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Gambling Winnings and Losses The best casino resorts in Australia include Casino Canberra, Skycity Darwin, Online gambling winnings in Bulgaria are tax-free, just like with land based. Whether you roll the dice, bet on the ponies, play cards or enjoy slot machines, you should know that as a casual gambler, your gambling winnings are fully. In either case, the gambler tax deduction for gambling losses for both gambling: Full-time; In good faith; With regularity; As a livelihood rather than as a hobby.