Background: Chronic leg ulcers present a global challenge in healthcare, necessitating precise wound measurement for effective treatment evaluation. This study is the first to validate the “split-wound design” approach for wound studies using objective measures. We further improved this relatively new approach and combined it with a semi-automated wound measurement algorithm. Method: The algorithm is capable of plotting an objective halving line that is calculated by splitting the bounding box of the wound surface along the longest side. To evaluate this algorithm, we compared the accuracy of the subjective wound halving of manual operators of different backgrounds with the algorithm-generated halving line and the ground truth, in two separate rounds. Results: The median absolute deviation (MAD) from the ground truth of the manual wound halving was 2% and 3% in the first and second round, respectively. On the other hand, the algorithm-generated halving line showed a significantly lower deviation from the ground truth (MAD = 0.3%, p < 0.001). Conclusions: The data suggest that this wound-halving algorithm is suitable and reliable for conducting wound studies. This innovative combination of a semi-automated algorithm paired with a unique study design offers several advantages, including reduced patient recruitment needs, accelerated study planning, and cost savings, thereby expediting evidence generation in the field of wound care. Our findings highlight a promising path forward for improving wound research and clinical practice.