Contralateral axillary metastasis (CAM) in breast cancer is presently treated as a stage IV disease. We hypothesized that this disease pattern is a manifestation of direct aberrant lymphatic drainage and would behave more similar to advanced locoregional disease. This is a single-site, retrospective review of patients with biopsy-proven CAM from 2008-2017. Descriptive analysis was performed. Twenty-three patients met the inclusion criteria. The median disease-free interval from primary tumor treatment to diagnosis of CAM was 68 months (range, 36-155 months). This population had aggressive disease (74% local recurrences and 61% clinical evidence of cutaneous or underlying muscular invasion) and extensive locoregional therapy (70% radiated, 57% mastectomy, and 65% axillary lymph node dissection) before their presentation with CAM. Fifteen (65.2%) patients recurred after treatment of CAM; the median recurrence-free interval was 11 months (range, 5-23 months), and 12 (52.2%) patients developed distant metastases. The median distant metastasis-free survival was 14 months (range, 11-23 months), and the median overall survival was 31 months (range, 22-67.5 months). Development of CAM is associated with aggressive disease and extensive prior locoregional surgery and/or radiation. The short recurrence-free interval and high progression to additional stage IV disease suggest these patients behave similar to traditional stage IV patients with resected oligometastatic disease.