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In most countries policy makers are seeking to raise the age at which people become eligible for state pensions due to population aging. Aging societies are also characterised by an increase in the number of people are living with chronic conditions and multi-morbidity which can affect employment later in life. This study examines the prevalence of multi-morbidity by age, birth-cohort, and socioeconomic status before assessing the impact that this has on employment status for workers approaching retirement age. It presents a comparative analysis of the UK and Canada and discusses the different policies that each have adopted regarding older workers with chronic conditions.We estimate the prevalence of multi-morbidity (composed of 6 broad categories of disease) for those aged between 50 and 64, by sex, educational level, and by two birth cohorts: the silent generation (pre-1946) and the baby boomers (1946–1964), using the Health Survey for England and the Canadian Community Health Survey. The prevalence of each condition and the changes in specific comorbidities between the generations were estimated. Finally, the association between multi-morbidity on the employment status (in employment or not) is assessed. Each of the analyses uses logistic regression models.Prevalence of multi-morbidities has increased between generations, particularly for the lower educated in England and higher educated groups in Canada. As the number of conditions increased the probability of being in employment decreased. While employment rates are similar for people with no-conditions in the UK and Canada there was a more negative impact of having more than one condition in the UK. For example, silent generation women with a low education in the England with 3+ conditions were much less likely to be employed than women with no health conditions (odds ratio of 0.095 (0.071–0.128), whilst the effect was lower for low educated silent generation women in Canada 0.318 (0.235–0.431)). The consequences of multi-morbidity for employment was found to be similar between generations. The increase in multi-morbidities may have led to reduced employment prospects particularly amongst the less educated groups in England.Many countries are facing the challenge of an aging population. The effect of multi-morbidity on employment for older workers has been understudied even though it presents a set of challenges which risk exacerbating existing social inequalities because they are concentrated among less advantaged groups and associated with reduced employment prospects. The research presented here suggests that different policy approaches might be effective in ameliorating these inequalities.