A simplified numerical engineering model for the design of the surrounding timber matrix of dowel groups, developed within the framework of a commercial structural analysis software, is presented herein. This model was applied to highlight and reflect various dowel arrangements in timber to steel connections from building practice subjected to arbitrary sets of internal forces against the background of both the real mechanical behavior and the present practice of design. A parameter study revealed the interdependence of stresses in the timber matrix and geometrical and mechanical properties of dowel groups.