Background: Despite increasing numbers of women surgeons globally, barriers to career advancement persist. While these barriers have been extensively discussed in high-income countries (HICs), the topic has received minimal attention in lower–middle-income countries (LMICs) like Pakistan. Methods: The Association of Women Surgeons of Pakistan (AWSP)—an organization in Pakistan consisting of female surgeons and trainees—carried out this international cross-sectional study over July–Sept 2019. An anonymous online survey was disseminated via social media platforms and various institutions across Pakistan and internationally. Results: A total of 218 female surgeons responded to the survey, with 146 (67%) from Pakistan and 72 (33%) from HICs. While HIC surgeons were more likely to report gender discrimination/bias (GD/bias) during residency (29.2% vs 11.6%; p = 0.001), more Pakistani surgeons reported that GD/bias negatively affected their job satisfaction (80.7% vs. 64.9%; p = 0.024). GD/bias manifested most commonly as differences in mentoring relationships (72%). A higher percentage Pakistani surgeons reported having experienced a family-related interruption in their career (24.7% vs. 11.1%; p = 0.019). The vast majority (95%) felt that surgery was perceived as a masculine field, and the majority (56.4%) of respondents reported having been told that they could not be a surgeon because of their gender. Conclusion: Our study highlights keys factors that must be addressed to provide equal career opportunities to women surgeons. It is the responsibility of surgical educators, policy makers, and healthcare organizations to facilitate women surgeons’ career progression by developing systems that support equitable career growth for women surgeons.