The purpose of the study was to evaluate the clinical effects of bicanalicular double silicone stents in endoscopic transnasal dacryocystorhinostomy with lacrimal trephinized canaliculoplasty for monocanalicular and common canalicular obstruction. Bicanalicular double silicone intubation in endoscopic transnasal dacryocystorhinostomy with lacrimal trephination was performed in 58 eyes of 54 patients (5 men, 49 women; mean age: 55.9 ± 14.9 years) with epiphora due to monocanalicular and common canalicular obstruction between November 2007 and August 2010. We reviewed the records of subjects who had undergone the same surgery with a bicanalicular single intubation for same disease between March 2004 and October 2007 as controls (56 eyes of 50 patients). We evaluated age, gender, the operative side, the site of canalicular obstruction, and the effects of double silicone intubation. Complications relating to the silicone tube were also investigated. The double-stent group showed higher anatomical success rates (91.4%) and functional success rates (82.8%) than the single-stent group (75.0 and 69.6%, respectively) (p = 0.034 and p = 0.103, respectively). Bicanalicular double silicone stenting in endoscopic transnasal dacryocystorhinostomy with lacrimal trephinized canaliculoplasty may be an effective treatment for monocanalicular and common canalicular obstructions. This may also reduce more invasive surgery including Jones tube insertion (p = 0.038).