The unfortunate distinction of being the only player in NFL history to lose five consecutive Super Bowl appearances belongs to backup quarterback Gale Gilbert. Gilbert experienced a uniquely painful stretch of championship game outcomes while serving as a reserve signal-caller during the 1990s. He was a member of the Buffalo Bills roster during their heartbreaking four-year streak of consecutive Super Bowl losses from Super Bowl XXV through Super Bowl XXVIII. In search of a change of scenery and a fresh start, he subsequently signed with the San Diego Chargers, only to reach Super Bowl XXIX the very next season, where the Chargers were decisively defeated by the San Francisco 49ers. This remarkable sequence left Gilbert with five straight conference championships and five consecutive Super Bowl defeats, making him a trivia footnote for enduring one of the most uniquely frustrating runs of championship game appearances in professional sports history.