Crown fractures are common detrimental consequences of dental traumatic injuries. Early management of such cases is mandatory in order to prevent subsequent pathological changes that could further complicate the treatment. Pulp necrosis, chronic and cystic apical periodontitis can be the fate if these teeth are left untreated. Despite these serious complications, root canal treatment followed by apical surgery is considered a valid treatment option when such cases become complicated with large periapical lesions. However, whether a retrograde filling is essential to be placed or not is still a matter of debate. This case report discusses the orthograde endodontic management, the surgical approach and the clinical outcomes of longstanding crown fractured teeth with large cyst-like periapical lesions with and without retrograde filling.