Underdog Fantasy tax documents

Checked against Underdog Fantasy’s own pages on 2026-10-09.

Do you owe tax on Underdog Fantasy 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 Underdog Fantasy issues

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  • A 1099 for pick’em profit. Underdog never names the variant.
  • Form 1099-B for Underdog Predict

Where to find it

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Underdog says the pick’em 1099 arrives by post and by email, and names no place in the app to download it. The in-app path, Account then Tax information, is for submitting your taxpayer details, not for collecting the form.

When it appears

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Sent in early March, later than most operators.

How it reaches you

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Underdog Fantasy delivers it by post and by email.

The thresholds, as Underdog Fantasy states them

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What Underdog Fantasy says triggers a form

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

  • A 1099 once you profit $2,000 or more in a year, on the How do taxes work? page, which gives no year
  • A 1099 once you profit $600 or more in a year, in the body of the Does Underdog tax my winnings? page, dated April 14, 2026
  • From the 2026 calendar year, net profits of $2,000 or more, which the same page calls an increase from the previous $600 threshold, for 1099s issued in 2027

Where these figures and the rule in force differ

  • $600: Superseded for 2026 payments, now $2,000

The Does Underdog tax my winnings? page still states $600 in its body. Its own 2027 Tax Update says profits in the 2026 calendar year need $2,000 for a 1099, and that the change does not affect 1099s issued for 2026 or prior years. Treat $600 as the rule for tax years before 2026 only.

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.

How many forms to expect

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Separate. Pick’em profit produces the mailed 1099. Underdog Predict runs through its own regulated Predictions account, and its tax information includes a 1099-B.

The win/loss statement, which is not your tax form

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A CSV of your full transaction history is available, but only by contacting support through the app. Underdog does not say whether it counts as a tax document.

This is the document a session log is built from, and the one most often mistaken for a tax form. Per wager or per session, and why it changes your bill.

Worth knowing

  • Underdog’s Predict tax collection promises 1099-B information, but its only article says nothing about taxes. That the Predict form arrives apart from the pick’em 1099 is an inference from the separate regulated account.
  • Underdog’s two tax pages disagree. How do taxes work? states only $2,000, with no year. Does Underdog tax my winnings? still states $600 in its body, then dates $2,000 to the 2026 calendar year, for 1099s issued in 2027. Read 2026-10-09.
  • The tax form gates your money. Once you pass the threshold you must complete your tax information before any withdrawal is processed, and you must also reply to their email.
  • Underdog no longer runs a sportsbook. Its North Carolina sportsbook help section is gone, so a former customer holding a W-2G from that period has no documented way to retrieve it.
  • The help centre moved to a new web address. Old links send you to the new one.

What we could not confirm

We could not confirm the company name that appears on the form from a page Underdog Fantasy publishes that we could read. We have left that out rather than guess.

Sources

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

  1. 1. Underdog Fantasy help centre, How do taxes work? read 2026-10-09
  2. 2. Underdog Fantasy help centre, Does Underdog tax my winnings? read 2026-10-09
  3. 3. Underdog help centre, Underdog Predict, Account, Funds & Taxes: tax info including your 1099-B read 2026-10-09
  4. 4. Underdog help centre, Your Prediction Picks Account: a regulated Predictions account read 2026-10-09

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.