This study seeks to analyse the rating by male and female school constituents of high performing principals on eight sub-scales, which represented the areas of effective school performance obtained from a questionnaire administered to constituents from 125 schools across Jamaica. The Principal Components Analysis (PCA) generated four dimensions or factors (philosophy and abilities, leadership, student support systems and community support and relationship) that conceptualized the areas of effective performance by high performing principals. The mean scores showed that male school constituents had a slightly more favourable rating of the four dimensions than female constituents. ?However, 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 community support and relationships. For the dimensions of personal philosophy and abilities and student support system there was no significant difference between male and female constituents on the rating of high performing principals. ?School constituents rating of high performing principals of above 4 on a rating scale of between 1 and 5, five being the highest, confirmed their selection as high performers by regional directors and senior education officers. Despite the slightly higher rating of male constituents, the significant differences (which were weak) applied to two of the four dimensions. ?The influence of personal characteristics, perceptions?and biases of male and female constituents in assessing the job performance of high performing principals may explain the differences reported for the dimensions of leadership and community support and relationship.