Provides an approach to osseous free flap selection for reconstruction of segmental mandible defects that takes into consideration general medical status of the patient and reconstruction requirements; demonstrates the complementary qualities of fibular and subscapular system free flaps; and describes the different surgical indications for lateral border scapular and scapular tip free flaps. To review our experience with osseous mandible reconstruction comparing the fibular and subscapular system free flaps, determine reconstruction-specific and general health variables that may differ between these patient groups, and present our approach to oromandibular reconstruction. Retrospective study. Academic tertiary care medical center. A total of 110 patients (68 male, 42 female) undergoing single-stage oromandibular reconstructions with free-tissue transfers between May 1, 2006, and May 30, 2012. Single-stage oromandibular reconstruction with free-tissue transfer. Differences in patient demographics, bone and soft-tissue aspects of the reconstruction, operative time, flap outcomes, and major postoperative complications between fibular, lateral scapular border, and scapular tip free flaps. A total of 110 patients underwent 113 reconstructions, including 58 fibular free flaps (FFFs) (51.3%) and 55 subscapular system flaps (48.7%). Of the subscapular system free flaps, 27 flaps (49%) were scapular tip free flaps (STFFs) based on the angular artery branch of the thoracodorsal pedicle; the remaining 28 cases were lateral scapular border flaps (LSBFs). Patients undergoing reconstruction with FFFs were significantly younger than their subscapular system flap counterparts (56 vs 70 years, P < .001). Mean mandible defect lengths were similar for patients undergoing FFF and LSBF reconstruction (7.8 and 7.7 cm, respectively); STFFs were used to reconstruct significantly shorter defects (mean, 6.0 cm, P < .001). The FFFs were more commonly used for anterior mandible defects in which multiple osteotomies and limited soft tissue were required, while subscapular flaps were more commonly used for linear mandible defects with complex soft-tissue requirements. A single complete flap loss occurred in a patient who underwent reconstruction with an STFF; other complication rates were similar between groups. The FFFs and subscapular flaps are complementary options for oromandibular reconstruction. The FFF is ideal for younger patients, extended defects, multiple osteotomies, and limited soft-tissue requirements. The subscapular system free flaps (LSBF and STFF) are excellent options for (1) elderly patients; (2) those with significant comorbidities, such as peripheral vascular disease; and (3) mandible defects associated with complex soft-tissue requirements. Furthermore, the STFF offers a reliable option to reconstruct short-segment defects, in particular, defects involving the angle of the mandible.