This study analyses the role that the gender difference of school constituents plays in rating the performance of high-performing principals in 125 schools across Jamaica. A Principal Components Analysis (PCA) generated four dimensions which conceptualized leadership performance in effective principals, and a confirmatory factor analysis (CFA) was used to assess the fit between the resulting data and the hypothesis of gender difference in the performance of high-performing principals. The analysis from the independent-samples "t"-test showed that there was a significant difference between the rating of male and female school constituents on the dimensions of leadership and management, and community support and relationships. For the dimensions of personal philosophy and abilities, and student support systems there was no significant difference between male and female constituents. The similarities and differences in the rating of the dimensions of performance of high-performing principals by male and female school constituents may be influenced by factors related to the gender of the principals, the nature of the dimensions being rated, and the gender of the school constituents themselves.