Objectives: To compare the outcomes of stenotic punctal dilation by means of a punctal dilator alone vs. a Kelly punch punctoplasty, both followed by insertion of a mini-monoka stent, for treatment of symptomatic punctal stenosis. Methods: A retrospective, comparative study. The participants were patients with punctal stenosis related epiphora treated at the Goldschleger Eye Institute, Sheba Medical Center. All patients were treated either by simple punctal dilation (group 1) or Kelly punch-assisted punctoplasty (group 2), both followed by mini-monoka stent insertion. Symptoms relief and subjective epiphora scoring (Munk score) were compared and analysed. Results: Fifty patients were included in the study; Mean age (+SD) of the participants was 60 years (±12, range 30–86 years). Baseline characteristics (age, gender distribution, and visual acuity) were similar in both groups. The mini-monoka stent was placed for an average period of 2 weeks, and all patients received postoperative steroids and antibiotic treatment for 1 week. The Munk score decreased significantly in both groups following the procedure, dropping from 4.9 to 1.9 in group 1 and from 4.3 to 1.2 in group 2 (P < 0.005 for both groups). There was no difference in the delta Munk score between the two groups. Conclusions: Simple punctal dilation followed by insertion of a mini-monoka stent is effective in alleviating the symptoms of punctal stenosis-related epiphora. There was no added benefit when the more invasive Kelly punch-assisted punctoplasty was used, raising some doubt about its justification in these cases.