Exploration of long-term health expenditure and longevity trends across three major sub-regions of Eastern Europe since 1989. 24 countries were classified as EU 2004, CIS, or SEE. European Health for All Database (HFA-DB) 1989-2012 data were processed using difference-in-difference (DiD) and data envelopment analysis (DEA). The strongest expenditure growth was recorded in EU 2004 followed by SEE and the CIS. A surprisingly similar longevity increase was present in SEE and EU 2004. In 1989, countries that joined EU in 2004 were relatively inefficient in the number of life-years gained yet had a lower life expectancy than the SEE region and was only slightly higher than the CIS region (DEA). By 2012 the revenue spent was roughly linear to additional life-year expectancies. EU 2004 members were the best performers in terms of balanced longevity increase followed by health expenditure growth. The SEE economies' longevity gains were lagging slightly behind at a far lower cost. An extrapolated CIS expenditure to longevity increase ratio has the fastest-growing long-term promise.