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I deposited crypto at different points, played with it, withdrew some when I was up, then eventually sold the withdrawn crypto through an exchange and moved the cash to my bank.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