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Introduction The modern availability in daily practice of different DICOM viewers allows physicians to routinely evaluate computed tomography (CT) and magnetic resonance (MR) scans of patients in the pre-, intra-, and postoperative settings. Their systematic use, together with a close surgeon-radiologist cooperation, may greatly improve outcomes of patients to be treated by transoral microsurgery for laryngeal cancer. Materials and methods We herein propose guidelines for systematic evaluation of CT/MR images taken from patients affected by supraglottic and glottic cancer to be treated by transoral microsurgery. Results A methodical, step-by-step approach focused on laryngeal anatomy, systematically looking at each true and false vocal folds, anterior commissure, laryngeal ventricle, subglottic area, epiglottis, thyroid, cricoid, and arytenoid cartilages, posterior commissure, crico-arytenoid unit, paraglottic and pre-epiglottic spaces, and possible extra-laryngeal extension is proposed. This checklist may be useful before imaging performance (to focus on specific issues to be detailed by the radiologist), as well before and during surgery for the specific evaluation of details to be cleared during transoral microsurgery. Conclusion Detailed preoperative evaluation of supraglottic and glottic anatomy is essential prior to any transoral approach for neoplastic disease. The proposed imaging checklist described herein represents a step-by-step guide to surgeons performing this kind of interventions and an aid in achieving a meticulous approach from a surgical perspective.