Occult breast cancer (OBC) is a rare presentation of breast cancer, characterised by breast carcinoma that has metastasized to the axillary lymph nodes with the absence of radiological disease in the breast. Contralateral axillary metastasis (CAM) in breast cancer is another rare occurrence with differentials including a contralateral metastasis from the primary breast cancer, metastasis from a separate primary ipsilateral breast cancer or metastasis from another primary cancer of extramammary origin. This poster presents a 67-year-old female with left axillary metastasis from an occult breast cancer with synchronous contralateral axillary metastasis. Although both axillary lesions were proven to be hormone receptor negative on histology, she remains a diagnostic dilemma due to the different HER-2 receptor status of both axillary lymph nodes. Her treatment included neoadjuvant chemotherapy, bilateral mastectomy with bilateral axillary lymph node dissection (ALND) and adjuvant radiotherapy. This case highlights the complexities and diagnostic dilemma of OBC and CAM. It is important for clinicians to have a high index of suspicion when there is evidence of metastatic breast cancer, regardless of a clear primary breast malignancy. While an ALND remains the mainstay surgical management of the axilla for OBC, there is yet to be consensus guidelines on the management of the breast. Previous treatment for OBCs involved mastectomies. However, modern practice involves breast preservation with radio-chemotherapy as an alternative treatment regimen. CAM is often managed with chemo-radiotherapy without the need for contralateral mastectomy, except for cases with different pathological or immunohistochemical features compared to the primary malignancy.