Extraskeletal cartilaginous, osseous, and chordoid tumors are extraordinarily rare in children and adolescents. These lesions are diagnostically challenging due to their rarity and their overlap with metastatic osteosarcoma, reactive or metabolic calcifying and bone-forming masses, various pseudosarcomatous proliferations such as myositis ossificans, and other rare genetic or metabolic disorders. This article reviews the clinicopathologic features and differential diagnosis of extraskeletal cartilaginous, osseous, and chordoid neoplasms in the first two decades of life and highlights the use of diagnostic adjuncts.