Spirocyclobutyl oxindoles, characterized by their unique three-dimensional structures, are valuable building blocks for many pharmacophores and drug units. However, stereoselective synthetic strategies for these scaffolds remain underdeveloped, with most existing methods relying on transition metal catalysts and stoichiometric redox reagents. In this work, we introduce an electrochemical strain-release driven cascade spirocyclization of bicyclo[1.1.0]butane (BCB) derivatives for the stereoselective synthesis of functionalized spirocyclobutyl oxindoles. Tetrabutylammonium bromide serves a dual purpose as both a supporting electrolyte and brominating agent. The method offers a broad substrate scope, high atom economy, and excellent diastereoselectivity. The stereoselectivity of the product is controlled by minimizing the dipolar repulsion between the amide C=O and the C-Br bonds. We also explored the methodology's versatility by applying it to various functionalizations and demonstrated its scalability for practical use. The efficient derivatization of the products allowed for the rapid creation of a diverse library of functionalized spirocyclobutyl oxindoles.