The article reviews the experience of development of industrial cooperation of small enterprises in Crimea in the run up to the World War I, October Revolution, and in the first years of formation of the Soviet Republic in Crimea. The authors draw economic and historic parallels of development between various cooperation forms, analyze certain social and economic effects of industrial cooperation development on the region’s economy. The results of the conducted studies will be of interest to researchers in the context of retrospective analysis of social and economic tendencies of entrepreneurship development, as well as to practitioners – in the part of application of the positive experience of small enterprises development regulation.