Background The coronavirus disease 2019 (COVID-19) global pandemic prompted a significant use of intensive care resources for managing hypoxic respiratory failure. A substantial portion of these patients required mechanical ventilation. While intubation is common, its impact on mortality improvement has been questionable. Tracheostomies have become crucial for patients needing prolonged ventilation. However, tracheostomies also risk infections, ranging from early-stage mild cellulitis to later-stage nosocomial pneumonia. Our study evaluates the incidence of bacterial infections in COVID-19 patients who underwent tracheostomy early (within 14 days) versus late (more than 14 days after initiation of mechanical ventilation) during their stay in the intensive care unit (ICU). Methods We conducted a retrospective single-center study at Royal Medical Services Military Hospital. The study included COVID-19 patients who underwent tracheostomy and were admitted to the ICU from March 2020 to March 2022. We analyzed the incidence of ventilator-associated pneumonia, the timing of weaning from mechanical ventilation, and outcomes between early and late tracheostomized patients. Analyzed variables included demographics, comorbidities, use of steroids, tocilizumab, inflammation parameters, tracheostomy timing, incidence of bacterial infections, complications, and outcomes. Results The study comprised 36 patients. We found no statistically significant difference in the incidence of bacterial infections between the early and late tracheostomy groups (P>0.05). Complications and overall outcomes did not show significant statistical associations. Inotropes use was more frequent in the late tracheostomy group (P=0.122). In contrast, continuous renal replacement therapy was higher in the early tracheostomy group, showing no significant association (P>0.05). Mortality was higher in the early tracheostomy group, with nine deaths compared to seven in the late tracheostomy group. Interestingly, infection with Acinetobacter baumannii was associated with a statistically significant lower mortality rate, with 75% survival following tracheostomy. Conclusions Findings suggest that tracheostomy timing does not significantly impact the incidence of bacterial pneumonia or other complications, such as the use of inotropes, continuous renal replacement therapy, or mortality rates. These results support the use of personalized decision-making while conducting tracheostomies. Further research is necessary to determine the impacts of tracheostomy timing on patient outcomes more definitively.