Background Male breast cancer incidence is rising. There may be a potential role in selective screening in men at elevated risk for breast cancer, but the effectiveness of such screening remains unexplored. Purpose To evaluate patterns of male breast imaging utilization, to determine high-risk screening outcomes, and to delineate risk factors associated with cancer diagnosis. Materials and Methods This retrospective study reviewed consecutive male breast imaging examinations over a 12-year period (between 2005-2017). Examination indications, biopsy recommendations, and pathologic results were correlated with patient characteristics. Fisher exact test, Mann-Whitney test, Spearman correlation, and logistic regression were used for statistical analysis. Results A total of 1869 men (median age, 55 years; range, 18-96 years) underwent 2052 examinations yielding 2304 breast lesions and resulting in 149 (6.5%) biopsies in 133 men; 41 (27.5%) were malignant and 108 (72.5%) were benign. There were 1781 (86.8%) diagnostic and 271 (13.2%) screening examinations. All men undergoing screening had personal or family history of breast cancer and/or genetic mutations. There was a significant increase in the number of examinations in men relative to the number of examinations in women over time (Spearman correlation, r = 0.85; P < .001). Five node-negative cancers resulted from screening mammography, yielding a cancer detection rate of 18 per 1000 examinations (95% confidence interval [CI]: 7, 41), with cancers diagnosed on average after 4 person-years of screening (range, 1-10 person-years). Mammographic screening sensitivity, specificity, and positive predictive value of biopsy were 100% (95% CI: 50%, 100%), 95.0% (95% CI: 93.1%, 98%), and 50% (95% CI: 22.2%, 77.8%). Older age (P < .001), Ashkenazi descent (P < .001), genetic mutations (P = .006), personal history (P < .001), and first-degree family history (P = .03) were associated with breast cancer. Non-first-degree family history was not associated with cancer (P = .09). Conclusion There is potential benefit in screening men at high risk for developing breast cancer. Such screening may have increased over time. © RSNA, 2019.