This chapter analyzes factors that may explain the existence and magnitude of starting price–based overrounds on Betfair, the leading and globally dominant person-to-person Internet betting site. Drawing on both finance and horse race betting literatures, several hypotheses are developed and tested, using data on 2,184 horse races in the United Kingdom between 2008 and 2010. Results are discussed and explanations offered for the findings, such as a positive relationship between grade of race and Betfair overround (the higher the grade, the higher the overround). More broadly, this research suggests that microstructure analysis of order-driven betting markets, such as Betfair, constitutes a fruitful line of enquiry for those interested in understanding market efficiency.