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Where does the Real Madrid game rank in your pantheon of Tottenham victories?


Tottenham Hotspur v Real Madrid - UEFA Champions League Photo by Clive Rose/Getty Images

If you’re anything like me you still can’t feel your face after yesterday’s win over Real Madrid and continue to explain to anyone who will listen that this was A BIG F***ING DEAL.

One of those kind souls who put up with me talking about the game non-stop for about an hour asked me where this ranks in the list of famous Tottenham victories in my lifetime. After some brief (Ed note: it was not brief) consideration, l came up with a top five.

This is obviously an extremely subjective ranking based on completely arbitrary criteria. Full disclosure: I’m 29, my first game was in 1996, so that rules out the FA Cup run in 1991. I’m also just the right age that Spurs were mostly terrible during my childhood, so there are wins that didn’t mean a ton in the grand scheme of things that hold immense sentimental value to me.

Anyway, here’s my list — we’d love to hear yours in the comments!

1. Tottenham 3-1 Inter Milan

This one takes the top spot mostly because it came first. Our first time in the Champions League, demolishing the holders, Gareth Bale ending Maicon’s career — that all made me feel like Spurs were the real deal, that those glory, glory nights were back at White Hart Lane.

2. Tottenham 3-1 Real Madrid

I’m not sure it’s really sunk in that we just beat the best team in the world, and pretty handily at that.

3. AC Milan 0-1 Tottenham

I thought we had zero chance going into this tie. Just getting to the knockout stage was an achievement. To actually grab a win at the San Siro with such a heroic performance felt immense.

4. Tottenham 2-1 Chelsea (League Cup Final)

I’ve only seen Spurs win two trophies: the League Cup over Leicester in 1999 when none of the big clubs cared about it, and the League Cup again in 2008. Putting one over on Chelsea made it feel especially sweet.

5. Tottenham 2-1 Chelsea (EPL 2006)

Spurs went 16 years(!!!) without beating Chelsea in the league. We were the butt of so many jokes over that period, getting that monkey off our backs was such a relief.

Honorable mention:

Man City 0-1 Tottenham: Qualifying for the Champions League was the first of many steps toward where we are today.

Tottenham 2-0 Arsenal: Finishing above our rivals with a dominant display in the final NLD at the Lane. What a beautiful day that was.

Man United 2-3 Tottenham: I thought this was the beginning of AVB’s long, successful reign. Alas… still fun!


What is the best Tottenham win in your lifetime?

This poll is closed

  • 19%
    Tottenham 3-1 Inter Milan
    (143 votes)
  • 60%
    Tottenham 3-1 Real Madrid
    (433 votes)
  • 2%
    AC Milan 0-1 Tottenham
    (21 votes)
  • 2%
    Tottenham 2-1 Chelsea (League Cup)
    (19 votes)
  • 0%
    Tottenham 2-1 Chelsea (EPL)
    (5 votes)
  • 13%
    Something else — let us know!
    (98 votes)
719 votes total Vote Now