Why this matters to owner-operators and fleet managers

A new Reddit post caught our eye because it mirrors questions trucking families ask every season: a dependent used fantasy sports apps (Underdog, Sleeper, PrizePicks), made deposits and withdrawals, received no tax forms, and wondered if anything needs to be reported. The numbers were modest, but the core issue is big for anyone whose teen or college-aged dependent dabbles in daily fantasy during downtime on the road: are those winnings taxable, and when does a dependent need to file?

First rule: Report all gambling and fantasy winnings—forms or not

The IRS is blunt: gambling and sports-betting winnings are fully taxable and must be reported on your federal return, even if you never receive a W‑2G or 1099. That includes cash payouts and the fair market value of prizes. Losses are deductible only if you itemize and only up to the amount of your reported winnings. There is no IRS “90% cap on gambling loss deductions” for casual gamblers—if you’ve seen that claim online, it’s not in current IRS guidance as of June 15, 2026.

Will the apps send a tax form in 2026?

Maybe—but don’t wait for one. IRS instructions updated in January 2026 note an inflation-adjusted minimum threshold for filing certain information returns, including Form W‑2G, with the minimum set at $2,000 for calendar year 2026. Separately, regular federal withholding (24%) can apply when net proceeds from certain wagers exceed $5,000 and are at least 300 times the wager, a rule that now explicitly includes sports wagering. Bottom line: a W‑2G isn’t guaranteed for smaller bets, but you must still report your winnings.

Platform policies can differ, too. PrizePicks says it may issue a 1099‑B for certain “event contract” pick types and a 1099‑MISC when a member’s net winnings reach $600 in a calendar year. Underdog’s help center likewise tells players to expect a 1099 if they earn $600 or more in profit. These are platform statements; your duty to report applies regardless.

When a dependent must file in 2026

For 2026 returns (generally filed in 2027), the IRS says a dependent’s standard deduction cannot exceed the greater of $1,350 or earned income plus $450, up to the basic standard deduction for their filing status. Winnings from fantasy sports and sports wagering are reported as “other income” and, for most dependents, function like unearned income for filing-threshold purposes. If a dependent’s total income (including these winnings) exceeds their standard deduction, they generally must file. Check whether your dependent also has wages from a summer job, which can change the math.

State taxes and multi-state considerations

Many states tax gambling and sports-related winnings, even when federal forms are not issued. Your resident state typically gets the first look; some states also require returns when you have taxable income sourced there. If your dependent places bets while you’re parked in another state (apps are geofenced), keep records; state rules vary.

Action checklist for trucking families

Don’t net deposits and withdrawals. Track wins and losses per wager (or export detailed history from the app) and save bank statements. The IRS expects accurate records if you claim losses.
Plan for filing even without a tax form. A missing W‑2G or 1099 doesn’t excuse reporting; it only means you’ll rely on your own records.
Watch 2026 thresholds. Some platforms still reference $600 1099 policies, but IRS W‑2G reporting and withholding rules changed for 2026; thresholds now vary by wager type and an inflation-adjusted minimum applies.
Run the dependent threshold test early. Compare your dependent’s 2026 income to the dependent standard deduction (greater of $1,350 or earned income + $450). If they clear it, plan to file.
Mind state rules. If your home base is in a state that taxes gambling income, expect to include the winnings on that return.
Avoid surprises at tax time. If winnings are mounting mid-year, consider estimated tax or extra withholding to avoid penalties.

The bottom line

For owner-operators and fleet managers, the guidance you give your household matters. If a dependent places fantasy or sports picks in 2026, assume the winnings are taxable, keep meticulous records, and check whether their income exceeds the dependent filing threshold. Whether or not a form shows up in January, the responsibility to report sits with your family.

Sources Consulted: IRS Topic No. 419 (Gambling Income and Losses); IRS Instructions for Forms W‑2G and 5754 (Jan. 2026); Internal Revenue Bulletin 2025‑45 (2026 dependent standard deduction); PrizePicks Help Center (Taxes); Underdog Fantasy Help Center (1099 policy); Nolo (state tax overview).

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This article was prepared exclusively for truckstopinsider.com. For professional tax advice, consult a qualified professional.