In May 2015, the European Commission adopted a Digital Single Market Strategy (2015), which identifies Europe as a potential leader in the global digital economy. If EU fragmentation and barriers are removed, Digital Single Market (DSM) could contribute an additional €415 billion to European GDP. Further, the Digital Single Market could create opportunities for new start-ups, and business can develop and create value for the 500 million consumers. The European Digital Single Market (DSM) has three policy areas: (1) access to digital goods and services, (2) conditions for digital networks and innovative services, and (3) digital as a driver for growth (https://ec.europa.eu/digital-single-market/en/digital-single-market ). In all these areas, data-driven services are an essential part of DSM. This research focuses on political, economic, social, technological, legal, and environmental (PESTEL) factors. Consider: To do this, a quantitative approach was used to analyze the data collected from four different data sources to understand major factors having impact on DSM:Digital Economy and Society Index (Desi), EU barometer, Digital Agenda key indicators, and public consultation. Based on our data analysis, we have found several data-based challenges in creating a digital single market as below: (a)Inequality within EU(b)Legislative gap with respect to digital content and data(c)Trust in a digital single market (in regard to data)(d)Privacy and security of digital software and systems Defining and understanding these challenges are vital to overcome obstacles hindering Digital Single Market goals.