As of Super Bowl XLII, there has never been a player to actually play in five consecutive Super Bowls, however, there has been one player, backup quarterback Gale Gilbert, who was on the roster of the Buffalo Bills that went to Super Bowls XXV-XXVIII and then was on the roster of the San Diego Chargers who went to Super Bowl XXIX.
No player has actually played in five consecutive Super Bowls. However, quarterback Gale Gilbert was a member of the four Buffalo Bills teams that went to Super Bowls XXV-XXVIII and a member of the San Diego Chargers that played in Super Bowl XXIX.
As of Super Bowl XLII, no quarterback nor team has won three consecutive Super Bowls.
Tom Brady.
The Cowboys' quarterback won three Super Bowls in four years (Super Bowls XXVII, XXVIII and XXX).
Through Super Bowl XLII, no quarterback has ever won three Super Bowls in a row.
John Elway.
Tom Brady (3).
Terry Bradshaw of the Pittsburgh Steelers and Joe Montana of the San Francisco 49ers each won four Super Bowls.
Tom Brady
Colts
The Cowboys quarterback started three Super Bowls in four seasons (Super Bowls XXVII, XXXVIII and XXX) and won all three.
Steve Young won three Super Bowls. One as a starting quarterback (XXIX) and two as Joe Montana's backup (XXIII and XXIV).
Joe Montana and Terry Bradshaw have each won 4 Superbowls.