Background: Ossifying fibroma in the nasal cavity and paranasal sinus is a benign tumor histologically, however clinically may show invasive characteristics. It usually invades the orbital bone, the base of the skull and calvarium to induce orbital and cranial manifestations. It has malignancy rate of 0.4-0.5%. Aim of the study: to present two cases of Juvenile ossifying fibroma of the paranasal sinuses with orbital involvement, with special consideration to the complex surgical approaches and documenting the radiological finding and histopathological entities. Patients and Methods: This study included two female children with Juvenile ossifying fibroma of the paranasal sinuses with orbital involvement. Research has been approved by the Research Ethical Committee of otolaryngology department, faculty of medicine for girls, AL -Azhar University. Both patients subjected to complete ENT and ophthalmological examination. CT study of the paranasal sinuses, orbit and brain were done using The two patients underwent excisional biopsy of the lesions through combined trans-nasal endoscopic and orbital approaches with repair of the orbital wall with titanium as in first case and/or high-density porous polyethylene sheets as in second case . Post-operative follow up included complete ENT and ophthalmological examination and CT scan. The radiological findings and histopathogical entities of both cases were described in details. Results: Both patients similarly presented with marked Swelling and masses of the right maxillary and ethmoidal sinuses that invaded the orbit with varying degree of proptosis, dystopia and visual affection. Our patients ages were 10 and 16 years. A histopathological feature of the first case is consistent with diagnosis of trabecular variant of ossifying fibroma, while the second case is consistent with the diagnosis of psammomatoid variant of ossifying fibroma. Radilogically were partially defined expansile heterogeneous fibro-osseous mass with ground glass appearance occupying the right maxillary, ethmoidal sinuses, and the right nasal cavity and invading the orbit. No intraoperative or Post-operative complication. Conclusion: An accurate Diagnosis of JOF is made by correlation of clinical, radiological, histopathological findings. A combined Trans-Nasal endoscopic and orbital approach is effective for excision.