Worst overall moment for me was watching the '99 Jaguars lose the AFC Championship to the Tennessee Titans after being the top team in the league, going 14-2 and the only losses coming from... the Titans.
I think the Jags are just starting to recover in recent years to get back to winning(aside from this year). I was younger then and it really affected me. I still have a disdain for that team. Losses to them are worse than to anyone else, no matter how more meaningful that game may or may not be.
Also anytime the Patties win a game.
(They beat both the Rams and Panthers in the Superbowl, both teams are among my favorites)
I think the Jags are just starting to recover in recent years to get back to winning(aside from this year). I was younger then and it really affected me. I still have a disdain for that team. Losses to them are worse than to anyone else, no matter how more meaningful that game may or may not be.
Also anytime the Patties win a game.
(They beat both the Rams and Panthers in the Superbowl, both teams are among my favorites)