Background Keeping older workers in employment is critical for societies facing the challenge of an ageing population. This study examined the association between types of health conditions and differentials in the probability of employment by level of education among men and women between 60-69 years of age in Canada, Denmark, Sweden and England. Methods Data were drawn from the Canadian Community Health Survey, Survey of Health, Ageing and Retirement in Europe and English Longitudinal Study of Ageing. We combined country data, applied logistic regression, adjusted for educational level, and stratified the analysis by sex to calculate the odds ratio (OR) of employment (>15 hours work per week) for persons with physical health conditions, mental health conditions (depression) and physical-mental health comorbidity. Results The odds of employment among men and women with physical-mental health comorbidity were lower compared to those with no/other conditions (men: OR 0.32, 95% CI: 0.25-0.42, women: OR 0.38 95% CI: 0.30-0.48). Women with low education had lower odds of employment compared to their counterparts with high education (OR 0.66, 95% CI: 0.57-0.76). The odds of employment at older ages was lower in Canada, Denmark and England compared with Sweden (e.g. English men: OR 0.48 95% CI 0.40-0.58; English women OR 0.33 95% CI 0.27-0.41). Conclusions The odds of employment beyond age 60 is lower for groups with low education, particularly women, and those with physical-mental health co-morbidities. As such, policies to extend working lives should not be 'one size fits all' but instead consider subgroups, in particular, these groups that we have shown to be most vulnerable on the labour market.