Stressful events may affect self-perceived general and oral health. While the working environment is known to expose military personnel to chronic stress, oral health reports in these populations is limited. This longitudinal study aimed to investigate the association of Oral Health Related Quality of Life (OHRQL) and stress in the military population aboard a training ship for 6 months. Three hundred and twenty-eight individuals were enrolled at baseline and three hundred and one at follow-up (six-month later). Completed questionnaires on Oral Health Impact Profile (OHIP-14) and Perceived Stress Scale (PSS-14) were assessed for analysis. Socio-demographic characteristics were also obtained. Multivariate Poisson regression analysis showed that PSS-14 predicted higher OHIP-14 scores at baseline and follow-up. At follow-up, besides PSS-14 (RR: 2.03; 1.42-2.90), being part of the crew group represented an increase of 87% on the OHIP-14 scores (RR:1.87; 1.27-2.74). Older individuals were 24% less likely to present higher OHIP-14 scores (RR:0.76; 0.58-0.99) than younger ones. OHRQL has worsened over time in this military population aboard (4.41±5.76 versus 5.95±6.88) and stress was an associated factor of that. The need to adjust management styles was highlighted as well as the need to prepare the staff to navigate stressful situations more effectively.