The current study focuses on the key roles that affect the success of a flipped classroom. The research was conducted with a questionnaire survey created from a study of literature review. Out of a total of 441 samples, 424 valid samples (96.14%) from teachers have been received. The study key conclusions are as follows: (1) a principal leadership has positive effect on student's learning achievement; (2) a principal leadership has positive effect on teacher's attitude of digital media teaching; (3) a teacher's attitude of using digital media has positive effect on student's learning achievement; (4) a teacher's attitude towards digital media teaching moderates the relationship between principal leadership and student's learning achievement; and (5) parental involvement has a positive effect on student's learning achievement. However, administrative support appeared to weakly influence teacher's attitudes towards digital media teaching. Very often in the culture of Taiwanese primary school, the teachers tend to only obey the principal and neglect the requirements of the administrative staff.