Background: Bacterial and fungal co-infections and superinfections have a critical role in the outcome of the COVID-19 patients admitted to the Intensive Care Unit (ICU). Methods: The present study is a retrospective analysis of 95 patients admitted to the ICU for COVID-19-related ARDS during the first (February–May 2020) and second waves of the pandemic (October 2020–January 2021). Demographic and clinical data, CT imaging features, and pulmonary and extra-pulmonary complications were recorded, as well as the temporal evolution of CT findings when more than one scan was available. The presence of co-infections and superinfections was registered, reporting the culprit pathogens and the specimen type for culture. A comparison between patients with and without bacterial and/or co-infections/superinfections was performed. Results: Sixty-three patients (66.3%) developed at least one confirmed co-infection/superinfection, with 52 (82.5%) developing pneumonia and 43 (68.3%) bloodstream infection. Gram-negative bacteria were the most common co-pathogens identified and Aspergillus spp. was the most frequent pulmonary microorganism. Consolidations, cavitations, and bronchiectasis were significantly associated with the presence of co-infections/superinfections (p = 0.009, p = 0.010 and p = 0.009, respectively); when considering only patients with pulmonary co-pathogens, only consolidations remained statistically significative (p = 0.004). Invasive pulmonary aspergillosis was significantly associated with the presence of cavitations and bronchiectasis (p < 0.001). Patients with co-infections/superinfections presented a significantly higher mortality rate compared to patients with COVID-19 only (52.4% vs. 25%, p = 0.016). Conclusions: Bacterial and fungal co-infections and superinfections are frequent in COVID-19 patients admitted to ICU and are associated with worse outcomes. Imaging plays an important role in monitoring critically ill COVID-19 patients and may help detect these complications, suggesting further laboratory investigations.