1. 2016 Week 1: San Diego Chargers 27, Kansas City Chiefs 33
I say this with every ounce of seriousness in my body: this might be the worst regular-season sports loss that I have ever had across any sport and it came in Week 1. That shows just how bad it was.
Not only did the Chargers do the perfect Charger thing and blow a huge lead to a division rival and lose in overtime, but they blew that lead because they lost their number one receiver, Keenan Allen, after a stellar first half.
At this point, Allen still could not shake the injury-prone narrative and the Chargers wound up without Allen for the entire year. He has since shaken that narrative with three-consecutive 16-game seasons, but this injury, man, was it rough.
It hurt the team for the entire season, obviously, but it also hurt them in this game. After Allen’s injury the Chargers could not get much going on offense and that fueled the Chiefs to overcome a 21-3 halftime deficit.
Heck, the Chargers still had a 24-10 lead heading into the fourth quarter and could only make a field goal while allowing the Chiefs to score 17 to take it into overtime.
The Chargers did not even get the ball in overtime. The Chiefs went 70 yards in 10 plays to score the game-winning touchdown and kickstart what would be an ugly 2016 season for the Chargers that felt very similar to the 2019 season.