The role of cross-border cooperation of Kaliningrad region’s of Russian Federation border municipalities in its development strategies are observed. Significance of cross-border cooperation of small and semi-medium cities for its socio-economic development is analysed. The main spheres of cooperation between small and semi-medium border settlements of Kaliningrad region, Poland and Lithuania have been defined. The theoretical base on cross-border cooperation (Russian and foreign researchers) was analysed, and five geographical methods were used on preparation the article.