The development of divergent methods to expedite structure-activity relationship studies is crucial to streamline discovery processes. We developed a rare example of regiodivergent ring expansion to access two regioisomers from a common starting material. To enable this regiodivergence, we identified two distinct reaction conditions for transforming oxindoles into quinolinone isomers. The presented methods proved to be compatible with a variety of functional groups, which enabled the late-stage diversification of bioactive oxindoles as well as facilitated the synthesis of quinolinone drugs and their derivatives.