Singapore's health system generates similar levels of health outcomes as does Sweden's but for only 4.4% rather than 11.0% of gross domestic product, with Singapore's resulting health sector savings being re-directed to help fund both long-term care and retirement pensions for its elderly citizens. This paper contrasts the framework of financial risk-sharing and the configuration and management of health service providers in these two high-income, small-population countries. Two main institutional distinctions emerge from this country case comparison: (1) Key differences exist in the practical configuration of solidarity for payment of health care services, reflecting differing cultural roots and social expectations, which in turn carry substantial implications for financing long-term care and pensions. (2) Differing arrangements exist in the organization of health service institutions, in particular balancing public as against private sector responsibilities for owning, operating and managing these two countries' respective hospitals. These different structural characteristics generate fundamental differences in health sector financial and delivery outcomes in one developed country in Far East Asia as compared with a well-respected tax-funded health system in Western Europe. In the post-COVID era, as Western European policymakers find themselves forced to adjust their publicly funded health systems to (further) reductions in economic growth rates and overall tax receipts, and as the cost of the information revolution continues to rise while efforts to fund better coordinated social and home care services for growing numbers of chronically ill elderly remain inadequate, this two-country case comparison highlights a series of health system design questions that could potentially provide alternative health sector financing and service delivery strategies.