The clinical dilemma of management of isolated contralateral axillary metastasis (CAM) in carcinoma breast remains unsolved. We report a case of metachronous contralateral left axillary metastasis in a 54-year-old postmenopausal woman, its management, and review of literature. After ruling out distant metastasis and occult primary in the opposite breast, curative treatment was planned. She underwent left axillary lymph node dissection which on histopathology showed metastatic carcinoma. Management of CAM with curative or palliative intent and whether to consider them as locoregional or distant metastasis remains controversial. CAM may occur due to the locoregional spread of disease, and hence, curative intent of treatment should be offered to these patients.