Background: The pain trajectory after ankle surgeries for osteoarthritis is relevant to describe. The purpose of this prospective study was to describe pain after ankle surgery and explore the link between perioperative factors and the development of postoperative pain. Methods: Duration, severity, type of preoperative pain, psychological distress, opioid consumption, and type of surgery were evaluated in 49 patients who were followed for 18 months. Acute postoperative pain in the first 10 days after surgery was modeled by a pain trajectory. Univariate analysis was conducted to identify predictors of acute pain trajectory and chronic pain. Results: Eighty-seven percent of patients had preoperative chronic pain, 34% had a high postoperative pain trajectory, 44% of whom reported chronic pain at 18 months. The patients who developed a high acute pain trajectory had higher preoperative opioid consumption (50% vs 19.4%, P = .04), a higher incidence of preoperative neuropathic pain (68.8% vs 32.3%, P = .02), a higher brief pain inventory score (51.5 vs 34, P = .01), and a higher psychological distress score (8 vs 3, P = .002). The patients who developed chronic pain had a higher brief pain inventory score (42 vs 33, P = .04), a higher psychological distress score (6 vs 4, P = .04), and a higher preoperative pain intensity (8 vs 6, P = .008). No association was found between the type of ankle surgery and pain. Conclusion: Patients with psychological distress and more severe preoperative pain were more at risk to develop acute pain and chronic pain after ankle surgery regardless of the surgery performed. Level of Evidence: Level II, prospective comparative study.