Weirdly, the one that really sticks in my mind is the 6-1 against Chelsea in 1997, Christian Gross' first home game.
We'd had a brick start to the season, the Badger was gone, our big summer signings were garbage, our kit was Pony, Arsenal were flying, we got deservedly done over by Crystal Palace, we hire a funny foreigner to match the one Arsenal have just hired and he turns out to be terrifyingly mental... but then Gross took over and we beat Everton with a smart, encouraging display, Ginola and Ferdinand suddenly looking like the players we'd just bought, finally smashing two past them after 70 minutes, beautiful. It really did feel like "wow, maybe this guy is onto something!" So I turn up at the Lane to watch us play Chelsea having feared the worst since I got my ticket (the jinx was still in its relative infancy back then but we still weren't tipped to get anything), the tide having suddenly turned, Chelsea fans at work suddenly not treating it as a joke any more... Christian, give us a wave!, followed by a deafening roar, probably louder than I've ever heard any new manager... bit of a ropey first half, Ian Walker having to scramble loads of long-range Chelsea pot-shots away, Ginola misses a golden chance by freezing up, Ferdinand tries a goalward volley and instead belts the ball in the general direction of the ****erel on the West Stand, and we're looking at each other thinking, okay, this isn't so good (but it's probably just nerves, right?), somehow going in 1-1 at the break (we headed in from a set piece, which shows you how long ago this was), and then... and then...
Literally the brickest, most incompetent, most diabolical second half performance I've ever seen us turn in at home (I'm tempted to say anywhere). Seriously, we weren't brick, we were some kind of brand new classification of brick. And every single person in the ground knew it - all our fans, all their fans, Gullit looked almost embarrassed at one point, Hughton dying of shame, Gross pictured on MOTD that night looking like a rabbit in the headlights - like, oh Jesus what is happening and why can't I fix it? - and even the players just had this resigned look about them, like "oh man, we really are bad." It wasn't that we gave up - we actually kept trying, to our credit, even when Zola and di Matteo were just carving us apart (they both should have had five each) - it was that we sort of knew our trying wasn't good enough. It's hard to explain, but I've never felt further away from being a success in the Premier League, not even when Gary Doherty was playing up front or Johnnie Jackson was claiming his goals would keep us up.
One of the discussion forums back then, in the days before GG>Spurs Update>Yidtalk>THUH - I think it was a Carling thing - had a thread the next day from some Coventry fans saying that when Spurs went down, Coventry should take a punt on buying Sol Campbell because he wasn't as brick as our performance against Chelsea had made him look. But he was, we all were. There've been plenty of times we've been crap, bottled it, choked, lost games we didn't deserve to lose, lost games we definitely deserved to lose, my uncle even tells me what it was like when we went down in the Seventies... but I've never felt so completely hopeless as trudging back up the freezing cold High Road in total silence after that game.