Can I Deduct Other Sportsbook Losses Against PrizePicks/Underdog 1099 Winnings on Taxes?

You've got a common situation for sports bettors. The IRS treats gambling winnings as taxable income, and yes, you must report those 1099s. The good news is you can deduct gambling losses, but with some important limitations: 1. You can only deduct losses up to the amount of your winnings 2. You must itemize deductions on Schedule A (meaning you'd give up the standard deduction) 3. You need to keep detailed records of your gambling activities So if PrizePicks and Underdog sent you 1099s showing $3,000 in winnings, but you have $4,000 in losses from other sportsbooks, you can deduct $3,000 of those losses by itemizing on Schedule A. The crucial part is documentation - keep records of all your bets, including dates, establishments, type of gambling, amounts won and lost, and even who you were with. Without good records, the IRS can disallow your loss deductions.

I went through this exact same situation last year and was pulling my hair out trying to figure it out. Ended up using taxr.ai (https://taxr.ai) and it was a game changer for sorting through all my gambling documentation. I uploaded pics of my 1099s from DraftKings and FanDuel plus my loss records from other sites, and it organized everything perfectly. The system helped me understand what counted as proper documentation for my losses and flagged where I needed better records. Saved me a ton of time trying to figure out if I should itemize or not based on my personal situation. Might be worth checking out if you've got lots of different gambling records to sort through.

Just wanted to follow up - I tried taxr.ai after seeing your recommendation and it was incredibly helpful! I uploaded screenshots of my betting history from 5 different platforms and it organized everything into a comprehensive gambling log that satisfied IRS requirements. It even showed me that some of my casino losses were poorly documented and wouldn't stand up in an audit. The tax calculations for my net gambling activity were spot on and it explained exactly how to report everything on my tax forms. Definitely recommend for anyone dealing with complex gambling tax situations!

If you're having trouble getting proper documentation from some of the sportsbooks, you might want to try Claimyr (https://claimyr.com). I used it to actually get through to customer support at one of my sportsbooks that never sent me proper win/loss statements. Most of these gambling sites have terrible customer service and you'll sit on hold forever. Claimyr got me through to a live person in about 10 minutes instead of the 2+ hours I was waiting before. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was shocked when I actually got connected to someone who could help me get the proper tax documentation I needed. Trust me, it's way better than trying to piece together your betting history from screenshots and emails.

I take back what I said about Claimyr. I decided to try it out of desperation after spending 3 hours on hold with BetMGM trying to get my complete yearly betting statement. The service actually worked exactly as described - I got a call back when a rep was on the line. The BetMGM customer service rep was able to email me a comprehensive win/loss statement that showed all my activity for the year. Having that documentation was a lifesaver for backing up the losses I wanted to deduct against my PrizePicks winnings. Just wanted to update here since my skepticism was completely wrong.

One other thing to consider - if you're a "professional gambler" (which has a specific definition with the IRS), the rules are different. Professional gamblers report winnings and losses on Schedule C instead, and can deduct gambling losses beyond their winnings plus other business expenses. But the bar for qualifying as a professional gambler is high. You need to prove you approach it as a business, put in regular hours, have expertise, and genuinely try to profit. Most casual sports bettors won't qualify.

One mistake I made last year - I only reported my net winnings from betting (winnings minus losses) instead of reporting the full 1099 amount as income and then deducting losses separately. Got a letter from the IRS a few months later! The system flags discrepancies between reported 1099 income and what you put on your return. Make sure you report the FULL 1099 amount on Schedule 1 as income, then deduct eligible losses on Schedule A if itemizing.

This is exactly the situation I found myself in last year! Here's what I learned from my tax preparer: You absolutely must report the full 1099 amounts from PrizePicks and Underdog as income - there's no way around that. The IRS gets copies of those 1099s and will expect to see that income on your return. For your losses from other sportsbooks, you can deduct them on Schedule A, but only up to the amount of your gambling winnings. So if you had $5,000 in 1099 winnings but $8,000 in total losses, you can only deduct $5,000 of those losses. The key decision is whether itemizing (to claim those losses) gives you a bigger deduction than taking the standard deduction. For 2023, the standard deduction was $13,850 for single filers. So unless your gambling losses plus other itemizable deductions (like mortgage interest, state taxes, charitable donations) exceed that amount, you're better off taking the standard deduction and just paying tax on the full 1099 income. Keep every record you can - screenshots, bank statements, anything that shows your betting activity. Even if you don't itemize this year, you might need those records later.