This article describes the idiosyncrasies towards information systems investment evaluation approaches in the emerging market of Greece. Five case studies are examined from the banking industry, each of them representing a different positioning in the market. The article discusses forms of formal and informal investment evaluation techniques used, relating them with the business and strategic concept of information systems and formulating a matrix that positions the organizations based on the techniques used and market maturity. The research highlights how the differentiation towards the concept of information systems investment evaluation correlates with market maturity and industry goals. C