Zechariah 9:5 - Matthew Poole's English Annotations on the Holy Bible

Ashkelon, threatened by Zephaniah, Zephaniah 2:4, which threat was executed by the Babylonians soon after the Jews captivity, when Nebuchadnezzar wasted the seacoast, and besieged and took Tyre; but this threat of Zechariah was fully executed by Alexander the Great, as is most likely. Shall see it; as cities see the fall of neighbouring cities, they shall have the news of it, and know it; perhaps some Ashkelonites may be there, and see the siege, and tell it. And fear; as men that have no power to defend themselves, nor means left of fleeing from the enemy. Gaza; another strong town, a principality of the Philistines, enemy to Israel; which in Nebuchadnezzar's time suffered with Tyre, Zephaniah 2:4, and shall again so suffer in Alexander's time, as here foretold. Be very sorrowful; at the news of Tyre's fall shall take a fright, and fall into sorrows of a travailing woman, as the word imports. Ekron, a city famous for idolatry, see Zephaniah 2:4, shall as much fear and grieve as Ashkelon or Gaza. Her expectation, her hope that Tyre would break Alexander's power, or hold out against it, and be a refuge to her citizens, who could not hope to withstand the conqueror, shall be ashamed; turned into shame and confusion. The king shall perish from Gaza; the government be overthrown; and perhaps this literally was fulfilled when Alexander the Great took Gaza after two months siege, and two slight wounds received, and finding Boetis, the king or roitelet, advanced to that dignity by Darius, thought good to put him to a cruel death, as Curtius, l. 4. Ashkelon shall not be inhabited, i.e. for some years it shall be as waste, or as it was laid by the Babylonian, according to Zephaniah 2:4.