This study aims to evaluate food impaction on three-dimensional (3D) printed models with periodontal ligament simulation. Based on a commercial typodont pair, 3D maxillary and mandibular models were created with no teeth and with tooth sockets that were 1 mm wider than the original ones from 24 to 27 or 34 to 37 for periodontal ligament simulation with vinyl polysiloxane impression material. In total, 35 pairs of 7 combinations, including maxillary/mandibular typodonts in occlusion with maxillary/mandibular 3D models with/without a distal gap of canines on 3D models (tooth 23 or 33) were mounted on hinge articulators and divided into seven groups (n = 5). Each sample experienced the same manual chewing simulation on a customized device. The proximal surfaces were photographed to measure the percentage of food impaction area using ImageJ software. Group with fixed maxillary and mandibular teeth showed more food impaction than other groups with significant differences in the average of maxilla and the average of all proximal areas. The flexibility of the periodontal ligament and the degree of freedom of the teeth in their sockets may contribute to the extent of food impaction in proximal spaces.