Oral squamous cell carcinoma (OSCC) is the most common oral cancer, with rising incidence rates due to several risk factors. In this study, the clinicopathological characteristics and disease-free survival (DFS) of OSCC patients are explored, emphasising age-related prognostic differences. A retrospective analysis was conducted on cases diagnosed in 2022 at an exclusive oral cancer hospital, using the College of American Pathologists (CAP) protocol and AJCC 8th edition staging. Demographic, clinical, and histopathological parameters were compared between patients ≤50 years and >50 years. Among the group, 57.8 % were older than 50 years, with a male predominance. While the younger group had a greater proportion of stage II cancers, the older patients presented more frequently with advanced stage III/IV disease. Lymph node involvement (p = 0.036) and invasion of adjacent structures (p = 0.048) were significantly higher in older patients. Interestingly, the mean depth of invasion (DOI) was greater in younger patients (p = 0.009). There was no discernible difference in DFS or recurrence rates between the groups. Age over 50, lymph node involvement, and DOI were all substantially linked to advanced stage in univariate binary logistic regression. However, in multivariate analysis, only DOI (OR = 1.18; p = 0.002) and nodal status (OR = 4.02; p < 0.001) remained independent predictors, while age lost statistical significance (p = 0.305). The model showed high predictive accuracy (AUC = 0.90). In conclusion, although age correlates with disease extent, DOI and lymph node status are stronger independent predictors, reinforcing the need for personalised risk-based management in OSCC.