Despite the availability of institutional guidelines, the practice of venous thromboembolism (VTE) risk assessment and thromboprophylaxis remains inadequate in Singapore. With hospital-associated VTE (HA-VTE) being a common cause of preventable mortality for medical patients, it is vital for prompt, appropriate prescription of thromboprophylaxis after VTE risk assessment. This study aimed to (1) assess the local practice of VTE risk assessment and prophylaxis according to institutional guidelines, (2) study the risk factors of potential preventable HA-VTE among hospitalized medical patients, and (3) improve the quality of care with respect to early prevention of HA-VTE. An audit was performed on daily new admissions to two general medical wards in a teaching hospital in Singapore (total capacity of 76 beds) over 2 weeks. Each new admission's medical records were reviewed to examine whether (1) VTE risk assessment was performed by the managing medical teams, (2) thromboprophylaxis was prescribed during admission in high VTE risk patients, and (3) any contraindications to pharmacological thromboprophylaxis for cases with high VTE risk but no pharmacological thromboprophylaxis prescribed was present. Only 1 out of 52 cases had VTE risk assessment performed. Thirty-one cases (59.1%) were identified to have high VTE risk using the Padua Prediction Score. However, only 1 out of the 31 cases (3.2%) had VTE prophylaxis prescribed. Adherence to local institutional guidelines remains poor despite increasing awareness of the importance of VTE risk assessment and prophylaxis in the prevention of associated morbidity and mortality. Certain patient profiles should prompt clinicians to perform VTE risk assessment.