A nickel‐catalyzed 1,4‐carbofluoroalkylation of 1,3‐enynes to access structurally diverse fluoroalkylated allenes has been established. This method has demonstrated high catalytic reactivity, mild reaction conditions, broad substrate scope, and excellent functional‐group tolerance. The key to success is the use of a nickel catalyst to generate different fluoroalkyl radicals from readily available and structurally diverse fluoroalkyl halides to access 1,4‐difunctionalization of 1,3‐enynes by a radical relay. This strategy provides facile synthesis of structurally diverse multisubstituted allenes, and offers a solution for batch production of various fluorinated bioactive molecules for drug discovery by further transformations. Radical relay: A nickel‐catalyzed 1,4‐carbofluoroalkylation of 1,3‐enynes provides fluoroalkylated allenes under mild reaction conditions and with excellent functional‐group tolerance. The key to success is the use of the nickel catalyst to generate different fluoroalkyl radicals from fluoroalkyl halides to realize the 1,4‐difunctionalization by a radical relay.