Background COVID-19 is a prothrombotic disease that can cause thromboembolism and microthrombi, which could lead to multiorgan failure and death. Since COVID-19 is a relatively new disease, there are guidelines for anticoagulation dosing for COVID-19 patients without consensus on the dosing. We studied the effects of different doses of anticoagulation in hospitalized patients with COVID-19 pneumonia and hypoxemia on any differences in need for high-flow oxygen, mechanical ventilation, and mortality. We also analyzed the patient population who benefited most from anticoagulation. Methodology We performed a retrospective chart review of all patients who were admitted with the diagnosis of COVID-19 infection with positive polymerase chain reaction, pneumonia (confirmed either by chest X-ray or CT chest), and hypoxemia (oxygen saturation of <94%, while on room air). These patients were studied for outcomes (the need for high-flow oxygen, the requirement for mechanical ventilation, and overall mortality) for different doses of anticoagulation (prophylactic, escalated, and therapeutic). Results The sample consists of 132 subjects, predominantly males (116, 87%), with a mean age of 59 years and a standard deviation of 15. About one-third of the participants had diabetes, and more than 50% had hypertension. Additionally, 27 (20.3%) had a history of heart disease, and 70 (53%) of the subjects were admitted to the intensive care unit (ICU) at some point during the study. Among those admitted to the ICU, about 11 (8%) subjects required mechanical ventilation and 16 (12%) passed away during the study. Those who died had higher use of high-flow oxygen, noninvasive mechanical ventilation, and invasive mechanical ventilation and had a longer stay on mechanical ventilation. There was no significant difference in mortality or need for mechanical ventilation for any strategy of anticoagulation. Conclusions Different doses of anticoagulation did not show any statistically significant relationship between the need for mechanical ventilation and mortality. More patients on high-flow oxygen had received escalated doses of anticoagulation as compared to those who were not on high-flow oxygen. Anticoagulation levels did not have any statistically significant effect on overall survival of patients.