Background/Objectives: The aim of the study was to compare dacryocystectomy (DCT) versus dacryocystorhinostomy (DCR) in patients with dacryocystitis in terms of tearing complaints. Methods: We conducted a retrospective and comparative study on 19 patients. The main outcome measure was defined as an improvement by 1 point of the Munk score postoperatively. Results: A total of 19 patients were included with 10 in the DCR group and 9 in the DCT group. The primary endpoint was reached in 7 (70%) and in 6 (67%) patients in the DCR and DCT groups, respectively (p > 0.999). All DCR procedures were performed under general anesthesia (GA), while almost all DCT procedures were performed under local anesthesia (LA) (p < 0.001). There was a higher need for hospitalization in the DCR group (p < 0.001). Conclusions: Our preliminary results indicate that DCR is not always the solution in the case of dacryocystitis. DCT is a viable surgical procedure, especially in elderly patients without any tearing complaint and with underlying dry eye disease.