Background: Chronic dacryocystitis is a common condition caused by an obstruction in the nasolacrimal duct, leading to excessive tearing, recurrent infections, and discomfort. The condition is often managed through dacryocystorhinostomy (DCR), which can be performed via two primary techniques: external DCR and endoscopic endonasal DCR. The external approach, a well-established procedure, requires an incision over the lacrimal sac, while the endoscopic technique offers a minimally invasive alternative with no external incision. The effectiveness, complication rates, and recovery times of these two methods are subjects of ongoing debate. Objective: This study aims to compare the outcomes of external versus endoscopic endonasal DCR in the management of chronic dacryocystitis. Methodology: An observational study was conducted at the Department of Ophthalmology, a tertiary hospital in Dhaka, from January 2024 to January 2025. A total of 30 patients diagnosed with chronic dacryocystitis were divided into two groups, with 15 undergoing endoscopic DCR and 15 undergoing external DCR. Demographic data, preoperative complications, and postoperative outcomes were recorded and analyzed using statistical methods to assess the efficacy of both approaches. Results: No significant differences were found between the two groups in terms of age, gender distribution, or preoperative complications. However, the mean duration of surgery was significantly longer in the endoscopic group (60.5 ± 7.9 minutes) compared to the external group (53.1 ± 6.2 minutes) (p = 0.042). Postoperative results revealed that 76.7% of the endoscopic group and 83.3% of the external group had patent drainage systems, with no statistically significant difference in epiphora rates or sac patency between the groups. Bleeding complications were mild to moderate, and no significant differences in severity were observed between the two techniques. Conclusion: Both external and endoscopic endonasal DCR are effective for treating chronic dacryocystitis, with comparable outcomes in terms of epiphora resolution, sac patency, and complications. While the endoscopic technique showed a longer surgical duration, the two approaches yielded similar results in postoperative follow-ups. The choice of technique should be guided by individual patient factors, surgeon expertise, and patient preferences, as both methods offer satisfactory results in chronic dacryocystitis management.