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