MOVIE
Winning the Bet
TMDb10.02008-03-25· 71 min
No genres
Watch Ryan, Devon and Brett use their “winnings” anyway they see fit. Whether it is Damien secured to posts, paddled, flogged, face and ass fucked or Riley put into stocks or Kyle drenched in hot wax, flogged, paddled plus face and ass fucked. Everyone wins in one way or another.
Below are the streaming services currently carrying the movie “Winning the Bet” in Canada, along with how each offers it (subscription, buy, or rent) and a direct link. Licensing differs by market, so availability in Canada can differ from other countries.
Where to watch Winning the Bet in Canada
Netflix
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OSN+
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Amazon Prime Video
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Shahid
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Watch It
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TOD
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Disney+
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Apple TV+
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Not currently available on the supported providers in Canada.
Availability can change as licenses rotate — confirm on the provider’s page before subscribing. Last checked: 15 Sept 2026.