Background and objectives: Abdominal wall endometriosis, also known as scar endometriosis, is a rare condition that is becoming increasingly common. The recent rise in incidence is attributed primarily to the surge of cesarean births, figures that could be influenced in a positive manner considering the improvements brought towards the ultrasound diagnostic methods that have been made in recent years. Materials and Methods: Here we report the cases of two Caucasian women of 38- (G2P2) and 36-years old (G1P1), both subjected to an ultrasound examination due to a specific symptomatic panel reported during anamnesis. Independently of the current status, in the first patient, there were no reported symptom-specific associations with endometriosis, but she had a known history of mild hereditary thrombophilia; the second woman suffered from two conditions positively associated with endometriosis. Results: In both cases, abnormal structures were revealed, with the diagnostic(s) of endometriosis being histologically confirmed based on a set of features observed during the investigation. Conclusions: This paper aims to highlight the importance of reducing cesarean births and to consider the diagnosis of scar endometriosis in women with a history of obstetric or gynaecological surgeries who present with cyclic, recurrent abdominal pain.