Surgical or percutaneous tracheotomy is one of the commonest operations in the ENT practice and one of the first procedures to be taught to residents. No study exists that demonstrates the safety of this surgical procedure performed by unexperienced surgeons. The purpose was to compare outcomes of tracheotomies performed by supervised residents and surgeons in terms of postoperative complications and mortality, and identify risk factors for the onset of complications. Retrospective cohort study. Otolaryngology-Head and Neck Surgery Department, University of Florence, Italy. We included all patients undergoing tracheotomy from July 2008 to January 2013 and compared tracheotomies performed by supervised residents or surgeons. During the study period, 304 patients were submitted to tracheotomy. Patients operated by surgeons had a significantly higher number of tracheal rings fracture (p = 0.05), subcutaneous emphysema (p = 0.003) and tracheostomy tube displacement (p = 0.003), while supervised residents had a higher number of tracheitis/pneumonia (p = 0.04) as early complications. Patients operated by supervised residents had a significantly higher number of tube obstructions as late complication (p = 0.04). Using multivariate model, risk factors for early postoperative complications were male sex (p = 0.04) and delayed time to substitution with cuffless tube (p = 0.01), while only a trend to statistical significance was observed for urgent tracheotomies concerning the risk for late postoperative complications (p = 0.08). The current practice where residents perform tracheotomies supervised by a surgeon should not be disheartened. Our study demonstrates that it is safe and does not lead to higher risk of complications nor negatively affects the quality of care.