The chapter aims to describe specific cases from the Italian context to introduce the role of grassroots sport organizations and their innovative practices and to analyze them in the context of the theoretical and managerial backgrounds introduced in the previous chapters. First, there is the analysis of the macro level, the European Union and its policies for innovation and sport. Then, there is the description of the Italian environment (meso level) through the introduction of the main grassroots sport organizations and of their sector (the Third Sector). Third, the chapter introduces three cases of grassroots sustainability innovations (green and coop management, education for sustainability and responsible sport events), which the author has been involved in, and potential future developments as practical examples of windows of opportunity for novel bottom up solutions. The cases and the future opportunities of development for grassroots innovative organizations will show that those initiatives are beneficial for society as a whole.