In the present study, we test the hypothesis whether experiential emotion regulation works more in-depth after repeated regulation, while top-down cognitive emotion regulation would have an initial advantage, which will decrease over time. Participants (N = 58; all women) viewed negative, arousing pictures three times. One group was randomly assigned to apply experiential emotion regulation, the other group, cognitive reappraisal. A ‘watch’ control condition, in which participants were instructed to focus on the colours in the picture, served as a within-subject control condition for both groups. Outcome measures included self-reported negative emotional experience, facial expression (EMG) of the corrugator and zygomaticus muscles, skin conductance, and heart rate. In line with our expectations, relative to the control ‘watch’ condition, the first instance of experiential emotion regulation was associated with higher subjective negative emotional experience, whereas cognitive reappraisal was associated with lower subjective negative emotional experience and increased positive facial expressivity. Repeating the same emotion regulation strategy resulted in a steeper relative decrease of negative emotional experience for experiential emotion regulation relative to cognitive appraisal. At the third instance of emotion regulation there was no significant difference in negative emotional experience between experiential emotion regulation and cognitive reappraisal. The findings provide insight into the mechanisms underlying experiential emotion regulation versus cognitive reappraisal.