Through Super Bowl XLIV, as far as head coaches are concerned, no head coach has won Super Bowls with different teams. Five head coaches have coached two different teams into the Super Bowl but neither won with two different teams.
1) Don Shula was the head coach the Baltimore Colts that lost Super Bowl III and of the Miami Dolphins that lost Super Bowl VI and won Super Bowls VII and VIII.
2) Bill Parcells was the head coach of the New York Giants that won Super Bowls XXI and XXV and the New England Patriots that lost Super Bowl XXXI.
3) Mike Holmgren was the head coach of the Green Bay Packers that won Super Bowl XXXI and the Seattle Seahawks that lost Super Bowl XL.
4) Dan Reeves was the head coach of the Denver Broncos that lost Super Bowls XXI, XXII, and XXIV and the Atlanta Falcons that lost Super Bowl XXXIII.
5) Dick Vermeil was the head coach of the Philadelphia Eagles that lost Super Bowl XV and the St. Louis Rams that won Super Bowl XXXIV.