Port site metastasis (PSM) is considered an uncommon and rare complication in gynecologic malignancies with unclear treatment recommendations or guidelines. Thus, we report the treatment strategies and outcomes of two cases of PSMs following gynecologic malignancies and a review of the literature to provide much information about the most frequent sites of PSMs and the incidence of PSMs in different gynecological tumors. A 57-year-old woman underwent laparoscopic radical surgery for right ovarian serous carcinoma in June 2016 followed by postoperative chemotherapy. Because PSMs were present near the port site of the bilateral iliac fossa, the tumors were completely removed on August 4, 2020, and the patient received chemotherapy. She has shown no signs of relapse. During the same period, a 39-year-old woman underwent laparoscopic type II radical hysterectomy for endometrial adenocarcinoma involving the endometrium and cervix on May 4, 2014, without adjuvant treatment. In July 2020, a subcutaneous mass under her abdominal incision was removed, and chemotherapy plus radiotherapy was administered. Metastasis was found in the left lung in September 2022, but there was no abnormality in the abdominal incision. We showed the two cases of PSMs, reviewed articles to provide some new insights about the incidences of PSMs in the gynecologic tumors, and discussed the proper preventive strategies.