Highly enantioselective 3+3 and 3+4 annulations of isatin‐derived enals with ethynylethylene carbonates and ethynyl benzoxazinanones are enabled by NHC/cooper cooperative catalysis, leading to a big library of spirooxindole derivatives in high structural diversity and enantioselectivity (up to 99 % ee). Both reactions represent a nicely synergistic integration of NHC and copper catalysis, in which both catalysts activate the substrates and the chiral NHC perfectly controls the stereochemistry. All together now: A cooperative N‐heterocyclic carbene (NHC)/cooper catalytic system was developed for the diversity‐oriented synthesis of spirooxindole derivatives through enantioselective 3+3 and 3+4 annulation reactions. Highly enantioselective 3+3 and 3+4 annulations of isatin‐derived enals with ethynylethylene carbonates and ethynyl benzoxazinanones were achieved.