Objectives: This study sought to identify tumor characteristics that associate with regional lymph node metastases in squamous cell carcinomas originating in the upper gingiva. Materials and methods: Data from 113 patients from Osaka University Dental Hospital were included. We measured each primary tumor’s width, length, depth, and the extent of bone invasion. Additionally, tumor signal intensity for T1 and T2-weighted images as well as the center of the tumor’s location and T classification was assessed, and a histopathological analysis was performed. Results: Tumor signal intensity was not found to be a significant prognostic factor. However, bucco-lingual width, histopathological classification as well as the tumor’s location were significantly different between metastatic and non-metastatic groups in both univariate and multivariate analysis. Superior–inferior depth and T classification were significant only in the univariate (and not the multivariate) analysis. Conclusions: Bucco-lingual width, histopathological grading as well as the tumor’s location are likely to be important predictors for the occurrence of LN metastasis in upper gingival carcinoma patients and should be considered when managing care for these patients.