There is growing evidence on the negative effects of perceived discrimination on health outcomes and their interactions with indicators of socioeconomic status. However, less has been studied on whether income and education lead individuals of a different race to encounter different discriminatory experiences in their lifetime. Using data from the national survey of the Midlife Development in the United States-MIDUS 1 (1995-1996) and MIDUS Refresher (2011-2014)-on eight measures of perceived lifetime discrimination, this study compares discriminatory experiences of Black and White persons in two time periods. We applied generalized structural equation models and generalized linear models to test multiplicative effects of income and education by race on lifetime discrimination. In both periods, we find substantive disparities between White and Black people in all types of lifetime discrimination, with Black people reporting much higher levels of discrimination. Such disparities exacerbated in the top cohorts of society, yet these associations have changed in time, with White individuals reporting increasing levels of discrimination. Results show that, for Black people in the mid-1990s, perceived discrimination increased as education and income increased. This finding persisted for education by the early 2010s; income effects changed as now both, low- and high-income Black people, reported the highest levels of discrimination. These findings highlight a policy conundrum, given that increasing income and education represent a desirable course of action to improve overall discrimination and health outcomes. Yet, we show that they may unintendingly exacerbate racial disparities in discrimination. We also show that the U.S. is moving toward a stagnation period in health outcomes improvement, with racial disparities in discrimination shrinking at the expense of a deterioration of whites' lifetime discriminatory experiences. Our results highlight the need for a multi-systems policy approach to prevent all forms of discrimination including those due to historical, institutional, legal, and sociopolitical structures.