As a boy, his tutor was the Athenian philosopher Aristotle. Alexander was so impressed with him that, as an adult, he did not wipe out the Greeks, though he did enslave them. He retained an interest in Greek theatre after beginning his conquests. (AUDIO: Mask of Tragedy)
Alexander was once targeted by android assassins, but was saved by Time Agents Jack Harkness and John Hart, who claimed them to be Persians. Giving the pair his thanks, Alexander had sex with both Jack and John before being caught in the act by Hephaestion. (AUDIO: The Death of Captain Jack)
In May 323 BC, the First Doctor, Susan, Ian and Barbara met Alexander in Babylon. During this time, the four became close friends with Alexander. To Alexander's great distress, his generals, friends, and designated successors - Cleitus, Calanus and Hephaestion - were murdered by Antipater and his co-conspirators, Antipater blamed the Doctor and his companions for the deaths, causing Alexander to imprison them. At their trial, Alexander realised that that they were probably innocent, but still demanded they prove their innocence before the gods to appease the superstitions of his army.
Thus, in June of that year, games were held to celebrate the life of the recently departed Hephaestion. To appease the gods, Ian chose to fight in the wrestling, while the Doctor was told to walk across scalding hot embers. Both did this successfully, pleasing Alexander and the onlooking crowd. Secretly, Antipater had poisoned Alexander's wine. Later that day, Alexander drew his generals together to out Antipater as a murderer, as he had recently deduced was the case. Antipater was then slayed by Seleucus, who did not want this part in the plot to become known. Alexander then collapsed as the poison began to take effect. With his dying breathe, with his wife Roxane by his side, Alexander bid that the successor should be "the best man". (AUDIO: Farewell, Great Macedon)
In an alternate timeline in 331 BC, Alexander was in Alexandria when the alien Rhakotis arrived in the city. He met Barbara Wright in this timeline, but eventually died some some disease which was extraterrestrial in origin. (PROSE: The Book of Shadows)
Immediately after his third regeneration, the Fourth Doctor recalled his encounter with Alexander the Great. Temporary memory loss caused him to refer to Brigadier Lethbridge-Stewart as Alexander. (TV: Robot)
In the 2190s, the Eighth Doctor's former companion Lucie Miller sarcastically referred to his great-grandson Alex Campbell as "Alexander the Great" due to his willingness to attack the Dalek occupation forces in North America. (AUDIO: Lucie Miller)