•Although a myriad of anatomical variations of the peroneal tendons have been described, a single muscular belly dividing into two separate tendons have not been previously reported as a cause of retromalleolar pain. However, anatomical evidence based guidelines on how to address this complex clinical problem are lacking.•Anatomic variants of the peroneal tendons can overcrowd the retromalleolar space and attenuate the superior peroneal retinaculum, leading to tendon pathology.•Successful reconstruction of the peroneal tendons using semitendinosus allograft has recently expanded the treatment armamentarium of peroneal tendon pathology and should be considered when addressing this problem.