How do you report crypto gambling winnings when there were tons of separate bets?

[u/abounding_art]

I’ve been gambling on Stake throughout the year and ended up around $50k ahead overall, but it wasn’t from one huge win. It was a lot of wins and losses across sportsbook bets and casino games over a bunch of different sessions.

I deposited crypto at different points, played with it, withdrew some when I was up, then eventually sold the withdrawn crypto through an exchange and moved the cash to my bank.

What I’m struggling with is how detailed the reporting is supposed to get.

My exchange can obviously see the crypto coming back from Stake and being sold, but it has no context for all the gambling activity that happened before that. On the Stake side, there are hundreds of individual bets, so I’m not sure whether I’m expected to account for every wager separately or if there’s a reasonable way to summarize wins and losses by session.

I’m also confused about what happens when the crypto leaves Stake. If I withdraw $10k worth of crypto after a winning stretch and sell it shortly after, am I treating the value at withdrawal as the new basis and only reporting the price movement after that as a crypto gain or loss?

For anyone who has dealt with this before, what records did you actually keep?

Did you export the full betting history, just deposits and withdrawals, or create your own summary of sessions and net results?

Also wondering whether this is something a regular CPA can usually handle or if it’s worth finding someone who specifically deals with both gambling and crypto.

I’m trying to report everything properly, I just don’t want to accidentally treat all the exchange proceeds as crypto gains when a lot of it came from gambling winnings.

[u/I__Know__Stuff]

If you can get and save the log of every bet, that's what you want.

On your tax return, you report the total of all the winning bets and (separately) the total of all the losing bets.

You only need the details if you get audited, which is unlikely; nevertheless you should be prepared for it.

Deposits and withdrawals are completely irrelevant.

[u/AurumFsg-CryptoTax → u/I__Know__Stuff]

This is your answer

[u/Garrett_CPAatCOS]

The best way to approach this is to treat the activity as two separate transactions: (1) the exchange of crypto for the wager, and (2) the wager itself.

The gains/losses from the crypto transactions can be tracked using crypto tax software, especially given the high volume you mentioned.

The wagering activity can be tracked separately by exporting the transaction history from Stake and calculating the gross winnings and losses.

For the tax return, the crypto gains/losses generally need to be reported at the transaction level. You can consolidate them into a single line on Form 8949, but you still need to include a statement with the underlying transaction-level detail.

The wagering activity is different: you generally report the gross winnings on Schedule 1 and gross losses on Schedule A, rather than reporting each individual wager on the return.

A coworker at Count on Sheep posted on this topic recently, which may be of interest: https://www.reddit.com/r/onlinegambling/comments/1wuk9b1/crypto_gambling_winnings_are_taxable_in_the_us/

[u/BillysView]

I used Koinly to look at all the transactions in all my wallets and exchanges, then once I got the list I ran that through Chat GPT to look for anomalies. It worked pretty good. If you have more than 1000 transaction Koinly will charge a fee though. I was able to finally get my taxes done using this approach.

[u/Tulex]

I have a crypto phone and I make hundred of micro transactions per day, plus sometimes 500$ wins or losses on pump.fun. I am told to enter wallets of the phone in Koinly but there are many discrepancies. Transactions can be purchases sells staking burning betting…

[u/summ_app → u/Tulex]

First thing is to split the two activities, because they're usually taxed differently. Bets on a casino or sportsbook site are gambling. Buying and selling tokens on pump. fun is not gambling in most tax systems, even if it feels like it. It's trading, and every sell or swap is a disposal with its own gain or loss.

With that many micro transactions, the Koinly discrepancies are almost always one of three things: a wallet that isn't connected so tokens appear from nowhere, failed transactions that still charged fees, or tokens with no price data so they come in at zero. Sort by the biggest missing cost basis warnings first and work down, the small ones rarely move the total.

Which country you file in changes the gambling side a lot.

[u/Ok_Cauliflower7436]

Hi, I am in a similar situation. Was wondering which exchange did you use and were they difficult about the source of funds? I have heard that some exchanges get tricky with crypto coming from stake or other sites! I’ll follow this thread to see if anyone have good tax advice. Are you US or EU based? Suppose the tax advice will be country specific

[u/chainglance_cm]

Biggest thing first: the IRS doesn't really let you report net. Winnings go in as income and losses only come off if you itemize, capped at your winnings. Take the standard deduction and $50k net can turn into taxes on way more than $50k of winnings. That's the number to get right before anything else.

The usual workaround is the session method, where you net wins and losses per session instead of per bet. It's widely accepted for casino play, murkier for sportsbook where each bet can be treated separately. A CPA should make that call, but it's why you want the full history.

On basis, yes, crypto you win gets a basis equal to its value when you won it. Technically that's when you won it rather than when you withdrew, but with session records those are close. Price movement after that is a normal capital gain or loss. Also don't forget that depositing crypto that had already gone up in value into Stake can count as selling it.

Records I'd keep: the full bet history export, all deposits and withdrawals with tx hashes, and your own session summary on top. Also heads up that starting with 2026, only 90% of gambling losses are deductible, so a breakeven year still leaves taxable income.

Find a CPA who's done both crypto and gambling. Tax software like Bitcoin.tax or Koinly can sort out the crypto side, but the gambling part is where a generalist can cost you.