Background: The aim of this cross-sectional study was to (i) determine the prevalence and distribution of developmental grooves in a young population and (ii) to evaluate the local periodontal conditions. Methods: Two hundred and fifty-one students with a mean age of 22.9 ± 4.7, attending the School of Dentistry and Dental Hygiene of Vita-Salute San Raffaele University (Milan, Italy) were included. The subjects underwent a clinical evaluation by two calibrated examiners. The following clinical parameters were recorded for each site presenting a radicular groove and for each corresponding site on an adjacent tooth used as control: probing pocket depth, plaque index, bleeding on probing, recession depth. Results: The prevalence of radicular grooves at patient and tooth level was 15.9% and 5%, respectively. When compared to control sites, the number of teeth with a radicular groove that presented plaque and bleeding on probing was higher. The logistic regression analysis showed that the presence of radicular grooves was significantly associated with the presence of plaque (OR, 6.14, p < 0.001) and of bleeding on probing (OR, 2.91, p = 0.01). Conclusions: The presence of radicular grooves increases the possibility of developing gingival inflammation by acting as a plaque retentive factor.