Introduction Venous thromboembolism (VTE) is the most preventable complication in hospitalized patients. The main objective of this study was to evaluate the adherence of current clinical practice to the established guidelines at a Palestinian teaching hospital. Methods This cross-sectional, retrospective, observational study was conducted at a Palestinian Teaching Hospital. The medical records of patients admitted to the medical floor over 18 years of age and hospitalized for longer than 24 hours between January 1 and May 31, 2019, were included. Patients taking anticoagulants with incomplete or duplicated medical records were excluded from the study. A data collection sheet was developed, and clotting and bleeding risks were assessed using the Padua and IMPROVE risk assessment models (scores). The data were analyzed using IBM SPSS (version 25). Results In total, 408 patients were included in the study, 222 of whom received thromboprophylaxis (54.4%). Of the hospitalized patients, 112 (27.5%) had a high risk of developing VTE (Padua score ≥ 4), and 73 patients were eligible for VTE pharmacological prophylaxis; however, only 44 (60.3%) received the appropriate prophylaxis. In addition, 296 patients had low Padua scores, indicating that pharmacological prophylaxis was not indicated. However, 144 (48.6%) patients received prophylaxis. The mean Padua and IMPROVE risk scores were 2.25 ± 2.08 and 4.44 ± 2.72, respectively. Among the patients, 17.6% had a high risk of bleeding (IMPROVE score ≥ 7). Conclusion VTE prophylaxis among hospitalized medically ill patients was mostly inappropriate; 80.18% of the patients received inappropriate prophylaxis, and only 60.3% of eligible patients received appropriate prophylaxis. Adapting assessment models or checklists in clinical practice based on clinical guidelines for VTE risk stratification is a practical and effective method to improve VTE prophylaxis management and select the appropriate therapy to prevent toxicity or complication.