Objective: To compare the clinical characteristics between women with primary and recurrent ovarian endometriomas. Methods: A total of 43 women who had undergone surgery for ovarian endometrioma from January 2017 through December 2017; 37 primary surgeries (group PS) and 6 reoperations for recurrent endometriomas (group RS). Age, CA125, AMH, intraoperative blood loss, surgical findings, the revised American Society for Reproductive Medicine (rASRM) score were reviewed. Results: Although the differences were not statistically significant, compared with patients of the group PS, the patients of the group RS were slightly older (40.83 ± 2.68 vs. 34.97 ± 1.46, p = 0.13) and rASRM score was higher (100 ± 33.32 vs. 69.19 ± 39.37, p = 0.078) and the change of hemoglobin level was higher (17 ± 3.74 vs. 11.28 ± 1.17, p = 0.087). Furthermore, the patients of the group RS showed significantly higher incidence of the involvement of mesosalpinx when compared with the group PS (100 vs. 35.1%, p = 0.004). In groups PS vs RS, respectively, there were significantly differences between the groups: the preoperative serum anti-Mllerian hormone (AMH) levels 2.71 ± 0.39 vs. 0.75 ± 0.12, p <0.001); the postoperative serum AMH levels 1.56 ± 0.27 vs. 0.16 ± 0.11, p <0.001); the rate of drop in the serum AMH levels 88.43 ± 10.32 vs. 48.8 ± 4.98%, p = 0.025. Conclusion: This study indicates that repetitive surgery for recurrent endometriosis may be associated with increased risk of post-surgical ovarian failure following surgery. Probably because the involvement of mesosalpinx associated with serious adhesion is more common in patients with recurrent endometriosis.