Combine raisins and 1/3 cup bourbon in small bowl. Soak for 30 minutes. Drain.
Preheat oven to 375°F Place bread in large bowl. Whisk milk, 3/4 cup sugar, cream, eggs, 2 egg yolks, vanilla and cinnamon in medium bowl to blend. Pour egg mixture over bread. Add raisins; mix gently to coat bread. Transfer mixture to 9×5x3-inch glass loaf baking dish.
Cover baking dish with foil. Bake pudding 40 minutes. Remove foil and bake until top is golden and tester inserted into center comes out clean, about 30 minutes longer. Cool slightly.
Melt butter in top of double boiler set over simmering water. Add 3 tablespoons bourbon, 1/4 cup sugar and 1 egg yolk. Whisk until mixture thickens slightly and candy thermometer registers 160°F, about 1 minute. Remove from heat.
Cut hot or warm bread pudding into 6 slices. Transfer to plates. Spoon bourbon sauce over each portion and serve.