The novel COVID-19 infection has demonstrated a spectrum of complications involving vascular, inflammatory, infectious, and metabolic conditions. These complications range from mild loss of smell to more severe acute respiratory distress syndrome (ARDS). Patients with more severe complications often require sedation and mechanical ventilation. Growing research has revealed the role of active malignancy and disease-in-remission status as possible risk factors contributing to the morbidity and mortality in COVID-19 patients. In our descriptive case series, we present three unique cases of complicated COVID-19 infection in patients with hematologic-oncologic risk factors and review the imaging features of their complications. The first patient was a 33-year-old male with sickle cell trait who developed rhabdomyolysis and myonecrosis of the paraspinal muscle in the setting of a physical fitness test; he subsequently developed an abscess at this site, presumably exacerbated by the hypoxemic state of his COVID-19 pneumonia. Our second patient was a 37-year-old male with COVID-19 pneumonia and a history of stage IV Non-Hodgkin's lymphoma in remission who developed spontaneous pneumomediastinum in the absence of positive pressure ventilation. The third COVID-positive patient was a 54-year-old male with a past medical history significant for grade 1 follicular non-Hodgkin's lymphoma in remission with sputum culture positive for mycobacterium avium complex and bronchoscopy positive for candida growth. 18-FDG/PET imaging was performed and demonstrated diffuse intense uptake throughout the lungs reflecting both the COVID-19 pneumonia and the multimicrobial superinfection.