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Using a convenience sample of 289 teachers in Singapore, this study examined: (1) whether there were significant differences between teachers’ perceptions of principal’s and immediate supervisor’s empowering behaviours; and (2) teachers’ perceptions of principal’s and immediate supervisor’s empowering behaviours in relation to teachers’ psychological empowerment. Results indicated that teachers perceived their principals and immediate supervisors as exercising empowering behaviours in their daily practices, but they also perceived their principal and immediate supervisor differing in magnitude in some specific dimensions of empowering behaviours such as delegation of authority, providing individualised concern and support, articulating a vision and fostering collaborative relationships. Results also indicated that teachers’ perceptions of principal’s and immediate supervisor’s empowering behaviours were positively associated with teachers’ psychological empowerment, and that they added unique variance to each other in predicting teachers’ psychological empowerment. This study suggests the importance of considering teachers’ perceptions of principal’s and immediate supervisor’s empowering behaviours as two distinct constructs in empirical research so that their unique predictive power could be more aptly captured. From a practical standpoint, it suggests the importance for school leadership developers to enhance school leaders’ awareness and capacity in exercising empowering behaviours towards their teachers in their daily practice. Essentially, schools may stand to gain from developing empowering leaders at different levels of management to promote teachers’ psychological empowerment.