gazza: My Story.
BBC commentator Barry Davies' call of the goal captured the moment perfectly (see above video). "Brilliant!" he cried, delighting at the England international's audacity. "That was one of the finest free-kicks that this stadium has ever seen."
Gary Lineker would score two either side of what proved a consolation goal from that season's league champions, Gascoigne involved in the creation of his England team-mate's first.
Spurs would go on to beat Nottingham Forest in the final, but it is their talisman's shining moment that is most fondly recalled from the run.
2008 League Cup Semi-Final Part One: Jenas Settles the Nerves
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Tied one-apiece from the first leg in the 2008 League Cup semi-final, Tottenham entered the deciding home fixture still without a win over Arsenal in almost nine years.
Since the Gascoigne-inspired win in 1991, they had also lost three times to the Gunners within reach of a final date. Twice in the FA Cup (in 1993 and 2001) and just a year prior in the League Cup when, despite taking the second leg to extra-time, they let the game get away from them.
Spurs had been unfortunate not to return to White Hart Lane with an advantage, Theo Walcott cancelling out Jermaine Jenas' opener at the Emirates Stadium with the benefit of a fortunate deflection.
Jenas led the way in making sure things would not be so close again.
Getting a head to Radek Cerny's long boot forward, the midfielder got the ball back two passes later. With space in front of him he advanced forward and—with a route to goal improved by Robbie Keane's run dragging William Gallas out of position—fired in off the far post.
White Hart Lane exploded with delight. Three minutes had not yet been played and Jenas had delivered the perfect, nerve-settling start.
2008 League Cup Semi-Final Part Two: Malbranque Seals a 5-1 Win
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A Nicklas Bendtner own goal and terrific counter-attack moves completed by Robbie Keane and Aaron Lennon all but put the 2008 semi-final beyond doubt (future Spurs striker Emmanuel Adebayor also netted to make it 5-2 on aggregate).
Either of the latter two Tottenham goals would have warranted their place here. Both scintillating examples of this Spurs side at their best—quick, clever and very entertaining.
Their fifth on the night gets the nod. The confirmation of their first final since 2001 and the knockout blow in a thrashing of Arsenal the likes of which they had not produced in decades.
Fittingly, arguably the player of the round in Jenas would set it up. Bounding down the pitch and past a leggy last challenge into the box, he teed up Steed Malbranque to sweep it home at the back post.
"In order to beat a team like Arsenal, you have to play well," then-manager Juande Ramos said, per BBC Sport. "We didn't make mistakes and were perfect in all areas of the team."
Tottenham would muster another great performance a month later, beating another London rival in Chelsea 2-1 in the final to secure their first major trophy of the 21st century.
Nayim from the Halfway Line!
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Out of the previous chronological order and testament to the relative paucity of great Tottenham cup moments against Arsenal, the final entry was not even scored in a north London derby.
Yet Nayim's incredible extra-time deciding goal for Real Zaragoza in the 1995 European Cup Winners' Cup final is more than worthy of honourary status.
The Spaniard had spent the best part of five years with Spurs at the turn of the decade and was part of the 1991 FA Cup-winning team.
Having left for Zaragoza in 1993, his strike at the Parc des Princes against his old rivals was not only a delightful quirk of fate. It was very much informed by his time as a Spurs man.
"I had played against Arsenal for five years with Tottenham and remembered they always played with a high defensive line, with the goalkeeper [Seaman] acting like a sweeper, so before the game I told my team-mates and our coach that we should try and shoot from the halfway line," Nayim told UEFA.com's Richard Martin in 2014.
The score was 1-1 with penalties looming when he decided to go for it. "I remember looking at Seaman the whole game and in the last minute I tried it—luckily everything went right."
Nayim controlled a tired Tony Adams header on his chest, looked up and proceeded to audaciously lob the England goalkeeper. He was not wearing a Spurs shirt, but heck, even the great Lilywhites would have struggled to deliver a moment as deliciously sweet as this.
A chant commemorating the goal would soon be heard echoing around Tottenham matches. With the Arsene Wenger era of north London dominance not long from starting, the White Hart Lane faithful would have to live off such memories for a while to come.
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