The results of surgical treatment of posterior tibial tendon insufficiency (PTTI) may be different at different stages of the disease. No single study has compared the results at different stages. This comparison can be helpful to the patient and physician if the patient asks “What if I wait and the disease progresses, how will my results be different?” A preliminary study comparing results for stage IIa, stage IIb (advanced stage II), and stage III was performed followed by a larger study comparing IIa and IIb with 26 and 22 patients, respectively. American Orthopaedic Foot and Ankle Society (AOFAS) outcome scores as well as radiographs and functional questions were used. Nearly all patients, regardless of stage, felt they were helped by surgical treatment. However, the lowest AOFAS score was in stage III, the most advanced stage investigated in this study. In comparing stage IIa and IIb patients, stage IIb patients had a statistically higher incidence of lateral discomfort. Although statistically significant differences were not found in all comparisons, this study suggests that the results of surgical treatment for PTTI declines with increasing stage or severity of disease.