Posterior tibial tendon problems are uncommon sources of disability in athletes. Awareness of the condition and early diagnosis are important to prevent disability and prolonged time away from sports. Appropriate imaging studies will aid in diagnosis. Tendon tears in younger patients are different than the typical ruptures seen in middle-aged and older adults. Treatment must be individualized based on the type of tear and degree of deformity present. Other conditions such as dislocation of the posterior tibial tendon, accessory navicular and exertional compartment syndrome can involve the tibialis posterior muscle and present as diagnostic dilemmas.