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(1) Abstract: Wound monitoring is an essential aspect in the evaluation of wound healing. This can be carried out with the multidimensional tool HELCOS, which develops a quantitative analysis and graphic representation of wound healing evolution via imaging. It compares the area and tissues present in the wound bed. This instrument is used for chronic wounds in which the healing process is altered. This article describes the potential use of this tool to improve the monitoring and follow-up of wounds and presents a case series of various chronic wounds with diverse etiology treated with an antioxidant dressing. (2) Methods: A secondary analysis of data from a case series of wounds treated with an antioxidant dressing and monitored with the HELCOS tool. (3) Results: The HELCOS tool is useful for measuring changes in the wound area and identifying wound bed tissues. In the six cases described in this article, the tool was able to monitor the healing of the wounds treated with the antioxidant dressing. (4) Conclusions: the monitoring of wound healing with this multidimensional HELCOS tool offers new possibilities to facilitate treatment decisions by healthcare professionals.