Introduction. Disorders of the Achilles tendon can be broadly classified into acute and chronic entities. Few studies have established chronic Achilles tendinopathy as a precursor to acute Achilles ruptures. In this study, we assessed the relationship between Achilles tendinopathy and rupture, clarifying the incidence of rupture in the setting of underlying tendinopathy. Methods. The United Healthcare Orthopedic Dataset from the PearlDiver Patient Record Database was used to identify patients with ICD-9 codes for Achilles rupture and/or Achilles tendinopathy. The number of patients with acute rupture, chronic tendinopathy, and rupture following a prior diagnosis of tendinopathy was assessed. Results. Four percent of patients with an underlying diagnosis of Achilles tendinopathy went on to sustain a rupture (7,232 patients). Older patients with tendinopathy were most vulnerable to subsequent rupture. Conclusions. The current study demonstrates that 4.0% of patients who were previously diagnosed with Achilles tendinopathy sustained an Achilles tendon rupture. Additionally, older patients with Achilles tendinopathy were most vulnerable. These findings are important as they can help clinicians more objectively council patients with Achilles tendinopathy.