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