Physical Education (PE) is beneficial for students’ mental and physical health, however, teenagers are increasingly becoming less motivated to actively participate in the current form of PE. Motivational studies show that collective physical activity augmented by playful interactions could encourage more participation and social engagement in physical activities (PA). In this paper, we present a within-subject field study with 20 teenagers formed into five groups sized equally. The study is conducted using Shuttlezap, a prototype that provides realtime playful audio augmentation to the process of the activity. Results show that the teenagers enjoyed playful audio augmentation and were socially engaged with an enhancement of their perception of competence. By further comparing the conditions between with and without the audio augmentation, we found that the playful audio augmentation positively contributed to the playfulness in terms of perceived relaxation and expression. We conclude with design implications for social play in the context of PE for teenagers.