This paper investigates early evidence of boxing as a sport in Ancient Egypt and Mesopotamia. Its representations were relatively rare in both cultures, because of the essentially static nature of their arts. In addition, it is also difficult to distinguish between wrestlers and boxers. The article examines the differences among early pictorial examples from the two cultures dating to the third and second millennia BCE. This article aims also to answer key questions concerning this sport in both cultures: Which culture did practice the sport first? Which one did borrow this sport from the other? It is worth noting that the evidence of boxing in Mesopotamia was earlier than that originating from Egyptian contexts. Moreover, the origins of boxing in Ancient Egypt are uncertain. The article raises another important question, stating, "Do all images in the article are Boxing Scenes or some of them can be considered as combat training?" Despite the disagreement in both cultures, it can be argued that boxing representation in Mesopotamia is clearer than in Ancient Egypt.