2005 AFC Playoffs vs New York Jets. Kaeding, maybe the most accurate kicker in the league at the time, misses a game winning FG in OT. Jets march down the field and hit the game winner.
2007 AFC Playoffs vs New England. Went into the game with a 14-2 team, arguably the greatest team in Chargers history. Complete meltdown in the 4th quarter as we had multiple mistakes that cost us the game. We intercept Brady late only to fumble it back on the same play. Leading 21-13, we lose 24-21 after a Pats TD, 2 point conversion, and late FG. I was absolutely crushed after this loss, probably the most devastating loss I have ever experienced as a fan.
2007 one game playoff vs Colorado Rockies. Holliday never touched home plate damn it! Padres had leads multiple times and Hoffman blows the save. Rockies win in extra innings on a bullshit play at home where Holliday is awarded the run while never touching home plate. Still irks me to this day because its the last time we have ever come close to making the postseason. I've never been so pissed off after a game.
2009 AFC Playoffs vs New York Jets. Entered the post season as the 2nd seed in the AFC on an 11 game winning streak. Kaeding misses another FG which essentially costs us the game. We lose 17-14 in LT's final game in a Chargers uniform.
2012 - Ray Rice 4th and 29. Ravens need to convert on a 4th and 29 to keep their chances of making the playoffs alive. 8 Chargers players miss the tackle during an absurd play where Rice converts. Ravens win and then go on to win the Super Bowl.
Not to mention we also lost Tony Gwynn, Junior Seau, and the San Diego Chargers football team. Its rough being a SD sports fan.