This case report highlights the clinical progression of a recurrent pyogenic granuloma (PG) in a 17-year-old male baseball player who experienced the transition of the lesion into a calcifying fibroblastic granuloma (CFG) extending into the periosteum and underlying bone. Adolescence, a period marked by significant hormonal changes and increased susceptibility to stress due to the demands of being an athlete, combined with a lack of proper oral hygiene, may have played a significant role in the lesion's development, recurrence, and progression to CFG. The initial treatment involved excisional biopsy, followed by more extensive surgical intervention, including excision of the periosteum and bone curettage, to ensure complete removal of the recurrent lesion. The surgical site healed without complications. This case underscores the importance of accurate diagnosis and the need for thorough excision to prevent recurrence. Furthermore, it highlights the significance of maintaining proper oral hygiene and managing risk factors such as stress, which can influence the recurrence and progression of PGs to CFGs.