Stenosing tenosinovitis of the peroneal tendons that results from hypertrophy of the peroneal tubercle, has been well described in the literature, but reports in our region are very rare. Surgical treatment is indicated to address the hypertrophy of the tubercle, the peroneal pulley and any intrinsic pathology of the tendon. Two cases of chronic lateral pain of the hindfoot and lateral inframalleolar prominence are reported, with poor response to conservative treatment. Both patients underwent a surgical procedure with relief of their symptoms. In the first case, we found a pulley hypertrophy without prominence of the tubercle, and in the second one, a hypertrophy of the tuber and a retinacular ganglion cist.