Background: The volume-outcome relationship is a well-known phenomenon in surgical oncology. The aim of this study was to quantify the impact of surgeon volume on the treatment outcome of oral squamous cell carcinoma (OSCC) patients. Methods: All new OSCC cases treated with curative intent between 2008 and 2013 were included. A heterogeneous set of predictor variables was collected, including patient, tumour and treatment factors. The outcomes of interest were recurrence-free survival (RFS), overall survival (OS) and disease-specific survival (DSS). To investigate the cut-off in surgeon volume, the number of OSCC resections was analysed in multiplies of 5 cases per annum according to DSS, using univariable regression analysis. Results: 534 cases were recruited. Independently, the negative predictors for patient survival were age, perineural invasion, worsening tumour staging, and extracapsular spread. High-volume surgeon was determined to be most significant at 20 cases per annum and significantly associated with improved RFS (HR: 0.67), OS (HR: 0.44), and DSS (HR: 0.39). Conclusions: Results from this study support the rationalisation of OSCC management at high-volume centres and in the hands of experienced surgeons for better patient survival. Head and neck surgeons should perform a minimum of 20 OSCC cases per year to maintain competency in OSCC ablation.