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Yes, the Buffalo Bills have lost four Super Bowls in which Jim Kelly was the quarterback.
Yes ... not only are the Bills the only team to lose four consecutive Super Bowls they are the only team to ever play in four consecutive Super Bowls.
The Dallas Cowboys lost Super Bowl V to the Baltimore Colts and Super Bowls X and XIII to the Pittsburgh Steelers.
Through Super Bowl XLII, the Cowboys have not lost back to back Super Bowls. They lost Super Bowl V to the Baltimore Colts and Super Bowls X and XIII to the Pittsburgh Steelers.
Pittsburgh Steelers in Super Bowls X and XIII.