Here we report the first example of iridium-catalyzed asymmetric N-allylation of pyrazoles with dienyl allylic alcohols under mild conditions with broad functional group tolerance, exhibiting excellent N1/C3-site selectivities and enantioselectivities (up to >99% ee). In addition to pyrazoles, other nucleophiles including benzotriazole, triazole, and pyrazole precursors (aryl vinyldiazos) are also suitable in this method. Notably, with the use of Sc(OTf)3 as additive and reactions performed at 30 °C for 24 h, the N1-C5 or N1-C1 selective alkylated pyrazoles are also obtained.