Purpose: To retrospectively investigate the agreement of diagnostic findings in syringing, dacryocystography (DCG), and dacryoendoscopy in the obstruction of the lacrimal drainage system (LDS).Design: Retrospective, analytical observational studyMethods: We examined 113 patients (211 LDS) who underwent syringing, DCG, and dacryoendoscopy to preoperatively evaluate LDS obstruction. Obstruction was compared by classifying the obstruction grade and site into three levels, respectively. The diagnostic agreement between tests was assessed by determining the weighted kappa value.Results: A total of 25 male (49 LDS) and 88 female patients (162 LDS) were included in this study. Obstruction was observed in 77.4%, 60.0%, and 81.3% of LDS by syringing, DCG, and dacryoendoscopy, respectively. Regarding the agreement in obstruction grade, Cohen’s kappa value for DCG and dacryoendoscopy was 0.65 (95% confidence interval [CI]: 0.56–0.74). DCG found no obstruction in 38.4% of all LDS, whereas 47.9% of them showed stenosis or obstruction by dacryoendoscopy. Meanwhile, DCG and dacryoendoscopy showed consistency in the obstruction site in 77.9% of LDS. When discrepancies were observed between syringing and dacryoendoscopy to detect the obstruction site, the combination of syringing and DCG reached dacryoendoscopy findings at the 99% level.Conclusions: “Substantial” agreements were found in the diagnostic findings among the three examinations. Then, the highest agreement was observed between syringing and dacryoendoscopy in determining the obstruction site. The lowest agreements were observed between syringing and DCG in diagnosing the obstruction grade and site.