Recently, the issue of the gender gap in dentistry and in the leadership in the dental field has placed new challenges on dental profession representatives and politicians. Indeed, the inequity between genders in healthcare workforces represents a limit to the progression of those in the professions, inhibiting talented colleagues from accessing high positions in the academic world and not providing adequate role models to inspire future generations. The Italian population practicing dentistry in 2021 was composed of 74% males and 26% females. The aim of this study is to analyze the level of the gender gap in the dental field in Italy by focusing on the gender distribution of professional leaders in institutional category associations and invited speakers at dental conferences accredited for the Continue Education in Medicine program. The search strategy considered three different fields in the national dentistry scene: the dental committee boards, the union category associations, and the cultural field. The roles in the dental boards were retrieved from the website of the National Medical and Dental Committee from 2018 to 2022; the roles in the union category associations at the provincial, regional, and national levels were retrieved from the related web pages, considering the period from 2018 to 2021; and the information about the speakers at national conferences from 1 January 2019 to 31 December 2021 was retrieved from the National Agency for Regional Health Services (Agenzia nazionale per i servizi sanitari regionali (AGENAS)) websites. The extracted data were grouped and examined using descriptive statistics (frequency), and due to the categorical nature of the data, non-parametric tests (chi-square tests) were used to assess any differences between the two genders. The null hypothesis was that there were no statistical differences between the two genders’ distributions. A p-value was considered significant when <0.05. In addition, aiming to understand the representation of male and female dentists, a comparison of the distributions of males and females in the dental boards with the percentages of female and male dentists operating in Italy in 2021 was performed using a binomial test. The analysis of the data regarding the composition of the dental boards and of the union category association boards revealed a statistically significant difference in the distribution of the roles between the two genders at the regional and local levels, with a p-value of <0.05, and a significantly low representation of the women practicing dentistry (p < 0.05). In Italy, women practicing dentistry are underrepresented in dental organizations and in cultural events, given the low numbers of female dentists in leadership and/or speaker roles in the years 2018–2021. Even though the glass ceiling effect continues to affect Italian female dentists, initiatives and political measures have been taken to improve this condition and reach gender equity.