Background: COVID-19 infection was linked to an increased risk of thromboembolism in high-risk individuals, so different anticoagulants were employed at varying doses. Anticoagulant-induced spontaneous retroperitoneal bleeding (SRB) is a rare condition. Objective: To analyze spontaneous retroperitoneal bleeding (SRB) associated with COVID-19 infection owing to anticoagulation on a larger scale in terms of comorbidities and factors related with SRB, as well as discuss existing therapeutics modalities, factors influencing decision, prognosis, and associated mortality. Patients and Methods: Twenty COVID-19 patients presented with SRB; 12 were treated surgically, and 8 were treated conservatively. Patients' demographic information, comorbidity evaluation, type of intervention, results, and prognostic factors were all evaluated. Results: Eight patients were treated conservatively; three died as a result of refractory shock. Twelve patients were operated on; eight of them died as a result of myocardial infarction, pulmonary problems, and multiple organ failure. The date of the surgical consultation influenced care and outcome significantly. Increased blood component requirements were found to be substantially associated to mortality. Conclusion: Management should be wise, yet not hesitate to intervene if necessary. In a progressive hematoma, this produces better results than conservation. Independent variables that necessitate intervention include vital instability, increasing hemoglobin decline, and transfusion requirements.