A bilateral patellar tendon rupture is extremely rare and has only been documented in case reports. Although the etiology remains unknown, predisposing factors include steroid usage, systemic diseases, and tendinopathies. In the present case, a healthy 33-year-old male with a prior history of bilateral patellar tendonitis and a diagnosis of Osgood-Schlatter disease during adolescence experienced simultaneous bilateral patellar tendon rupture after playing volleyball. He underwent bilateral patellar repair without complications. In the absence of trauma, spontaneous bilateral patellar tendon ruptures are associated with several predisposing factors, including systemic diseases, prior corticosteroid or fluoroquinolone usage, and history of tendinopathy. Injuries can be classified based on the location of the rupture. Bilateral patellar tendon ruptures can be misdiagnosed due to the rarity of cases and the lack of a normal comparative knee. Radiographic techniques can aid in the diagnosis, leading to early surgical treatment and improved outcomes. Early diagnosis and prompt surgical repair contribute to good functional outcomes in this potentially debilitating injury pattern.