The assessment of dental issues is done nowadays both clinically and radiologically. The latter includes radiographs that are based on X-ray radiation, i.e. intraoral radiography, panoramic radiography, and three-dimensional (3D) cone beam computed tomography (CBCT). In several cases, radiographs have limitations, as they do not reveal dental issues such as small cavities, enamel cracks, or tooth erosion. These aspects can be visible with another medical imaging technique, Optical Coherence Tomography (OCT). The aim of this study is to present a few results obtained with an in-house developed swept-source OCT (SS-OCT) system on several dental issues that cannot be visible on radiographs. These results prove that OCT can be utilized in dentistry, with advantages such as radiation free technique and superior resolution. This study presents both radiography and OCT images for different dental issues which include small cavities, metal crowns cracks, or crowns manufactured with different materials (i.e., zirconia, ceramics, or composite). Firstly, samples have been analyzed radiologically and some abnormalities could be detected, but they could be correctly assessed. Secondly, these abnormalities have been analyzed with the SS-OCT system and finally all images and collected data from both medical imaging techniques have been compared. One of the conclusions is that OCT is more appropriate than radiography for several dental issues such as those presented in this study. These two medical imaging techniques can therefore be complementary in dental medicine.