This chapter presents the results of the empirical analysis of the situation of the business economy in Greece. The research covers the period of 2006–2016, which gives the 11 years of observation of the financial results of selected companies. This period covers three years (2006–2008) before the economic crisis in Greece and the eight years of the adverse economic conditions (2009–2016). The study used correlation and regression analysis to analyse data. The aim of the present chapter is twofold. First, it attempts to evaluate the profitability and business dependence on debt. Second, it purports to explore the relationship between determinants which are specific for firms and their capital structure. Data for the study were collected from the small- and medium-sized sector in the Region of Epirus in Greece. There are three main data sources used in this research. Financial data were extracted from the ICAP database, containing detailed financial reports annuals of Greek companies (income statements and annuals balance sheets). Other complementary data were collected from the Chambers of Epirus and the national statistics on Greek companies.