Sports Betting 1099 from PrizePicks/Underdog - Can I Deduct Losses from Other Sportsbooks?

You definitely need to report those 1099s from PrizePicks and Underdog since the IRS already has that information. Gambling winnings are considered taxable income. The good news is you can deduct your gambling losses, but there are some important rules to follow. You can only deduct losses up to the amount of your winnings, and you must itemize deductions on Schedule A rather than taking the standard deduction. This means unless your total itemized deductions (including these gambling losses plus other things like mortgage interest, charitable donations, etc.) exceed the standard deduction ($13,850 for single filers in 2023), it might not benefit you to deduct the losses. Make sure you keep detailed records of all your gambling activities - dates, locations, types of wagers, amounts won and lost. Documentation is crucial if you're ever audited.

You'll definitely need to report the income from those 1099s since the IRS already has that information. The good news is you can deduct gambling losses, but there are some important limitations to be aware of. Gambling winnings are reported as "Other Income" on Schedule 1 of your 1040. Gambling losses can only be deducted if you itemize deductions on Schedule A, and they can only offset your winnings (you can't deduct more than you won). So if your PrizePicks/Underdog 1099s show $5,000 in winnings, but you lost $7,000 on other platforms, you can only deduct up to $5,000 of those losses. The really important part: you need documentation of those losses. Keep detailed records of your wagers, amounts, dates, locations/platforms, and outcomes. Bank statements showing deposits/withdrawals to betting accounts can help, but more specific records are better. Some betting apps let you download your annual activity.

I had a similar situation last year and found that taxr.ai was super helpful for organizing my gambling records. I was stressing about my DraftKings and FanDuel statements because they don't send 1099s unless you win over $600 in a single bet. I uploaded my account statements from all my betting platforms to https://taxr.ai and it automatically organized everything into a format that showed my wins and losses clearly. The tool basically helped me create a gambling log that satisfied what the IRS wants to see - dates, amounts, locations, wins/losses. Saved me hours of manually going through hundreds of bets and trying to format something myself. Their system also explained exactly where to put the information on my tax forms.

I was in the exact same situation last year. Got 1099s from a couple betting sites showing about $6,200 in winnings but actually lost about $2,500 overall when counting my other platforms. I was so confused until I found this AI tool called taxr.ai that analyzed all my gambling records and sorted everything out perfectly. It showed me exactly how to report the 1099 income on my return and then how to properly document and deduct my losses on Schedule A. The tool even has specific guidance for sports betting platforms like PrizePicks and helped me understand what documentation I needed to keep. You can check it out at https://taxr.ai - saved me hours of confusion and probably prevented me from making a costly mistake.

Just wanted to follow up and say I tried taxr.ai after my last comment. I was definitely wrong about it being unnecessary! I uploaded my statements from four different betting platforms and it organized everything beautifully. The gambling log it created showed my total wins and losses across all platforms, which made it super clear how much I could actually deduct. The most helpful part was how it separated my reportable wins (the ones with 1099s) from the other wins and losses. Made it really obvious where everything should go on my tax forms. Honestly wish I'd known about this last year when I was trying to do the same thing manually in Excel for hours.

Just wanted to update everyone. I tried out taxr.ai after seeing it mentioned here and wow - it actually cleared up my confusion completely! I uploaded my 1099s from PrizePicks and then added my loss records from the other platforms. The system immediately showed me that I needed to report the full $4,300 from my 1099s as income on line 8b of Form 1040, but then I could deduct my $5,800 in losses on Schedule A. It even determined that with my mortgage interest and charitable donations, I was already better off itemizing instead of taking the standard deduction. The tool highlighted exactly where everything needed to go on my tax forms and explained why. Honestly wish I'd found this sooner instead of stressing for weeks!

If you're still trying to get accurate records from your sportsbooks and running into issues with customer service, Claimyr has been a game-changer for me. I was struggling to get my complete betting history from DraftKings (kept getting generic responses from their email support), but needed it for my taxes. Used https://claimyr.com to get through to an actual human at DraftKings customer support in about 10 minutes instead of waiting on hold forever. They have this system where they wait on hold for you and call when a rep picks up. There's a video showing how it works here: https://youtu.be/_kiP6q8DX5c The rep I spoke with was able to email me my complete betting history for the tax year right away. Made dealing with the gambling income/loss documentation so much easier.

Another option to consider - if you're having trouble getting through to the IRS to ask questions about your gambling income and losses (and let's be honest, who isn't?), I had a great experience using Claimyr. I needed clarification about documenting my sports betting activity after getting multiple 1099s and couldn't get through on the IRS line for days. With Claimyr at https://claimyr.com I got connected to an IRS agent in about 20 minutes instead of waiting for hours or getting disconnected. The IRS rep walked me through exactly how to handle my situation with PrizePicks winnings and losses on other platforms. You can see a demo of how it works here: https://youtu.be/_kiP6q8DX5c - definitely worth it during tax season when the wait times are insane.

