2011 CL Final, I knew the gulf was big between us and Barcelona. But, they were simply so much better. We never really stood a chance, that was a really humbling experience and really broke me given how far away we were from the worlds' best.
2005 FA Cup Final, this loss stings the most. Even over 2011 CL Final, won't say it broke me. But, to this day remains the most bullshit game we've lost despite playing brilliant.
Post-Fergie era, there are simply too many games and moments. If I were to go down the memory lane, I'll genuinely get depressed. But, I have to say the lowest was our abysmal end to 2018/19 campaign where we were in relegation form and had given Ole a 3 year deal. Instead of sacking him, we gave him the reigns to rebuild the club with infamous "cultural reboot". I knew we had made a mistake which we'd pay for dearly, but not a lot of fans were ready to listen.