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