Background: The aim of this retrospective study was to evaluate patient-reported clinical outcomes, prosthesis survival, and causes of revision of cemented humeral surface replacement (Durom-Cup) in a large population. Methods: Between 1997 and 2015, 266 patients underwent 279 implantations of Durom-Cup. Overall, 81 patients died, 39 patients were lost to follow-up, and 21 patients were excluded according to pre-defined exclusion criteria, and dementia; this left 125 patients (135 shoulders) with a mean follow-up of 8.0 years (range, 1–20 years). To report long-term follow-up a subgroup of 51 patients with a minimum follow-up of 9 years and a mean follow-up of 12.4 years (range, 9–20 years) was evaluated. The mean age at the time of surgery was 65.8 years (range, 25–91 years). Results: The indications were primary osteoarthritis (52%) and rheumatoid arthritis (48%). Patient satisfaction at final follow-up was as follows: very satisfied, 59.2%; satisfied, 29.2%; and not satisfied, 11.6%. On a visual analogue scale (VAS) from 0 to 10, the mean pain on weight-bearing was 2.4 (range, 0–10). Overall, 55.4% were able to perform leisure activities without major limitations. Patients with rheumatoid arthritis were significantly younger than patients with primary osteoarthritis at the time of surgery (mean difference, 11.5 years, p < 0.001). The overall survival rates (prosthesis without revision surgery) of the Durom-Cup were 94.0 ± 5.0% at 5 years, 90.8 ± 9.86% at 10 years, and 90.8 ± 17.1% at 15 years. However, 9 shoulders (6.7%) required revision arthroplasty after a mean 4.3 years (range, 0.5–9 years).Conclusions: These data demonstrated a relatively low revision rate of the Durom-Cup and high satisfaction levels, suggesting an acceptable quality of life post-surgery.