NFL head coach career: Cleveland Browns (1991–1995), New England Patriots (2000–2023)
Super Bowl years won: 2002, 2004, 2005, 2015, 2017, 2019
Considered to be perhaps the greatest coach of all time, Bill Belichick holds the record for most Super Bowl wins as a head coach, but he also earned two wins as the defensive coordinator of the New York Giants, giving him a total of eight victories as coach and coordinator.
Part of the Bill Parcells coaching tree, Belichick worked with Parcells for the New York Giants, became head coach of the Cleveland Browns in 1991 and then rejoined Parcells as assistant head coach and defensive backs for the Patriots in 1996.
Of course, Belichick played a huge role in the New England Patriots’ football dynasty from 2001 to 2019, working with Tom Brady to secure multiple victories.