The knee is the most complex and largest joint in the body. Injuries to any part of this joint affect the entire body. There are multiple injuries that can occur to the knee, with the most common being ligament and meniscus tears. A not-so-common injury to the knee is a patellar tendon rupture. A bilateral patellar tendon rupture is extremely rare. A case study of a 43-year-old man who sustained a bilateral patellar tendon rupture while playing softball is used to present this devastating injury. This discussion includes the incidence and diagnosis of the tear, surgical repair, as well as a description of the comprehensive rehabilitation process necessary to allow the patient to return to normal physical activity. Risks and complications of this surgery and the expected outcomes are also presented.