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The purpose of this work was to evaluate the potential of functional imaging with ¹⁸F-FDG PET, ¹⁸F-fluoromisonidazole PET, diffusion-weighted MRI, and dynamic contrast-enhanced MRI to provide an appropriate and reliable biologic target for dose painting in radiotherapy for head and neck squamous cell carcinoma (HNSCC). Fifteen patients with locally advanced HNSCC, treated with concomitant chemoradiotherapy, were prospectively enrolled in a bioimaging protocol. Sequential PET (¹⁸F-FDG and ¹⁸F-fluoromisonidazole) and MRI (T1, T2, dynamic enhanced, and diffusion-weighted sequences) were performed before, during, and after radiotherapy. Median follow-up was 30.7 mo (range, 6.3–56.3 mo); in 7 patients, disease recurred. Disease-free survival correlated negatively with the maximum tissue-to-blood ¹⁸F-fluoromisonidazole ratio (T/B_max) on the baseline ¹⁸F-fluoromisonidazole …