Spirocyclic frameworks have attracted synthetic practitioners due to their unique three-dimensional assembly, improved metabolic stability, solubility, and increased molecular complexity with regard to planar architectures. A recent surge in the number of spirocyclic oxindoles inhibiting enzymes, moderating unique protein-protein interactions, modulating receptors and transporters is testament to their prevalence. Against this background, the construction of spirocyclic frameworks containing an oxindole moiety as a torsional switch via stereoselective methods is in great demand. Herein we present a summary of the past three years in the progress of metal, organic molecule, nanostructured particle mediated, and even uncatalyzed versions of the highly diastereo- and enantioselective pathways leading to oxindole spirocycles.