Dermatomyositis (DM) is an idiopathic inflammatory myopathy. The incidence of malignancy in DM patients is quite high. Anti-transcription intermediary factor 1-γ (anti-TIF1-γ) antibody is more prevalent in DM patients with malignancy than in those without malignancy. A 70-year-old woman developed hoarseness and difficulty swallowing. A physical examination revealed skin abnormalities. Breast cancer was found in her right breast. She was positive for anti-TIF1-γ antibody. Chemotherapy reduced the tumor size, decreased the anti-TIF1-γ antibody level, and improved her symptoms. About 2.5 years later, however, her skin symptoms worsened, and anti-TIF1-γ antibody levels increased again, and colorectal cancer was found. Treatment with endoscopic mucosal resection (EMR) improved her symptoms again. Our case suggests that the exacerbating skin symptoms and parallel increase in the anti-TIF1-γ antibody level led to the detection of a second cancer after treatment of the first cancer in this case of DM.