The purpose of this study was to evaluate a series of patients undergoing a single platelet-rich plasma (PRP) injection for the treatment of chronic midsubstance Achilles tendinopathy, in whom conservative treatment had failed. Thirty-two patients underwent a single PRP injection for the treatment of chronic midsubstance Achilles tendinopathy and were evaluated at a 6-month final follow-up using the Foot and Ankle Outcome Score and Short Form 12 general health questionnaire. Magnetic resonance imaging was performed on all patients prior to and 6 months after injection. Twenty-five of 32 patients (78%) reported that they were asymptomatic at the 6-month follow-up visit and were able to participate in their respective sports and daily activities. The remaining 7 patients (22%) who reported symptoms that did not improve after 6 months ultimately required surgery. Four patients went on to have an Achilles tendoscopy, while the other 3 had an open debridement via a tendon splitting approach. A retrospective evaluation of patients receiving a single PRP injection for chronic midsubstance Achilles tendinopathy revealed that 78% had experienced clinical improvement and had avoided surgical intervention at 6-month follow-up. Levels of Evidence: Therapeutic, Level IV: Retrospective case series