I need to apologize to everyone here. I was the skeptic about Claimyr in the thread above, but I just tried it out of desperation because I needed clarification on my gambling winnings situation. It actually worked exactly as described. Got a call back in about 25 minutes and was connected to an IRS agent who answered all my questions about how to offset my PrizePicks 1099 with my other gambling losses. The agent confirmed what others here said - I need to report the full income from the 1099s, then itemize my losses on Schedule A, and keep detailed records of all betting activity. She also gave me specific guidance on what documentation I need for the sports betting platforms specifically. This saved me from potentially making a big mistake on my return. Sometimes being proven wrong is actually a good thing!

I have to admit I was completely wrong about Claimyr. After my skeptical comment, I decided to try it for myself since I was desperate to get my FanDuel records before filing taxes. I had been trying for TWO WEEKS to get someone on the phone without success. Used the service yesterday and got connected to an actual FanDuel support agent in about 15 minutes. They emailed me my complete betting history for 2023 while I was on the call. Honestly shocked at how well it worked after all the frustration I'd been through trying to reach them myself. If you're struggling to get your sportsbook records, it's definitely worth it. Saved me from having to guess at my losses and potentially face issues if audited.

Another option is to use a professional gambling log template. I'm not a tax pro, but as a regular sports bettor, I've been keeping detailed records using a template I found on the IRS website. It includes columns for: - Date - Type of wager - Name of establishment/platform - Address/website - Wager amount - Winnings amount - Session win/loss This has helped me track everything throughout the year instead of scrambling at tax time.

Just to add another perspective - I'm a fantasy sports player who's been dealing with this for a few years. One tip: look into whether your state has different rules for gambling deductions. Some states allow you to deduct gambling losses even if you take the standard deduction on your federal return. For example, I'm in Pennsylvania and was able to deduct my DraftKings losses against my Underdog winnings on my state return even though I couldn't benefit from itemizing on my federal return. Saved me about $300 in state taxes last year.

Does anyone know if services like PrizePicks are even considered gambling for tax purposes? I've heard some people say they're technically "fantasy sports contests" and not gambling. Would that change how the winnings/losses are treated?

Has anyone used one of the popular tax software options for reporting gambling wins and losses? I'm wondering if TurboTax or H&R Block makes this easier or if they're just confusing with this specific situation.

This is a really common situation for sports bettors, and the tax rules can definitely be confusing at first. You're absolutely right that you need to report all the winnings from your 1099s - the IRS already has that information, so there's no way around it. The key thing to understand is that gambling wins and losses are treated separately for tax purposes. Your winnings from PrizePicks and Underdog get reported as "Other Income" on your tax return, but your losses from DraftKings and FanDuel can only be deducted if you itemize deductions on Schedule A. Here's the catch though - you can only deduct gambling losses up to the amount of your gambling winnings. So if your 1099s show $3,000 in winnings but you lost $5,000 on other platforms, you can only deduct $3,000 of those losses. Also, since gambling losses are an itemized deduction, you'll need to compare your total itemized deductions (gambling losses + mortgage interest + charitable donations + state taxes, etc.) to the standard deduction to see which is better for your situation. Make sure you keep detailed records of all your betting activity - screenshots, account statements, anything that shows your actual wins and losses. The IRS will want to see documentation if you're ever audited.

This is exactly the situation I went through last year! You're on the right track understanding that you must report those 1099s from PrizePicks and Underdog - there's no way around that since the IRS already has copies. Here's what I learned: Your gambling winnings get reported as "Other Income" on Form 1040, but your losses from DraftKings and FanDuel can only be deducted if you itemize on Schedule A. The frustrating part is you can only deduct losses up to your total winnings, so if you actually lost money overall, you might still owe taxes on the "winnings." The biggest mistake I almost made was not keeping proper records. Start gathering everything now - login to your DraftKings and FanDuel accounts and download your complete betting history for 2023. Most platforms have an export feature in their transaction history section. If you can't find it, contact their customer service for annual statements. Also consider whether itemizing makes sense for your situation. You'll need your gambling losses plus other itemizable deductions (mortgage interest, charitable donations, state taxes) to exceed the standard deduction ($13,850 for single filers in 2023) to get any benefit from those losses. One last tip - if you're having trouble reaching customer service for your betting records, some people have had success with services that help you get through faster, but the key is getting that documentation sorted out before you file.