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.