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#3 - Dan Reeves
Dan Reeves has appeared in four Super Bowls during his career, tied for the fourth-most by any NFL head coach ever. He unfortunately lost all four of them. He joined Bud Grant and Marv Levy as the only head coaches in history to appear in at least three Super Bowls without winning any of them.
Reeves impressively helped the Denver Broncos reach the Super Bowl three times in a four-year span. But he was defeated in all three by three different teams. He later became the head coach of the Atlanta Falcons and appeared in Super Bowl XXXIII, where he was defeated by the Broncos, his former team.
#4 - Andy Reid
Andy Reid had a long and successful run as the head coach of the Philadelphia Eagles. He made it to the playoffs nine times during his 14 seasons there. He helped the Eagles reach Super Bowl XXXIX, where they were defeated by the New England Patriots.
Reid was often considered one of the best head coaches in NFL history to never have won a Super Bowl, but he changed that narrative with the Kansas City Chiefs. They defeated the San Francisco 49ers in Super Bowl LIV. The Chiefs returned to Super Bowl LV the following season, but were defeated by the Tampa Bay Buccaneers.
#5 - Don Shula
Don Shula is one of the greatest head coaches in NFL history. He is the all-time leader with 347 career wins and his six Super Bowl appearances are the second-most ever, trailing only Bill Belichick. His first appearance came in Super Bowl III with the Baltimore Colts, where they were defeated by the New York Jets.
Shula is best known for his legendary run with the Miami Dolphins. He coached the only perfect season in NFL history when the Dolphins went undefeated and won Super Bowl VII against Washington. He won another ring the following season against the Minnesota Vikings. Shula also made two other Super Bowl appearances with the Dolphins during his Hall of Fame career.
