Cognitive reappraisal is an important strategy for emotion regulation. Studies show that even healthy people may not be able to implement this strategy successfully, but the underlying neural mechanism behind the behavioral observation of success or failure of reappraisal is unclear. In this paper, 28 healthy college students participated in an experiment of emotional regulation with the cognitive reappraisal strategy. They were asked to complete the cognitive psychological questionnaires before the experiment. Their behavioral scores and scalp electroencephalogram (EEG) signals were collected simultaneously during the experiment. We divided all the subjects into two groups, according to the statistical test of valence scores. Then we analyzed their questionnaires, early event-related potential (ERP) components N200, P200, and late positive potential (LPP), and calculated the correlation between the valence score and the amplitude of LPP. The results showed that, in both groups, compared with negative-watching, the reappraisal induced larger N200 and P200 components and there were two modulation patterns (“increase” and “decrease”) of the reappraisal effect on the amplitude of early LPP (300−1 000 ms after stimulus onset). Moreover, correlation analysis showed that significant positive correlation between two differences in the successful group, i.e., the greater difference in the valence scoresin between reappraisal and negative-watching, the greater difference in the amplitude of early LPP between reappraisal and negative-watching; but no such effect was found in the failure group. These results indicated that, whether reappraisal was successful or not, no significant effect on early ERP components was found; and there were different patterns of the reappraisal effect on early LPP. The difference between successful and failure groups was mainly reflected in early LPP, that is, the EEG characteristics and behavioral scores of successful group were significantly positively correlated. Furthermore, the small sample analysis showed that this correlation only existed in the pattern of "increase". In the future, more research of this modulation mode is necessary in order to find more stable EEG characteristics under successful cognitive reappraisal in emotion regulation.