For crypto dice: I've won ~12M Doge on Dogedice in the span of a few hours. This was back when the BTC price was ~$650 and the Doge Price was ~140 satoshis.
For crypto poker: I've won 11 BTC when BTC was ~$500 in one day at Seals with Clubs.
WOW, awesome, how did you bet, at what rate?
I pretty much implemented a silly martingale / bet by feel strategy for fun.
I'd usually bet 25k < 66.4 and continue betting until I felt I was on a cold streak. When I wasn't feeling it i'd scale down to 10k and 5k. When I felt I was due, I'd yolo bet it.
It was a pretty fun night. I received some pretty terrible news the day after and I decided to super yolo it. Didn't turn out too well.