These are in chronological order, but I've not rated them 1-5, they are just 5 moments that stand out for me as low points.
1) Relegation against Liverpool in 1996, the first time I saw City relegated. I couldn't believe what I was seeing when we subbed Niall Quinn and he came back out, hair still wet from his shower, screaming at the players that we needed another goal. Why did non of the coaching staff not have a radio?
2) Relegation against Stoke despite winning 5-2 in 1998, to see the club I loved so much, sink that low...terrible.
3) Being 2-0 down in the play off final against Gillingham, thinking we were destined for another season in division 2, the abyss. (Fortunately this one had a happy ending but I'll never forget how despondent I was at 2-0 down)
4) Leaving Maine Road and the untimely death of Marc-Vivien Foe.
It was sad to leave Maine Road, it was the home of so many great footballing memories for me and many thousands of blues. To no longer be able to go to the place you saw your first game was sad, however it was put in to context only a short time later by the untimely death of Marc - Vivien Foe. Pele was in town the night Foe died at an event at Flannels, I queued up to get his autograph. Was so happy on the way home, then flicked on the news and couldn't believe what I was seeing. I went to Maine Road to sign the condolence book and saw all the flowers, shirts and tributes. I remember a really hard looking bloke with tears in his eyes pointing out a poem he'd read earlier, it was surreal. I'll never forget what it was like outside Maine Road that day.
5) Blackburn 2 City 0 FA Cup 1/4 final 2007
To see City play with so little passion in an important game was bad enough, but the vibe around the club with Pearce at the time was like the bad old days. I remember the TV footage of the woman literally screaming in frustration. A horrible day, but we'd seen far worse and at least we were in the Premier league at the time. Still a low point though.