Social entrepreneurship is an underrated subject in the field of sports. For Romanian society, the fall of communism opened up new opportunities in the entrepreneurial domain. At the same time, entrepreneurship began to intersect with sports, and the results were often productive. Sport is seen as a domain that could inspire entrepreneurship through its principles. The similarities between these two fields have created the perspective of common action in sport and entrepreneurship, and this coexistence has improved during times of social change. After 1989, Romania was confronted with many challenges at the societal level, and sport offered a way to address and to tackle social problems. Through sport, some athletes decided to contribute to issues of individuals or communities. They assumed the status of a social entrepreneur, and developed activities that could inspire others. This paper intends to gather examples of such social entrepreneurship from Romania, and to identify the elements that lead to success. The research takes into consideration case studies from various domains, and this diversity helps us to better understand the challenges of Romanian sport when it interacts with social entrepreneurship.