The chapter seeks to explain the relationship between employment–unemployment and flexible working in the Greek labor market. More specifically, we study the evolution of flexible forms of employment during the period 2000–2013 and examine whether these changes had an impact on the overall scale of employment and unemployment. In recent years, particularly in the European Union, it is believed that the reduction of labor costs will contribute to the competitiveness and adaptability of enterprises and thus to maintain existing jobs and create new ones. Since the early 1990s, Greece, following the guidelines of the European Union, gradually pushed a series of legislative changes relating to wages, working time, and so on aiming to promote flexible working. The main conclusion of the study supports findings of other researches that the significant increase in flexible working, particularly after 2009, failed to increase employment and reduce unemployment in the Greek labor market.