Spirocyclic o-quinone analogues show a broad spectrum of applications as biologically active compounds. We herein report the chiral bifunctional squaramide catalysed asymmetric vinylogous aldol-cyclization cascade reaction between 3-alkylidene oxindoles and o-quinones. A wide range of enantioenriched spirocyclic o-quinone analogues with a quaternary stereocenter could be smoothly synthesized in good to excellent yields (up to 99%) with high enantioselectivities (up to 99%).