Background and Objectives: Despite the expected positive association between subjective functional difficulties (SFD) and subjective cognitive decline (SCD), their mediation by mentally unhealthy days (MUDs) is under-studied. Moreover, few SCD studies have examined affective reactivity to functional difficulties by age cohort. This study examined the mediation effect of MUDs on the association between SFD and SCD by age cohorts’ moderation among older adults. Methods: Using a cross-sectional design approach, we used the 2019 BRFSS dataset on 13,377 older adults aged 65 to ≥80 (44% males and 56% females). Results: The bias-corrected percentile bootstrap with 5000 samplings revealed that MUDs partially mediate the relationship between SFD and SCD (14.12% mediation effect), controlling depressive symptoms, education, income levels, and race. Age cohorts moderated the relationship between SFD and SCD and between SFD and SCD but not between MUDs and SCD. The predictive effects of the path from SFD to MUDs and from MUDs to SCD were stronger in the younger-old (65–69) than the middle-old (70–79) and oldest-old (≥80) age cohorts. Worse SCD was associated with being Asian, in female older adults, and in those with lower education and income levels. Conclusions: These findings extend the chronic stress theory predictions that accentuated emotional vulnerability to subjective functional difficulties may magnify SCD, particularly in the younger-old age group. By implication, preventive SCD interventions should seek to support younger-old adults in their activities of daily life for successful aging transitioning into older-age cohorts.