Objectives: This study aimed to analyze caregivers and care recipients’ health characteristics and caregiving context changes during a one-year follow-up. Methods: A total of 204 informal caregivers and oldest-old care recipients ( ≥ 80 years) were assessed on two occasions, 12 months apart. Information was retrieved on the dyad’s sociodemographic profile, caregiver’s health/caregiving outcomes, care recipients’ dependency level, and caregiving context. Descriptive analysis was performed for all variables and comparisons between the two moments using paired t tests or McNemar tests. Results: Caregiving hours, caregiver burden, and negative aspects of caregiving got significantly worse over one year. The number of unmet needs, in-home services utilization, and self-perception of mental health improved. Care recipients declined in their functional and health status and on their cognitive performance. Conclusions: This study provides information about caregiving trajectory changes over one year and stresses a probable caregiver adaptation even when facing increasing caregiving demands.