Background Haglund syndrome is a common disease that causes posterior heel pain. The objective of this study was to compare the clinical outcomes between the dorsal closing wedge calcaneal osteotomy (DCWCO) and the posterosuperior prominence resection (PPR) for the treatment of this disease. Methods The retrospective study included 12 patients who received DCWCO and 32 who patients received PPR from January 2010 to August 2016. The patients were evaluated in terms of the American Orthopedic Foot Ankle Society ankle-hindfoot scale (AOFAS), the Victorian Institute of Sport Assessment Scale for Achilles tendinopathy (VISA-A), the Fowler-Philip angle, Bohler’s angle, and the calcaneal pitch angle, both pre- and postoperatively (at 3 months, 6 months, 1 year, and the latest follow-up). Results Both groups showed a significance increase in their AOFAS and VISA-A scores after the operation. The DCWCO group showed a lower AOFAS score than the PPR group after 6 months (77.6 ± 5.1 vs. 82.8 ± 7.8, P =0.037), but received higher scores in the latest follow-up (98.2 ± 2.3, vs. 93.4 ± 6.1, P =0.030). For the VISA-A scores, the DCWCO group had lower scores for 3 months (56.9 ± 13.9, vs. 65.2 ± 11.0, P =0.044), but showed higher scores in the latest follow-up (98.2 ± 2.6, vs. 94.3 ± 5.0, P =0.010) when compared with the PPR group. Both groups had a significant change in the Fowler-Philip angle and Bohler’s angle after the operation. The postoperative Fowler-Philip angle in the DCWCO group was greater than that of the PPR group (35.9° ± 4.9°, vs. 31.4° ± 6.2°, P =0.026). However, there was no statistical difference in any other angle between the two groups, postoperatively. Conclusions The DCWCO group had poorer short-term clinical outcomes but better long-term function and symptom remission, as compared with the PPR group, in the treatment of Haglund syndrome.