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Abstract Background Chronic quadriceps tendon rupture is technically challenging for surgeons due to scarring and tendon retraction. The presence of concurrent ipsilateral knee osteoarthritis compounds the issue even further. Although a combined presentation is rare, treatment options to manage each coexisting pathology simultaneously are scarcely reported. We describe the case of a 67-year-old Caucasian male who had such a presentation, and was subsequently treated with a one-stage extensor mechanism autograft reconstruction and total knee replacement with computer navigation. Case The patient was a 67-year-old male Caucasian, who had previously sustained an acute rupture of his right quadriceps tendon that was adequately repaired 6 months prior. Despite an initial satisfactory result, he reported deterioration in his mobility in the few months thereafter, with worsening knee pain. His comorbidities consisted of hypertension, asthma, and a body mass index of 40.4 kg/m2. Otherwise, there were no risk factors for tendon rerupture. Clinical examination later revealed a large palpable gap in the right suprapatellar region and weakness of active knee extension. No traumatic cause for this new presentation was identified. Suspicion of a chronic quadriceps tendon rupture was confirmed on radiological imaging, but the investigations also noted the presence of severe tricompartmental osteoarthritis of the ipsilateral, native knee joint. The combined procedure took place in one surgical sitting. The total knee replacement with patella resurfacing was performed first and assisted by computer navigation. The quadriceps tendon reconstruction was then conducted sequentially using the patient’s hamstring tendons (semitendinosus and gracilis). The tensile strength was reinforced with use of a Ligament Augmentation and Reconstruction System (LARS) ligament. Initial outcomes were excellent, and these results were maintained at 6 months postoperatively, with the patient reporting no pain and having full range of movement. Conclusion Our techniques used have not previously been reported, but are successful options in treating coexisting chronic quadriceps tendon rupture and ipsilateral knee osteoarthritis. The advantage of using computer navigation with an extramedullary femoral jig can lead to improved accuracy of bone cuts, which is important in the presence of anatomical disruption. Chronic failures of the extensor mechanism require different approaches depending on the inherent and underlying pathology. We feel that the multidisciplinary team approach to the management and use of two surgeons with differing expertise added to the successful outcome of this complex case.