Three contextual factors, the gender of the principal, the choice of subject matter used for the demonstration of competence, and number of years of teaching experience, have been shown to have an effect on the outcome of teacher evaluation. The annual evaluations of 521 elementary personnel using the Florida state-mandated single assessment were investigated. Significant differences were recorded in initiating instruction, presenting instruction, and managing student conduct when examined from the reference point of the gender of the principal. Significant differences were recorded in managing student conduct when examined from the reference point of the subject matter used for the demonstration of competence. Significant differences were recorded in communicating with students when examined from the reference point of teachers' years of experience. A qualitative follow-up study of the principals identified distinctive differences in professional preparation and career patterns between the 5 male and 10 female elementary principals in the study. (JD)