Objectives: This observational cross-sectional study aimed to evaluate and compare the oral health-related quality of life (OHRQoL) and clinical performance between dentate subjects and edentulous patients restored with conventional dentures or implant overdentures. Methods: 85 edentulous patients were grouped as follows: Group-1 (CD): conventional denture wearers (n = 42), and Group-2 (IO): implant-retained overdenture wearers (n = 43). For the OHRQoL comparisons, a control group of subjects with a healthy natural dentition (Group-3, ND; n = 50) was included. Participants completed three validated questionnaires (OHIP-14sp, OHIP-20sp, and QoLIP-10). Socio-demographic data, prosthesis-related factors, clinical condition of the mouth, and patient subjective evaluations, were gathered. Descriptive and non-parametric probes were run (alpha = 0.05). Results: The ND group was the most unsatisfied (OHIP-14sp; p <= 0.001). The OHIP-20sp attributed significantly worse Psychological disability (p = 0.029) and Handicap (p = 0.027) to CD wearers when compared to IO wearers. The CD group showed the significantly highest need for relining (p = 0.041), and the lowest retention (p = 0.011). The OHIP-14sp disclosed a significantly worse OHRQoL for those volunteers who had a job (p = 0.003), a basic education instead of a secondary one (p = 0.022), and no partner (p = 0.006). Conclusions: The overall OHRQoL was comparable for both prosthodontic groups, being modulated by sociodemographic and prosthesis-related features. Nonetheless, CD wearers presented prosthetic complications more frequently. Clinical significance: While dentate subjects were the most critical about their oral condition and its repercussion in their life, implant overdenture wearers tended to observe a better OHRQoL and clinical performance compared to conventional denture wearers.