Am I required to pay taxes if I win online? February 06, 2020 6:05 am by Tom Wilson A Am I required to pay taxes if I win online? Only professional gamblers and poker players are required to pay taxes on online winnings. (No Ratings Yet)Loading... PREVIOUS ARTICLE Do offshore casinos accept residents of Alberta? NEXT ARTICLE Is sports betting allowed in Alberta? 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