Cutting speed plays a crucial role for the behavior during and the final quality of viscoelastic foods after cutting and is, in industrial applications, usually adjusted on an empirical basis. Although previous studies investigated the interplay between the time-dependent properties and cutting behavior of model systems on an elastomer basis, there is still a need to elaborate such cause-effect relations for real foods. The aim of this study was to establish a reproducible manufacture of model caramels on a laboratory scale and to investigate the influence of the compositional parameters, moisture, and solid fat content, as well as cutting speed, on cutting behavior. It was possible to visualize ductile-brittle transitions in cutting force profiles, with an increase in cutting speed resulting in effects similar to that induced by a decreasing moisture content or an increasing solid fat content. Quantitatively, the progression of both maximum force and cutting energy reversed when cutting speed increased and composition changed in favor of a more brittle behavior. This work provides the basis for further research on distinct loading phenomena observed during the cutting of foods and for numerical modeling of the cutting process.