Background: This study aimed to investigate the relationship between the Curve of Spee (COS) depth and malocclusion characteristics in a population from Sibiu County, Romania. The research sought to understand how the COS’s anatomical dimensions correlate with different classes of malocclusion and the position of the frontal teeth. Methods: A total of 265 participants from the Dentistry Ambulatory of the Military Hospital of Sibiu were included in this study. It employed digital intraoral scanning technology to measure the COS, overjet, and overbite, with malocclusion classification. Statistical analyses, including correlation and regression, were conducted to examine the relationships between COS depth, frontal teeth position, and malocclusion characteristics. Results: The average COS depth measured was 1.0564 mm, presenting variability when compared to existing literature. Most of the study participants had Class I malocclusion. A significant positive correlation between COS depth and overjet was identified, with no notable gender-based differences in these occlusal parameters. Conclusions: The findings affirm the integral role of COS in occlusal dynamics and malocclusion diagnosis. The COS measurement of a mean of 1.0564 mm, when compared to other results emphasizes the differences in occlusal curvature among various populations. The results contribute to a refined understanding of occlusal relationships, supporting the need for personalized orthodontic and prosthetic treatments based on precise anatomical measurements.