Purpose: To compare oral function and health-related quality of life (HRQoL) in patients reconstructed with either a reconstruction plate or a free vascularized bone flap with or without 3D planning. Materials and Methods: Patients from the Institute for Reconstructive Sciences in Medicine, University Medical Center Utrecht, and Radboud University Medical Center were included. This cross-sectional study assessed objective masticatory performance with the mixing ability test (mixing ability index [MAI]), maximum bite force, maximum mouth opening, and HRQoL. Differences between groups were analyzed using analysis of variance or Kruskal-Wallis test for continuous variables and chi-square test for categorical variables. Results: Six patients with digitally planned resections and reconstructions were included. For comparison, five patients treated with freehand bone reconstruction and four patients treated with plate reconstruction were also included. Mixing ability was superior in 3D-planned reconstructions (MAI: 20.7 ± 6.7) compared to plate reconstructions (MAI: 30.0 ± 0.1, P = .017) and freehand reconstructions (MAI: 29.5 ± 1.1, P = .017). Maximum mouth opening, bite force, and HRQoL differences did not reach statistical significance. Conclusion: This study indicated a possible benefit to masticatory performance of adequate surgical planning for one-phase reconstruction using 3D technology. A larger prospective study is necessary to gain more evidence regarding this finding.