Design thinking is associated with prescriptions for the innovation of products and services with business and social contexts and one of the important topics in the technology management field. The Design Thinking Test (DTT) was developed by VISITS Technologies Inc. and was released to the market in 2019. The DTT is an assessment tool for measuring creativity and judgment ability which reflect methodology of design thinking, and design thinking scores are calculated as an output of the DTT. In this study, what kind of experiences of university students enhance design thinking skills was examined using the data of 11,040 university students who took the DTT. Regression analyses using data of design thinking scores and experiences of 11,040 university students were executed. It was found that long-term intern or work at firms, business contests, and work experiences such as business planning enhanced design thinking scores of university students. Among these 3 kinds of experiences, long-term intern or work at firms is the most effective, business contests are the second most effective, and work experiences such as business planning is the third most effective to enhance design thinking skills of university students.