Unintentional islanding can be a harmful event, requiring the fast actuation of the anti-islanding protection to disconnect the distributed generators. Although passive techniques are mostly used, they have non-detection zones and fail to detect islanding under specific conditions. Therefore, knowing in advance such operative conditions and the risks associated with the islanding occurrence can be a strategic information to support grid operators in the decision-making process regarding the effectiveness of distributed generators interconnection protection. In this context, this paper proposes a probabilistic method to assess the risk of energized island formation by combining the probability of breaker (or recloser) opening with the probability of anti-islanding protection failure. The method employs probabilistic short circuit associated with overcurrent protection actuation by using Monte Carlo simulation and time-domain analysis to obtain the cases of unintentional islanding and to calculate the risk of distributed generator islanded operation. The results drove more realistic and less conservative conclusions than previous literature. Additionally, it is shown that faults as the cause of breaker opening do play a relevant role in the performance of the anti-islanding protection.