The long-term effects of multiple sport-related concussions are currently at the center of debate in the popular press and scientific community. The question, "How many concussions are too many," is frequently asked in the competitive sport environment by parents, athletes, and coaches. While research suggests that a history of concussion influences the risk and recovery from subsequent concussion, studies investigating the long-term effects of multiple concussions are less conclusive. This paper reviews the literature on multiple concussions and the potential long-term consequences of these injuries. Furthermore, this paper addresses how concussion history can inform clinical and return-to-play decisions. Recent studies incorporating novel brain imaging and electrophysiological technology for assessing residual impairment from multiple concussions are reviewed and the clinical implications of this work are discussed.