4. Forrest Gregg - 32 wins
Forrest Gregg played in the NFL from 1956 to 1971 before turning to coaching in 1972. He got his coaching start with the San Diego Chargers where he was an offensive line coach for two years. He took the same job with the Browns in 1974 and then got promoted to head coach in 1975.
Despite putting together a winning season in 1976, Gregg only spent one more year in Cleveland. He was the Toronto Argonauts head coach in 1979 and then was hired by the Bengals in 1980 to become their fourth head coach in franchise history.
Gregg went on to compile a 32-25 record during his four years in charge. He was the first head coach in Bengals history to lead the team to a Super Bowl appearance, a feat that occurred in just his second year at the helm.
Gregg left the Bengals following the 1983 season to coach the Green Bay Packers, where he had played for the majority of his pro career. He never notched a winning record in Green Bay in four seasons.
Even with the lackluster finish for Gregg, he was one of the best coaches in Bengals history and is only one of two coaches to have a winning record in franchise history.