From about 1985-2000 it might have been easier to pick out the ones who did well for us! Most of the players we signed in that era were turkeys! :)
Some players I remember getting excited about and then disappointed with a few weeks later:
I was at Maine Road for Alphonse Groenendijk's debut against QPR and at the time, we didn't get many Dutch players in England - especially from Ajax! The guy had a decent debut and could pick out a pass. I was sure he was going to become a legend at City.... it goes without saying he didn't become a legend and don't remember him playing much either.
I was also really excited about Ricky Holden. Oldham had produced some top class players and Holden was the one who would put in these insanely accurate crosses with plenty of whip on them. I honestly think that he could cross the ball as well as Beckham. In my mind, Holden would whip in the crosses and Quinn and White would be 25 goals each. He was absolutely awful. Not only that, he looked well out of shape too.
David Sommeil was one who should've been ideal next to Distin, but he just looked absolutely out of his depth. Many of these players had decent careers up until they signed for us then just lost whatever they had. Sommeil wasn't bad, but just disappointing.
Tony Vaughan was a big name signing in 1997 from Ipswich - around £1.5m I think it was. He was supposed to be a City fan but played like he'd had 10 pints before getting on the pitch. I remember one game where he was played as a full back and was just awful there - slicing the ball out of play. They swapped him around in the second half and he sliced it out on the other side then! He was just a poor player.
Wayne Bridge had shown glimpses of being a decent player before he came to us. When he got here, he did nothing. He was probably one (as well as Mills) of the worst pound-for-pound signings we made. He had no interest in playing for us, no desire and had no intention of getting fit.