Aside from the obvious, the worst football period of my life started in about January 2008, and now, three years later, hasn't finished.
We were twice behind to Havant and Waterlooville, and then knocked out by Barnsley. We were playing dreadfully with no passion and no depth, and at that point I knew that Rafa was going to take us nowhere - I wanted him out. We recovered a little, made the top 4, and went on to miss out on the title the following season by just 4 points...but it didn't stop me thinking that when it came to it, the team that wore Liverpool red simply weren't good enough, and (a few exceptions aside) didn't give a fuck and wouldn't put their balls on the line for us.
We kept Rafa for 2 and a half years from that point, and Roy has been here for six months, and we have slowly disintegrated as a team further and further, just winning enough important games (Man U 4-1, Madrid 4-0, Chelsea 1-0 (away) and 2-0) to ensure we stay there or there abouts and keep the board from sacking the manager. Just enough talent to perform when they can be arsed.
If we had of thought, after the Barnsley game, lets fucking mix this up and get a decent young manager (obviously those Yank cunts wouldn't have done that though) - where would we be now? Maybe the rebuilding would have taken 3, 5, maybe 10 years, but we would be in a better shape than we are now.
Fucking depressing when you see how good Spurs looked as an attacking threat in the second half, with the majority of players who would have joined us if we had wanted them...instead of the attacking fucking 'threat' that Babel, Jovanovic, Voronin et al have given us over the last few years.
Barring all that, the worst I have ever felt in football terms was in May 1989, Michael Thomas. As a 14 year old I just wanted to curl up and die. Now I'm just left with apathy.
