Emotion regulation (ER) is the process by which individuals can modulate the intensity of their emotional experience and it plays a crucial role in daily life. So far, behavioral analyses seem to suggest that ER ability remains stable throughout the lifespan. However, imaging studies evaluating the neural correlates of ER performance during the aging process have shown mixed results. In this study, we used the “Cambridge Centre for Ageing and Neuroscience cohort sample” to investigate: (1) ER behavioral performance and (2) the differential association between brain measures (based on both structural and functional connectivity data) and ER performance, in a group of younger/middle‐aged participants (N = 159; age range: 18y < x < 58y) relative to a group of older healthy subjects (N = 136; age range: 58y < =x < 89y). Whereas we found no group‐related differences either in ER behavioral data or the association between ER performance and structural data, we did observe that ER performance was differentially correlated in our two study groups to functional connectivity measures in the fronto‐insular‐temporal network, which has been shown to be involved in emotional processing. Group‐related differences were specifically localized in a cluster of voxels within the anterior cingulate areas which revealed a reverse pattern between our study groups: in younger/middle‐aged participants better ER performance was associated with increase connectivity, whereas among older participants better ER performance was related to reduced connectivity. Based on our results, we suggest that a de‐differentiation mechanism, known to affect the frontal lobes brain activity and connectivity in older subjects, might explain our findings.