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