Ashamed/distraught
1. Southampton at home in 2004, lost 3-1. Seem to remember Kevin Phillips notching a couple for them. It was right at the end of the season and we only had a couple of home games left - we were staring relegation in the face. We'd just got good points away at Spurs and Villa and we thought we were on the way to safety, only for James Beattie and Phillips to batter us pretty convincingly. After that game I think we were a point above the dropzone and I was convinced that was it. My first year as a season-ticket holder at the City of Manchester Stadium, I thought it was all over and I cried - it's the only City loss I've ever cried over. Thank fuck for that win against Newcastle a couple of weeks later - big man Paolo Wanchope with his first goal of the season in fucking April saved our bacon.
2. Wigan FA Cup final in 2013. Not because of the result. I was happy enough for Wigan to win, and I knew we'd be back each season, challenging for top honours and trying to win trophies. Wigan were down anyway and were allowed their day in the sun. What made the day so shameful was the drip-feed of rumours in the morning coming from City that Roberto Mancini was going to be sacked regardless of the result. It killed the atmosphere in the car immediately. And when we got to Wembley it was clear everyone knew. City outnumbered Wigan three-to-one and all of us were tense. There was loads of blue-on-blue fighting in the crowd over the Mancini/Manuel Pellegrini rumours and the weather made everything worse after full-time. A bad day that started to put me off going to Wembley.
3. Blackburn away in the FA Cup 2007. As others have said, that Blackburn game was the absolute lowest point just before the takeover. We'd been playing abject football all season (and for the majority of our time under Stuart Pearce) but we'd somehow ended up in the FA Cup quarter-finals with a game against Blackburn. Cue an absolute shitfest of a game at Ewood Park that we lost 2-0. The performance was so bad that I remember watching on TV as Joey Barton threw his shirt in the crowd as a souvenir for a fan, only to see it get chucked straight back at him. That was a dark, dark day. A big collective realisation that this was it for City. A boring mid-table finish, just about escaping relegation, and losing to the first decent team we played in the FA Cup. Every year. Thank god things changed.
Proud
Can't think of many, but Newcastle away in the FA Cup in 2002 stands out. We went away to Newcastle in the FA Cup when we were top of the Championship under Kevin Keegan, and I remember it being seen as a 'test of our Premier League credentials'. Newcastle were flying high under Bobby Robson, playing in the Champions League, and had players like Alan Shearer, Nol Solano, Craig Bellamy, etc. They eventually finished 4th. In 2024, the equivalent would be, say, Sheffield United or Leeds United going away to Chelsea or Aston Villa now. We got reduced to 10 men in the first half but we kept battling and battling and battling. Eventually Newcastle scored and won 1-0 but it was only because of a Nicky Weaver mistake in the end, and we gave them a proper scare throughout and had some big chances. It showed we were more than ready to come up in 2002, and it proved true - we beat that same Newcastle team at Maine Road seven months later in the most one-sided 1-0 game I've ever watched.