Dental residents experience high stress in their demanding programs and gender-based harassment/discrimination can contribute to their stress. The objectives were to compare stress, satisfaction, experienced sexual harassment and observed discrimination of women in dental graduate programs with high, medium, and low percentages of women and to explore relationships between these constructs of interest. Note that, 112 pediatric dentistry (PD), 44 prosthodontics, and 56 oral and maxillofacial surgery (OMS) residents responded to a survey. PD residents had the lowest personal life-related stress (4-point scale with 4=very stressful: PD=2.99/P=3.67/OMS=3.56; p<0.001), faculty-related stress (2.68/3.66/3.03; p<0.001), lack of confidence-related stress (2.79/3.31/2.96; p<0.01) and academic stress (2.65/3.24/3.02; p<0.001), while prosthodontics residents had the highest stress levels. The average frequency of experiencing sexual harassment was highest for OMS residents and lowest for PD residents (5-point scale with 1=never: 1.15/2.62/2.74; p<0.001). PD residents observed least and OMS residents most frequently that female residents were treated less positively by other residents because of their gender (1.59/2.57/3.00; p <0.001). Prosthodontics residents had the lowest job satisfaction score (5-point scale with 1=lowest satisfaction: 4.12/3.14/4.20; p<0.001). The more frequently male and female residents experienced sexual harassment, the higher their personal life-related stress, faculty-related stress, lack of confidence-related stress, and academic stress, and the lower their career satisfaction, specialty content satisfaction, and stress-related satisfaction. Women's frequencies of observed gender-based discrimination were associated with higher stress and lower satisfaction, while men's frequencies of these observations were not associated with stress, but associated with increased satisfaction. Dental residents' stress, career satisfaction, experienced sexual harassment, and observed discrimination of women residents differ depending on the dental specialty program. Both male and female residents report more stress and less satisfaction the more they experience sexual harassment. The more women observe discrimination of women, the more stressed and the less satisfied they are. For men, the frequencies of these observations are not associated with stress, but positively associated with increased satisfaction.