The main goal of root canal treatment (RCT) is to eradicate or essentially diminish the microbial population within the root canal system and to prevent reinfection by a proper chemo-mechanical preparation and hermetic final obturation of the root canal space. The aim of this study was to assess the quality of the root canal filling and the number of visits needed for completing RCT by operators with different experience, including dentistry students (4th and 5th year), general dental practitioners (GDPs), and endodontists. Data from medical records of 798 patients were analyzed, obtaining 900 teeth and 1773 obturated canals according to the inclusion and exclusion criteria. A similar number of teeth was assessed in each group in terms of density and length of root canal filling and number of visits. The larger number of visits and the lower quality of treatment was observed for 4th year students than for other groups (p < 0.05); in contrast, the endodontists needed the lowest number of visits to complete RCT and more often overfilled teeth than other operator groups (p < 0.05). Interestingly, no statistical difference in quality of root canal filling was noted between 5th year students, GPDs and endodontists. The treatment of lower teeth demanded statistically more visits than that of upper teeth (p < 0.05). The results of the study emphasize that most of the root canal filling performed by operators was considered adequate, regardless of tooth type, files used and number of visits.