Background There is limited research on supplemental screening breast US in women with a personal history of breast cancer (PHBC). Purpose To compare the performance of supplemental screening breast US in women with and women without a PHBC by using a matched cohort. Materials and Methods Consecutive asymptomatic women who underwent radiologist-performed supplemental breast US and mammography between January 2013 and December 2013 at a tertiary referral university hospital were retrospectively identified. Inclusion criteria were negative or benign findings at mammography, follow-up data for at least 1 year, first cancer stage of 0 to II in women with a PHBC, and incidence screening in women without a PHBC. The two groups were matched 1:1 according to age and breast density. Performance measures were compared with McNemar test, generalized estimating equation, or penalized likelihood logistic regression. Results A total of 3226 women with a PHBC were matched with 3226 women without a PHBC (mean age ± standard deviation, 52 years ± 9; mammographic breast density, fatty in 603 and dense in 2623). Fourteen cancers (six screen-detected, eight interval cancers) were found in women with a PHBC and 13 cancers (12 screen-detected, one interval cancer) in women without a PHBC. Supplemental US in women with a PHBC compared with women without a PHBC showed lower sensitivity (43% [95% confidence interval {CI}: 18%, 71%; six of 14 cancers] vs 92% [95% CI: 64%, 100%; 12 of 13 cancers]; P = .03), higher interval cancer rates (2.5 [95% CI: 1.1, 4.9; eight of 3226 women] vs 0.3 [95% CI: 0, 1.7; one of 3226 women] per 1000; P = .02), and higher specificity (92.8% [95% CI: 91.9%, 93.7%; 2982 of 3212 women] vs 89.3% [95% CI: 88.2%, 90.4%; 2870 of 3213 women]; P < .001), respectively. Conclusion Supplemental US screening in women with a personal history of breast cancer had lower sensitivity and higher interval cancer rate but higher specificity relative to women without a personal history of breast cancer. © RSNA, 2020 Online supplemental material is available for this article. See also the editorial by Lee and Lee in this issue.