It is expected that the number of elected female mayors in local government will increase globally, yet no major progress has been registered lately despite the increased focus on the topic. At the European level, no country exceeds 40% female mayors or other leaders of the municipal council (or equivalent), with the highest descriptive representation of 39.1% in Iceland. Following the 2020 elections in Romania, only around 5% of mayors were female with a strong over-representation of male mayors. The current study aims to analyze the male–female distribution of mayors, the degree of re-election, the relationship between the number of candidates and re-election of incumbents, and how these factors impact female political representation at the local level in Romania. Thus, we argue that a high degree of re-election of incumbents may be a barrier to women’s access to the position of mayor. In addition, it is important to determine whether female incumbents are as successful as their male counterparts in being re-elected. While there is an extensive body of literature on incumbency that covers a range of topics, there is a gap in the literature regarding the proposed subject. The present research aims to fill the gap and contribute to a better understanding of the political representation of women in Eastern Europe. We utilized a dataset of Romanian elections from 2008 to 2020 to test our hypotheses. Our findings indicate that during the studied period, more than 95% of mayors were male, the re-election was a frequent occurrence in Romania with a percentage ranging from 70.82% (2008–2012) to 72% (2012–2016 and 2016–2020), and female incumbents were just as likely to be re-elected as their male counterparts.