Building on that success, Madden was hired by Al Davis as linebackers coach for the AFL's Oakland Raiders in 1967, putting him in the Sid Gillman coaching tree. He helped the team reach Super Bowl II that season. A year later, after Raiders head coach John Rauch resigned to take the same position with the Buffalo Bills, Madden was named the Raiders' head coach on February 4, 1969, becoming professional football's youngest head coach at the age of 32.
Madden's Raiders reached and lost five AFC title games in seven years, which left the Raiders with the same image that the Dallas Cowboys had previously had—as a team unable to "win the big one." Despite a 12–1–1 mark in 1969, the team lost 17–7 to the Kansas City Chiefs in the final American Football League championship game. Three years later, in what appeared to be a last-minute victory over the Steelers instead became a part of football lore when Franco Harris' "Immaculate Reception" gave Pittsburgh a 13–7 win. Then, in 1974, after defeating the two-time, and defending Super Bowl champion Miami Dolphins in dramatic fashion, the Raiders lost again to the Steelers in the AFC Championship game.
In 1976, the Raiders went 13–1 in the regular season, and escaped the first round of the playoffs with a dramatic and controversial victory over the New England Patriots. In the second round of the playoffs they defeated the Steelers for the AFC Championship. On January 9, 1977, Madden's Raiders finally captured their first Super Bowl with a convincing 32–14 win over the Minnesota Vikings.
The Raiders lost the AFC Championship Game in 1977 to the Denver Broncos with Madden battling an ulcer for most of the season. He retired after the 1978 season when the Raiders failed to make the playoffs.
Madden retired as a Super Bowl winning head coach and was the youngest coach ever to reach 100 career regular season victories, a record he compiled in only ten full seasons of coaching at the age of 42. He is still the coach with the most wins in Raiders history.
Madden's overall winning percentage including playoff games ranks second in league history. He won a Super Bowl and never had a losing season as a head coach. Madden has a winning record as a head coach against other future Hall of Fame head coaches.[8]