Ocular imaging has developed rapidly and plays a critical role in clinical care and ocular disease management. Development of image processing technologies pertinent to ocular diseases has paved the way for automated diagnostic systems including detection techniques using deep learning (DL) approaches. The prevalence of an abnormal tissue layer in the conjunctiva, known as pterygium eye disease, is increasing due to lack of awareness. Despite the non-cancerous/benign nature of pterygium, a clinical diagnosis from an ophthalmologist is still required to prevent the pterygium tissues from extending into the pupil, which would result in blurred vision. However, current diagnostic methods are mostly dependent on human expertise. Automated detection can potentially serve as an assistive method to reduce diagnosis time by applying a DL approach. Considering the lack of comprehensive research work on pterygium detection using DL, we propose a new architecture consisting of an improved CNN-based trained network named VggNet16-wbn that is derived from VggNet16, a pre-trained CNN algorithm. This paper presents an overview of the DL as a core approach to the transfer learning (TL) concept, as well as current efforts towards automated ocular detection approaches. A new architecture of a CNN-based trained network was proposed based on a network assessment from six CNN pre-trained networks to detect pterygium. This work consists of two main modules, namely, data acquisition and DCNN classification. The proposed trained network, VggNet16-wbn, shows the best performance with 99.22% accuracy, 98.45% sensitivity, and a perfect score on specificity and area under the curve metrics. This work has high potential for creating a pterygium screening system that can be used as a baseline for fully automated detection using a DL approach.