Dental enamel manifests high transparency in the near-IR. Previous work demonstrated that near-IR light at 1310-nm is ideally suited for the transillumination of interproximal dental caries (dental decay in between teeth) . However, most new dental decay occurs in the pits and fissures of the occlusal (biting) surfaces of posterior teeth. These caries lesions cannot be detected by x-rays during the early stages of decay due to the overlapping topography of the crown of the tooth. In this study, a near-IR imaging system operating at 1310-nm was used to acquire occlusal images by launching the near-IR light into the buccal surface of the tooth just above the gingival margin (gum-line). The near-IR light diffuses through the highly scattering dentin providing uniform back illumination of the enamel of the crowns allowing imaging of the occlusal surfaces. The near-IR images show high contrast between sound and demineralized areas. Demineralization (decay) can be easily differentiated from stains and pigmentation. Moreover, the high transparency of the enamel enables imaging at greater depth for the detection of subsurface decay hidden under the enamel. These early images suggest that the near-IR offers significant advantages over conventional visual, tactile and radiographic caries detection methods.