The primary aim of our retrospective chart review is to compare open surgical (OS) tracheostomies performed by specialist and supervised resident surgeons, focusing on surgical time and post-surgical complications. The secondary objective was to compare these data based on the years of surgical experience for both specialists and residents. All patients undergoing surgical tracheostomy at the Unit of Otorhinolaryngology, Head & Neck Department, University of Verona between 1 January 2017, and 31 December 2022, were subjected to a retrospective analysis. A total of 385 OS tracheostomies were included in the study. Procedures conducted by supervised residents across various training years were compared with those performed by junior and senior specialists, focusing on surgical duration and postoperative complications. Subsequently, these data were stratified based on the surgical experience of subgroups: residents were categorized into 4 years of training, and specialists were categorized into junior (with less than 5 years of experience) and senior (with at least 5 years). Statistical analysis concerning patients' anatomy revealed a significant increase in operative times among those with no palpable neck landmarks (p = 0.006) and those with previous neck surgery (p = 0.039). Among patients' comorbidities, only anticoagulant or antiaggregant therapy was found to prolong operative time (p = 0.018), while the ASA score did not correlate with the duration of surgery. Finally, no statistically significant differences in surgical time were observed (p = 0.287), and no significant differences in complication frequency were reported between supervised residents and specialists (p = 0.908), regardless of years of experience. Under appropriate supervision, OS tracheostomy has demonstrated safety for residents as early as their first year of residency. Residents can perform tracheostomies without significantly prolonging the duration of the operation or increasing the risk of peri- and post-operative complications.