Globalization and the multitude of technological changes that have affected societies in recent years have introduced complex and diverse problems into the daily lives of individuals. Indeed, great effort is expended to create rich and abundant lives, especially in the age of the knowledge economy. In this context, “creativity” has come to be seen as the most precious human asset. Many scholars have suggested that foundational knowledge in certain academic fields is necessary for creative thinking. Thus, this study will focus on creativity in the field of mathematics. Additionally, many studies have found that playfulness enhances creativity and exploration. This study sought to explore the role of playfulness learning mathematics to gain in-depth understandings of the relationship between playfulness and creativity as well as the effect of playfulness on creativity. This study used questionnaires to collect data relating to the playfulness and creativity of junior high school students who were gifted in mathematics and science. Data were analyzed using SPSS17.0 to explore the relationships among dimensions. This study used a random-sampling approach to select a sample of junior high school students who were gifted in mathematics and science. A total of 360 questionnaires were distributed, and our valid return rate was 94%. This study confirmed that playfulness enhances individual creative performance and that personal playfulness can predict and has a positive influence on creativity.