Fliff tax documents

Checked against Fliff’s own pages on 2026-09-13.

Do you owe tax on Fliff contest winnings?

IRS Publication 525 says winnings from fantasy sports leagues are gambling winnings, and you must include them in your income. IRS Tax Topic 419 says you must report all gambling winnings, including winnings that no Form W-2G reports.

Gambling losses come off only if you itemize, and only up to your winnings. From tax year 2026 you may deduct just 90 percent of them. A 2020 IRS legal memo concluded that the fee you pay to enter a daily fantasy contest is paid for a wager under 26 U.S.C. 165(d) as it stood then, the rule the 90 percent limit now amends. The IRS says the memo may not be used or cited as precedent.

None of these sources names pick’em contests, and we could not confirm whether the IRS treats them as fantasy sports leagues. Either way the winnings are income: Publication 525 also says you must include a prize you win in a contest in your income. What stays unconfirmed is whether pick’em entry fees count as gambling losses.

This section does not cover event contracts or sweepstakes.

Find your state’s guide and calculator.

Sources for this section

This is a fantasy operator, so there is usually no W-2G. It may report on a 1099 instead, which is a different form on a different rule. Some fantasy 1099s show your net winnings for the year and some show your total prizes, so check which one yours measures.

What Fliff issues

1, 2
  • Form 1099-MISC for Fliff Pick’em, and Fliff says "may issue" rather than will
  • For the Fliff Cash sweepstakes, no form is named at all

Where to find it

1

There is no self-service location. The sweepstakes rules say only that Fliff will provide tax forms if a participant requests them.

The name on the form may not be the one you know

1, 2

Fliff Inc., of King of Prussia, Pennsylvania. This is the only company we found under that name.

The thresholds, as Fliff states them

2

What Fliff says triggers a form

Fliff’s own wording, not the rule. Operators restate the law, and their wording is not always correct.

  • Form 1099-MISC where aggregate contest prize winnings total $600 or more in a calendar year, for Pick’em only

Where these figures and the rule in force differ

  • $600: Superseded for 2026 payments, now $2,000

Fliff’s Pick’em terms still state the pre-2026 figure, with no mention of the increase for payments after 31 December 2025. Its sweepstakes rules state no figure.

For a prize reported on Form 1099-MISC, the reporting threshold is set by 26 U.S.C. 6041(a), which section 70433(a) of Public Law 119-21 raised from $600 to $2,000 for payments made after 31 December 2025. Every dollar of gambling winnings is taxable whether or not a form arrives, so do not read a missing form as a missing tax bill.

Worth knowing

  • We found no working Fliff help centre and no tax page. Every tax fact on this page comes from legal terms most customers would not think to open. Fliff’s two sets of terms cover different products and treat forms differently.
  • Only the sweepstakes rules make a form depend on your request. The Pick’em terms say Fliff may issue a 1099-MISC and set no such condition, and neither says how a form reaches you.
  • Sites that promote Fliff all say that it issues a 1099 at $600. Fliff’s own sweepstakes rules say only that forms come on request, with no threshold.
  • Fliff describes prize winnings and prize redemptions, and never uses the word net. For a player who bought coins, a figure based on redemptions could exceed their actual gain.
  • Fliff Cash must be played through once before it can be redeemed, so taxable prize income is timed by redemption rather than by winning.

What we could not confirm

We could not confirm the date the form appears, how the form reaches you, how many forms to expect or whether a win/loss statement is available from a page Fliff publishes that we could read. We have left those out rather than guess.

Sources

Fliff’s own pages. Operator help centres change without notice, so each source shows the date we read it.

  1. 1. Fliff, sweepstakes rules, section 6.8 read 2026-09-13
  2. 2. Fliff Pick’em, terms of use, section 8.18 read 2026-10-11

Work out your tax by state

Each state has a guide to its rules and a calculator for your own numbers.

The calculators treat all your losses, entered or estimated, as gambling losses. For pick’em entry fees, no source we found confirms that.