Even as we mark the fortieth anniversary of Title IX, evidence indicates that pregnant and parenting high school students continue to struggle with stigmatization and discrimination within the public school system. To remind school social work practitioners and other concerned administrators of the provisions of this historic legislation, this article will commemorate its passage by examining the special policies and practices that it mandates for female students who have undertaken parenting responsibilities while attending high school. Specifically, this article will take a historic journey through the development of Title IX by discussing the inconsistencies between federal provisions and educational policies. The recommendations for school social work intervention are intended to ensure that current educational practices comply with Title IX directives. These recommendations include strategies for educating stakeholders, involving teenage fathers, and advocating for gender equality.