We report a case of bilateral Descemet membrane detachment (DMD) after canaloplasty in a 70-year-old Portuguese man with primary open-angle glaucoma. The patient developed bilateral DMD immediately following consecutive (1 week apart) canaloplasty surgery in both eyes. Slit lamp biomicroscopy, gonioscopy, and Fourier-domain optical coherence tomography (FD-OCT) findings are described. On postoperative day 1, in both cases, slitlamp biomicroscopy revealed an unscrolled inferonasal DMD and a clear cornea with deep and quiet anterior chambers. Gonioscopy showed an intact, lightly pigmented, and distended trabecular meshwork with no evidence of suture extrusion. High-resolution FD-OCT revealed a widely dilated canal of Schlemm, trabecular distention, and a retrocorneal hyperreflective membrane corresponding to a DMD. At 3 months, the DMD resolved spontaneously in both eyes. Although DMD is a known complication of canaloplasty, the occurrence of bilateral symmetrically located DMDs in our case suggests a possible anatomical predisposition in addition to factors induced by the surgical technique.