Radiological diagnosis of oral squamous cell carcinoma (OSCC) is one of the main steps in treatment planning. T (tumor size), DOI (depth of invasion) (AJCC 8th edition), and nodal metastases (N+) were evaluated using CT and MRI to assess the most effective imaging method. The effectiveness of the radiological imaging methods was compared with histopathological results. Imaging diagnostic studies were performed and retrospectively analyzed in 125 patients with OSCC (CT n = 54 and MRI n = 71). Histopathology evaluated T, DOI, and N+. The radiological T results of CT in comparison with histopathological examination showed agreement in 62.5% of cases for T1, 56.25% for T2, 25% for T3, and 42.8% for T4 (p-value = 0.07), and regarding MRI, 52.2% for T1, 36.4% for T2, 33.3% in T3, and 33.3% for T4. The DOI results of CT and MRI juxtaposed against the histopathological findings were as follows: for CT, n = 18 for DOI ≤ 10 mm and n = 36 for >10 mm; for MRI, n = 29 for DOI ≤ 10 mm and n = 42 for >10 mm (DOI CT vs. DOI hist. pat. p-value = 0.23; DOI MRI vs. DOI hist. pat. p-value = 0.006). Regarding nodal metastasis, n = 21 for N0 and n = 32 for N+ for CT (p-value = 0.02), and n = 49 for N0 and n = 22 for N+ for MRI (p-value = 0.1). In the radiological N+ group, the histopathological findings coincided with the results of MRI and CT in 27% and 62.5% of cases, respectively (N0: 83.6% for MRI; 85.7% for CT). Upon evaluating T, a decreasing percentage of overlapping results with an increasing tumor size was observed. The accuracy of both imaging studies was at a similar level, with a slight advantage for MRI. Among the patients on whom CT was performed, DOI analysis did not show statistically significant differences. This led to the conclusion that, in most cases, the DOI results based on CT overlapped with those described via histopathological examination. However, among the group of patients with MRI as the imaging method of choice, the differences proved to be statistically significant (p-value = 0.006). The results of this study indicate that CT is a more accurate method for DOI assessment. The results of the radiologic metastasis evaluation (N+ group) overlapped more in the CT group, while the percentage of corresponding results in the radiologic N0 vs. hist. pat. N0 group was high and similar in both groups. These results indicate that it is easier to confirm the absence of a metastasis than its presence.