My personal lowest moment following Coventry City came on December 4th 2016 - We lost 4-0 away at Cambridge who were a League below us at the time in the FA Cup having let Luke Berry, a central midfielder score all 4 goals against us, it was beyond doubt the worst most clueless performance I have ever seen a City side put in
Walking out of that ground (about 60 mins in) was the only time I have ever questioned my support for the club, I turned round to my dad and asked 'What is the point in all of this time, money and effort we waste on this club?' - I could have at that point happily not attended another game that season and the only reason I did was to A) Keep my dad company and B) Despite how shit we were I did enjoy the camaraderie of away matches back then
If you would have told me less than 10yrs later we would even be a Championship side, yet alone a Premier League one that day I would have put you in straight jacket myself