This multi-method study aimed to disentangle objective and subjective components of job stressors and determine the role of each for hypertension risk. Because research on job stressors and hypertension has been exclusively based on self-reports of stressors, the tendency of some individuals to use denial and repressive coping might be responsible for the inconclusive results in previous studies. Stressor measures with different degrees of objectivity were contrasted, including (1) an observer-based measure of stressors (job barriers, time pressure) obtained from experts, (2) self-reported frequency and appraised intensity of job problems and time pressures averaged per workplace (group level), (3) self-reported frequency of job problems and time pressures at the individual level, and (4) self-reported appraised intensity of job problems and time pressures at the individual level. The sample consisted of 274 transit operators working on 27 different transit lines and four different vehicle types. Objective stressors (job barriers and time pressure) were each significantly associated with hypertension (casual blood pressure readings and/or currently taking anti-hypertensive medication) after adjustment for age, gender and seniority. Self-reported stressors at the individual level were positively but not significantly associated with hypertension. At the group level, only appraisal of job problems significantly predicted hypertension. In a composite regression model, both observer-based job barriers and self-reported intensity of job problems were independently and significantly associated with hypertension. Associations between self-reported job problems (individual level) and hypertension were dependent on the level of objective stressors. When observer-based stressor level was low, the association between self-reported frequency of stressors and hypertension was high. When the observer-based stressor level was high the association was inverse; this might be indicative of denial of stress or alexithymia. We feel that multi-method studies are useful for disentangling the relations between objective and subjective stress and hypertension.