Am I required to pay taxes if I play online? February 11, 2020 5:14 am by Tom Wilson A Am I required to pay taxes if I play online? You are not required to pay any taxes on your winnings generated in offshore casinos. (No Ratings Yet)Loading... PREVIOUS ARTICLE Is sports betting allowed in New Brunswick? NEXT ARTICLE What is the legal gambling age in Ontario? 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