How do I report daily fantasy sports taxes if I'm up on Underdog Fantasy but down on Prizepicks?

So I've had kind of a rollercoaster year with my fantasy sports gambling. On Underdog Fantasy, I'm sitting on about $5,200 in winnings for the year (lucky me!), but I'm down like $3,300 on Prizepicks and another $1,400 in the hole on DraftKings. The issue I'm running into is that Underdog is going to send me a tax form since I won over $600, but I won't get any kind of loss documentation from the other platforms where I'm down money. When you add everything up, I'm only actually up about $500 total across all platforms, but the IRS is going to think I made $5,200 without seeing my losses. Has anyone dealt with this situation before? What kind of documentation do I need to show my losses on these other platforms? I talked to customer support and they just showed me my total deposits and withdrawals history. Is that enough to document my losses when filing taxes? I don't want to pay taxes on $5,200 when my actual net winnings are way less.

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19 comments

Alejandro Castro

•1y

This is a common issue with fantasy sports and gambling taxes. The IRS allows you to deduct your losses up to the amount of your winnings, but you need to itemize deductions on Schedule A to do this (rather than taking the standard deduction). For documentation, you should keep detailed records of all your gambling activities. This includes your deposits, withdrawals, wins, and losses. The transaction history from Prizepicks and DraftKings showing your deposits and withdrawals can serve as evidence, but it's even better if you can get statements that clearly show your win/loss record. Some platforms offer annual gambling statements or win/loss statements if you request them specifically - check if Prizepicks and DraftKings provide these. Print and save all electronic records and take screenshots of your account histories. You should also keep a personal log or spreadsheet tracking all your gambling activities throughout the year. Remember that you'll report the full $5,200 from Underdog on your tax return as income, and then you can deduct your losses on Schedule A if you itemize.

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Alejandro Castro

•1y

Yes, that's unfortunately the case. You'd have to report the full $5,200 as income, but if the standard deduction is better for your overall tax situation, you won't be able to deduct your gambling losses. This is one of those situations where the tax code isn't very friendly to casual gamblers. If the difference between itemizing and taking the standard deduction is close, you might want to calculate your taxes both ways to see which gives you the better overall result. Sometimes the gambling loss deduction can push itemizing into being the better option.

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Jackie Martinez

•1y

I was in almost the exact same situation last year! I was up about $4k on one platform but down around $2.5k across three others. I found this AI tax assistant that really helped me figure it all out - https://taxr.ai - they specialize in handling gambling and fantasy sports income situations. What I liked is they helped me understand exactly what documentation I needed from each platform and even analyzed my transaction histories to verify what could count as losses. They also helped me decide whether itemizing made sense in my situation (it did). The whole process was way easier than I expected, and I ended up saving a bunch of money by properly documenting my losses.

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Jackie Martinez

•1y

For crypto gambling, absolutely! They actually have specific tools for tracking crypto gambling transactions and determining the proper basis for wins/losses. They helped a friend of mine with his bitcoin casino situation last year. You don't need to provide login access to your accounts at all. You just upload screenshots or downloaded transaction histories from your platforms. They never asked for passwords or anything like that. You can download your transaction PDFs or CSV files from the platforms and upload those. Super secure and I felt comfortable with the process.

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Haley Stokes

•1y

Just wanted to follow up on my experience with taxr.ai after I checked it out. I was skeptical at first (as you could probably tell from my question), but I went ahead and tried them for my sports betting situation. The service was actually really helpful - I uploaded my transaction histories from FanDuel, DraftKings and Underdog, and they organized everything to properly document my losses against my winnings. They even found some transactions I had forgotten about that actually helped my tax situation! Definitely made tax season less stressful and saved me from overpaying. Much better than trying to explain everything to my regular tax guy who kept getting confused about fantasy sports vs traditional gambling.

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Asher Levin

•1y

If you're having trouble getting through to support at any of these gambling platforms, I had good results using Claimyr (https://claimyr.com) to actually get a human on the phone at DraftKings. I needed a detailed loss statement and kept getting generic responses through email support. Claimyr basically navigated the phone tree for me and got me connected to a real person who could help. You can see how it works here: https://youtu.be/_kiP6q8DX5c - it's pretty cool actually. The rep I spoke with was able to generate a more detailed annual statement that showed my losses properly, which was exactly what I needed for tax purposes. Worth it if you're stuck trying to get the right documentation and just can't get through to anyone who can actually help.

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Asher Levin

•1y

It's not sketchy at all - they basically use an automated system that navigates through the phone menus and waits on hold for you. Instead of you personally waiting on hold for an hour, their system does it, then calls you once a real person is on the line. I was absolutely able to talk to a real person at DraftKings. It took about 45 minutes of hold time (which I didn't have to personally sit through), but I got connected to their tax documentation department. The rep was actually really helpful once I explained my situation and sent me a detailed transaction history with wins and losses clearly marked, which is exactly what I needed for my tax records.

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Issac Nightingale

•1y

Alright I'll admit I was completely wrong. After waiting on hold for over an hour last week and getting nowhere with DraftKings, I decided to try Claimyr. The service actually worked exactly as described. Their system waited on hold (for like 50 minutes!) and then called me when they got a real person. I was connected to someone in their tax documentation department who explained they could generate a detailed annual statement showing all my wins and losses. They emailed it to me within an hour after our call. This statement was WAY more detailed than what I could see in my app history and clearly showed my losses for the year. Definitely solved my documentation problem for tax filing.

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Romeo Barrett

•1y

Former tax preparer here - one thing to keep in mind is that the IRS treats each gambling "session" separately. So technically you're supposed to report each winning session as income and each losing session as a deduction (if you itemize). You can't just net everything together before reporting. The officially correct way is to report the full $5,200 as gambling income on your 1040, and then deduct the $4,700 in losses on Schedule A if you're itemizing. Also, make sure to keep a "contemporaneous gambling diary" that records dates, locations, type of gambling, who was with you, and amounts won/lost. The IRS loves documentation!

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Romeo Barrett

•1y

That's correct! The tax code isn't very friendly to gamblers. You have to report all your gambling winnings as income, regardless of your losses. Then you can only deduct your losses (up to the amount of your winnings) if you itemize deductions instead of taking the standard deduction. For your example, yes, you would technically need to report the $100 win as income and then potentially deduct the $100 loss on Schedule A if you itemize. Many casual gamblers end up paying taxes on their winnings without being able to deduct their losses because the standard deduction is more beneficial overall. It's definitely not a fair system for most people.

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Owen Jenkins

•1y

@Alana Willis is absolutely right - this would be considered structuring to avoid tax reporting requirements, which is illegal. The platforms require SSN verification for withdrawals anyway, so you'd still be linked to the winnings. Plus, even if you don't receive a 1099, you're still legally required to report all gambling income on your tax return. The IRS can easily cross-reference bank deposits with unreported income during an audit. Much better to just properly document your losses and file correctly!

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