The first asymmetric hydrogenation of 3‐ylidenephthalides has been developed using the IrI complex of a spiro4,4‐1,6‐nonadiene‐based phosphine‐oxazoline ligand (SpinPHOX) as the catalyst, affording a wide variety of chiral 3‐substituted phthalides in excellent enantiomeric excesses (up to 98 % ee). The utility of the protocol has been demonstrated in the asymmetric synthesis of chiral drugs NBP and BZP precursor, as well as the natural products chuangxinol and typhaphthalide. A shortcut to a wide variety of chiral 3‐substituted phthalides with pharmacological interests has been realized by SpinPHOX/Ir catalyzed asymmetric hydrogenation of 3‐ylidenephthalides in high enantioselectivities (up to 98 % ee).