The career path of women in Canadian public education has, in general, continued to follow quite a different course from that of men. In most instances, the careers of Canadian educators place the majority of women in teaching positions while men dominate school administration. Women, who are school administrators, have tended to be appointed to elementary school positions or, when assigned to the secondary level, are more likely to be designated to support positions such as vice-principalships. In Manitoba, the provincial pattern is not dissimilar. However, the data for the Winnipeg School Division stands in marked contrast. The twenty-five year period between 1972-3 and 1997-8 saw a change from women occupying some 22 percent of the Division's administrators at the start of the period to 56 percent. These substantial shifts in the gender representation of school administrators within the Winnipeg School Division, their impact on the career paths of women and men administrators in the Division, and the perceptions of high school principals regarding the significance of gender and gender discrimination in administrator career development over the twenty-five year period provide the focus of this study. Data was collected from School Board minutes and Divisional records of all school-based administrative appointments (principals and vice-principals) during the period of the study, and in addition a series of interviews were conducted with fourteen high schools principals between June and November 2000. An analysis of the date presented in this study suggests that these substantial changes in gender representation - which occurred in waves, beginning with the elementary school vice-principalship, moving through the secondary vice-principalship and the elementary school principalship - were achieved, not by recruiting from outside of the division, nor by "fast-tracking women administrators. Rather it was achieved by a sustained effort to recruit women into entry administrative positions as they became open and then to support them through a career path of promotion that paralleled the scope and speed of traditional male careers. Both female and male high school principals recognized the significance of gender and gender discrimination as a salient feature of both community and professional attitudes towards school administration and saw the benefits of the division's policies and practices directed towards affirmative action.