Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) is a novel coronavirus that has caused a global pandemic and unfortunately has caused a health crisis. When severe, coronavirus disease 2019 (COVID-19) can manifest with bilateral pneumonia and hypoxemic respiratory failure but also can affect different organ systems. SARS-CoV-2 infection is known to cause a hypercoagulable state resulting in acute thrombotic events, including venous thromboembolism, acute myocardial infarction, acute stroke, acute limb ischemia, and clotting of ECMO (extracorporeal membrane oxygenation) and CRRT (continuous renal replacement therapy) catheters. Even though it commonly causes thrombotic complications, bleeding complications of COVID-19 due to coagulopathy and use of anticoagulation are less commonly reported. We herein present a case of a patient with COVID-19 complicated by spontaneous retroperitoneal bleeding and massive deep vein thrombosis (DVT), which was later complicated by compartment syndrome. To the best of our knowledge, coexistence of spontaneous bleeding with massive DVT has not been reported in the current literature. This case emphasizes that COVID-19 induced hypercoagulable state can cause massive thrombosis, and patients might need anticoagulation therapy. However, clinicians should also consider the risk of hemorrhagic complications of the disease and be cautious when administering anticoagulant therapy in selected cases.