Chronic lateral ankle instability is a condition commonly encountered by the podiatric physician. Chronic instability usually occurs after injuries to the lateral collateral ligamentous complex. The purpose of this article is to report subjective results of a retrospective study comparing delayed primary ligamentous repair and a new secondary ligamentous reconstruction. Our patient population includes 23 patients who responded to a detailed questionnaire. Three patients had bilateral ligamentous repair for a total of 26 ankles. Sixteen ankles underwent delayed primary ligamentous repair, while 10 ankles had a secondary reconstruction utilizing the authors' technique. The overall postoperative improvement was 90% in those with a delayed primary repair and 82% in those with the new secondary reconstruction. The average return to full activity for both groups was 10 weeks. Average follow-up for both groups was 12 months. The authors feel these results demonstrate that delayed primary repair and the authors' new secondary reconstruction both provide favorable clinical and surgical outcomes.