Chronic wounds affect millions of people worldwide every year. An adequate assessment of a wound’s prognosis is a critical aspect of wound care since it assists clinicians in understanding wound healing status, severity, triaging and determining the efficacy of a treatment regimen, thus guiding the clinical decision making. The current standard of care involves using wound assessment tools, such as Pressure Ulcer Scale for Healing (PUSH) and Bates-Jensen Wound Assessment Tool (BWAT), to determine wound prognosis. However, these tools involve manual assessment of a multitude of wound characteristics and skilled consideration of a variety of factors, thus, making wound prognosis a slow process which is prone to misinterpretation and high degree of variability. Therefore, in this work we have explored the viability of replacing subjective clinical information with deep learning-based objective features derived from wound images, pertaining to wound area and tissue amounts. These objective features were used to train prognostic models, that quantified the risk of delayed wound healing, using a dataset consisting of 2.1 million wound evaluations derived from more than 200,000 wounds. The objective model, which was trained exclusively using image-based objective features, achieved at minimum a 5% and 9% improvement over PUSH and BWAT, respectively. Our best performing model, that used both subjective and objective features, achieved at minimum an 8% and 13% improvement over PUSH and BWAT, respectively. Moreover, the reported models consistently outperformed the standard tools across various clinical settings, wound etiologies, sexes, age groups and wound ages, thus establishing the generalizability of the models.