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The present study simulates an enduring intergroup conflict in which each of two interacting groups is represented by a single representative elected for a given period. The authors assume that the conflict between the two groups can be modeled as an iterated prisoner's dilemma game played by the groups' representatives, and that the performance of each representative influences her constituents which, in turn, affects her prospects for reelection. At the end of a constituency period, new elections are called, and their results determine whether the delegate remains in her position or is replaced by another representative. The main objectives are: (1) to investigate the effect of this common democratic procedure, namely, the periodic election of group representatives, on the evolution of cooperation between the groups; and (2) to investigate the effect of the frequency of elections in the two groups on evolving intergroup relations. Outcomes of 360 simulations yielded the following main results: (1) the dynamics of the intergroup conflict evolve into five phases of well-defined patterns; (2) for most election frequencies, mutual defection was not an enduring pattern whereas mutual cooperation evolved as an enduring pattern; and (3) there exists an election frequency that optimizes the likelihood that the intergroup process converges to mutual cooperation.