This study aims to investigate the differences in the learning path and value between students of different genders and educational backgrounds in digital game-based learning in Taiwan’s higher vocational education. A game-based digital Supply Chains Learning System was used to explore the value network based on “system attributes—learning consequences—target value” from the perspective of the student. To investigate the research question, this study conducted a cross-analysis of differences in gender and education background. Findings from the study revealed that irrespective of gender and educational background in higher vocational education in Taiwan, students developed distinctively different learning paths, values, and emphasis from specific system attributes. These findings will not only enable trainers and educators to learn more about the differences in learning by individuals but will also serve as useful guidelines for the improvement of the teaching strategy used by digital games developers.