3 times Tottenham beat Arsenal against the odds

A repeat of any of these would be most welcome.
Paul Gascoigne and Gary Lineker
Paul Gascoigne and Gary Lineker | David Cannon/GettyImages

My confidence of a good result leading up to the North London Derby typically fluctuates from extremely sure of a win to feelings of dread. Just as quickly as I can convince myself 3 points is ours, I can also see how a crushing loss is on the cards. After a season where Tottenham have played some of the worst football I can remember (and I’ve seen some bad teams), confidence is sticking on the low side now.

We always hear that derbies are unpredictable, anything can happen, and cries of “the form book goes out of the window”. This time there is also talk of a “new manager bounce” for Spurs. There is some truth to all these things of course, but the situation is potentially bleak. We must admit to being one of the worst teams in the league this season, on terrible form, and up against an Arsenal team who should still be favorites for the title despite some surprising recent away draws.

There have been many times in the past, however, where we have got the win over Arsenal in these unexpected situations. I will delve (a short distance) into the history books and recall 3 of the very best of these wins that I remember.

Note these are not to say they were the greatest performances ever against Arsenal, or that we had the greatest team on that day. Instead, they stick in the memory because of the situation at the time and the unexpected way the performance played out.

1. Tottenham 3 Arsenal 1 (FA Cup Semi-final, 1991)

A clear number 1 spot. In the 90s (and in the decades before), the FA Cup held a much greater significance than it does now. The final itself was a major event with TV coverage in the UK beginning early in the morning before the traditional 3pm kick off. Teams that reached the final even released songs before the big game (yes, really).

There was talk of it being fate for Spurs to win the cup that year because “the year ends in one” and we often won a trophy when that was the case. In truth though, it was Arsenal who came in as heavy favorites. They had recently won the league and would go on to do so again that season, conceding only 18 goals in the process. We, meanwhile, finished 34 points behind in midtable. The cup offered respite from an average league season and, crucially, a chance to stop Arsenal’s effort to win the double. It was also the first FA Cup semi-final to be played at Wembley which added to the occasion.

Arsenal’s boasted a famously miserly back four of Lee Dixon, Nigel Winterburn, Steve Bould, and Tony Adams. Behind them was an excellent goalkeeper, David Seaman. They had a creative midfield and a consistent goalscorer up front in Alan Smith. Despite Tottenham having two genuine superstars in Paul “Gazza” Gascoigne and Gary Lineker, it was difficult to see how we would score enough to win the game. How wrong the predictions were.

We attacked from the start. After only 5 minutes, Gazza, who was recently back from injury, took one of the best free kicks the competition has ever seen. Driving the ball from distance into the top corner, giving Seaman no chance. An iconic goal (with iconic commentary from Barry Davies) and it set the standard for what was to follow.

Lineker made it 2-0 on the half hour with a goal from close range. Harry Kane may be England’s top scorer now, but Lineker held that record for a long time and was truly a master at reading the game to be in the right place at the right time.

Predictably, Alan Smith got a goal just before half time to reduce the score to 2-1 but the Arsenal comeback never happened. Instead, Lineker ran through on goal from nearly the halfway line in the second half to make it 3-1.

We went on to win the FA Cup that year. Our song  for the final? “When the Year Ends in One.”

2. Tottenham 5 Arsenal 1 (League Cup Semi-final, 2008)

Another semi-final win over Arsenal, and another time we then went on to lift the trophy. It is not the occasion that gives this game recognition, however, nor is it even the scoreline (although that did make it even better). This game is recognized because it ended a grueling run of fixtures vs Arsenal.

North London Derbies over the last decade or so have been reasonably even affairs with wins for both teams. The emergence of Harry Kane and Son Heung-Min having much to do that. Between 1999 and 2008, however, we actually went 21 games vs Arsenal without a win. In 2004, we even scored 4 goals at home in the derby and lost 5-4. It seemed like it was to never be and even after a 1-1 draw away in the first leg there was a familiar sense before the game.

Just like at Wembley in 1991, we started strongly and took a lead after a few minutes from Jermaine Jenas. A Nicklas Bendtner own goal made it 2-0 and at half time we were starting to believe. Then came a superb second half as goals from Robbie Keane (linked with the Tottenham manager job recently) and Aaron Lennon made it 4-0. Emmanuel Adebayor scored a consolation for Arsenal, but Steed Malbranque wrapped it up with a simple finish in injury time to make the final score 5-1. Spurs were on their way to Wembley.

3. Arsenal 2 Tottenham 3 (Premier League, 2010)

There are many ways to win a football match but one of the best must be the late winner. Even better than that is when you are losing, looking finished, and you come back to get a late winner. Even better than that is when this happens away from home. And one better than that? When it’s away to Arsenal.

That is exactly what happened in this league game. Arsenal, again performing better than us in the league that season, cruised to a 2-0 halftime lead. It looked like a routine win, but the second half was a different story.

Rafa van der Vaart, in his short time at the club, really seemed to get what games vs Arsenal meant, and he led the charge. He set up Gareth Bale early in the second half to bring us back into the game. Then van der Vaart’s free kick led to a handball which gave us a penalty. He dispatched it to make it 2-2. Finally, van der Vaart’s late free kick was headed on by defender Younes Kaboul for the winner.

We are currently on another bad run against our North London rivals. We are also on a bad run of form in general. We may not have Gazza, Lineker, or van der Vaart. We barely have enough fit players this week. But at least history tells us what can happen. COYS!

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