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Our daf includes one of the most famous stories in the Gemara, when the kohen gadol, Shimon HaTzaddik met Alexander Mokdon (the Macedonian). The story is taken from Megillat Ta’anit (where the baraita explains why during the second Temple period the 25th day of Tevet was celebrated as a minor holiday, which was called “the day of Mount Gerizim.”
The Samaritans approached Alexander Mokdon and requested permission from him to be permitted to destroy the Temple in Jerusalem. Alexander agreed. When word of this got to Jerusalem, the kohen gadol, Shimon HaTzaddik dressed in his priestly garments and headed north together with an entourage to greet Alexander.
These stories have some parallels in Josephus but further exploration reveals little historticity. The only historical event connecting Alexander the Great with the Jews is his visit to Jerusalem, which is recorded by Josephus in a somewhat fantastic manner. According to "Ant." xi. 8, §§ 4-6, Alexander went to Jerusalem after having taken Gaza.