Purpose To investigate the accuracy of dynamic contrast material-enhanced (DCE) breast MRI for determining residual tumor size after neoadjuvant chemotherapy (NAC). Materials and Methods For this retrospective study, 487 consecutive women (mean age, 47.0 years ± 10.3 [standard deviation]; range, 24-78 years) underwent preoperative DCE MRI following NAC and subsequent surgeries between 2008 and 2011. Tumor size was measured at early-phase, conventional delayed-phase, and late delayed-phase MRI (90, 360, and 590 seconds after contrast material injection, respectively). At histopathologic examination, total tumor size (both invasive and in situ) and the size of invasive tumor alone were separately recorded. Absolute agreement between tumor size at MRI and histopathologic examination was assessed by using intraclass correlation coefficient (ICC) analysis. Factors affecting size discrepancy were assessed by using multiple linear regression analysis. Results Compared with tumor size at histopathologic examination, total tumor sizes showed higher agreement at conventional delayed-phase MRI than at early-phase MRI (ICC, 0.76 vs 0.56; P ˂ .001) and comparable agreement at conventional and late delayed-phase MRI (ICC, 0.76 vs 0.74; P = .55). Lobular histologic features and tumor subtype were independently associated with greater size discrepancy (P ˂ .001). Lobular cancers were underestimated in size compared with ductal cancers (mean size discrepancy, -2.8 cm ± 3.2 vs -0.3 cm ± 1.8; P = .004). Estrogen receptor-positive/human epidermal growth factor receptor 2 (HER2)-negative cancers were underestimated compared with HER2-positive cancers (-0.8 cm ± 2.0 vs -0.3 cm ± 1.7, P = .006) and triple-negative cancers (-0.8 cm ± 2.0 vs 0.3 cm ± 1.7, P ˂ .001). Conclusion Delayed-phase MRI is more accurate than early-phase MRI for evaluating residual breast tumor size after neoadjuvant chemotherapy. Lobular or estrogen receptor-positive/human epidermal growth factor receptor 2-negative cancers are underestimated in size at MRI compared with ductal or other subtypes. © RSNA, 2018 Online supplemental material is available for this article.