Residual cholesteatoma is a cholesteatoma that remains incompletely excised during the initial surgical procedure. Management options for residual disease typically include either the traditional postauricular mastoidectomy or a transcanal endoscopic approach, depending on the location and extent of the residual pathology. We report the case of a 22-year-old male who presented with recurrent left-sided otorrhea lasting seven months. He had previously undergone a left modified radical mastoidectomy for chronic otitis media with cholesteatoma seven months prior to his current symptoms. A high-resolution computed tomography (HRCT) scan of the temporal bone, performed postoperatively, revealed soft tissue density in the epitympanum, mesotympanum, and mastoid bowl, along with evidence of ossicular chain disruption. A transcanal endoscopic approach was utilized for the removal of the residual disease. This case highlights the viability of the transcanal approach in selected patients with residual cholesteatoma, provided that high quality preoperative imaging is available and the procedure is performed by an experienced otologist skilled in endoscopic ear surgery.