Background: Oncologic resection of the scalp confers several obstacles to the reconstructive surgeon dependent upon patient-specific and wound-specific factors. We aim to describe our experiences with various reconstructive methods, and delineate risk factors for coverage failure and complications in the setting of scalp reconstruction. Methods: A retrospective chart review was conducted, examining patients who underwent resection of fungating scalp tumors with subsequent soft-tissue reconstruction from 2003 to 2019. Patient demographics, wound and oncologic characteristics, treatment modalities, and outcomes were recorded and analyzed. Results: A total of 189 patients were appropriate for inclusion, undergoing a range of reconstructive methods from skin grafting to free flaps. Thirty-three patients (17.5%) underwent preoperative radiation. In all, 48 patients (25.4%) suffered wound site complications, 25 (13.2%) underwent reoperation, and 47 (24.9%) suffered from mortality. Preoperative radiation therapy was an independent risk factor for wound complications (odds ratio [OR], 2.85; 95% confidence interval [CI], 1.1–7.3; p = 0.028) and reoperations (OR, 4.45; 95% CI, 1.5–13.2; p = 0.007). Similarly, the presence of an underlying titanium mesh was an independent predictor of wound complications (OR, 2.49; 95% CI, 1.1–5.6; p= 0.029) and reoperations (OR, 3.40; 95% CI, 1.2–9.7; p= 0.020). Both immunosuppressed status (OR, 2.88; 95% CI, 1.2–7.1; p= 0.021) and preoperative radiation therapy (OR, 3.34; 95% CI, 1.2–9.7; p= 0.022) were risk factors for mortality. Conclusion Both preoperative radiation and the presence of underlying titanium mesh are independent risk factors for wound site complications and increased reoperation rates following oncologic resection and reconstruction of the scalp. Additionally, preoperative radiation, along with an immunosuppressed state, may predict patient mortality following scalp resection and reconstruction.