Background: Several operative interventions are available to alleviate pain in hallux rigidus, and the optimal operative technique is still a topic of debate among surgeons. Three of these are arthrodesis, cheilectomy, and Keller’s arthroplasty. Currently, it is unclear which intervention yields the best long-term result. The aim of this study was to assess which of these interventions performed best in terms of patient-reported outcome, pain scores, and disease recurrence at long-term follow-up. Methods: These data are the follow-up to the initial study published in 2006. In the original study, 73 patients (n = 89 toes) with symptomatic hallux rigidus were recruited and underwent first metatarsophalangeal joint arthrodesis (n = 33 toes), cheilectomy (n = 28 toes), or Keller’s arthroplasty (n = 28 toes). Outcome measures were AOFAS hallux metatarsophalangeal-interphalangeal (HMI) score, and pain was assessed with a visual analog scale (VAS) at a mean follow-up period of 7 years. Patients of the original study were identified and invited to participate in the current study. Data were collected in the form of AOFAS-HMI score, VAS pain score, Manchester-Oxford Foot Questionnaire (MOXFQ), and Forgotten Joint Score (FJS-12). In addition, a clinical examination was performed and radiographs were obtained. Data were available for 37 patients (45 toes), with a mean follow-up period over 22 years. Results: AOFAS-HMI and VAS pain score improved during follow-up only in arthrodesis patients. Furthermore, no statistically significant differences in clinical and patient-reported outcome were detected between groups based on AOFAS-HMI, VAS pain, MOXFQ, or FJS-12. However, clinically important differences in patient-reported outcomes and pain scores were detected, favoring arthrodesis. Radiographic disease progression was more evident after cheilectomy compared with Keller’s arthroplasty. Conclusion: Arthrodesis, cheilectomy, and Keller’s arthroplasty are 3 sucessful operative interventions to treat symptomatic hallux rigidus. Because clinically important differences were detected and symptoms still diminish many years after surgery, a slight preference was evident for arthrodesis. Level of Evidence: Level III, comparative study.