October 1, 331 B.C. - On this date, Alexander the Great soundly defeated Darius III of Persia in the Battle of Gaugamela. Though the size of the Persian army was far greater than that of Alexander, darius' infantry was no match for the Macedonian leader's hoplites.
October 3, 42 B.C. - In the First Battle of Philippi, Mark Antony and Octavian (who were allies at this point) fought against Brutus and cassius, to avenge the assassination of Julius Caesar. Though Antony's army was able to defeat Cassius' troops, the battle ended in a draw, forcing a second battle a few weeks later.
October 3, 42 B.C. - Roman Senator and Julius Caesar assassin Cassius was killed by his own men, on his own order, after his defeat by Mark Antony at the First Battle of Philippi.
October 6, 105 B.C. - The Battle of Arausio, waged between the Roman armies and the ancient tribes of modern France (including the Gauls), was fought on this date. Conflicts among the Roman armies led to disorganization of the troops, and a horrible defeat. There were approximately 80,000 Roman casualties, and a period of political dissention and reorganization followed.