Dislocation of the posterior tibial tendon is an uncommon condition. Although surgery is usually performed in most cases of posterior tibial tendon dislocation, postoperative repeat dislocation of the posterior tibial tendon has not been reported in the published data. We report the case of a 27-year-old male patient who experienced repeat dislocation of the posterior tibial tendon after a gymnastic landing, 44 months after initial retinaculum repair. For revision surgery, we reconstructed the flexor retinaculum in conjunction with deepening of the retromalleolar groove, because the groove was hypoplastic. He returned to competitive gymnastics and had not experienced subluxation or dislocation of the posterior tibial tendon at the 1-year follow-up examination.