Purpose: To compare the safety and efficacy of enoxaparin versus unfractionated heparin for venous thromboembolism prophylaxis in hospitalized patients with chronic liver disease by evaluating in-hospital bleeding and thromboembolic events. Methods: This retrospective, single-center cohort study included adult patients (> 18 years) with a documented diagnosis of cirrhosis or chronic liver disease as identified by relevant ICD-10 codes from January 2020 to June 2025 that have received VTE prophylaxis with UFH or enoxaparin during hospitalization. The data collected includes baseline patient characteristics, admission diagnosis, prior to admission medications, important baseline laboratory values, MELD score, Child-Pugh score, VTE and bleed risk assessment tools, and VTE prophylaxis administered. The primary endpoint is the incidence of in-hospital bleeding events. Secondary endpoints include incidences of in-hospital International Society on Thrombosis and Haemostasis (ISTH) major and minor bleeding, in-hospital VTE events, drug discontinuations due to thrombocytopenia or anemia, and mortality. Data analysis was completed using descriptive statistics. Results: A total of 82 patients were included (enoxaparin n=46; UFH n=36). Baseline demographics, laboratory values, and liver disease severity were similar, with median age 60 years and most patients classified as Child-Pugh C. All patients were high VTE risk by PADUA and IMPROVE scores. New bleeding events occurred in 8.6% with enoxaparin and 5.6% with UFH. Major bleeding occurred only with UFH (5.6%), while minor bleeding occurred only with enoxaparin (8.6%). VTE events were rare and comparable (2.2% vs 2.7%). Therapy discontinuation for non-bleeding events was more frequent with enoxaparin (32.6% vs 22.2%). In-hospital mortality was numerically lower with enoxaparin (6.5% vs 13.8%). Conclusion: In hospitalized patients with cirrhosis requiring VTE prophylaxis, enoxaparin demonstrated similar efficacy to UFH in preventing thromboembolic events. Although bleeding occurred more often with enoxaparin, events were minor and did not require discontinuation of therapy, whereas fewer but more severe bleeding events were seen with UFH. These findings suggest that enoxaparin may be a safe alternative, though larger prospective studies are needed.