Different from the well-investigated enynes, transition-metal-catalyzed carbocyclization reactions of allenynes are more attractive as a result of the unique structure and versatile reactivity of allenes. Herein, we report the first cobalt-catalyzed highly chemo- and stereoselective arylative carbocyclization of 1,6-allenynes with arylboronic acids, affording five-membered carbocycles and heterocycles with moderate to high yields, broad substrate scope, and wide functional group compatibility. Moreover, several mechanistic experiments were conducted to gain insight into the reaction process.