In terms of Bitcoin involved those were not as big (no more than a few mBTCs), but now I can remember two (one positive and one negative):
First one, I was going to bet on total goals for a match between two Asian teams (Bangladesh was one, cannot remember the second), I saw over 1.5 goals @ 2.76 and thought "woah, some easy money"... so, I placed my bet as fast as I could, but as soon as it confirmed I looked closer and noticed: "First half goals". I wanted to kill myself, but I decided to give it a try since I was too sleepy to message customer support and ask them to cancel the bet. Next morning I woke up and... I had won!, first half ended 3 - 0 for Bangladesh.
Second one, similar to what happened to you, but with worse results. Someone tipped me while playing at rollin, since I wanted to level up faster I decided to set up the bot to go all-in at 98% winning chance, but... accidentally I configured it to play at 1% chance. I lost all my balance in a single roll
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And martingaling, of course, I think I have lost 0.1+ BTC doing that. At least I think I learned my lession.