The importance of entrepreneurship in economic development has long been recognized. Men are responsible for many entrepreneurial operations; nonetheless, women entrepreneurs play an important role in economic development. Despite this, women entrepreneurs confront a slew of obstacles and hurdles that impede their productivity and profitability. Therefore, the main purpose of this research is to investigate the Impact of constraints and challenges on the progress of women entrepreneurs in the Colombo District in Sri Lanka. This research is explanatory and descriptive in nature. This study used quantitative analysis to conduct this research and establish whether various constraints and challenges have an influence on the progress of women entrepreneurs. A structured questionnaire was filled out through an online survey to gather data for this study, and data was collected from 90 respondents. Reliability analysis, factor analysis, and regression analysis were statistical tools used to analyze the data. This study categorized constraints and challenges into four independent variables, which are socio-cultural issues, economic issues, psychological issues, and managerial issues. The findings of this research confirmed that economic issues and socio-cultural issues have a more significant influence on the progress of women entrepreneurs. The implications of this study based on the findings can be stated as; government programs and services that can foster women’s decisions to be involved in entrepreneurial activity; develop credit guarantee plans to allow banks to make low-risk loans by government, educate both women and their spouses; and encourage the educational level of women entrepreneurs. To acquire a holistic perspective, a similar study might be conducted in different districts across the country. More research is needed to understand how cross-cultural trade affects women entrepreneurs around the world, as well as how women entrepreneurs manage their survival and growth in today’s globalized society.