2000: Chargers win just one game
The 2000 season doesn’t make this list because expectations were high (though the team went a respectable 8-8 in 1999), but because the team was just….. awful.
To this point, no team had ever gone 0-16 in a season. There had been a few winless teams before, but those teams didn’t play 16 games. The Chargers came incredibly close to being the first.
Their lone win of the season came over the Chiefs in Week 13. The Chargers came into that game 0-11 and Ryan Leaf found a way to outduel Warren Moon in that game but it took a 52-yard field goal by John Carney late in the fourth quarter to give the Chargers a one-point victory.
The team then finished the season the way it started it, losing its last four games by an average of 17.5 points per game.
Harbaugh, who had beaten the Chargers in that 1995 playoff game, was on this team as a backup quarterback, but he didn’t fare much better than Leaf in the games he started and played in.
The Chargers were simply atrocious in 2000. The team allowed 40 or more points in three games (including 57 in Week 5 against the St. Louis Rams) and at least 30 points six times.
It was also the season in which it became abundantly clear that Leaf, the team’s first-round pick in 1998, was not going to work out. That season, Leaf completed exactly half of his passes while throwing 18 interceptions and posting a 1-8 win-loss record.
2000 was a miserable season and that year’s Chargers should be considered among the worst teams in league history.