Limitations on loss deductions The amount of gambling losses you can deduct exxpense never exceed the winnings you report as income. The regular place of business for many professional poker players is their residence, regardless of whether they predominantly play live or online. Quicken products provided by Quicken Inc.why is gambling unheathy UNTIL YOU BY JUDITH MCNAUGHT ONLINE Today we review the extent a professional gambler may deduct business expenses and the rules governing some common types of business. Win or lose, know IRS' rules that govern gambling It's tempting to deduct travel and other gambling costs as business expenses. But just. A professional gambler, on the other hand, who is engaged in the trade or business of gambling, is allowed to offset losses and expenses of.