Transverse testicular ectopia (TTE) is a condition characterized by migration of both testes towards the same hemiscrotum. The mean age of presentation is 4 years, with a typical presentation of a symptomatic inguinal hernia with contralateral impalpable testis. There is no reported predisposition to either left or right side. The diagnosis is usually intraoperative however, imaging modalities and diagnostic laparoscopy are useful in aiding pre-operative diagnosis. We present a case of a 5-year-old boy with a history of a painful swelling in the left inguinal region, with palpable left testis and contralateral empty scrotum. During the planned herniotomy in view of his pain, he was diagnosed with transverse testicular ectopia intra-operatively. Herniotomy on the left side with left testicular orchiopexy and transseptal fixation for the right testis was performed. He recovered well in the post-operative period. This rare congenital anomaly is often diagnosed intraoperatively as an incidental finding, and long-term follow up would be required due to the risk of malignant transformation.