The alveolar ridge reconstruction of vertical and combined bone defects is a non-predictable procedure with varying percentages of success. The greatest challenge for vertical and combined bone augmentation is to maintain mechanical stability of the bone graft; therefore, it is mandatory to provide and preserve space for bone regeneration. The development of biomaterials and 3D printing has enabled the use of polymer scaffolds in the reconstruction of alveolar ridge defects. The aim of this pilot study was to evaluate the mechanical characteristics of an innovative individualized biodegradable polylactic acid (PLA) scaffold, under dynamic conditions, simulating biodegradation and the influence of masticatory forces. After the design and 3D printing of PLA scaffolds, two groups of 27 scaffolds were formed according to the compression testing procedure. The compression tests were performed in occlusal and lateral directions. In each of the two groups, nine subgroups of three scaffolds were formed for different testing periods during in vitro degradation with a total period of 16 weeks. Results showed that biodegradation and load application had no significant influence on mechanical characteristics of tested scaffolds. It can be concluded that simulated masticatory forces and biodegradation do not significantly influence the mechanical characteristics of an individualized biodegradable augmentation scaffold.