Intraoperative bleeding represents serious problems during tooth extractions. We describe two cases of intraoperative massive bleeding at upper wisdom tooth extraction. Case 1: 27‐year‐old male (right side). Local anesthesia, compression hemostasis, tie‐over, and a hemostatic plate were applied. Case 2: 27‐year‐old female (right side). She was taken to the nearest emergency. Radiopaque gauze was inserted. Seven cases of intraoperative bleeding of upper wisdom teeth are previously reported. Medical history and X‐ray images must be carefully reviewed. If unexpected bleeding starts in healthy patients, damage to vascular malformation and/or to the posterior superior alveolar artery should be considered. Facilitate the preparation of local hemostatic items before the operation is recommended.