Purpose: To compare the success rates of external dacryocystorhinostomy (EXT-DCR) with 5-fluorouracil (5-FU) augmented endonasal laser dacryocystorhinostomy (ENL-DCR) and to record the complications associated with 5-FU augmented ENL-DCR Materials and Methods: This was a retrospective non-randomised study. Forty-one patients with primary acquired nasolacrimal duct obstruction underwent an EXT-DCR (19 patients) or an ENL-DCR (22 patients) over a 3-year period. A Holmium YAG laser (Ho:YAG) was used in the latter group of patients. Silicone tubes intubated in all patients were removed at three months. 5-FU was applied intraoperatively at the site of the ostium in the ENL-DCR patients. The median follow-up was 12 months (range 3-24 months) for the ENL-DCR group and 22 months (range 6-28 months) for the EXT-DCR group. The patency of the lacrimal system and the severity of epiphora were assessed at a final-review. Results: The median age of the EXT-DCR group was 77 years (range 53-87) and that of the ENL-DCR group was 71 years (range 23 to 84). There were 12 female patients in the former group and 19 in the latter. The percentage of success in the EXT-DCR group was 94.7% (95% confidence interval (CI) = 75.4-99.1) = ), and 63.6% in the ENL-DCR group (95% CI= 43.0-80.3). The confidence interval for the difference of 31.1% was 5.6-52.2. There was a statistically significant difference between the two groups, p=0.024 (Fisher exact test). Conclusions: These data suggest that EXT-DCR provides better results than 5-FU augmented ENL-DCR. However, ENL-DCR is the procedure of choice in certain circumstances such as in elderly, frail or medically unfit patients. Our results of 5-FU augmented ENL-DCR compare favourably with other published series.