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Diagnosing joint pain in the pediatric patient can be difficult considering the wide variety of possible pathology. Concurrent disease processes around the same joint confound assessment and can introduce cognitive bias where the surgeon most often focuses on the most common diagnoses, precluding further workup of other less common pathologies. Here, this concept is reiterated through two cases in which a synovial sarcoma, an extremely uncommon pediatric malignancy, was coincident with more common pathologies of the hip and knee. These cases highlight the importance of an unbiased evaluation of the patient and critical diagnostic workup as concurrent, unrelated pathologies do occur. Additionally, they highlight the importance of considering previously undiagnosed concurrent pathologies when patients deviate from normal recovery after surgery for their primary initially diagnosed pathology.