A methyl phenyl sulfoximine (MPS) is used as a directing group in the ruthenium‐catalyzed intramolecular hydroarylation of alkene‐tethered benzoic acid derivatives to afford dihydrobenzofurans and indolines in good to excellent yields. A one‐pot, unsymmetrical, twofold C−H functionalization involving intramolecular C−C and intermolecular C−C/C−N bond formations is successfully demonstrated by using a single set of catalytic reaction conditions, which is unprecedented thus far. A novel isoquinolone‐bearing dihydrobenzofuran is constructed through an unsymmetrical twofold C−H functionalization. In a single shot: A methyl phenyl sulfoximine (MPS) is used as a directing group in the ruthenium‐catalyzed intramolecular hydroarylation of alkene‐tethered benzoic acid derivatives to afford dihydrobenzofurans and indolines in excellent yields. A one‐pot, unsymmetrical, twofold C−H functionalization involving intramolecular C−C and intermolecular C−C/C−N bond formations is successfully demonstrated.