To evaluate the clinical outcomes of resin composite CAD/CAM restorations in a prospective cohort study, and to assess patient and operator satisfaction after restoration placement, 59 indirect resin composite were placed by supervised undergraduate students, of which 43 restorations were followed over a mean period of 28 months (14–44 months) and evaluated using USPHS criteria. Patient and operator satisfaction levels were assessed using a visual analogue scale (VAS) after restoration placement. A total of 37 patients and 47 restorations were included for further study. Four teeth were extracted—three due to extensive drug-induced secondary caries in the same patient, and one tooth due to large periapical periodontitis after 44 months of service. The overall survival rate was 91.4%, and success rate was 87.2%. Differences between baseline and endpoint scores were significant for marginal discoloration (p < 0.05) and adaptation (p < 0.001). Color match (p < 0.05) and surface texture (p < 0.001) differed significantly, affecting all restoration types. VAS scores for patient and operator satisfaction showed a significant rank correlation (p < 0.01), and pairwise comparison showed significant differences for mean overall patient and operator VAS scores (p < 0.001). Lava Ultimate CAD/CAM may be considered a suitable material for overlays and endocrown restorations when combined with IDS, air abrasion, and MDP-containing adhesive systems. Marginal disintegration may present in inlays and onlays over time.