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