Gregory is third in school history in coaching victories and his 1979 team had a single season best record of 9–2.
In 1984 Winnipeg won the Grey Cup in part due to Gregory's offensive line that helped set a CFL single season rushing record.
After the 1986 season he was hired to coach Saskatchewan Roughriders, a team that had no playoff appearances in the past 10 years.
In 1995, Jim Foster hired Gregory to build an Arena Football League expansion team in Des Moines, Iowa.
Gregory coached the Iowa Barnstormers to five division titles in six seasons and led the team to two ArenaBowls.
Quarterbacks Kurt Warner and Aaron Garcia are considered two of the greatest AFL players ever.
[1] However, the Cobras suffered a losing streak that dropped them to 3–7, leading to Gregory's dismissal with six games left in the season.