The evolution of structural changes and the textural features during the ripening process of four varieties of Spanish sheep cheese were studied using Magnetic Resonance Imaging (MRI). Specifically, longitudinal (T1) and transverse (T2) relaxation times and apparent diffusion coefficient maps were analyzed. Also, proton density was used to improve the description of the structure of the cheeses. The MRI results displayed important information about cheese matrix structure, associated with different manufacturing processes (industrial vs. traditional), ripening times (RTs, from 2 to 180 days), and geographical origins. A significant interaction between RT and cheese variety related to the variations in physicochemical and textural parameters was found. Linear regression models were developed per the abundant literature. Logarithmic regression models showed the highest R2 when monitoring the dependency on T1 and T2 parameters of water content, water activity, RT, and some texture parameters. Therefore, these results support that MRI is a useful technology to monitor the ripening process, predict textural behavior and physicochemical variables, and characterize the structure of different varieties of sheep cheese.