The article examines the influence of Xenophon’s didactic works on the military activities of Alexander the Great. It is re-vealed that messages from ancient sources containing direct in-dications of the fact that Alexander was familiar with Xeno-phon’s works are either fundamentally unreliable or subject to different interpretations. Nevertheless, a comparison of the rec-ommendations proposed in “Kyropedia” and other Athenian au-thor’s writings the with Alexander’s practical activities reveals obvious similarities in their views on training military personnel, organizing competitions in military skill, providing soldiers with richly decorated weapons, and caring for the sick and wounded. A set of coincidences is associated with the political and admin-istrative activities of Alexander, who, like Cyrus the Elder in Xenophon’s writings, demonstratively showed mercy towards the vanquished, attracted representatives of the local elite to the ser-vice, wore clothes traditional for a conquered country. A large number of similarities, good education of Alexander and the popularity of Xenophon’s writings in the second half of the 4th century BCE allow us to conclude that the Macedonian king was familiar with the works of the Athenian author. However, the components of Xenophon's didactic legacy associated with the methods of warfare do not correlate well with Alexander's mili-tary leadership practice. The fundamental differences are re-vealed in the armament of the cavalry and their tactics, the depth of the infantry formation, the role of army branches on the battle-field. They were caused by a significant breakthrough in the art of war that took place in Macedonia during the time of Philip II. This breakthrough also led to the emergence of new tactics that provided for crushing the enemy not with a frontal attack of heavy infantry, but through the combined use of various types of troops. Alexander as a military leader was raised under the con-ditions of a new, more developed military art. Thus, the over-whelming majority of Xenophon's recommendations, which de-scribed the cavalry as a purely auxiliary branch of the army and considered the classical hoplite phalanx a decisive force in battle, were clearly irrelevant for him and therefore ignored.