Jon Gruden:Mike Tomlin, Pittsburgh - XLIII (36 yrs, 323 days)Jon Gruden, Tampa Bay - XXXVII (39 yrs, 162 days)John Madden, Oakland - XI (40 yrs, 274 days)Joe Gibbs, Washington - XVII (42 yrs, 66 days)Chuck Noll, Pittsburgh - IX (43 yrs, 7 days)Don Shula, Miami - VII (43 yrs, 10 days)
Bill Callahan was head coach of the Raiders last Super Bowl team (SB XXXVII).
No. Both were head coach of two teams in the Super Bowl. Vermeil was head coach of the Philadelphia Eagles that lost Super Bowl XV to the Oakland Raiders and the St. Louis Rams that defeated the Tennessee Titans in Super Bowl XXXIV. Vermeil's record in the Super Bowl as a head coach was 1-1. Reeves was the head coach of the Denver Broncos that lost Super Bowl XXI to the New York Giants, Super Bowl XXII to the Washington Redskins, and Super Bowl XXIV to the San Francisco 49ers, and the Atlanta Falcons that lost Super Bowl XXXIII to the Denver Broncos. Reeves record in the Super Bowl as a head coach was 0-4. As a player, Reeves won Super Bowl VI with the Dallas Cowboys and as an assistant coach, won Super Bowl XII with the Cowboys. Through Super Bowl XLIII, three other head coaches have led two teams to the Super Bowl but no coach has won Super Bowls with 2 different teams. Bill Parcells won Super Bowls XXI and XXV as head coach of the New York Giants and lost Super Bowl XXXI as head coach of the New England Patriots. Mike Holmgren won Super Bowl XXXI as head coach of the Green Bay Packers and lost Super Bowl XL as head coach of the Seattle Seahawks. Don Shula won Super Bowls VII and VIII as head coach of the Miami Dolphins and lost Super Bowl III as head coach of the Baltimore Colts.
No Miami Dolphin assistant coach has ever moved on from the team and won a Super Bowl title as the Head Coach of another franchise. In fact, no Mimai Dolphin assistant coach has ever brought another NFL franchise to the Super Bowl and lost as a head coach.
Through Super Bowl XLIV, there have been several ... 1) Tom Flores - player for the Chiefs in Super Bowl I and head coach of the Raiders in Super Bowls XV and XVIII. 2) Forrest Gregg - player for the Packers in Super Bowls I and II and head coach of the Bengals in Super Bowl XVI. 3) Mike Ditka - player for the Cowboys in Super Bowls V and VI and head coach of the Bears in Super Bowl XX. 4) Dan Reeves - player for the Cowboys in Super Bowls V and VI and head coach of the Broncos in Super Bowls XXI, XXII, and XXIV and Falcons in Super Bowl XXXIII. 5) Sam Wyche - player for the Redskins in Super Bowl VII and head coach of the Bengals in Super Bowl XXIII. 6) Tony Dungy - player for the Steelers in Super Bowl XIII and head coach of the Colts in Super Bowl XLI.
Yes, Tom Coughlin is the oldest head coach to win a Super Bowl.
If you meant Super Bowl XVIII, Washington's head coach was Joe Gibbs.