Ryan Dinwidde won two Grey Cups in Toronto. That places him alongside Cito Gaston and Don Matthews as all-time bench bosses coaches. Ryan Dinwiddie, head coach and general manager of the Ottawa Redblacks, stands on the field during the team’s annual Fan Fest earlier this year. Ashley Fraser/Postmedia Network Article content See more Toronto Sun on Google —save as a Preferred Source Advertisement 2 This advertisement has not loaded yet, but your article continues below.