The usefulness of magnetic resonance imaging (MRI) has been questioned in evaluating patients with chronic ankle sprain pain. The purpose of this study was to determine the effectiveness and reliability of routine MR imaging in the diagnosis of anterolateral soft tissue impingement. Inclusion criteria required that the MR examinations be performed by the same musculoskeletal radiologist after the most recent scanner upgrade and using a dedicated ankle/hindfoot coil. The surgical and MRI reports of 24 patients who had an arthroscopic diagnosis of anterolateral soft tissue impingement of the ankle were tabulated and categorized. Unlike previous studies, sagittal T1 and Short Tau Inversion Recovery (STIR) images were used primarily in the diagnosis of these lesions. Using this technique, we report a 78.9% accuracy in diagnosis, a sensitivity of 83.3% and a specificity of 78.6%. Fifty-eight percent of patients had an associated diagnosis, which in 33% of patients altered our surgical plan. Although not indicated in all cases of anterolateral ankle impingement, we advocate the use of MR imaging in complicated clinical presentations where the exclusion of additional pathology in the ankle or subtalar joint, and the confirmation of anterolateral soft tissue impingement would be beneficial.