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