Following a review of the etymology and modern usage of the term ‘arbitrage’, this article explores the relevance of historical context to possible instances of ancient arbitrage activity. Types of possible ‘arbitrage’ associated with the use of overvalued coinage in regions of Greek influence are considered. Comparison with Roman civilization reveals the relevance of social attitudes and legal institutions to the ability to execute arbitrage trades. Specific attention is given to the possibility of arbitrage across the Roman frontier to India and the impact of debasements during the imperial period. Recognizing that sources prior to early modern times are scant, numismatic, epigraphic and literary evidence that is available to make inferences about ancient arbitrage activity is assessed.