- "Make I'm betting dollars to doughnuts that you will! 3. Dollars to donuts Gary Heller's I bet you dollars to donuts he knows exactly where the money is. 1. I won my bet. Place your bets. · 2. It means, "I bet you (something), and I'm very confident. . a sum of money betted. This is a faux bet in which one person agrees to put up the same amount of dollars to another person's donuts in a bet (where a donut is considered to be worth. Dollars to doughnuts" means something that is sure to happen. Hundreds of millions of dollars betting against this bubble. "I'll bet my dollars to your donuts (or buttons, cobwebs--whatever. It's an expression. This is a faux bet in which one person agrees to put up the same amount of dollars to another person's donuts in a bet (where a donut is considered to be. Make a fast buck. I bet you dollars to donuts our boy's upstairs somewhere. " Example: Dollars to doughnuts she quits her new job in a month. an act of betting. "Dollars to donuts"--an old-world expression meaning a certainty, a pseudo-betting term.