Depending on the reactant property and reaction mechanism, one major regioisomer can be favored in a reaction that involves multiple active sites. Herein, an orthogonal regulation of nucleophilic and electrophilic sites in the regiodivergent hydroamination of isoprene with indazoles is demonstrated. Under Pd‐hydride catalysis, the 1,2‐ or 4,3‐insertion pathway with respect to the electrophilic sites on isoprene could be controlled by the choice of ligands. In terms of the nucleophilic sites on indazoles, the reaction occurs at either the N1‐ or N2‐position of indazoles is governed by the acid co‐catalysts. Preliminary experimental studies have been performed to rationalize the mechanism and regioselectivity. This study not only contributes a practical tool for selective functionalization of isoprene, but also provides a guide to manipulate the regioselectivity for the N‐functionalization of indazoles. The Pd‐catalyzed regiodivergent coupling reactions between indazoles and isoprene have been developed through the orthogonal regulation of nucleophilic and electrophilic sites.