Membranous dysmenorrhoea is an uncommon condition characterized by the spontaneous flaking of endometrium into a single piece that maintains the shape of the uterus. The common symptom of membranous dysmenorrhoea is a colicky pain caused by uterine contractions. Because only a limited number of cases have been published in the literature, the case report we present is peculiar. This report describes a case of membranous dysmenorrhoea that occurred after an artificial frozen thawed embryo transfer cycle using vaginal progesterone. The patient, during hormone replacement treatment, reported an intense abdominal colicky pain resulting in the loss of membranous endometrial tissue. A histopathological exam was performed with a clear diagnosis of membranous dysmenorrhoea. Moreover, photos were recorded and provided together with this article. The importance of such a case report relies on the actual debate about the appropriate progesterone route of administration. Although different medical approaches exist, progesterone administration is the most widespread. However, the intramuscular, oral, and subcutaneous means of administration are gaining popularity. On this peculiar case report, the patient underwent a subsequent frozen thawed embryo transfer cycle with subcutaneous progesterone administration. The embryo transfer resulted first in a clinical pregnancy and subsequently in a spontaneous delivery without any complications.