The Pentathlon is a combined athletic discipline of the ancient Olympic Games. A detailed exploration of the ancient Olympic competitions in general and of the pentathlon, in particular, allow us to discover1200 years of sport history. The spectacle of the pentathlon contest, the method of determining a winner, the order of the five disciplines is simply fascinating. The modern Olympic Games redefined the pentathlon among the Olympic disciplines. Under the name of the modern pentathlon, it gradually regained its fame won in antiquity. The military pentathlon is a variant of the modern pentathlon deployed within the military organization and is considered the king of military sports. The evolution of the modern battlefield, strongly influenced by the modern combat technique, will surely change the pentathlon contest register. Even if respect for the Olympic spirit is desired, the pentathlon must take into account the evolution of the contemporary society to keep its attractiveness.