Port-site hernia (PSH) of less than 10 mm is an exceptionally rare complication of minimally invasive surgery (MIS). To date, there have been no cases in the literature reporting recurrence of PSH from a 5 mm incision. We present the first case of PSH recurrence in a woman who underwent surgery for benign gynaecological pathology via a MIS approach. Her post-operative course was complicated by an episode of symptomatic hernia arising from a 5 mm accessory trocar which was surgically managed. A few months later she re-presented with the same symptoms and had a PSH recurrence of the same port-site. Two corrective surgeries employing different techniques were performed. The first episode was managed laparoscopically using interrupted stitches. On the other hand, the PSH recurrence was managed by placement of a mesh. Ultrasound played a crucial role in diagnostics, especially in the recurrent setting. Due to the complete absence of similar cases in the literature, the decision making around the management of a PSH recurrence from a 5 mm trocar site proved to be challenging. As MIS is the current standard of care, more cases are likely to occur, however despite the increasing number of surgical procedures performed via MIS, no established guidelines for managing such complications have been proposed. Trying to bridge this gap, we present the case report of the first case of PSH recurrence from a 5 mm accessory port and a review of the most significant literature available to date. We finally summarise the reported cases of PSH and the types of surgical repair conducted to highlight the absence of a standard of care.