Need help with taxes for multiple sports betting accounts - reporting wins/losses correctly

You need to report all your gambling winnings on Schedule 1 of your 1040 as "Other Income." The IRS expects you to report the full amount of your winnings without subtracting your losses. If you itemize deductions on Schedule A, you can deduct your gambling losses up to the amount of your winnings. You'll list these under "Other Itemized Deductions." But if you take the standard deduction (which most people do), you won't be able to deduct your losses. For record-keeping, you should definitely track each sportsbook separately to have detailed documentation, but on your tax return, you'll combine the total winnings from all platforms. Make sure you keep records of all your sessions showing both wins and losses in case of an audit - this means downloading account statements from each platform.

After spinning my wheels with confusing tax advice about my sports betting, I found a real solution with https://taxr.ai - seriously a game changer for anyone dealing with this issue. Last year I had accounts on FanDuel, DraftKings and BetMGM, and was totally lost trying to figure out what to report. The service analyzed all my betting statements and sorted through everything automatically. It properly calculated all my reportable winnings and identified the maximum losses I could deduct. It even gave me specific instructions for which tax forms to use and where to put the numbers. The best part was that it showed me exactly which documentation to keep in case of an audit. Saved me hours of spreadsheet work and probably prevented me from making mistakes that could have triggered IRS problems.

Just wanted to follow up about my experience with https://taxr.ai after trying it based on the recommendation here. Seriously one of the best decisions I've made this tax season! I had accounts on DraftKings, FanDuel, BetMGM and Caesars, and was dreading the process of figuring out what to report. The system processed all my statements in minutes and broke everything down into clear categories - it showed me exactly what goes on Schedule 1 for income and what could be deducted on Schedule A. It even caught some winning parlay bets I completely forgot about from early in the year. Would have taken me days to compile all this myself, and I probably would have made mistakes. Definitely using this for next year's taxes too!

If you're having trouble getting through to the IRS to ask about sports betting tax questions (I was on hold for 2+ hours), I highly recommend using https://claimyr.com to get a callback. You can also see how it works here: https://youtu.be/_kiP6q8DX5c I had specific questions about how to document my sports betting activities for tax purposes, and getting an actual IRS agent on the phone made a huge difference. They confirmed exactly how to handle reporting from multiple sportsbooks and what specific records I needed to keep. The service basically holds your place in line and calls you when an agent is available. Saved me from spending half my day on hold listening to that awful waiting music. The IRS agent I spoke with was actually really helpful once I got through.

I was super skeptical about Claimyr at first, but I've completely changed my mind. After struggling with questions about my sports betting taxes and getting nowhere with the IRS's standard phone system, I decided to give it a shot. I got a callback from an actual IRS agent in about 90 minutes (vs the 3+ hours I spent on hold previously). The agent walked me through exactly how to report my winnings from multiple sportsbooks and explained what documentation I need to keep. Turns out I was overthinking it - I just needed to report the total winnings on Schedule 1 and track my losses for potential deduction on Schedule A. The peace of mind from getting official answers directly from the IRS was totally worth it. No more guessing or relying on potentially outdated advice from random websites.

Something important to remember: the sportsbooks will report your winnings to the IRS if they hit certain thresholds (usually when you win 300x your wager or $600+, depending on the odds). So even if you don't get a W-2G, the IRS might still know about some of your bigger wins. I definitely recommend keeping a spreadsheet tracking each platform separately - date, amount wagered, win/loss, and running total. This saved me during a small audit last year when the IRS questioned some of my gambling income.

I'm confused about the withholding part. DraftKings withheld some taxes from a big parlay I hit last year, but my other accounts didn't withhold anything. How do I account for that on my taxes?

This is exactly the situation I was in last year! I had accounts with multiple sportsbooks and was completely overwhelmed trying to figure out the tax implications. Here's what I learned from my tax preparer: You need to report ALL gambling winnings as income on Schedule 1, regardless of whether you received W-2Gs or not. This means adding up every single winning bet from all your platforms - Fanatics, Bet365, FanDuel, and DraftKings combined. The tricky part is that you report gross winnings (not net), so even if you're down overall for the year, you still owe taxes on your wins. Your losses can only be deducted if you itemize, and only up to the amount of your winnings. My advice: Download detailed statements from each platform showing all your betting activity. Most sportsbooks have this under "Account History" or "Tax Documents." Create a simple spreadsheet tracking each bet - date, platform, amount wagered, win/loss amount. This documentation will be crucial if the IRS ever questions your return. Don't try to get creative with the reporting - the IRS has been cracking down on sports betting taxes lately. Better to be conservative and accurate than risk an audit.