Background: Nasolacrimal duct obstruction is a common ophthalmic condition that frequently presents with persistent tearing (epiphora) and episodes of dacryocystitis, significantly affecting patients’ quality of life. The purpose of this study was to compare the functional and anatomical outcomes of endoscopic versus external dacryocystorhinostomy in patients with nasolacrimal duct obstruction. Methods: This prospective, non-randomized study at the Department of Ophthalmology, National Institute of Ophthalmology and Hospital, Dhaka, Bangladesh, included 72 patients undergoing endoscopic or external dacryocystorhinostomy, followed for six months to assess anatomical and functional outcomes, intraoperative bleeding, and postoperative recovery. Preoperative evaluation used syringing, fluorescein dye, and dacryocystography when needed; data were analyzed with SPSS, with p < 0.05 considered significant. Results: Seventy-two patients (80 eyes) underwent DCR: 42 patients (50 eyes) EN-DCR, 30 patients (30 eyes) EX-DCR. Bilateral surgery was performed in 19.0% of EN-DCR patients (p = 0.018). EN-DCR patients were younger (33.6 ± 10.5 vs 46.0 ± 11.8 years, p < 0.001) with similar female predominance (57.1% vs 53.3%, p = 0.936) and eye laterality (p = 1.000). Anatomical and functional success were comparable (92.0% vs 93.3%). Minimal bleeding was more common in EN-DCR (56.0% vs 20.0%, p < 0.001). Hospital stay was shorter (1.3 ± 0.5 vs 2.6 ± 0.8 days, p < 0.001) with faster recovery (83.3% vs 60.0%, p = 0.025). Conclusion: Endoscopic and external DCR are equally effective for NLDO, with endoscopic DCR offering less bleeding and faster recovery.