Oxa(aza)benzonorbornadienes are utilized as important synthetic intermediates and useful building blocks in organic synthesis due to their structural features and reactivity. In addition to ring‐opening reactions, the transition‐metal‐catalyzed ring‐retentive addition reactions of oxa(aza)bicyclic alkenes have increasingly drawn the attention of various researchers. Numerous efficient protocols in this field have been investigated that enable facile and efficient transformations of oxa(aza)benzonorbornadienes to related valuable adducts, which are summarized and discussed in detail in this review.