19. 1999 Miami Dolphins
Regular season: 9-7 | Playoffs: 1-1
This marked the final NFL season for Hall of Fame quarterback Dan Marino and legendary head coach Jimmy Johnson in a relationship that lasted four seasons and was fraught with difficulties. Johnson was supposed to be the guy who could finally get Marino a ring, but the teams Johnson inherited and tried to build upon just weren’t there. Marino started just 11 regular-season games in 1999, with Damon Huard as his backup, and though the Dolphins started their season 7-1, they backed into the playoffs at 9-7 following a late-season collapse. After beating the Seahawks 20-17 on the road in the wild-card round, Miami was absolutely demolished by the Jaguars, 62-7, in the divisional frame. The Dolphins have made the postseason just four times since and haven’t won a playoff game since 2000.