Primary squamous cell carcinoma (SCC) of the temporal bone is an extremely rare malignancy, comprising only 0.2% of head and neck cancers. There is currently no universally accepted staging system for these tumors. This study evaluates the utility of the Pittsburgh staging system for temporal bone SCC, examines prognostic factors, and reports clinical outcomes. A retrospective review was conducted on a small cohort of 15 patients diagnosed with temporal bone SCC between 2020 and 2023. Imaging included high-resolution CT and MRI (T1W, T2W, and DWI). Staging accuracy was assessed, and Cohen’s Kappa coefficient was used to compare radiological and pathological staging. Results showed a 73% accuracy in preoperative radiological staging, with higher agreement for T3/T4 tumors (86%) compared to T1/T2 (63%). MRI provided additional information, revealing dural enhancement in two patients and parotid involvement in one. Survival analysis indicated 100% survival in T1/T2 patients, 25% in T3, and 0% in T4, supporting the prognostic value of the Pittsburgh system. While limited by the small sample size, the study confirms that the Pittsburgh staging system offers a reliable approach to stratifying patients with temporal bone SCC and underscores the importance of combined CT and MRI for accurate staging and treatment planning.