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

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.

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.

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.

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.

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.

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!

Would it be worth it to sign up for fantasy sports apps using different emails/accounts to avoid getting 1099s? Asking for a friend...

I'm dealing with a very similar situation this year! I'm up about $3,800 on FanDuel but down around $2,200 combined on other platforms. What I've learned is that you absolutely need to keep detailed records of everything. Here's what I did: I downloaded transaction histories from all platforms (CSV files when available), took screenshots of my account summaries showing net wins/losses, and created a spreadsheet tracking every deposit, withdrawal, and net result by platform. Some platforms are better than others at providing clear loss documentation. FanDuel actually has a pretty good year-end summary if you dig into your account settings. For the platforms that don't provide clear loss statements, the deposit/withdrawal history should be sufficient as long as you can show more money went in than came out. The key thing is being able to prove to the IRS that your losses are legitimate gambling losses, not just money you spent on other things. Keep everything organized and don't wait until tax time to gather this info - some platforms make it harder to access older transaction data. Also worth noting that you need to decide whether itemizing makes sense for your overall tax situation. In my case, itemizing to claim gambling losses actually pushed me over the threshold where it was better than taking the standard deduction.

I went through this exact situation last year and it was a nightmare until I got organized. Here's what worked for me: First, contact each platform's support and specifically ask for an "annual gambling statement" or "win/loss statement" - don't just ask for transaction history. Some platforms have these available but don't advertise them. I had to escalate with DraftKings support twice before finding someone who knew how to generate one. Second, create a master spreadsheet with columns for: Date, Platform, Deposit Amount, Withdrawal Amount, Net Win/Loss, and Running Total. This becomes your gambling diary that the IRS expects to see. Third, take screenshots of everything NOW before the platforms potentially change their interfaces or make older data harder to access. I learned this the hard way when one platform updated their system and I lost access to some older transaction details. The key insight that saved me money: calculate whether itemizing vs standard deduction works better AFTER adding in your gambling losses. In my case, I was borderline on itemizing, but the gambling loss deduction of $4,200 pushed itemizing into being clearly the better choice, which saved me about $800 compared to taking the standard deduction and paying full taxes on my winnings. Don't try to get cute with under-reporting your winnings - the platforms report to the IRS and it's not worth the audit risk. Just make sure you can properly document and claim your losses.

Hey Maggie! I went through almost the exact same situation last year - won about $4,800 on one platform but had losses totaling around $3,200 across two others. The transaction histories from your deposit/withdrawal records should definitely be sufficient documentation for the IRS, but I'd recommend organizing everything into a clear spreadsheet. What really helped me was creating a simple tracking sheet with columns for: Date, Platform, Amount Deposited, Amount Withdrawn, and Net Result. This makes it crystal clear to show your actual losses versus just spending money. One tip - try reaching out to Prizepicks and DraftKings support and specifically ask for an "annual win/loss statement" rather than just transaction history. Some platforms have these but don't automatically provide them. It might take a few tries with different support reps, but it's worth it for cleaner documentation. The biggest thing to remember is that you'll need to decide whether itemizing deductions makes sense for your overall tax situation. With $4,700 in losses to deduct against your $5,200 in winnings, it might actually push you into itemizing territory if you're close to the standard deduction threshold. Run the numbers both ways - you might be surprised which option saves you more money overall. Keep all your screenshots and records organized now while the platforms still have the data easily accessible. Good luck!

I'm in a very similar boat this year! I won around $3,400 on BetMGM but I'm down about $2,100 across FanDuel and Caesars. Reading through everyone's advice here has been super helpful. One thing I wanted to add that I learned from my accountant - make sure you're keeping track of the dates for all your gambling activity. The IRS technically wants to see that your losses occurred in the same tax year as your winnings. So if you won money in 2024 but some of your losses were in 2023, you can't use those older losses to offset this year's winnings. Also, I found that taking screenshots of your year-to-date totals from each platform's app or website can be really helpful backup documentation. Some platforms show a clear "net winnings/losses" figure right on your account dashboard that makes it obvious what your position is. The itemizing vs standard deduction calculation is definitely worth running both ways. I used FreeTaxUSA's calculator and was surprised that itemizing actually saved me about $300 more than taking the standard deduction once I factored in the gambling losses. Thanks to everyone who shared their experiences - this thread has been way more helpful than trying to figure this out on my own!

I'm dealing with a similar situation but with sports betting apps - won about $2,800 on Bet365 but down around $1,900 across other platforms. Reading through all these responses has been incredibly helpful! One thing I'd add is that some of the newer sportsbooks are actually pretty good about providing year-end statements if you know where to look. I found that Bet365 has a "Responsible Gambling" section in account settings where you can download a detailed activity report showing all your deposits, withdrawals, bets, and net position for any date range you specify. For platforms that don't make it easy, I've been using the approach several people mentioned - screenshot everything now and create that master spreadsheet. I'm organizing mine by date with columns for Platform, Activity Type (deposit/withdrawal/bet), Amount, and Running Balance. This way I can clearly show the IRS my actual gambling activity vs just moving money around. The tax year timing point that Ethan mentioned is crucial - I almost made the mistake of trying to count some December 2023 losses against my 2024 winnings until my tax software flagged it. Thanks everyone for sharing your experiences - this community is way more helpful than the generic tax advice you find elsewhere online!