o-Hydroxyphenyl substituted p-quinone methides (p-QMs) belong to a class of p-QMs with unique advantages.They not only maintain the high reactivity of p-QMs, but also have more reactive and activation sites owing to the introduction of hydroxyl group.Therefore, o-hydroxyphenyl substituted p-QMs have wide applications in synthetic and medicinal chemistry.The catalytic asymmetric 1,6-conjugate addition and [4+n] cycloaddition of o-hydroxyphenyl substituted p-QMs have developed very rapidly in recent years, which have become efficient strategies for the synthesis of chiral oxygen-containing heterocycles and arylmethanes with potential bioactivity.This review summarizes the catalytic asymmetric reactions involving o-hydroxyphenyl substituted p-QMs and points out the remaining challenges in this research area, which will open a new window for the design of new type of o-hydroxyphenyl substituted p-QMs and their involved catalytic asymmetric reactions.