I won some money from sports betting websites. However I did not win more than $600, or really even come close to it. What do I need to do?

[ToddL99]

If you win money betting on sports from sites like DraftKings, FanDuel or Bovada, it is taxable income and should be reported on your tax return. If you itemize deductions, you can claim gambling losses up to the amount of your reported winnings (see the attached article for additional details),

If your winnings are $600 or more, the payor should send both you and the IRS a tax form (1099-MISC) or a Form W2-G, Certain Gambling Winnings. If you receive your winnings through PayPal, the reporting form may be a 1099-K.

The 1099 tax forms (or Form W-2G or 1099-K) report your winnings to the taxing authorities and also let you know the amount you must report on your taxes. Even if you don’t receive a Form 1099, you still need to report the net profits on your federal and state income tax returns. 

If you receive a Form 1099-MISC for gambling winnings, enter it in the 1099-MISC interview (Other Common Income tab under Income and Expenses section).  In completing this interview, remember this type of gambling income is generally not related to your trade or business, did not involve an intent to "earn" money ("earning" implies "working"), and was not a recurring form of income (received in the past or expected in future). Answering the interview with these facts in mind will avoid having the program think you owe employment taxes on gambling/gaming winnings.

If you receive a Form W-2G (or didn't receive any tax forms), you would enter your winnings in the Gambling Winnings interview under the Less Common Income tab of Income and Expenses section.

Again, for additional details, see:  Sports Betting Taxes Guide (How to Pay Taxes on Sports Betting)

[Grand1]

I've read various interpretations from sports betting and how they define sessions.

For example,  if on one site (say DK) you had 10,000 in wagers, and 11,000 in wins, since it was from the same site, you can report the session (2020) as 1,000 in gross winnings, however, if you had a separate site (say FD) and had 1,000 in wagers and 900 in wins, you wouldn't take the net of both sites combined, instead you would do 1K in winnings, and for itemized deductions you can take the 100 in losses.     Can this logic be applied?

Otherwise you are adding 11,900 of income to be taxed on, and unless you itemize, you wouldn't be able to write off any of the 11,000 you lost (wagered).     So it would result in you being net positive 900 for the year, but having to pay taxes on quite a bit more income than that.

[JohnB5677]

There may be various interpretations from sports betting on how they define sessions.  However, the IRS says:

"You may deduct gambling losses only if you itemize your deductions on Schedule A (Form 1040) and kept a record of your winnings and losses.

The amount of losses you deduct can't be more than the amount of gambling income you reported on your return. Claim your gambling losses up to the amount of winnings, as "Other Itemized Deductions."

Topic No. 419 Gambling Income and Losses (irs.gov)

[Grand1]

Can the approach using the time period of the full year one site towards a "session', where if you had 100K in wagers and 90K in winnings, that you wouldn't report any winnings as the "session" was not a winning one?

[Irene2805]

Keep in mind that you are preparing your 2020 tax return.  If you are on a cash basis (as are most taxpayers), you report your income, including gambling income, using a calendar year.  You would also report any gambling losses for the calendar year to offset any winnings, if you are itemizing deductions on Schedule A.  If you are not itemizing deductions, you cannot use the losses to offset the gambling income.

@Grand1