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Simple Summary: Oral cancers are associated with high mortality in advanced stages. Early diagnosis is associated with better patient outcomes, but this is challenging to achieve as benign lesions look similar to lesions of concern, and multiple biopsies may be required to ensure the most pathologic tissue is sampled. This work leverages a previously developed endoscopic imaging system and deep learning segmentation tool to provide measurements of subsurface changes in the first few millimeters of oral tissue. We present seven quantitative features that allow for rapid examination of tissue, which we propose may be useful for biopsy site or treatment margin selection. Optical coherence tomography is a noninvasive imaging technique that provides three-dimensional visualization of subsurface tissue structures. OCT has been proposed and explored in the literature as a tool to assess oral cancer status, select biopsy sites, or identify surgical margins. Our endoscopic OCT device can generate widefield (centimeters long) imaging of lesions at any location in the oral cavity—but it is challenging for raters to quantitatively assess and score large volumes of data. Leveraging a previously developed epithelial segmentation network, this work develops quantifiable biomarkers that provide direct measurements of tissue properties in three dimensions. We hypothesize that features related to morphology, tissue attenuation, and contrast between tissue layers will be able to provide a quantitative assessment of disease status (dysplasia through carcinoma). This work retrospectively assesses seven biomarkers on a lesion-contralateral matched OCT dataset of the lateral and ventral tongue (40 patients, 70 sites). Epithelial depth and loss of epithelial–stromal boundary visualization provide the strongest discrimination between disease states. The stroma optical attenuation coefficient provides a distinction between benign lesions from dysplasia and carcinoma. The stratification biomarkers visualize subsurface changes, which provides potential for future utility in biopsy site selection or treatment margin delineation. [ABSTRACT FROM AUTHOR]