While dental caries represents the major chronic disease of humans, visual and tactile inspection are the methods of choice in daily dental practice. Several optical technologies have been developed in recent years for the purpose of dental examination, including near-infrared light transillumination as a promising tool for the supplementation and partial replacement of radiography. In case of occlusal alterations, the incidence of surface discolorations impedes the visual assessment, whereas tactile inspection appears to yield little diagnostic information or might be detrimental. Optical coherence tomography (OCT) facilitates depth-resolved imaging with μm resolution, utilizing near-infrared light, and has already shown its potential for various dental applications. We have recently demonstrated that depolarization imaging utilizing the degree of polarization uniformity (DOPU) extends those abilities by the detection of early carious lesions, as it provides an unambiguous demineralization contrast. Here, we show that this approach also enables the assessment of occlusal enamel lesions in the presence of stains, and compare PS-OCT cross sections with polarized light microscopy (PLM) images of thin sections. For tooth samples with discoloration or demineralization, respectively, PS-OCT and PLM results are in good agreement.