Diabetic mastopathy is a rare benign condition associated with long-standing diabetes mellitus and presents with breast lumps. This report describes two cases in which diffusion-weighted images (DWI) on magnetic resonance imaging were quite different from each other. In case 1, there were hyperintense lesions on DWI, and surgically removed specimens revealed ductitis with marked lymphocytic infiltration. In case 2, no abnormal intensity was depicted on DWI, and biopsy specimens showed dense stromal fibrosis with mild perivascular lymphocytic infiltration that corresponded to previous reports. Although it is reported that diabetic mastopathy is composed of dense fibrous tissue with low cellularity that results in no hyperintense lesion on DWI, in cases with marked lymphocytic infiltration, strong hyperintensity can be seen on DWI mimicking malignant breast tumors.