We present some of our recent investigations in Dental Medicine using Optical Coherence Tomography (OCT). Time Domain (TD), Spectral Domain (SD), and Swept Source (SS) OCT in-house developed systems are being used, for both ex vivo and in vivo investigations in the oral cavity. We study ex vivo the interface between the tooth and the dental sealant and demonstrate the limitations of the X-rays investigations that are now the gold standard for such procedures. Using OCT, defects in the interface that cannot be identified in radiographs can be determined both as position and magnitude. The drilling process of teeth can also be characterized in real time using OCT, to monitor the remaining dentin thickness (RDT) in order to avoid opening the pulp chamber. We demonstrate in this respect that an RDT of 0.5 mm is the minimum value to assure the integrity of the dentin wall between the drilled cavity and the pulp chamber; at an RDT of 0.3 mm or less a fracture is initiated, the dentin is punctured and endodontic treatment must follow. In vivo OCT investigations in the oral cavity were also performed (i.e., for metalloceramic prostheses and for ceramic inlay tooth interfaces), with the low cost, light weight and versatile handheld probes with 1D galvoscanners that we have developed and applied for a range of in-house developed OCT systems, in various clinical applications. They are briefly discussed, as well as some of our current and future work in the field, including for studies of soft tissue in the mouth.