Background and Objectives: Dental caries is a preventable, reversible disease in its early stages. This study evaluated the intra-rater agreement of International Caries Assessment and Detection System (ICDAS) scores with Medit i500® and Omnicam® scanners versus traditional clinical examinations and the inter-rater agreement using the Omnicam® among senior dentists and dental students and between these two groups. Materials and Methods: A total of 24 patients aged between 21 and 34 years, randomly selected from dental students and interns, underwent four examinations (three intraoral scans and one clinical examination), and the corresponding ICDAS scores were recorded by a randomly selected rater out of the 31 available examiners. The examination team consisted of dental students, dentists with less than 3 years, and dentists with more than 5 years of clinical experience. The following inter- and intra-rater agreement tests for the ordinal data were chosen: Fleiss’ kappa coefficient, Cohen’s weighted kappa, and inter-class correlations. Results: For all examination techniques, there was statistically significant agreement for the experienced raters (p < 0.05). The highest positive interclass correlation was obtained for inter-rater agreement tests of 288 observations recorded by senior dentists: ICC = 0.969 (95% CI 0.949–0.981). Conclusions: Intra-rater reliability was excellent for Omnicam compared to clinical exams conducted by senior dentists but moderate for Medit i500. Although inter-rater agreement using Omnicam was poor between students and between senior dentists and students, it was excellent among senior dentists.