An asymmetric organocatalytic domino oxa‐Michael/1,6‐addition reaction of ortho‐hydroxyphenyl‐substituted para‐quinone methides and isatin‐derived enoates has been developed. In the presence of 5 mol % of a bifunctional thiourea organocatalyst, this scalable domino reaction affords 4‐phenyl‐substituted chromans bearing spiro‐connected oxindole scaffolds and three adjacent stereogenic centers in good to excellent yields (up to 98 %) and with very high stereoselectivities (up to >20:1 d.r., >99 % ee). Hydroxy‐substituted para‐quinone methides were successfully used in an asymmetric organocatalytic oxa‐Michael/1,6‐addition domino reaction. In the presence of a bifunctional thiourea organocatalyst, this reaction afforded a wide range of 4‐aryl‐substituted chromans with an oxindole scaffold and three contiguous stereocenters in high yields and stereoselectivities.