The dissertation investigates gender inequalities in Italian academia concerning career progression and tenure, and how these inequalities intersect with parenthood and fertility. Structured around three empirical chapters, it examines the impact of parenthood on men's and women's academic careers and how academic progression influences men's and women's fertility behaviour. The research uses an extensive empirical dataset, including administrative records of PhD holders and unique primary data collected from Italian academics. Advanced regression-based techniques and event history analysis are applied to analyse the data. The first chapter focuses on the academic journey from PhD to employment, assessing potential gender differences in career choices. The second chapter examines gender differences in academic progression in terms of the time elapsed between obtaining a PhD and being appointed to different academic positions, assessing the role of fertility in contributing to gender disparities. The third chapter aims to understand how academic careers shape the fertility behaviour of academic women and men. The findings shed light on the complex interplay between gender, parenthood and academic careers, revealing significant challenges faced by women in academia, particularly in terms of career progression and balancing fertility decisions.