Several in vitro studies have demonstrated the potential for transillumination imaging and optical coherence tomography operating at 1310-nm for imaging caries lesions on tooth proximal and occlusal surfaces. Recently, we demonstrated that lesions on proximal surfaces could be imaged in vivo using NIR transillumination and that PS-OCT can be used in vivo to measure early demineralization on tooth buccal and occlusal surfaces. In this paper we report the first in vivo measurements using OCT and NIR imaging of occlusal lesions that have been scheduled for restoration. Occlusal lesions were chosen that were scheduled for restoration based on conventional diagnosis that consists of visual and tactile examination. Occlusal lesions were visible in the NIR. OCT looks promising for confirming the lateral spread of occlusal caries under the dentinal-enamel junction adjacent to fissures. These studies suggest that both near infrared transillumination imaging at 1310-nm and OCT provide valuable information about the severity of caries lesions.