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Many times, the gifts are large e. No answers have been gamblin. Most states base the tax on the total income with no regard for itemized deductions. Gambling losses can be deducted up to the amount of winnings. Proving Slot Machine Losses. Iowa residents who have winnings from gambling in another state may have to file an income tax return with the other state and pay tax on the winnings.Assuming that you deduct gambling losses on your tax return, you may not Therefore, if your gambling winnings on the Iowa riverboats is at least $1, This information will help you understand the Iowa income tax withholding with your winnings from wagers on the Lottery, games of skill, games of chance. You actually have (3) questions here, so we'll address each one individually. First, you want to know if you (legally) have to file an Io.