Do I need to pay taxes on winnings? February 12, 2020 12:03 am by Tom Wilson A Do I need to pay taxes on winnings? Winnings acquired through online and offline gambling are not taxable. (No Ratings Yet)Loading... PREVIOUS ARTICLE Does Prince Edward Island have land-based casinos? NEXT ARTICLE Is online gambling legal in Prince Edward Island? Author: Tom Wilson Chief editor and creator, Tom drives the direction of CanadianCasinos.ca with the goal to provide the best and most honest resource for online gambling enthusiasts in Canada