This article explores the growth and development of the agricultural co-operative associations in Estonia from the 1860s up to the 1930s in a comparative fashion. The primary focus is on the expansion of dairy co-operative associations. Hence, the comparative approach puts Estonia in the light of the contemporary organisational development, foremost in the Nordic countries and Bulgaria and to some extent also related to the Latvian and Lithuanian development. It is shown here that the co-operative expansion taking place prior to the interwar independence was of major importance for the relative export success that took place in the 1920s, i.e. prior to the trade contraction during the inter-war depression. Several uniting developmental features are elucidated and discussed from the perspective of co-operative organisation and education, as well as the relations between the state and the co-operative associations. The 1930s here represents a period of deviation in relation to the Nordic countries because of the impact from the depression, the rise of authoritarianism and not least the expansion of state control, which preceded the formal Soviet occupation in 1940.