The purpose of this study was to evaluate the correlation between the acrylamide (AA) content and the antioxidant activity (AOA) of self-prepared cookies. Cookies were baked in the laboratory under defined conditions following four different recipes. The parameters of investigation were the influence of the type and relative content of sugar (glucose and fructose) and the baking time on the AA content as well as AOA of the final products. Parameters depending on the recipe and baking conditions such as the moisture content, the total nitrogen concentration, and the color of the products were evaluated for all samples as well. To prove the transferability of the findings gained with model cookies to samples from industry, the same measurements were performed on seven different types/brands of cookies that were purchased in local markets. A direct correlation was found between the concentration of AA and the AOA. With increasing baking time, the moisture content of the cookies decreased. The latter parameter correlated well with the AA concentration and AOA. The use of fructose enhanced the concentration of AA and the AOA of the final products, when compared with the use of sucrose. However, a simple model for the prediction of acrylamide contents and the AOA of samples from the baking time, color, protein, or moisture content of the samples was not found.