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The problem here is, if you had a win and did not file it on your Income Tax. Your tax return for that year is where you would have had the opportunity to file your losses against the gain. The IRS is not going to say "oh okay, in 2005 you won $5000 that you did not claim, but you lost $5000, so we're cool go ahead and go home". They are going to say you didn't claim the income. You have three years to amend a return, but I don't think you can do it once you are being audited. I am wondering if the safest thing to do would be to go back and amend returns.
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