Persistent pain and swelling in the anterior part of the upper ankle are encountered very frequently in sports traumatology. Classically, in the patient with a long history of typical anterior ankle pain there is no instability, but pinching effects, a sense of impingement, blocking and a feeling of unsteadiness combined with a certain restriction of movement due to the pathology. By analogy with the anatomical structures, various pathologic changes can lead to the classic clinical symptoms: adhesions, cicatrices, meniscoid-type lesions, osteophytes with synovitis, folds, fibrotic subcutaneous fatty tissue, free arthroliths, osteochondral lesions and arthrotic changes. When long-term conservative therapy has not provided a cure for the clinical syndrome surgical intervention becomes necessary. Arthroscopic interventions were carried out in a total of 21 patients, with follow-up times between 6 and 36 months. About two-thirds of all the patients showed good or very good results, while in one-third the results were unsatisfactory, mainly because of degenerative changes. An precise diagnosis is essential, but the significance of a pathologic change as the cause of symptoms can be problematical.