The purpose of this research was to evaluate the efficacy of utilizing the anterolateral flap from the thigh region for reconstructing the oro-mandibular defects when compared to other forms of flap reconstruction. A propensity score-matched analysis of patients with an oncologic head and neck defect who underwent microvascular reconstruction was performed. Two surgical groups, i.e., ALT (anterolateral thigh flap and bridging Plate) only and DFF (simultaneous soft tissue and vascularized bone flap), were created. Incidence and subsequent management strategies for postoperative plate exposure were evaluated along with complications, overall survival, and postoperative quality of life (QoL). Sixty-two patients were 1:1 propensity matched (31 per group). The DFF group had a significantly larger soft tissue and bone defect than the single-flap group. The 5-year probability of not having a plate exposure was 45.5 and 47.4% for the double-flaps and single-flap groups, respectively (p = 0.186). The ALT-only group had a significantly higher rate of wound infections (38.7% vs. 12.9%, p = 0.02). The incidence of flap loss, re-exploration, inpatient mortality, plate fracture, medical complications, and overall survival were not significantly different.