Christ. It's amazing looking at that list how many more humiliations I can think of.
The Notts County one always makes me laugh a bit although the story is a bit grim. I was about 15 at the time and one of the few Spurs supporters in my school. I used to get even more upset about games back then than I do now. Anyway, the morning after, someone started a rumour that I tried to top myself by using my coat after the game. Lo and behold, the next day I was late into school for an unrelated reason so the rumour caught fire and most people thought I was in hospital because of us losing to Notts County. When I eventually showed up a few hours late, I was plagued with people inspecting my neck for the day...
I think the City one was spectacular. IIRC they hadn't won in about 10 games, were 3-0 down at HT and down to 10 men. There is no other club they could have won against that night except maybe themselves. Spectacular. For me the ultimate humiliation.
The Saudi Sportswashing Machine one runs it close though. We don't just fudging lose, we lose on steroids. To lose 5-1 to 10 relegated men ensuring we finished third in a two horse race and behind our fiercest rivals has Tottenham written all over it.
We don't do glorious failure, we do spectacular failure.