Medical image segmentation of tissue abnormalities, key organs, or blood vascular system is of great significance for any computerized diagnostic system. However, automatic segmentation in medical image analysis is a challenging task since it requires sophisticated knowledge of the target organ anatomy. This paper develops an end-to-end deep learning segmentation method called Contextual Multi-Scale Multi-Level Network (CMM-Net). The main idea is to fuse the global contextual features of multiple spatial scales at every contracting convolutional network level in the U-Net. Also, we re-exploit the dilated convolution module that enables an expansion of the receptive field with different rates depending on the size of feature maps throughout the networks. In addition, an augmented testing scheme referred to as Inversion Recovery (IR) which uses logical “OR” and “AND” operators is developed. The proposed segmentation network is evaluated on three medical imaging datasets, namely ISIC 2017 for skin lesions segmentation from dermoscopy images, DRIVE for retinal blood vessels segmentation from fundus images, and BraTS 2018 for brain gliomas segmentation from MR scans. The experimental results showed superior state-of-the-art performance with overall dice similarity coefficients of 85.78%, 80.27%, and 88.96% on the segmentation of skin lesions, retinal blood vessels, and brain tumors, respectively. The proposed CMM-Net is inherently general and could be efficiently applied as a robust tool for various medical image segmentations.