Background: The primary aim of this study is to evaluate the functional outcomes of two surgical treatment groups with hallux rigidus. Our goal was to better understand the post-surgical outcomes between the two treatment groups from a practical, patient-centered point of view. Methods: A retrospective case series of 63 patients with hallux rigidus undergoing cheilectomy (C group) or a cheilectomy plus proximal phalanx osteotomy (CPP group) over a 4-year period with a minimum clinical follow up of 12 months. Evaluation of the study was based on satisfaction scores, VAS score, functional outcomes, and radiographs. Results: There were 32 patients in the C group and 31 in the CPP group. The median months to "100% recovery" was 3.5 months in the C group vs. 9 months for the CPP group. Time to normal shoes and overall satisfaction with either surgery was nearly identical in both groups (30 days for C vs. 28 days for CPP and a mean satisfaction score of 8.4 for group C and 8.2 for group CPP). Both treatment groups had similar percentages of patients report less post-operative pain than expected (34% C vs. 33% CPP). A higher percentage of patients in the C group (56%) reported more pain than expected compared to the CPP group (40%). Also in both groups the VAS pain level decreased significantly. Discussion: In our study, we found that although CPP is a longer procedure, patients had an earlier return to full weight bearing but a much longer subjective, patient reported "100% recovery." However, the time to regular shoes remained the same in each group and overall means satisfaction score was similar. Interestingly, more patients in the cheilectomy only group reported their post-op pain to be higher than expected suggesting patients were underestimating their post-op course or receiving sub-optimal pre-operative counselling.