This study aims to investigate how a teacher’s creative teaching is affected by the teacher’s imagination and his or her school principal’s visionary leadership and how the contextual moderating effects are at play among the cross-hierarchical factors. The research framework is divided into two levels, the individual level on how “teacher’s imagination” affects “teacher’s creative teaching”, and the group level on the impact of “the principal’s visionary leadership”. From the teachers of 65 primary schools in southern Taiwan invited to participate the survey study, 861 valid data were returned. The demographic variables were analyzed by the use of descriptive statistics. The cross-level moderating effects were further examined via Hierarchical Linear Modelling (HLM). The results show that the “teacher’s imagination” will impact the “creative teaching” positively. The “vision practice” will affect “autonomous learning and challenge-presenting” positively as well. Moreover, the “vision feedback” plays a positive moderator role in how “creative imagination” contributes to “interactive discussion and open-mindedness”.