This study explored changes in the associations between and coexistence of disadvantages in several dimensions of living conditions in the oldest old people in Sweden. We used nationally representative data from 1992 (n = 537), 2002 (n = 621) and 2011 (n = 931). Indicators of limited social resources, limited political resources, limited financial resources, psychological health problems, physical health problems and functional limitations were used. The probability of reporting coexisting disadvantages tended to increase and was particularly elevated in 2002. Physical health problems became more common, and functional limitations, limited financial resources and limited political resources became less common during the studied period. Associations between health-related disadvantages remained fairly stable, whereas associations including other kinds of disadvantages varied somewhat over the studied period. These changes suggest that in general, the composition of coexisting disadvantages is likely to have altered over time. Consequently, the challenges faced by disadvantaged groups in 2011 may have been different from those in 1992. Moreover, the healthcare and social care services directed to older people have undergone significant changes during the past decades. These changes to the system accentuate the vulnerability of people experiencing coexisting disadvantages.