Hallux rigidus (HR) is a prevalent arthritic condition in the foot. Cheilectomy is a common joint-preserving procedure for HR, involving the removal of prominent osteophytes to relieve impingement of the 1st MTPJ. This study aims to identify factors associated with the failure of cheilectomy in the treatment of HR. A retrospective review of a prospectively collected database from 2007 to 2021 identified all cheilectomy cases. The minimum follow-up was 2 years. Preoperative demographic data, patient-reported outcome measures (PROMs) and foot radiographs were collected. PROMs were reassessed in post-operative reviews, and cases were categorized as successes or failures. Failure was defined by meeting at least one of the following criteria at the latest review: 1) Visual analog pain score (VAS) more than or equal to 4, 2) undergoing subsequent revision procedures, or 3) reporting poor or terrible satisfaction with the surgery. The analysis involved 66 patients, with 19 failure and 47 success cases. Both groups showed similar age, BMI, and gender profiles. Preoperative radiographic parameters were comparable between groups. However, preoperative VAS was significantly higher in the failure group: 7.16 vs. 5.23 (P = 0.0029). Logistic regression confirmed preoperative VAS as a predictor of non-response (P = 0.023). Receiver Operating Characteristic analysis established an optimal cut-off VAS score of 7.0. Patients with a preoperative VAS score of more than 7 had an odds ratio of 5.11 (P = 0.0055) for failure. A higher preoperative VAS score is significantly associated with cheilectomy failure in HR treatment, suggesting a cutoff score of 7.0.