Background: Previous studies have demonstrated that preoperative patient-reported outcome measures are associated with postoperative outcomes in foot and ankle surgery, and also in specific procedures such as bunionectomy, flatfoot reconstruction, and total ankle replacement. The primary purpose of this study was to determine if preoperative Patient-Reported Outcomes Measurement Information System (PROMIS) physical function, pain interference, pain intensity, and depression scores were associated with the ability of patients undergoing cheilectomy for hallux rigidus to achieve a minimal clinically important difference (MCID) of improvement. Methods: This retrospective study included preoperative and ≥2-year postoperative PROMIS physical function, pain interference, pain intensity, and depression scores for 125 feet in 118 patients undergoing cheilectomy collected from an institutional review board (IRB)–approved foot and ankle registry database. MCIDs were established using distribution-based methods to determine clinical significance of improvements in PROMIS scores. Receiver operating characteristic (ROC) curves and area under the curve analyses were used to determine which preoperative PROMIS scores were associated with patients meeting the MCID. Results: ROC analysis found statistically significant areas under the curve (AUCs) for the physical function domain (AUC 0.71), pain intensity (AUC 0.70), and depression (AUC 0.79) PROMIS domains. Subsequent analyses were unable to identify clinically useful 95% sensitivity and specificity preoperative thresholds, with the exception of the 95% sensitivity PROMIS physical function threshold. A preoperative physical function score of greater than 53.2 resulted in a 63% probability of achieving the MCID. The pain interference PROMIS domain did not demonstrate a statistically significant AUC. Conclusion: Preoperative PROMIS physical function, pain interference, pain intensity, and depression scores are minimally associated with preoperative to 2-year postoperative improvement in patients undergoing cheilectomy. It may be difficult to determine which patients improve from a cheilectomy based on the severity of symptoms they exhibit preoperatively. Level of Evidence: Level IV, retrospective case series.