A combinatorial nickel‐catalyzed monofluoroalkylation of aryl halides with unactivated fluoroalkyl halides by reductive cross‐coupling has been developed. This method demonstrated high efficiency, mild conditions, and excellent functional‐group tolerance, thus enabling the late‐stage monofluoroalkylation of diverse drugs. The key to success was the combination of diverse readily available bidentate and monodentate pyridine‐type nitrogen ligands with nickel, which in situ generated a variety of readily tunable catalysts to promote fluoroalkylation with broad scope with respect to both coupling partners. This combinatorial catalysis strategy offers a solution for nickel‐catalyzed reductive cross‐coupling reactions and provides an efficient way to synthesize fluoroalkylated druglike molecules for drug discovery. Combining forces: Aryl halides undergo efficient monofluoroalkylation with unactivated fluoroalkyl halides by reductive cross‐coupling with excellent functional‐group tolerance (see scheme). The mild and efficient transformation was developed by the combination of diverse readily available bidentate and monodentate pyridine‐type nitrogen ligands with nickel to generate a variety of readily tunable catalysts in situ.