Chronic ankle instability (CAI) leads to the ankle osteoarthritis (OA), and ligament repair is performed to restore ankle stability. However, anterior talofibular ligament (ATFL) repair alone is not sufficient to stabilize the ankle in some cases, which additionally require calcaneofibular ligament (CFL) repair. This study aimed to explore characteristics of CAI that necessitated the repair of both ATFL and CFL. Forty-three patients (44 ankles) with CAI treated operatively were retrospectively reviewed. After ATFL repair, patients with residual ankle instability revealed by the varus stress under fluoroscopy additionally underwent CFL repair. Preoperative condition and intraoperative findings of the combined ATFL and CFL repair (AC) (n = 24) and only ATFL repair (A) (n = 20) groups were compared. The ankle activity score of group AC was significantly higher (p < .05) than that of group A. OA changes at the medial gutter were observed in 62.5% (15/24) in the group AC and 20% (4/20) in group A. Chondral/osteochondral lesions were seen in 66.7% (16/24) in the group AC and 20% (4/20) in group A. The remnant quality in group AC was inferior to that of group A. CAI that necessitated both ATFL and CFL repair exhibited characteristic findings such as high ankle activity score, high rate of chondral/osteochondral lesions and/or OA changes, and poor quality of ATFL remnants compared to those in CAI that required only ATFL repair. The repair of both ATFL and CFL should be considered in CAI which exhibit these characteristics to ensure complete correction of the instability.