Background <p>Teachers constitute a distinct occupational group that is at risk of work-related psychological distress. The present study examined associations among psychological distress, work-related burden, and oral health–related quality of life (OHRQoL) among schoolteachers.</p> Methods <p>A cross-sectional survey was conducted among teachers in Jeddah, Saudi Arabia. The Depression, Anxiety, and Stress Scale (DASS-21) and Oral Health Impact Profile (OHIP-14) were used to assess psychological distress and OHRQoL, respectively.</p> Results <p>Of the 347 teachers, 28.5%, 43.8%, and 29.0% reported severe or extremely severe depression, anxiety, and stress, respectively. Teachers who rated their oral or general health as poor had significantly higher OHIP-14 scores than those who rated their oral or general health as excellent (<i>p</i> &lt; 0.0001). Higher DASS-21 severity levels were significantly associated with higher OHIP-14 scores (<i>p</i> &lt; 0.0001). Higher stress levels were reported among female teachers than among male teachers (<i>p</i> = 0.002), those with chronic diseases (<i>p</i> = 0.02), and those without family or personal support (<i>p</i> = 0.03), but these differences did not hold for the depression and anxiety subscales of DASS-21. Job dissatisfaction was strongly associated with more severe forms of depression, anxiety, and stress (<i>p</i> &lt; 0.007). Regression analysis showed that poorer OHRQoL, female sex, perceived lack of colleague support, spending time on out-of-school work tasks, and job dissatisfaction were associated with higher psychological distress (<i>p</i> &lt; 0.0001).</p> Conclusions <p>Psychological distress was common among teachers and significantly associated with poorer OHRQoL. Work-related burdens and lack of social support predicted higher distress levels. Interventions promoting teachers’ well-being should integrate mental and oral health components and target modifiable workplace factors.</p>