The Republic of Singapore Air Force (RSAF) provides Helicopter Search-and-Rescue (SAR) and Helicopter Medical Evacuation (Heli-Medevac) coverage for the Singapore Aeronautical Search and Rescue Region (ASSR) in the South China Sea, spanning 840,000 km2. This region contains busy international shipping lanes and air traffic routes. Each year, Singapore's Helicopter SAR and Heli-Medevac service is activated multiple times to rescue personnel lost at sea or to evacuate ill and injured ship sailors or passengers to tertiary hospitals in Singapore for stabilization and advanced care. This is a retrospective review on all civilian SAR and Heli-medevac activations by the RSAF over a 5-year period from 2016 to 2020. Case profiles, presenting conditions, in-flight treatment, and patient outcomes are reviewed and discussed. Key operational observations made from RSAF's SAR and Heli-Medevac, as well as lessons learned from these missions, are discussed in this article.