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You are able to buy "The Challenge - Season 1" on Microsoft Store as download.
There are no options to watch The Challenge for free online today in Canada. You can select 'Free' and hit the notification bell to be notified when season is available to watch for free on streaming services and TV.
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Road Rules: All Stars is the first season of the MTV reality game show, The Challenge. Unlike later seasons the show followed alumni of The Real World as they went on a typical Road Rules-type adventure around the United States in a non-competitive format. It is the only season without the term Challenge in its title. The season premiered on June 1st, 1998.