Unlike the Achilles tendon, the posterior tibial tendon does not typically undergo acute rupture. We report two cases of posterior tibial tendon tears occurring in young, athletic individuals (<30 years old) that required operative intervention before the patients could return to competitive sports. We believe that these are the first two reports of posterior tibial tendon tears occurring in this population without the patient having a prior history of steroid injections in the tendon. The tears we observed and described at surgical exploration were chronic and degenerative in nature. We also comment on our approach to treatment of posterior tibial tendon injuries in the athletic population.