The Opportunity 2000 Campaign has recognized that equal opportunity policy change has to be accompanied by a process of culture change in organizations. However, sustaining commitment to an equal opportunity culture may be a difficult task in times of rapid and varied organizational change. In particular, the volume and scope of 'restructuring' that follow mergers, acquisitions, divestment, the introduction of internal markets, and other changes in business strategy often lead to 'downsizing', 'delayering', and outsourcing of business functions. This can have very variable outcomes for the careers of women managers. For them the experience of organizational restructuring is akin to participation in a lottery in which they are occasionally winners, but usually losers. This is the main finding from in-depth case studies of three large organizations in the public sector, pharmaceuticals, and financial services, which have all experienced some form of 'restructuring' over the last five years. The main conclusion of this research is that unless restructuring involves an expansion of managerial positions it is likely to disadvantage women managers. The reasons for this are that it leads to job losses in functions where women are concentrated; highlights the disadvantages of poor line manager support; reinforces exclusion from the valuable informal organizational networks that provide access to career development opportunities; and renders formal equal opportunity policy monitoring ineffective. These findings have considerable implications for organizational and national policy initiatives to achieve an equal opportunity business culture.