Despite the universal social policies of Sweden’s welfare state, recent decades have seen decreasing public benefits and increasing socio-economic disparities, affecting the financial wellbeing of older adults and their younger family members. This repeated cross-sectional study explores the development of intergenerational financial transfers in Sweden over the past two decades, examining transfers involving older parents and their children and grandchildren, and patterns related to gender and social class. It utilises data from the Swedish Panel Study of Living Conditions of the Oldest Old, from 2002 to 2021, along with descriptive statistics and logistic regression models, to study shifts in donor–receiver proportions and gender/social-class disparities. The findings revealed that approximately one in four parents provided financial support to younger generations, while very few received such support. Downward financial transfers increased over time, with growing focus on grandchildren. No significant gender differences in providing were identified; however, women’s contributions increased in frequency and amount, compared to previous cohorts of women. Men’s contributions remained relatively stable over time. Parents in higher social classes were more inclined to provide financial support than parents in lower classes; this difference grew over time. Additionally, parents in higher social classes more frequently provided higher amounts than their counterparts. In conclusion, this study underscores changing gender and social-class patterns in financial contributions made by parents to their children and grandchildren in contemporary Sweden. Understanding these levels and subgroup differences is crucial for shaping policies and mitigating the potential growth of socio-economic inequality in future generations.