High quality performance of image segmentation methods presents one leading priority in design and implementation of image analysis systems. Incorporating the most important image data information into segmentation process has resulted in development of innovative frameworks such as fuzzy systems, rough systems and recently rough - fuzzy systems. Data analysis based on rough and fuzzy systems is designed to apprehend internal data structure in case of incomplete or uncertain information. Rough entropy framework proposed in [12,13] has been dedicated for application in clustering systems, especially for image segmentation systems. We extend that framework into eight distinct rough entropy measures and related clustering algorithms. The introduced solutions are capable of adaptive incorporation of the most important factors that contribute to the relation between data objects and makes possible better understanding of the image structure. In order to prove the relevance of the proposed rough entropy measures, the evaluation of rough entropy segmentations based on the comparison with human segmentations from Berkeley and Weizmann image databases has been presented. At the same time, rough entropy based measures applied in the domain of image segmentation quality evaluation have been compared with standard image segmentation indices. Additionally, rough entropy measures seem to comprehend properly properties validated by different image segmentation quality indices.