This study provides novel insights into older adults' cognitive functioning before and after widowhood onset and possible effect channels. It further examines gender heterogeneity in the adaptation to (anticipated or actual) spousal bereavement, comparing objective evidence with subjective evidence of cognitive abilities. We used longitudinal data of up to 26,584 participants of the Health and Retirement Study, aged over 50 at recruitment, assessed biennially between 1998 and 2016. Two-way fixed effects with dynamic treatment effects were estimated for various cognitive measures, including six aggregated indices and six single item scales. After adjusting for effect channels including depression, social vulnerability, and stress, there remained significant widowhood effects on older adults' cognitive health. Using single item scales, we established the adverse contemporaneous and adaptation effects on bereaved older females' short-term memory, semantic memory, and numeracy. For bereaved older males, working memory and focus-of-attention deteriorated after widowhood onset. Meanwhile, subjective memory rating remained intact, contrary to objective evidence. We conclude that cognitive transitions to and from widowhood can exhibit distinctive patterns across objective and subjective cognitive domains. With the effect channels in mind, cognitive intervention for widowed older adults should be tailored to the temporal distance to spousal loss, gender, and task.