The objectives of the present work are to use computational fluid dynamics (CFD) to studythe airflow pattern and to evaluate the effectiveness of the passive cooling design of theproposed Jurong General Hospital (JGH) using natural wind. The complex three-dimensionalCFD model is used to assess the environmental conditions at the deep podium inside the JGHcomplex with prevailing wind conditions in Singapore, corresponding to the monsoon(November-February) and hot (March-October) seasons. The results include mean velocityvectors, streamlines and pressure distribution around the building as well as inside the podiumspace and walkway. It is shown that the effective depth for human comfort at the podiumspace may not be satisfied for all the prevailing wind conditions for the existing design. Theeffects of wind scoop, placement of wind baffle, openings, hybrid ventilation system,chamfering of sharp building edge (L corner) and many other novel architectural features areinvestigated.