Deep learning models (DLMs) can achieve state of the art performance in medical image segmentation and classification tasks. However, DLMs that do not provide feedback for their predictions such as Dice coefficients (Dice) have limited deployment potential in real world clinical settings. Uncertainty estimates can increase the trust of these automated systems by identifying predictions that need further review but remain computationally prohibitive to deploy. In this study, we use a DLM with randomly initialized weights and Monte Carlo dropout (MCD) to segment tumors from microscopic Hematoxylin and Eosin (H&E) dye stained prostate core biopsy RGB images. We devise a novel approach that uses multiple clinical region based uncertainties from a single image (instead of the entire image) to predict Dice of the DLM model output by linear models. Image level uncertainty maps were generated and showed correspondence between imperfect model segmentation and high levels of uncertainty associated with specific prostate tissue regions with or without tumors. Results from this study suggest that linear models can learn coefficients of uncertainty quantified deep learning and correlations ((Spearman's correlation (p<0.05)) to predict Dice scores of specific regions of medical images.