You can't enter gambling losses unless you first enter gambling winnings. Enter your Raffle/gambling winnings under Other Common Income > Income from Form 1099-MISC as follows:
- Type 1099-misc in the search bar
- Click on Jump to 1099-misc.
- Enter your 1099-misc.
- Enter a description.
- On the Does one of these uncommon situations apply? screen, check This was prize winnings.
- On the 1099-MISC Summary screen, click Done.
- Continue until you get to the Enter Gambling Losses screen. Enter your losses.
Note: Gambling losses are not always a dollar for dollar reduction of gambling winnings.
From the information you provided, it appears that the standard deduction gives you a bigger refund, or less of an amount due, than taking the itemized deductions.
1. If the federal standard deduction is greater than your Itemized Deductions, the gambling losses are considered to be part of your standard deduction. The standard deduction is a fixed dollar amount, based on your filing status and age, that the IRS lets you take off (deduct) from your taxable income.
2. If you itemize instead of taking the standard deduction, you can deduct gambling losses up to the amount of your winnings.