2002 Oakland Raiders

The Raiders went 11-5 in the regular season, and boasted the league’s MVP, quarterback Rich Gannon.  They even cruised to two easy wins in the playoffs, getting past the 9-7 Jets and 11-5 Titans with an average margin of victory of 18.5 points, and found themselves four-point favorites in Super Bowl XXXVII against the Buccaneers.  But then the game actually happened, and along with it came Gannon’s five interceptions, Tampa Bay’s 24 first downs, Dexter Jackson's MVP award and ultimately, a comically bad 48-21 loss. 

After the game, the Bucs' players said they knew all the signals and audibles the Raiders were calling - maybe that's why Oakland managed just two offensive scores, while Tampa Bay's defense racked up three touchdowns.

Worst still: since that shocking Sunday, the Raiders are just 24-72 in the six losing seasons that have followed.