Introduction: Patients with degenerative Achilles tendon rupture and those with a chronic nonresponding Achilles tendinopathy form a major surgical population in foot and ankle surgery. Simple debridement and repair of the tendon will not be sufficient in these patients because the Haglund bump and retrocalcaneal spur, which is seen in both groups, is an important contributing factor. Calcaneoplasty and spur excision are required in addition to get good results. In this study, the clinical significance of Haglund bump and the role of calcaneoplasty and spur excision in treating these related pathologies are discussed. Materials and methods: This is a retrospective study of two groups of patients. The first group comprised 20 patients with chronic Achilles tendinopathy, who underwent tendo-achilles (TA) detachment debridement and reattachment after calcaneoplasty. The second group comprised 19 patients with degenerative TA rupture, who underwent tendon repair with calcaneoplasty. Postoperative outcomes at 6 months followup were compared between these groups, and a multinomial logistic regression was done to analyze the preoperative variables to predict the strong factor that causes tear. Results: Mean pre- and postoperative American Orthopedic Foot & Ankle Society (AOFAS) score of the tendinopathy group was 54.25 [standard deviation (SD) = 13.1] and 95.15 (SD = 6.13), whereas it was 45.68 (SD = 13.33) and 93.11 (SD = 4.90) in the tendon rupture group. In both the groups, there was a marked increase in postoperative outcome, but there was no significant difference in between the two groups (p-value = 0.259). Multinomial logistic regression proved Haglund bump, measured using Vega angle, to be the only significant predictor of tendon rupture. Conclusion: Haglund bump and spur are the significant lesions of the posterior heel pathologies. Surgical treatment of these pathologies should always include calcaneoplasty and spur excision when there is an abnormally prominent Haglund bump as predicted by Vega angle.