Taking the Michael: The first highly enantio ‐ and diastereoselective Michael addition of various 3 ‐ benzyl ‐ substituted oxindoles to 2 ‐ cyclopentenone has been developed. A variety of 3,3 ‐ disubstituted oxindoles as Michael adducts were obtained in 69–99 % yield with 73–98 % ee and 9:1 to >20:1 d.r.