Giant juvenile fibroadenomas in patients with hemihypertrophy are exceptionally rare. We present a very interesting case of a 13 year old girl with hemihypertrophy of the left side presenting with recurrent giant juvenile fibroadenomas of the left breast. The giant fibroadenomas occurred twice in the left breast over two years. The first had a diameter of 12 cm and was excised through an inframammary incision. The second occurred a year later, had a diameter of 11 cm, and was associated with three smaller fibroadenomas. These lesions were removed through a single periareolar incision. The procedures were complicated by keloid scarring but the results were improved with steroid impregnated tape dressing and local methylprednisolone injection. This report adds to our experience in managing patients with recurrent giant juvenile fibroadenomas complicated by hemihypertrophy and raises awareness to anticipate keloid scarring.