I first played Championship Manager in 1999, playing the 1997/98 version. After a little more than season, I'd been sacked by Celtic. What a start! I played around a bit with other teams, with the UEFA Cup win with Derby in my 8th season and the World Cup win in the 20th season of the same game the major highlights, but none greater than Monaco's 29-28 penalty shoot out win in the second round (or something) of the French Cup. I later moved on to the CM3 versions, and started off by getting sacked by Derby halfway into my third season. Having now managed to actually win some of my matches, I've moved onto CM4, in which I'm currently anxiously awaiting my first sacking.
Below are some of the stranger screenshots that I've accumulated in my games, (unfortunately, the Monaco penalty shoot out one couldn't be screenshotted), plus my greatest victory.