Am I required to pay taxes if I win online? February 11, 2020 4:32 am by Tom Wilson A Am I required to pay taxes if I win online? No, only professional punters have to pay taxes on winnings, so donβt have to worry about it. (No Ratings Yet)Loading... PREVIOUS ARTICLE Can I bet on Greyhound racing in Manitoba? NEXT ARTICLE Who regulates gambling in Nova Scotia? 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